Persist file categories on the index and classify archives and unknown types during idle maintenance.

Co-authored-by: Cursor <cursoragent@cursor.com>

Backlog.md

@@ -457,14 +457,14 @@ Goal: Understand what files and folders represent rather than relying only on ex
 ## Detection signals
 
 - [x] File extension
-- [ ] MIME/content signature
+- [x] MIME/content signature (light idle magic-byte; never hydrates)
 - [x] Folder structure
 - [x] Git metadata
 - [x] Media metadata
 - [x] Known application structures (`node_modules`, `bin`, `obj`, `.vs`)
 - [x] File age (old installers flagged in preview)
 - [ ] File relationships
-- [ ] Index metadata
+- [x] Index metadata
 
 ---
 

docs/Documentation.md

@@ -343,7 +343,22 @@ Classification **suggests** moves. Nothing moves until you Preview and Queue.
 
 Build output names (`node_modules`, `bin`, `obj`, `.vs`, and similar) are never moved. Online-only cloud items are skipped. Old installers (older than one year) still propose a move and show a warning. Destinations may sit *inside* the source folder (Downloads → Downloads\Software). Destinations are remembered in preferences.
 
-Never auto-reorganizes. No MIME/content sniffing (that would hydrate cloud files).
+Organize uses the **indexed category** when one exists (including ZIP contents that are mostly photos, and **Classify as…** overrides). Extension heuristics fill in the rest.
+
+Never auto-reorganizes. A light magic-byte peek for unknown extensions runs only during idle maintenance on local files — never on online-only cloud items.
+
+---
+
+## Classification
+
+The index stores a category on each entry (Photos, Video, Documents, Archive, and so on) plus a short reason.
+
+- Details shows a **Category** column (tooltip has the reason)
+- Search accepts `category:photos` or the category dropdown
+- Storage analysis has **By category** next to **By file type**
+- Context menu **Classify as…** writes a user override that later scans do not replace
+
+ZIP/7z files stay Archive until their contents are indexed; idle maintenance then promotes them when a category dominates.
 
 ---
 
@@ -416,7 +431,7 @@ Left open on purpose:
 - Multi-PC search, sharing, encrypted vaults
 - Robocopy as a second transfer engine
 - Scheduled profiles and folder-watcher triggers
-- MIME/EXIF classification
+- Full EXIF / ffprobe classification
 - Duplicate “backup copy” auto-tagging
 
 ---

src/Explorer.Analysis/AnalysisService.cs

@@ -76,6 +76,16 @@ public sealed class AnalysisService
             ct => _store.Analysis.UsageByExtensionAsync(sourceId, pathRelPrefix, take, ct),
             cancellationToken);
 
+    public Task<IReadOnlyList<CategoryUsage>> UsageByCategoryAsync(
+        long? sourceId,
+        string? pathRelPrefix,
+        int take = AppConstants.AnalysisTopN,
+        CancellationToken cancellationToken = default)
+        => CachedAsync(
+            $"categories:{sourceId}:{pathRelPrefix}:{take}",
+            ct => _store.Analysis.UsageByCategoryAsync(sourceId, pathRelPrefix, take, ct),
+            cancellationToken);
+
     public Task<IReadOnlyList<SourceUsage>> UsageBySourceAsync(CancellationToken cancellationToken = default)
         => CachedAsync("sources", ct => _store.Analysis.UsageBySourceAsync(ct), cancellationToken);
 

src/Explorer.App/MainWindow.xaml

@@ -44,6 +44,17 @@
       </MenuItem>
       <MenuItem Header="Organize this folder…" Click="OnOrganizeFolder"
                 Visibility="{Binding ShowOrganizeFolder, Converter={StaticResource BoolVis}}"/>
+      <MenuItem Header="Classify as" Visibility="{Binding ShowClassifyAs, Converter={StaticResource BoolVis}}">
+        <MenuItem Header="Photos" Command="{Binding ClassifyAsCommand}" CommandParameter="Photos"/>
+        <MenuItem Header="Video" Command="{Binding ClassifyAsCommand}" CommandParameter="Video"/>
+        <MenuItem Header="Audio" Command="{Binding ClassifyAsCommand}" CommandParameter="Audio"/>
+        <MenuItem Header="Documents" Command="{Binding ClassifyAsCommand}" CommandParameter="Documents"/>
+        <MenuItem Header="Installer" Command="{Binding ClassifyAsCommand}" CommandParameter="Installer"/>
+        <MenuItem Header="Archive" Command="{Binding ClassifyAsCommand}" CommandParameter="Archive"/>
+        <MenuItem Header="Backup" Command="{Binding ClassifyAsCommand}" CommandParameter="Backup"/>
+        <MenuItem Header="Code repository" Command="{Binding ClassifyAsCommand}" CommandParameter="CodeRepository"/>
+        <MenuItem Header="Unknown" Command="{Binding ClassifyAsCommand}" CommandParameter="Unknown"/>
+      </MenuItem>
       <Separator Visibility="{Binding ShowExtractArchive, Converter={StaticResource BoolVis}}"/>
       <MenuItem Header="Extract here" Click="OnExtractHere"
                 Visibility="{Binding ShowExtractArchive, Converter={StaticResource BoolVis}}"/>
@@ -537,6 +548,13 @@
                           <GridViewColumn Header="Date modified" Width="148" DisplayMemberBinding="{Binding ModifiedLabel}"/>
                           <GridViewColumn Header="Date created" Width="148" DisplayMemberBinding="{Binding CreatedLabel}"/>
                           <GridViewColumn Header="Type" Width="100" DisplayMemberBinding="{Binding TypeLabel}"/>
+                          <GridViewColumn Header="Category" Width="110">
+                            <GridViewColumn.CellTemplate>
+                              <DataTemplate>
+                                <TextBlock Text="{Binding CategoryLabel}" ToolTip="{Binding CategoryTooltip}"/>
+                              </DataTemplate>
+                            </GridViewColumn.CellTemplate>
+                          </GridViewColumn>
                           <GridViewColumn Header="Size" Width="110" DisplayMemberBinding="{Binding SizeLabel}"/>
                           <GridViewColumn Header="Git" Width="110" DisplayMemberBinding="{Binding GitLabel}"/>
                           <GridViewColumn Header="Cloud" Width="100" DisplayMemberBinding="{Binding CloudLabel}"/>
@@ -661,6 +679,13 @@
                           <GridViewColumn Header="Date modified" Width="148" DisplayMemberBinding="{Binding ModifiedLabel}"/>
                           <GridViewColumn Header="Date created" Width="148" DisplayMemberBinding="{Binding CreatedLabel}"/>
                           <GridViewColumn Header="Type" Width="100" DisplayMemberBinding="{Binding TypeLabel}"/>
+                          <GridViewColumn Header="Category" Width="110">
+                            <GridViewColumn.CellTemplate>
+                              <DataTemplate>
+                                <TextBlock Text="{Binding CategoryLabel}" ToolTip="{Binding CategoryTooltip}"/>
+                              </DataTemplate>
+                            </GridViewColumn.CellTemplate>
+                          </GridViewColumn>
                           <GridViewColumn Header="Size" Width="110" DisplayMemberBinding="{Binding SizeLabel}"/>
                           <GridViewColumn Header="Git" Width="110" DisplayMemberBinding="{Binding GitLabel}"/>
                           <GridViewColumn Header="Cloud" Width="100" DisplayMemberBinding="{Binding CloudLabel}"/>
@@ -768,6 +793,11 @@
               <TextBlock Grid.Row="1" Text="Extension" Foreground="{DynamicResource FgMuted}" VerticalAlignment="Center" Margin="0,0,8,0"/>
               <StackPanel Grid.Row="1" Grid.Column="1" Orientation="Horizontal" Margin="0,0,16,0">
                 <TextBox Width="90" Text="{Binding Search.Extension, UpdateSourceTrigger=PropertyChanged}"/>
+                <ComboBox Width="140" Margin="8,0,0,0"
+                          ItemsSource="{Binding Search.CategoryChoices}"
+                          DisplayMemberPath="Label"
+                          SelectedValuePath="Value"
+                          SelectedValue="{Binding Search.Category}"/>
                 <CheckBox Content="Files" Margin="16,0,8,0" VerticalAlignment="Center" Foreground="{DynamicResource Fg}"
                           IsChecked="{Binding Search.FilesOnly}"/>
                 <CheckBox Content="Folders" VerticalAlignment="Center" Foreground="{DynamicResource Fg}"
@@ -795,6 +825,7 @@
                 <GridView>
                   <GridViewColumn Header="Name" Width="220" CellTemplate="{StaticResource NameWithOverlays}"/>
                   <GridViewColumn Header="Path" Width="420" DisplayMemberBinding="{Binding FullPath}"/>
+                  <GridViewColumn Header="Category" Width="110" DisplayMemberBinding="{Binding CategoryLabel}"/>
                   <GridViewColumn Header="Size" Width="100" DisplayMemberBinding="{Binding SizeLabel}"/>
                   <GridViewColumn Header="Free space" Width="100" DisplayMemberBinding="{Binding FreeSpaceLabel}"/>
                 </GridView>

src/Explorer.Application/BackgroundMaintenance.cs

@@ -36,6 +36,27 @@ public interface IHistoryMaintenance
     Task<bool> TryCaptureAsync(CancellationToken cancellationToken = default);
 }
 
+public interface IIdleClassifyWork
+{
+    bool IsPaused { get; }
+    string? CurrentPath { get; }
+    void Pause();
+    void Resume();
+    /// <summary>Returns true when any classification work was performed.</summary>
+    Task<bool> ProcessPendingAsync(CancellationToken cancellationToken = default);
+}
+
+public sealed class NullIdleClassifyWork : IIdleClassifyWork
+{
+    public static NullIdleClassifyWork Instance { get; } = new();
+    public bool IsPaused => true;
+    public string? CurrentPath => null;
+    public void Pause() { }
+    public void Resume() { }
+    public Task<bool> ProcessPendingAsync(CancellationToken cancellationToken = default)
+        => Task.FromResult(false);
+}
+
 public interface IForegroundWorkSignal
 {
     bool HasForegroundWork();

src/Explorer.Application/BrowseService.cs

@@ -395,7 +395,11 @@ public sealed class BrowseService
             Cloud = entry.CloudAvailability is { } availability
                 ? new CloudPresence(null, availability, entry.SizeBytes, entry.AllocatedSizeBytes, availability == CloudAvailability.OnlineOnly)
                 : null,
-            Hydration = ItemHydrationFlags.All
+            Hydration = ItemHydrationFlags.All,
+            IndexEntryId = entry.Id,
+            Category = entry.Category,
+            CategoryReason = entry.CategoryReason,
+            CategorySource = entry.CategorySource
         };
 
     private async IAsyncEnumerable<BrowseDelta> ListLiveProgressiveAsync(
@@ -609,7 +613,11 @@ public sealed class BrowseService
             fileId: item.FileId ?? entry.FileId,
             cloud: cloud,
             indexedChildCount: entry.ChildFileCount + entry.ChildDirCount,
-            hydration: item.Hydration | ItemHydrationFlags.Index);
+            hydration: item.Hydration | ItemHydrationFlags.Index,
+            indexEntryId: entry.Id,
+            category: entry.Category,
+            categoryReason: entry.CategoryReason,
+            categorySource: entry.CategorySource);
         return Annotate(hydrated, sizeFromIndex: item.IsDirectory && entry.AggregateSize > 0, preferences, probeAccess: false);
     }
 
@@ -785,7 +793,11 @@ public sealed class BrowseService
             Attributes = c.Attributes,
             FileId = c.FileId,
             ReparseTag = c.ReparseTag,
-            AllocatedSizeBytes = c.AllocatedSizeBytes
+            AllocatedSizeBytes = c.AllocatedSizeBytes,
+            IndexEntryId = c.Id,
+            Category = c.Category,
+            CategoryReason = c.CategoryReason,
+            CategorySource = c.CategorySource
         }).ToList();
 
         var hint = isArchiveFile && items.Count == 0

src/Explorer.Application/EntryClassificationService.cs

@@ -0,0 +1,173 @@
+using Explorer.Domain;
+using Explorer.Domain.Abstractions;
+using Microsoft.Extensions.Logging;
+
+namespace Explorer.Application;
+
+public sealed class EntryClassificationService : IIdleClassifyWork
+{
+    private readonly IIndexStore _store;
+    private readonly IFileSystemEnumerator _enumerator;
+    private readonly IHydrationGuard _hydration;
+    private readonly ILogger<EntryClassificationService> _logger;
+    private readonly IHostActivitySink _activity;
+    private volatile bool _paused = true;
+    private volatile string? _currentPath;
+
+    public EntryClassificationService(
+        IIndexStore store,
+        IFileSystemEnumerator enumerator,
+        IHydrationGuard hydration,
+        ILogger<EntryClassificationService> logger,
+        IHostActivitySink? activity = null)
+    {
+        _store = store;
+        _enumerator = enumerator;
+        _hydration = hydration;
+        _logger = logger;
+        _activity = activity ?? NullHostActivitySink.Instance;
+    }
+
+    public bool IsPaused => _paused;
+    public string? CurrentPath => _currentPath;
+
+    public void Pause() => _paused = true;
+    public void Resume() => _paused = false;
+
+    public async Task<bool> ProcessPendingAsync(CancellationToken cancellationToken = default)
+    {
+        if (_paused)
+        {
+            return false;
+        }
+
+        var backfill = await _store.Entries.BackfillCheapCategoriesAsync(80, cancellationToken)
+            .ConfigureAwait(false);
+        if (backfill > 0)
+        {
+            _activity.Record("Classify", "Backfilled " + backfill + " extension categories");
+            return true;
+        }
+
+        var archives = await _store.Entries.GetArchiveIdsNeedingContentClassifyAsync(20, cancellationToken)
+            .ConfigureAwait(false);
+        if (archives.Count > 0)
+        {
+            foreach (var id in archives)
+            {
+                if (_paused || cancellationToken.IsCancellationRequested)
+                {
+                    break;
+                }
+
+                await _store.Entries.RefreshCategoryFromChildrenAsync(id, cancellationToken)
+                    .ConfigureAwait(false);
+            }
+
+            _activity.Record("Classify", "Updated " + archives.Count + " archive(s) from contents");
+            return true;
+        }
+
+        return await TrySignatureClassifyAsync(cancellationToken).ConfigureAwait(false);
+    }
+
+    private async Task<bool> TrySignatureClassifyAsync(CancellationToken cancellationToken)
+    {
+        var unknowns = await _store.Entries.GetUnknownFilesForSignatureAsync(12, cancellationToken)
+            .ConfigureAwait(false);
+        if (unknowns.Count == 0)
+        {
+            return false;
+        }
+
+        var sources = await _store.Sources.GetAllAsync(cancellationToken).ConfigureAwait(false);
+        var byId = sources.ToDictionary(s => s.Id);
+        var changed = 0;
+        foreach (var entry in unknowns)
+        {
+            if (_paused || cancellationToken.IsCancellationRequested)
+            {
+                break;
+            }
+
+            if (!byId.TryGetValue(entry.SourceId, out var source) || string.IsNullOrEmpty(source.LastRootPath))
+            {
+                continue;
+            }
+
+            var full = PathRules.Combine(source.LastRootPath, entry.PathRel);
+            _currentPath = full;
+            try
+            {
+                var item = _enumerator.GetItem(full);
+                if (item is null)
+                {
+                    MarkSignatureSkip(entry, "File was not found.");
+                    await _store.Entries.UpsertAsync(entry, cancellationToken).ConfigureAwait(false);
+                    continue;
+                }
+
+                if (_hydration.WouldHydrateOnRead(item)
+                    || await _hydration.WouldHydrateOnReadAsync(full, cancellationToken).ConfigureAwait(false))
+                {
+                    MarkSignatureSkip(entry, "Skipped online-only cloud file.");
+                    await _store.Entries.UpsertAsync(entry, cancellationToken).ConfigureAwait(false);
+                    continue;
+                }
+
+                await using var stream = new FileStream(
+                    PathRules.ToExtended(full),
+                    FileMode.Open,
+                    FileAccess.Read,
+                    FileShare.ReadWrite | FileShare.Delete,
+                    bufferSize: 64,
+                    FileOptions.SequentialScan | FileOptions.Asynchronous);
+                var buffer = new byte[16];
+                var read = await stream.ReadAsync(buffer.AsMemory(0, buffer.Length), cancellationToken)
+                    .ConfigureAwait(false);
+                var hit = FileSignatureClassifier.TryClassify(buffer.AsSpan(0, read));
+                if (hit is null)
+                {
+                    entry.CategorySource = CategorySources.Mime;
+                    entry.CategoryConfidence = 10;
+                    entry.CategoryReason = "No known file signature.";
+                    entry.CategoryUtc = DateTimeOffset.UtcNow;
+                    await _store.Entries.UpsertAsync(entry, cancellationToken).ConfigureAwait(false);
+                    continue;
+                }
+
+                EntryCategoryAssigner.Apply(entry, hit, CategorySources.Mime, 70);
+                await _store.Entries.UpsertAsync(entry, cancellationToken).ConfigureAwait(false);
+                changed++;
+            }
+            catch (Exception ex) when (ex is not OperationCanceledException)
+            {
+                _logger.LogDebug(ex, "Signature classify failed for {Path}", full);
+                try
+                {
+                    MarkSignatureSkip(entry, "Could not read file signature.");
+                    await _store.Entries.UpsertAsync(entry, cancellationToken).ConfigureAwait(false);
+                }
+                catch (Exception markEx) when (markEx is not OperationCanceledException)
+                {
+                    _logger.LogDebug(markEx, "Could not mark signature skip for {Path}", full);
+                }
+            }
+        }
+
+        _currentPath = null;
+        if (changed > 0)
+        {
+            _activity.Record("Classify", "Signature-classified " + changed + " file(s)");
+        }
+
+        return changed > 0 || unknowns.Count > 0;
+    }
+
+    private static void MarkSignatureSkip(IndexEntry entry, string reason)
+        => EntryCategoryAssigner.Apply(
+            entry,
+            new FileClassification(entry.Category, reason),
+            CategorySources.Mime,
+            5);
+}

src/Explorer.Application/ReorganizePlanner.cs

@@ -15,7 +15,8 @@ public sealed class ReorganizePlanner
         Func<string, bool> isRepoRoot,
         Func<FileSystemItem, bool>? wouldHydrate = null,
         Func<string, bool>? pathExists = null,
-        DateTimeOffset? now = null)
+        DateTimeOffset? now = null,
+        IReadOnlyDictionary<string, IndexEntry>? indexedByName = null)
     {
         if (string.IsNullOrWhiteSpace(sourceRoot))
         {
@@ -63,13 +64,16 @@ public sealed class ReorganizePlanner
             var childCategories = item.IsDirectory && !FileClassifier.SkipDescent(item.Name)
                 ? ChildCategories(item, enumerator, isRepoRoot)
                 : null;
-            var classification = FileClassifier.Classify(
+            var classification = PreferIndexed(
+                item,
+                indexedByName,
+                FileClassifier.Classify(
                     item.Name,
                     item.FullPath,
                     item.IsDirectory,
                     item.Attributes,
                     item.IsDirectory && isRepoRoot(item.FullPath),
-                childCategories);
+                    childCategories));
 
             if (FileClassifier.ShouldLeave(classification.Category))
             {
@@ -143,6 +147,28 @@ public sealed class ReorganizePlanner
         };
     }
 
+    private static FileClassification PreferIndexed(
+        FileSystemItem item,
+        IReadOnlyDictionary<string, IndexEntry>? indexedByName,
+        FileClassification fallback)
+    {
+        if (indexedByName is null
+            || !indexedByName.TryGetValue(item.Name, out var stored))
+        {
+            return fallback;
+        }
+
+        if (CategorySources.IsUser(stored.CategorySource)
+            || stored.Category is not FileCategory.Unknown)
+        {
+            return new FileClassification(
+                stored.Category,
+                stored.CategoryReason ?? "Indexed category.");
+        }
+
+        return fallback;
+    }
+
     private static IReadOnlyList<FileCategory> ChildCategories(
         FileSystemItem folder,
         IFileSystemEnumerator enumerator,

src/Explorer.Application/WorkbenchHost.cs

@@ -57,4 +57,53 @@ public sealed class LocalIndexMutations : IIndexMutations
         => _store.Hashes.EnqueueSizeCollisionsAsync(sourceId, cancellationToken);
     public Task UpsertRelationAsync(FileRelation relation, CancellationToken cancellationToken = default)
         => _store.Relations.UpsertAsync(relation, cancellationToken);
+
+    public async Task SetUserCategoryByPathAsync(
+        string fullPath,
+        FileCategory category,
+        string? reason = null,
+        CancellationToken cancellationToken = default)
+    {
+        if (string.IsNullOrWhiteSpace(fullPath))
+        {
+            return;
+        }
+
+        var sources = await _store.Sources.GetAllAsync(cancellationToken).ConfigureAwait(false);
+        Source? best = null;
+        var bestLen = -1;
+        var path = PathRules.FromExtended(fullPath).TrimEnd('\\');
+        foreach (var source in sources)
+        {
+            if (string.IsNullOrEmpty(source.LastRootPath))
+            {
+                continue;
+            }
+
+            var root = PathRules.FromExtended(source.LastRootPath).TrimEnd('\\');
+            if (path.Equals(root, StringComparison.OrdinalIgnoreCase)
+                || path.StartsWith(root + "\\", StringComparison.OrdinalIgnoreCase))
+            {
+                if (root.Length > bestLen)
+                {
+                    best = source;
+                    bestLen = root.Length;
+                }
+            }
+        }
+
+        if (best?.LastRootPath is null)
+        {
+            return;
+        }
+
+        var rel = PathRules.MakeRelative(best.LastRootPath, fullPath) ?? "";
+        var entry = await _store.Entries.GetByPathAsync(best.Id, rel, cancellationToken).ConfigureAwait(false);
+        if (entry is null)
+        {
+            return;
+        }
+
+        await _store.Entries.SetUserCategoryAsync(entry.Id, category, reason, cancellationToken).ConfigureAwait(false);
+    }
 }

src/Explorer.Contracts/IWorkbenchHost.cs

@@ -83,4 +83,6 @@ public interface IIndexMutations
     Task MarkRenameBatchUndoneAsync(long id, CancellationToken cancellationToken = default);
     Task EnqueueHashCollisionsAsync(long? sourceId, CancellationToken cancellationToken = default);
     Task UpsertRelationAsync(FileRelation relation, CancellationToken cancellationToken = default);
+    Task SetUserCategoryByPathAsync(string fullPath, FileCategory category, string? reason = null, CancellationToken cancellationToken = default)
+        => Task.CompletedTask;
 }

src/Explorer.Domain/Abstractions/IIndexStore.cs

@@ -59,6 +59,11 @@ public interface IEntryStore
     Task DeleteExpiredTombstonesAsync(DateTimeOffset cutoffUtc, CancellationToken cancellationToken = default);
     Task RenameSubtreePathAsync(long sourceId, string oldPathRel, string newPathRel, CancellationToken cancellationToken = default);
     Task<long> CountPresentAsync(long sourceId, CancellationToken cancellationToken = default);
+    Task RefreshCategoryFromChildrenAsync(long folderOrArchiveId, CancellationToken cancellationToken = default);
+    Task SetUserCategoryAsync(long entryId, FileCategory category, string? reason = null, CancellationToken cancellationToken = default);
+    Task<int> BackfillCheapCategoriesAsync(int take, CancellationToken cancellationToken = default);
+    Task<IReadOnlyList<long>> GetArchiveIdsNeedingContentClassifyAsync(int take, CancellationToken cancellationToken = default);
+    Task<IReadOnlyList<IndexEntry>> GetUnknownFilesForSignatureAsync(int take, CancellationToken cancellationToken = default);
 }
 
 public interface IExcludeStore
@@ -109,6 +114,7 @@ public sealed class SearchRequest
     public bool DirectChildrenOnly { get; init; }
     public bool IncludeOffline { get; init; } = true;
     public bool IncludeDeleted { get; init; }
+    public FileCategory? Category { get; init; }
     public int Skip { get; init; }
     public int Take { get; init; } = 500;
 }
@@ -121,6 +127,7 @@ public interface IAnalysisStore
     Task<IReadOnlyList<IndexEntry>> LargestDirectoriesAsync(long? sourceId, long? parentId, int take, CancellationToken cancellationToken = default);
     Task<IReadOnlyList<IndexEntry>> LargestFilesAsync(long? sourceId, string? pathRelPrefix, int take, CancellationToken cancellationToken = default);
     Task<IReadOnlyList<ExtensionUsage>> UsageByExtensionAsync(long? sourceId, string? pathRelPrefix, int take, CancellationToken cancellationToken = default);
+    Task<IReadOnlyList<CategoryUsage>> UsageByCategoryAsync(long? sourceId, string? pathRelPrefix, int take, CancellationToken cancellationToken = default);
     Task<IReadOnlyList<SourceUsage>> UsageBySourceAsync(CancellationToken cancellationToken = default);
     Task<IReadOnlyList<IndexEntry>> ChildrenBySizeAsync(long parentId, int take, CancellationToken cancellationToken = default);
 }
@@ -132,6 +139,13 @@ public sealed class ExtensionUsage
     public long FileCount { get; init; }
 }
 
+public sealed class CategoryUsage
+{
+    public required string Category { get; init; }
+    public long TotalSize { get; init; }
+    public long FileCount { get; init; }
+}
+
 public sealed class SourceUsage
 {
     public long SourceId { get; init; }

src/Explorer.Domain/Entities.cs

@@ -68,6 +68,11 @@ public sealed class IndexEntry
     public long ScanGeneration { get; set; }
     public long? AllocatedSizeBytes { get; set; }
     public CloudAvailability? CloudAvailability { get; set; }
+    public FileCategory Category { get; set; } = FileCategory.Unknown;
+    public string? CategoryReason { get; set; }
+    public int CategoryConfidence { get; set; }
+    public string CategorySource { get; set; } = CategorySources.None;
+    public DateTimeOffset? CategoryUtc { get; set; }
 }
 
 public sealed class ExcludeRule
@@ -150,6 +155,10 @@ public sealed class FileSystemItem
     public bool AvailableToImport { get; init; }
     public ItemHydrationFlags Hydration { get; init; } = ItemHydrationFlags.All;
     public int IndexedChildCount { get; init; }
+    public long? IndexEntryId { get; init; }
+    public FileCategory Category { get; init; }
+    public string? CategoryReason { get; init; }
+    public string? CategorySource { get; init; }
     public bool IsReparsePoint => (Attributes & AttributeFlags.ReparsePoint) != 0;
 
     public FileSystemItem Overlay(
@@ -168,7 +177,11 @@ public sealed class FileSystemItem
         long? capacityBytes = null,
         bool? availableToImport = null,
         ItemHydrationFlags? hydration = null,
-        int? indexedChildCount = null)
+        int? indexedChildCount = null,
+        long? indexEntryId = null,
+        FileCategory? category = null,
+        string? categoryReason = null,
+        string? categorySource = null)
         => new()
         {
             FullPath = FullPath,
@@ -189,7 +202,11 @@ public sealed class FileSystemItem
             CapacityBytes = capacityBytes ?? CapacityBytes,
             AvailableToImport = availableToImport ?? AvailableToImport,
             Hydration = hydration ?? Hydration,
-            IndexedChildCount = indexedChildCount ?? IndexedChildCount
+            IndexedChildCount = indexedChildCount ?? IndexedChildCount,
+            IndexEntryId = indexEntryId ?? IndexEntryId,
+            Category = category ?? Category,
+            CategoryReason = categoryReason ?? CategoryReason,
+            CategorySource = categorySource ?? CategorySource
         };
 }
 

src/Explorer.Domain/EntryCategoryAssigner.cs

@@ -0,0 +1,129 @@
+namespace Explorer.Domain;
+
+/// <summary>Where an <see cref="IndexEntry"/> category came from.</summary>
+public static class CategorySources
+{
+    public const string None = "none";
+    public const string Extension = "extension";
+    public const string Folder = "folder";
+    public const string Children = "children";
+    public const string ArchiveContents = "archive_contents";
+    public const string Mime = "mime";
+    public const string User = "user";
+
+    public static bool IsUser(string? source)
+        => string.Equals(source, User, StringComparison.OrdinalIgnoreCase);
+
+    public static bool IsAutomatic(string? source)
+        => !IsUser(source);
+}
+
+public static class EntryCategoryAssigner
+{
+    public static void ApplyAutomatic(
+        IndexEntry entry,
+        string? rootPath = null,
+        bool isRepoRoot = false,
+        IReadOnlyList<FileCategory>? childCategories = null)
+    {
+        if (CategorySources.IsUser(entry.CategorySource))
+        {
+            return;
+        }
+
+        var full = string.IsNullOrWhiteSpace(rootPath)
+            ? (string.IsNullOrEmpty(entry.PathRel) ? entry.Name : entry.PathRel)
+            : PathRules.Combine(rootPath, entry.PathRel);
+        var result = FileClassifier.Classify(
+            entry.Name,
+            full,
+            entry.IsDirectory,
+            entry.Attributes,
+            isRepoRoot,
+            childCategories);
+        Apply(entry, result, InferSource(entry, result, childCategories), Confidence(result, childCategories));
+    }
+
+    public static void ApplyUser(IndexEntry entry, FileCategory category, string? reason = null)
+        => Apply(
+            entry,
+            new FileClassification(category, reason ?? "Set by user."),
+            CategorySources.User,
+            100);
+
+    public static void Apply(
+        IndexEntry entry,
+        FileClassification classification,
+        string source,
+        int confidence)
+    {
+        entry.Category = classification.Category;
+        entry.CategoryReason = classification.Reason;
+        entry.CategorySource = source;
+        entry.CategoryConfidence = Math.Clamp(confidence, 0, 100);
+        entry.CategoryUtc = DateTimeOffset.UtcNow;
+    }
+
+    public static FileCategory ParseCategory(string? value)
+        => Enum.TryParse<FileCategory>(value, ignoreCase: true, out var cat) ? cat : FileCategory.Unknown;
+
+    public static string InferSource(
+        IndexEntry entry,
+        FileClassification classification,
+        IReadOnlyList<FileCategory>? childCategories)
+    {
+        if (childCategories is { Count: > 0 } && classification.Category != FileCategory.Unknown)
+        {
+            return entry.IsDirectory
+                ? CategorySources.Children
+                : CategorySources.ArchiveContents;
+        }
+
+        if (entry.IsDirectory)
+        {
+            return classification.Category == FileCategory.Unknown
+                ? CategorySources.None
+                : CategorySources.Folder;
+        }
+
+        if (ArchiveFormats.IsArchive(entry.Name))
+        {
+            return CategorySources.Extension;
+        }
+
+        return classification.Category == FileCategory.Unknown
+            ? CategorySources.None
+            : CategorySources.Extension;
+    }
+
+    public static int Confidence(FileClassification classification, IReadOnlyList<FileCategory>? childCategories)
+    {
+        if (classification.Category == FileCategory.Unknown)
+        {
+            return 0;
+        }
+
+        if (childCategories is { Count: > 0 })
+        {
+            var known = childCategories.Count(c => c is not FileCategory.Unknown);
+            if (known == 0)
+            {
+                return 40;
+            }
+
+            var majority = childCategories
+                .Where(c => c == classification.Category)
+                .Count();
+            return Math.Clamp(40 + majority * 60 / known, 40, 95);
+        }
+
+        return classification.Category switch
+        {
+            FileCategory.SystemData or FileCategory.BuildOutput => 95,
+            FileCategory.Archive or FileCategory.Photos or FileCategory.Video
+                or FileCategory.Audio or FileCategory.Documents => 85,
+            FileCategory.Installer or FileCategory.Backup or FileCategory.CodeRepository => 80,
+            _ => 50
+        };
+    }
+}

src/Explorer.Domain/FileClassifier.cs

@@ -87,6 +87,13 @@ public static class FileClassifier
         {
             if (ArchiveFormats.IsArchive(name))
             {
+                if (TryMajority(childCategories, out var archiveMajority))
+                {
+                    return new FileClassification(
+                        archiveMajority,
+                        "Archive contents are mostly " + OrganizeDestinations.Label(archiveMajority).ToLowerInvariant() + ".");
+                }
+
                 return new FileClassification(FileCategory.Archive, "Archive file.");
             }
 
@@ -147,24 +154,62 @@ public static class FileClassifier
             return new FileClassification(FileCategory.Backup, "Backup folder name.");
         }
 
-        if (childCategories is { Count: > 0 })
+        if (TryMajority(childCategories, out var folderMajority))
         {
-            var known = childCategories.Where(c => c is not FileCategory.Unknown and not FileCategory.BuildOutput and not FileCategory.SystemData).ToList();
+            return new FileClassification(
-            if (known.Count > 0)
+                folderMajority,
-            {
+                "Folder contents are mostly " + OrganizeDestinations.Label(folderMajority).ToLowerInvariant() + ".");
-                var majority = known.GroupBy(c => c).OrderByDescending(g => g.Count()).First();
-                if (majority.Count() * 10 >= known.Count * 7)
-                {
-                    return new FileClassification(majority.Key, "Folder contents are mostly " + OrganizeDestinations.Label(majority.Key).ToLowerInvariant() + ".");
-                }
-            }
         }
 
         return new FileClassification(FileCategory.Unknown, "No matching signal.");
     }
 
+    private static bool TryMajority(IReadOnlyList<FileCategory>? childCategories, out FileCategory majority)
+    {
+        majority = FileCategory.Unknown;
+        if (childCategories is not { Count: > 0 })
+        {
+            return false;
+        }
+
+        var known = childCategories
+            .Where(c => c is not FileCategory.Unknown and not FileCategory.BuildOutput and not FileCategory.SystemData)
+            .ToList();
+        if (known.Count == 0)
+        {
+            return false;
+        }
+
+        var top = known.GroupBy(c => c).OrderByDescending(g => g.Count()).First();
+        if (top.Count() * 10 < known.Count * 7)
+        {
+            return false;
+        }
+
+        majority = top.Key;
+        return true;
+    }
+
     public static bool ShouldLeave(FileCategory category)
         => category is FileCategory.Unknown or FileCategory.SystemData or FileCategory.BuildOutput or FileCategory.Backup;
 
     public static bool SkipDescent(string name) => BuildNames.Contains(name);
+
+    public static bool IsPhotoFile(string name)
+    {
+        var ext = NameNormalizer.Extension(name);
+        return ext is not null && Photos.Contains(ext);
+    }
+
+    public static bool IsVideoFile(string name)
+    {
+        var ext = NameNormalizer.Extension(name);
+        return ext is not null && Videos.Contains(ext);
+    }
+
+    public static bool IsAudioFile(string name)
+    {
+        var ext = NameNormalizer.Extension(name);
+        return ext is not null && Audio.Contains(ext);
+    }
 }

src/Explorer.Domain/FileSignatureClassifier.cs

@@ -0,0 +1,84 @@
+namespace Explorer.Domain;
+
+/// <summary>Light magic-byte hints for files with no useful extension category.</summary>
+public static class FileSignatureClassifier
+{
+    public static FileClassification? TryClassify(ReadOnlySpan<byte> header)
+    {
+        if (header.Length < 4)
+        {
+            return null;
+        }
+
+        if (header[0] == 0xFF && header[1] == 0xD8 && header[2] == 0xFF)
+        {
+            return new FileClassification(FileCategory.Photos, "JPEG signature.");
+        }
+
+        if (header.Length >= 8
+            && header[0] == 0x89 && header[1] == 0x50 && header[2] == 0x4E && header[3] == 0x47)
+        {
+            return new FileClassification(FileCategory.Photos, "PNG signature.");
+        }
+
+        if (header[0] == 0x47 && header[1] == 0x49 && header[2] == 0x46 && header[3] == 0x38)
+        {
+            return new FileClassification(FileCategory.Photos, "GIF signature.");
+        }
+
+        if (header[0] == 0x25 && header[1] == 0x50 && header[2] == 0x44 && header[3] == 0x46)
+        {
+            return new FileClassification(FileCategory.Documents, "PDF signature.");
+        }
+
+        if (header[0] == 0x50 && header[1] == 0x4B && (header[2] == 0x03 || header[2] == 0x05 || header[2] == 0x07))
+        {
+            return new FileClassification(FileCategory.Archive, "ZIP-family signature.");
+        }
+
+        if (header.Length >= 12
+            && header[0] == 0x52 && header[1] == 0x49 && header[2] == 0x46 && header[3] == 0x46)
+        {
+            var form = System.Text.Encoding.ASCII.GetString(header.Slice(8, 4));
+            if (form is "WAVE" or "AVI ")
+            {
+                return new FileClassification(
+                    form == "WAVE" ? FileCategory.Audio : FileCategory.Video,
+                    "RIFF " + form.Trim() + " signature.");
+            }
+        }
+
+        if (header.Length >= 12
+            && header[4] == 0x66 && header[5] == 0x74 && header[6] == 0x79 && header[7] == 0x70)
+        {
+            return new FileClassification(FileCategory.Video, "ISO BMFF (ftyp) signature.");
+        }
+
+        if (header[0] == 0x49 && header[1] == 0x44 && header[2] == 0x33)
+        {
+            return new FileClassification(FileCategory.Audio, "ID3 signature.");
+        }
+
+        if (header[0] == 0x7F && header[1] == 0x45 && header[2] == 0x4C && header[3] == 0x46)
+        {
+            return new FileClassification(FileCategory.Installer, "ELF binary signature.");
+        }
+
+        if (header[0] == 0x4D && header[1] == 0x5A)
+        {
+            return new FileClassification(FileCategory.Installer, "PE/MZ signature.");
+        }
+
+        if (header[0] == 0x37 && header[1] == 0x7A && header[2] == 0xBC && header[3] == 0xAF)
+        {
+            return new FileClassification(FileCategory.Archive, "7z signature.");
+        }
+
+        if (header[0] == 0x52 && header[1] == 0x61 && header[2] == 0x72 && header[3] == 0x21)
+        {
+            return new FileClassification(FileCategory.Archive, "RAR signature.");
+        }
+
+        return null;
+    }
+}

src/Explorer.Domain/OrganizeDestinations.cs

@@ -48,6 +48,51 @@ public sealed class OrganizeDestinations
             _ => "Unknown"
         };
 
+    public static bool TryParse(string? value, out FileCategory category)
+    {
+        category = FileCategory.Unknown;
+        if (string.IsNullOrWhiteSpace(value))
+        {
+            return false;
+        }
+
+        var key = value.Trim().Replace(" ", "", StringComparison.Ordinal).Replace("_", "", StringComparison.Ordinal);
+        if (Enum.TryParse(key, ignoreCase: true, out category) && category != FileCategory.Unknown)
+        {
+            return true;
+        }
+
+        category = key.ToLowerInvariant() switch
+        {
+            "photo" or "photos" or "image" or "images" or "picture" or "pictures" => FileCategory.Photos,
+            "video" or "videos" or "movie" or "movies" => FileCategory.Video,
+            "audio" or "music" or "sound" => FileCategory.Audio,
+            "doc" or "docs" or "document" or "documents" => FileCategory.Documents,
+            "code" or "repo" or "repository" or "git" or "development" => FileCategory.CodeRepository,
+            "installer" or "installers" or "setup" => FileCategory.Installer,
+            "backup" or "backups" => FileCategory.Backup,
+            "archive" or "archives" or "zip" => FileCategory.Archive,
+            "system" or "systemdata" => FileCategory.SystemData,
+            "build" or "buildoutput" => FileCategory.BuildOutput,
+            "unknown" => FileCategory.Unknown,
+            _ => (FileCategory)(-1)
+        };
+        return (int)category >= 0;
+    }
+
+    public static readonly FileCategory[] UserChoices =
+    [
+        FileCategory.Photos,
+        FileCategory.Video,
+        FileCategory.Audio,
+        FileCategory.Documents,
+        FileCategory.Installer,
+        FileCategory.Archive,
+        FileCategory.Backup,
+        FileCategory.CodeRepository,
+        FileCategory.Unknown
+    ];
+
     private static string? EmptyToNull(string value)
         => string.IsNullOrWhiteSpace(value) ? null : value.Trim();
 }

src/Explorer.FileOperations/ReorganizeService.cs

@@ -13,6 +13,7 @@ public sealed class ReorganizeService
     private readonly IHydrationGuard _hydration;
     private readonly IGitStatusProvider _git;
     private readonly UiPreferencesStore _preferences;
+    private readonly IIndexStore _store;
 
     public ReorganizeService(
         ReorganizePlanner planner,
@@ -21,7 +22,8 @@ public sealed class ReorganizeService
         IFileSystemEnumerator enumerator,
         IHydrationGuard hydration,
         IGitStatusProvider git,
-        UiPreferencesStore preferences)
+        UiPreferencesStore preferences,
+        IIndexStore store)
     {
         _planner = planner;
         _ops = ops;
@@ -30,6 +32,7 @@ public sealed class ReorganizeService
         _hydration = hydration;
         _git = git;
         _preferences = preferences;
+        _store = store;
     }
 
     public OrganizeDestinations LoadDestinations()
@@ -63,14 +66,24 @@ public sealed class ReorganizeService
     }
 
     public OperationPlan Preview(string sourceRoot, OrganizeDestinations destinations)
-        => _planner.Build(
+        => PreviewAsync(sourceRoot, destinations).GetAwaiter().GetResult();
+
+    public async Task<OperationPlan> PreviewAsync(
+        string sourceRoot,
+        OrganizeDestinations destinations,
+        CancellationToken cancellationToken = default)
+    {
+        var indexed = await LoadIndexedChildrenAsync(sourceRoot, cancellationToken).ConfigureAwait(false);
+        return _planner.Build(
             sourceRoot,
             destinations,
             _enumerator,
             path => _volumes.IsPathReachable(path),
             path => _git.IsRepoRoot(path),
             item => _hydration.WouldHydrateOnRead(item),
-            RenameBatchService.PathExists);
+            RenameBatchService.PathExists,
+            indexedByName: indexed);
+    }
 
     public async Task<OperationPlan> EnqueueAsync(
         string sourceRoot,
@@ -78,7 +91,7 @@ public sealed class ReorganizeService
         OperationPlan? plan = null,
         CancellationToken cancellationToken = default)
     {
-        plan ??= Preview(sourceRoot, destinations);
+        plan ??= await PreviewAsync(sourceRoot, destinations, cancellationToken).ConfigureAwait(false);
         if (!plan.CanEnqueue)
         {
             return plan;
@@ -97,6 +110,62 @@ public sealed class ReorganizeService
         return plan;
     }
 
+    private async Task<IReadOnlyDictionary<string, IndexEntry>> LoadIndexedChildrenAsync(
+        string sourceRoot,
+        CancellationToken cancellationToken)
+    {
+        if (string.IsNullOrWhiteSpace(sourceRoot))
+        {
+            return new Dictionary<string, IndexEntry>(StringComparer.OrdinalIgnoreCase);
+        }
+
+        try
+        {
+            var sources = await _store.Sources.GetAllAsync(cancellationToken).ConfigureAwait(false);
+            Source? best = null;
+            var bestLen = -1;
+            foreach (var source in sources)
+            {
+                if (string.IsNullOrEmpty(source.LastRootPath))
+                {
+                    continue;
+                }
+
+                var root = PathRules.FromExtended(source.LastRootPath).TrimEnd('\\');
+                var path = PathRules.FromExtended(sourceRoot).TrimEnd('\\');
+                if (path.Equals(root, StringComparison.OrdinalIgnoreCase)
+                    || path.StartsWith(root + "\\", StringComparison.OrdinalIgnoreCase))
+                {
+                    if (root.Length > bestLen)
+                    {
+                        best = source;
+                        bestLen = root.Length;
+                    }
+                }
+            }
+
+            if (best?.LastRootPath is null)
+            {
+                return new Dictionary<string, IndexEntry>(StringComparer.OrdinalIgnoreCase);
+            }
+
+            var rel = PathRules.MakeRelative(best.LastRootPath, sourceRoot) ?? "";
+            var dir = await _store.Entries.GetByPathAsync(best.Id, rel, cancellationToken).ConfigureAwait(false);
+            if (dir is null)
+            {
+                return new Dictionary<string, IndexEntry>(StringComparer.OrdinalIgnoreCase);
+            }
+
+            var children = await _store.Entries.GetChildrenAsync(best.Id, dir.Id, EntryStatus.Present, cancellationToken)
+                .ConfigureAwait(false);
+            return children.ToDictionary(c => c.Name, StringComparer.OrdinalIgnoreCase);
+        }
+        catch (Exception)
+        {
+            return new Dictionary<string, IndexEntry>(StringComparer.OrdinalIgnoreCase);
+        }
+    }
+
     private static string Known(Environment.SpecialFolder folder)
         => Environment.GetFolderPath(folder);
 

src/Explorer.Hosting.Client/Ipc/WorkbenchPipeClient.cs

@@ -579,6 +579,17 @@ public sealed class WorkbenchPipeClient : IWorkbenchHost, ICloudOverlay, IHostCo
             => _client.CallAsync("Mutations.EnqueueHashCollisions", cancellationToken, n: sourceId ?? 0);
         public Task UpsertRelationAsync(FileRelation relation, CancellationToken cancellationToken = default)
             => _client.CallAsync("Mutations.UpsertRelation", cancellationToken, payload: Json(relation));
+        public Task SetUserCategoryByPathAsync(
+            string fullPath,
+            FileCategory category,
+            string? reason = null,
+            CancellationToken cancellationToken = default)
+            => _client.CallAsync(
+                "Mutations.SetUserCategory",
+                cancellationToken,
+                s: fullPath,
+                dest: reason,
+                payload: category.ToString());
         private static string Json<T>(T value) => JsonSerializer.Serialize(value, WorkbenchIpc.Json);
     }
 }

src/Explorer.Hosting/BackgroundMaintenanceCoordinator.cs

@@ -14,6 +14,7 @@ public sealed class BackgroundMaintenanceCoordinator : BackgroundService, IBackg
     private readonly IForegroundWorkSignal _foreground;
     private readonly IIdleIndexWork _indexing;
     private readonly IIdleHashWork _hash;
+    private readonly IIdleClassifyWork _classify;
     private readonly IHistoryMaintenance _history;
     private readonly IIndexStore _store;
     private readonly IVolumeService _volumes;
@@ -44,7 +45,8 @@ public sealed class BackgroundMaintenanceCoordinator : BackgroundService, IBackg
         IIndexStore store,
         IVolumeService volumes,
         ILogger<BackgroundMaintenanceCoordinator> logger,
-        IHostActivitySink? activity = null)
+        IHostActivitySink? activity = null,
+        IIdleClassifyWork? classify = null)
     {
         _idle = idle;
         _power = power;
@@ -52,6 +54,7 @@ public sealed class BackgroundMaintenanceCoordinator : BackgroundService, IBackg
         _foreground = foreground;
         _indexing = indexing;
         _hash = hash;
+        _classify = classify ?? NullIdleClassifyWork.Instance;
         _history = history;
         _store = store;
         _volumes = volumes;
@@ -71,6 +74,7 @@ public sealed class BackgroundMaintenanceCoordinator : BackgroundService, IBackg
     protected override async Task ExecuteAsync(CancellationToken stoppingToken)
     {
         _hash.Pause();
+        _classify.Pause();
         using var timer = new PeriodicTimer(TimeSpan.FromSeconds(1));
         while (await timer.WaitForNextTickAsync(stoppingToken).ConfigureAwait(false))
         {
@@ -115,10 +119,7 @@ public sealed class BackgroundMaintenanceCoordinator : BackgroundService, IBackg
         {
             _idleScanQueued.Clear();
             _idleVerified.Clear();
-            if (!_hash.IsPaused)
+            PauseBackgroundWorkers();
-            {
-                _hash.Pause();
-            }
 
             if (_lastAllowed)
             {
@@ -147,10 +148,7 @@ public sealed class BackgroundMaintenanceCoordinator : BackgroundService, IBackg
 
         if (_indexing.IsBusy || _indexing.HasIdleWork)
         {
-            if (!_hash.IsPaused)
+            PauseBackgroundWorkers();
-            {
-                _hash.Pause();
-            }
 
             // Keep the idle-maintenance caption only while idle work is still queued/running.
             // Watcher/user jobs must not keep showing a stale "checking External" line.
@@ -165,10 +163,7 @@ public sealed class BackgroundMaintenanceCoordinator : BackgroundService, IBackg
         var verify = BackgroundMaintenancePlanner.NextLocalVerify(sources, _idleVerified);
         if (verify is not null && verify.LastRootPath is not null && _volumes.IsPathReachable(verify.LastRootPath))
         {
-            if (!_hash.IsPaused)
+            PauseBackgroundWorkers();
-            {
-                _hash.Pause();
-            }
 
             _idleVerified.Add(verify.Id);
             _indexing.EnqueueIdleVerify(verify.Id, "");
@@ -183,10 +178,7 @@ public sealed class BackgroundMaintenanceCoordinator : BackgroundService, IBackg
         var scan = BackgroundMaintenancePlanner.NextLocalScan(sources, DateTimeOffset.UtcNow, _idleScanQueued);
         if (scan is not null && scan.LastRootPath is not null && _volumes.IsPathReachable(scan.LastRootPath))
         {
-            if (!_hash.IsPaused)
+            PauseBackgroundWorkers();
-            {
-                _hash.Pause();
-            }
 
             _idleScanQueued.Add(scan.Id);
             _indexing.EnqueueIdleFullScan(scan.Id);
@@ -196,6 +188,16 @@ public sealed class BackgroundMaintenanceCoordinator : BackgroundService, IBackg
             return;
         }
 
+        PauseHash();
+        _classify.Resume();
+        if (await _classify.ProcessPendingAsync(cancellationToken).ConfigureAwait(false))
+        {
+            _workMessage = "Idle maintenance · classifying";
+            Publish(decision, _workMessage);
+            return;
+        }
+
+        _classify.Pause();
         _hash.Resume();
         if (hashPending)
         {
@@ -232,6 +234,23 @@ public sealed class BackgroundMaintenanceCoordinator : BackgroundService, IBackg
         Publish(decision, _workMessage);
     }
 
+    private void PauseBackgroundWorkers()
+    {
+        PauseHash();
+        if (!_classify.IsPaused)
+        {
+            _classify.Pause();
+        }
+    }
+
+    private void PauseHash()
+    {
+        if (!_hash.IsPaused)
+        {
+            _hash.Pause();
+        }
+    }
+
     private string PauseMessage(BackgroundWorkDecision decision)
     {
         if (decision.SkipReason == MaintenanceSkipReason.ForegroundOperations)

src/Explorer.Hosting/ExplorerHostServices.cs

@@ -100,8 +100,10 @@ public static class ExplorerHostServices
             sp.GetRequiredService<IIndexMutations>()));
         services.AddSingleton<DuplicateHashWorker>();
         services.AddSingleton<HistoryRollupService>();
+        services.AddSingleton<EntryClassificationService>();
         services.AddSingleton<IIdleIndexWork>(sp => sp.GetRequiredService<IndexingCoordinator>());
         services.AddSingleton<IIdleHashWork>(sp => sp.GetRequiredService<DuplicateHashWorker>());
+        services.AddSingleton<IIdleClassifyWork>(sp => sp.GetRequiredService<EntryClassificationService>());
         services.AddSingleton<IHistoryMaintenance>(sp => sp.GetRequiredService<HistoryRollupService>());
         services.AddSingleton<BackgroundMaintenanceCoordinator>();
         services.AddSingleton<IBackgroundMaintenance>(sp => sp.GetRequiredService<BackgroundMaintenanceCoordinator>());

src/Explorer.Hosting/Ipc/WorkbenchPipeServer.cs

@@ -462,6 +462,16 @@ public sealed class WorkbenchPipeServer : BackgroundService
                 case "Mutations.UpsertRelation":
                     await Workbench.Mutations.UpsertRelationAsync(Read<FileRelation>(request.Payload)).ConfigureAwait(false);
                     return reply;
+                case "Mutations.SetUserCategory":
+                    if (OrganizeDestinations.TryParse(request.Payload, out var userCategory)
+                        || Enum.TryParse(request.Payload, true, out userCategory))
+                    {
+                        await Workbench.Mutations.SetUserCategoryByPathAsync(
+                            request.S ?? "",
+                            userCategory,
+                            request.Dest).ConfigureAwait(false);
+                    }
+                    return reply;
                 case "Cloud.Places":
                     reply.Payload = JsonSerializer.Serialize(_overlay!.GetPlaces(), WorkbenchIpc.Json);
                     return reply;

src/Explorer.Indexing/FolderReconciler.cs

@@ -190,6 +190,9 @@ public sealed class FolderReconciler
             }
         }, cancellationToken).ConfigureAwait(false);
 
+        await _store.Entries.RefreshCategoryFromChildrenAsync(parent.Id, cancellationToken)
+            .ConfigureAwait(false);
+
         foreach (var path in archivesToTomb)
         {
             await _store.Entries.TombstoneByPathPrefixAsync(source.Id, path, now, cancellationToken)
@@ -202,6 +205,8 @@ public sealed class FolderReconciler
             {
                 await _archives.ExpandIfNeededAsync(source, archive, now, source.ScanGeneration, cancellationToken)
                     .ConfigureAwait(false);
+                await _store.Entries.RefreshCategoryFromChildrenAsync(archive.Id, cancellationToken)
+                    .ConfigureAwait(false);
             }
         }
 

src/Explorer.Presentation/ViewModels/AnalysisViewModel.cs

@@ -69,6 +69,7 @@ public sealed partial class AnalysisViewModel : ObservableObject
     public const string PageFolders = "Biggest folders";
     public const string PageFiles = "Biggest files";
     public const string PageTypes = "By file type";
+    public const string PageCategories = "By category";
     public const string PageSources = "By source";
 
     private readonly AnalysisService _analysis;
@@ -93,7 +94,7 @@ public sealed partial class AnalysisViewModel : ObservableObject
         Rows = [];
     }
 
-    public string[] Pages { get; } = [PageTree, PageFolders, PageFiles, PageTypes, PageSources];
+    public string[] Pages { get; } = [PageTree, PageFolders, PageFiles, PageTypes, PageCategories, PageSources];
     public ObservableCollection<StorageScopeItem> Scopes { get; }
     public ObservableCollection<StorageNodeViewModel> TreeRoots { get; }
     public ObservableCollection<StorageNodeViewModel> VisibleNodes { get; }
@@ -461,6 +462,25 @@ public sealed partial class AnalysisViewModel : ObservableObject
                 0,
                 (string?)null)).ToList();
         }
+        else if (page == PageCategories)
+        {
+            var cats = await _analysis.UsageByCategoryAsync(sourceId, null, AppConstants.AnalysisTopN, cancellationToken)
+                .ConfigureAwait(false);
+            items = cats.Select(t => (
+                OrganizeDestinations.TryParse(t.Category, out var cat)
+                    ? OrganizeDestinations.Label(cat)
+                    : string.IsNullOrEmpty(t.Category) ? "Unknown" : t.Category,
+                t.TotalSize,
+                (string?)null,
+                (string?)null,
+                (string?)null,
+                (long?)null,
+                sourceId,
+                false,
+                (int)t.FileCount,
+                0,
+                (string?)null)).ToList();
+        }
         else
         {
             var usage = await _analysis.UsageBySourceAsync(cancellationToken).ConfigureAwait(false);

src/Explorer.Presentation/ViewModels/FolderItemViewModel.cs

@@ -85,6 +85,27 @@ public sealed partial class FolderItemViewModel : ObservableObject
     };
     public bool HasCloudStatus => !string.IsNullOrEmpty(CloudLabel);
 
+    public string CategoryLabel
+        => Item.Category == FileCategory.Unknown
+           && (string.IsNullOrEmpty(Item.CategorySource) || Item.CategorySource == CategorySources.None)
+            ? ""
+            : OrganizeDestinations.Label(Item.Category);
+
+    public string CategoryTooltip
+    {
+        get
+        {
+            var label = CategoryLabel;
+            if (string.IsNullOrEmpty(label))
+            {
+                return "";
+            }
+
+            var reason = Item.CategoryReason;
+            return string.IsNullOrEmpty(reason) ? label : label + " · " + reason;
+        }
+    }
+
     [ObservableProperty] private string _gitLabel = "";
     public bool HasGitLabel => !string.IsNullOrEmpty(GitLabel);
 
@@ -122,18 +143,8 @@ public sealed partial class FolderItemViewModel : ObservableObject
 
 internal static class MediaKinds
 {
-    private static readonly HashSet<string> Images = new(StringComparer.OrdinalIgnoreCase)
+    public static bool IsImage(string name) => FileClassifier.IsPhotoFile(name);
-    {
+    public static bool IsVideo(string name) => FileClassifier.IsVideoFile(name);
-        ".jpg", ".jpeg", ".png", ".gif", ".bmp", ".webp", ".tif", ".tiff", ".ico", ".jfif"
-    };
-
-    private static readonly HashSet<string> Videos = new(StringComparer.OrdinalIgnoreCase)
-    {
-        ".mp4", ".mkv", ".avi", ".mov", ".wmv", ".webm", ".m4v", ".mpg", ".mpeg"
-    };
-
-    public static bool IsImage(string name) => Images.Contains(Path.GetExtension(name));
-    public static bool IsVideo(string name) => Videos.Contains(Path.GetExtension(name));
 }
 
 file static class ItemExt

src/Explorer.Presentation/ViewModels/MainViewModel.cs

@@ -34,6 +34,7 @@ public sealed partial class MainViewModel : ObservableObject
     private readonly ConversionPlanner _conversionPlanner;
     private readonly IFileSystemEnumerator _enumerator;
     private readonly IMediaConversionProvider _conversion;
+    private readonly IIndexMutations _mutations;
     private readonly IThumbnailService? _thumbnails;
     private readonly IHostConnection? _host;
     private readonly IBackgroundMaintenance? _maintenance;
@@ -65,6 +66,7 @@ public sealed partial class MainViewModel : ObservableObject
     [ObservableProperty] private bool _showTags;
     [ObservableProperty] private bool _showRunProfile;
     [ObservableProperty] private bool _showOrganizeFolder;
+    [ObservableProperty] private bool _showClassifyAs;
     [ObservableProperty] private bool _canUndoRenameBatch;
     [ObservableProperty] private bool _showExtractArchive;
     [ObservableProperty] private bool _showCompress;
@@ -141,6 +143,7 @@ public sealed partial class MainViewModel : ObservableObject
         _conversionPlanner = conversionPlanner;
         _enumerator = enumerator;
         _conversion = conversion;
+        _mutations = mutations;
         _thumbnails = thumbnails;
         _host = hostConnection;
         _maintenance = maintenance;
@@ -737,6 +740,36 @@ public sealed partial class MainViewModel : ObservableObject
     public ReorganizeViewModel CreateReorganizeViewModel()
         => new(_reorganize, OrganizeSourcePath());
 
+    [RelayCommand]
+    public async Task ClassifyAsAsync(string? category)
+    {
+        if (!OrganizeDestinations.TryParse(category, out var parsed)
+            && !Enum.TryParse(category, true, out parsed))
+        {
+            Footer = "Unknown category.";
+            return;
+        }
+
+        var items = ActivePane.SelectedItems.Where(IsRealFileSystemItem).ToList();
+        if (items.Count == 0)
+        {
+            Footer = "Select a file or folder to classify.";
+            return;
+        }
+
+        var n = 0;
+        foreach (var item in items)
+        {
+            await _mutations.SetUserCategoryByPathAsync(item.FullPath, parsed, "Set by user.").ConfigureAwait(true);
+            n++;
+        }
+
+        await ActivePane.RefreshAsync().ConfigureAwait(true);
+        Footer = n == 1
+            ? "Classified as " + OrganizeDestinations.Label(parsed) + "."
+            : "Classified " + n + " items as " + OrganizeDestinations.Label(parsed) + ".";
+    }
+
     public GitChangesViewModel CreateGitChangesViewModel()
         => new(_gitCommands, _workspace, _hydration);
 
@@ -984,6 +1017,7 @@ public sealed partial class MainViewModel : ObservableObject
         ShowRunProfile = ShowBatchRename;
         ShowOrganizeFolder = OrganizeSourcePath() is not null;
         var real = ActivePane.SelectedItems.Where(IsRealFileSystemItem).ToList();
+        ShowClassifyAs = real.Count > 0;
         ShowExtractArchive = real.Count > 0 && real.All(i => !i.IsDirectory && ArchiveFormats.IsArchive(i.Item.Name));
         ShowCompress = real.Count > 0;
         ShowConvert = real.Any(i => i.IsDirectory || ConversionFormats.IsConvertible(i.Item.Name));

src/Explorer.Presentation/ViewModels/ReorganizeViewModel.cs

@@ -44,7 +44,7 @@ public sealed partial class ReorganizeViewModel : ObservableObject
     {
         Status = "Analyzing…";
         CanQueue = false;
-        var plan = await Task.Run(() => _organize.Preview(SourcePath.Trim(), CurrentDestinations())).ConfigureAwait(true);
+        var plan = await _organize.PreviewAsync(SourcePath.Trim(), CurrentDestinations()).ConfigureAwait(true);
         ApplyPlan(plan);
     }
 

src/Explorer.Presentation/ViewModels/SearchViewModel.cs

@@ -9,6 +9,7 @@ using Explorer.Search;
 namespace Explorer.Presentation.ViewModels;
 
 public sealed record SearchScopeChoice(SearchScopeKind Kind, string Label);
+public sealed record CategoryChoice(string Value, string Label);
 
 public sealed partial class SearchViewModel : ObservableObject
 {
@@ -20,6 +21,7 @@ public sealed partial class SearchViewModel : ObservableObject
     [ObservableProperty] private string _text = "";
     [ObservableProperty] private SearchScopeKind _scope = SearchScopeKind.AllKnown;
     [ObservableProperty] private string? _extension;
+    [ObservableProperty] private string _category = "";
     [ObservableProperty] private bool _foldersOnly;
     [ObservableProperty] private bool _filesOnly;
     [ObservableProperty] private string? _minSizeText;
@@ -46,6 +48,12 @@ public sealed partial class SearchViewModel : ObservableObject
         new(SearchScopeKind.OfflineMedia, "Offline media")
     ];
 
+    public CategoryChoice[] CategoryChoices { get; } =
+    [
+        new("", "Any category"),
+        .. OrganizeDestinations.UserChoices.Select(c => new CategoryChoice(c.ToString(), OrganizeDestinations.Label(c)))
+    ];
+
     public void OpenWithoutSearch()
     {
         IsOpen = true;
@@ -103,6 +111,7 @@ public sealed partial class SearchViewModel : ObservableObject
                 Scope = scope,
                 Text = Text,
                 Extension = Extension,
+                Category = OrganizeDestinations.TryParse(Category, out var cat) ? cat : null,
                 IsDirectory = DirectoryFilter(FoldersOnly, FilesOnly),
                 MinSize = ParseSize(MinSizeText),
                 MaxSize = ParseSize(MaxSizeText),
@@ -139,7 +148,11 @@ public sealed partial class SearchViewModel : ObservableObject
                     FileId = entry.FileId,
                     ReparseTag = entry.ReparseTag,
                     FreeSpaceBytes = space.FreeBytes,
-                    CapacityBytes = space.CapacityBytes
+                    CapacityBytes = space.CapacityBytes,
+                    IndexEntryId = entry.Id,
+                    Category = entry.Category,
+                    CategoryReason = entry.CategoryReason,
+                    CategorySource = entry.CategorySource
                 }, entry.IsDirectory));
             }
 

src/Explorer.Search/Explorer.Search.csproj

@@ -9,4 +9,7 @@
     <ProjectReference Include="..\Explorer.Application\Explorer.Application.csproj" />
     <ProjectReference Include="..\Explorer.Domain\Explorer.Domain.csproj" />
   </ItemGroup>
+  <ItemGroup>
+    <InternalsVisibleTo Include="Explorer.Search.Tests" />
+  </ItemGroup>
 </Project>

src/Explorer.Search/SearchService.cs

@@ -15,6 +15,7 @@ public sealed class SearchQuery
     public DateTimeOffset? CreatedBefore { get; init; }
     public DateTimeOffset? ModifiedAfter { get; init; }
     public DateTimeOffset? ModifiedBefore { get; init; }
+    public FileCategory? Category { get; init; }
     public IReadOnlyList<long>? SourceIds { get; init; }
     public string? PathRelPrefix { get; init; }
     public bool IncludeOffline { get; init; } = true;
@@ -33,9 +34,19 @@ public sealed class SearchService
         var text = query.Text?.Trim();
         string? extension = query.Extension;
         string? name = text;
-        if (!string.IsNullOrEmpty(text) && text.StartsWith("*.", StringComparison.Ordinal) && !text.Contains(' ', StringComparison.Ordinal))
+        var category = query.Category;
+        if (!string.IsNullOrEmpty(text))
         {
-            extension = text[2..];
+            (name, var hinted) = SplitCategoryHint(text);
+            if (hinted is not null)
+            {
+                category = hinted;
+            }
+        }
+
+        if (!string.IsNullOrEmpty(name) && name.StartsWith("*.", StringComparison.Ordinal) && !name.Contains(' ', StringComparison.Ordinal))
+        {
+            extension = name[2..];
             name = null;
         }
 
@@ -43,6 +54,7 @@ public sealed class SearchService
         {
             Name = name,
             Extension = extension,
+            Category = category,
             IsDirectory = query.IsDirectory,
             MinSize = query.MinSize,
             MaxSize = query.MaxSize,
@@ -62,4 +74,25 @@ public sealed class SearchService
 
         return _store.Search.SearchAsync(request, cancellationToken);
     }
+
+    internal static (string? Name, FileCategory? Category) SplitCategoryHint(string text)
+    {
+        FileCategory? category = null;
+        var name = System.Text.RegularExpressions.Regex.Replace(
+            text,
+            @"\b(?:category|cat):([A-Za-z]+)\b",
+            match =>
+            {
+                if (OrganizeDestinations.TryParse(match.Groups[1].Value, out var parsed))
+                {
+                    category = parsed;
+                    return "";
+                }
+
+                return match.Value;
+            },
+            System.Text.RegularExpressions.RegexOptions.IgnoreCase);
+        name = name.Trim();
+        return (string.IsNullOrEmpty(name) ? null : name, category);
+    }
 }

src/Explorer.Storage.Sqlite/AnalysisHistoryHashStores.cs

@@ -91,6 +91,24 @@ internal sealed class AnalysisStore : IAnalysisStore
         return rows.AsList();
     }
 
+    public async Task<IReadOnlyList<CategoryUsage>> UsageByCategoryAsync(long? sourceId, string? pathRelPrefix, int take, CancellationToken cancellationToken = default)
+    {
+        await using var conn = await _store.OpenReadAsync(cancellationToken).ConfigureAwait(false);
+        var sql = """
+            SELECT ifnull(category, 'Unknown') AS Category, SUM(size_bytes) AS TotalSize, COUNT(*) AS FileCount
+            FROM entries
+            WHERE is_dir=0 AND status=0
+            """;
+        if (sourceId is not null) sql += " AND source_id=@sourceId";
+        if (!string.IsNullOrEmpty(pathRelPrefix))
+            sql += " AND (path_rel=@pathRelPrefix OR path_rel LIKE @like ESCAPE '\\')";
+        sql += " GROUP BY category ORDER BY TotalSize DESC LIMIT @take";
+        var like = string.IsNullOrEmpty(pathRelPrefix) ? null : pathRelPrefix.Replace("\\", "\\\\") + "\\\\%";
+        var rows = await conn.QueryAsync<CategoryUsage>(new CommandDefinition(
+            sql, new { sourceId, pathRelPrefix, like, take }, cancellationToken: cancellationToken)).ConfigureAwait(false);
+        return rows.AsList();
+    }
+
     public async Task<IReadOnlyList<SourceUsage>> UsageBySourceAsync(CancellationToken cancellationToken = default)
     {
         await using var conn = await _store.OpenReadAsync(cancellationToken).ConfigureAwait(false);

src/Explorer.Storage.Sqlite/EntryStore.cs

@@ -88,14 +88,41 @@ internal sealed class EntryStore : IEntryStore
 
     internal static async Task<long> UpsertCore(SqliteConnection conn, IndexEntry entry)
     {
-        var existing = await SqliteExec.ScalarAsync<long?>(
+        var existingId = await SqliteExec.ScalarAsync<long?>(
             conn,
             "SELECT id FROM entries WHERE source_id=@SourceId AND ifnull(parent_id,-1)=ifnull(@ParentId,-1) AND name_norm=@NameNorm",
             new { entry.SourceId, entry.ParentId, entry.NameNorm }).ConfigureAwait(false);
 
-        if (existing is > 0)
+        if (existingId is > 0)
         {
-            entry.Id = existing.Value;
+            entry.Id = existingId.Value;
+            var existingSource = await SqliteExec.ScalarAsync<string>(
+                conn,
+                "SELECT ifnull(category_source, 'none') FROM entries WHERE id=@Id",
+                new { entry.Id }).ConfigureAwait(false);
+            if (CategorySources.IsUser(existingSource))
+            {
+                entry.Category = EntryCategoryAssigner.ParseCategory(
+                    await SqliteExec.ScalarAsync<string>(conn, "SELECT category FROM entries WHERE id=@Id", new { entry.Id })
+                        .ConfigureAwait(false));
+                entry.CategoryReason = await SqliteExec.ScalarAsync<string>(
+                    conn, "SELECT category_reason FROM entries WHERE id=@Id", new { entry.Id }).ConfigureAwait(false);
+                entry.CategoryConfidence = await SqliteExec.ScalarAsync<long>(
+                    conn, "SELECT ifnull(category_confidence, 0) FROM entries WHERE id=@Id", new { entry.Id })
+                    .ConfigureAwait(false) is { } conf
+                    ? (int)conf
+                    : 0;
+                entry.CategorySource = CategorySources.User;
+                var utc = await SqliteExec.ScalarAsync<string>(
+                    conn, "SELECT category_utc FROM entries WHERE id=@Id", new { entry.Id }).ConfigureAwait(false);
+                entry.CategoryUtc = string.IsNullOrEmpty(utc) ? null : DateTimeOffset.Parse(utc);
+            }
+            else if (string.IsNullOrWhiteSpace(entry.CategorySource)
+                     || entry.CategorySource == CategorySources.None)
+            {
+                EntryCategoryAssigner.ApplyAutomatic(entry);
+            }
+
             await SqliteExec.ExecuteAsync(conn, """
                 UPDATE entries SET
                   name=@Name, extension=@Extension, is_dir=@IsDir, size_bytes=@SizeBytes,
@@ -103,21 +130,32 @@ internal sealed class EntryStore : IEntryStore
                   last_indexed_utc=@LastIndexedUtc, attributes=@Attributes, file_id=@FileId,
                   parent_file_id=@ParentFileId, reparse_tag=@ReparseTag, status=@Status,
                   deleted_utc=@DeletedUtc, path_rel=@PathRel, scan_generation=@ScanGeneration,
-                  allocated_size=@AllocatedSizeBytes, cloud_availability=@CloudAvailability
+                  allocated_size=@AllocatedSizeBytes, cloud_availability=@CloudAvailability,
+                  category=@Category, category_reason=@CategoryReason,
+                  category_confidence=@CategoryConfidence, category_source=@CategorySource,
+                  category_utc=@CategoryUtc
                 WHERE id=@Id
                 """, ToArgs(entry)).ConfigureAwait(false);
             return entry.Id;
         }
 
+        if (string.IsNullOrWhiteSpace(entry.CategorySource)
+            || entry.CategorySource == CategorySources.None)
+        {
+            EntryCategoryAssigner.ApplyAutomatic(entry);
+        }
+
         var id = await SqliteExec.InsertAsync(conn, """
             INSERT INTO entries (source_id, parent_id, name, name_norm, extension, is_dir, size_bytes, aggregate_size,
               child_file_count, child_dir_count, created_utc, modified_utc, last_seen_utc, last_indexed_utc,
               attributes, file_id, parent_file_id, reparse_tag, status, deleted_utc, path_rel, content_hash, hash_state, scan_generation,
-              allocated_size, cloud_availability)
+              allocated_size, cloud_availability,
+              category, category_reason, category_confidence, category_source, category_utc)
             VALUES (@SourceId, @ParentId, @Name, @NameNorm, @Extension, @IsDir, @SizeBytes, @AggregateSize,
               @ChildFileCount, @ChildDirCount, @CreatedUtc, @ModifiedUtc, @LastSeenUtc, @LastIndexedUtc,
               @Attributes, @FileId, @ParentFileId, @ReparseTag, @Status, @DeletedUtc, @PathRel, @ContentHash, @HashState, @ScanGeneration,
-              @AllocatedSizeBytes, @CloudAvailability)
+              @AllocatedSizeBytes, @CloudAvailability,
+              @Category, @CategoryReason, @CategoryConfidence, @CategorySource, @CategoryUtc)
             """, ToArgs(entry)).ConfigureAwait(false);
         entry.Id = id;
         return id;
@@ -262,6 +300,121 @@ internal sealed class EntryStore : IEntryStore
             new { sourceId }).ConfigureAwait(false);
     }
 
+    public Task RefreshCategoryFromChildrenAsync(long folderOrArchiveId, CancellationToken cancellationToken = default)
+        => _store.WriteAsync(async conn =>
+        {
+            var row = await conn.QuerySingleOrDefaultAsync<EntryRow>(
+                "SELECT * FROM entries WHERE id=@id", new { id = folderOrArchiveId }).ConfigureAwait(false);
+            if (row is null)
+            {
+                return;
+            }
+
+            var entry = row.ToModel();
+            if (CategorySources.IsUser(entry.CategorySource))
+            {
+                return;
+            }
+
+            var children = (await conn.QueryAsync<string>(
+                "SELECT ifnull(category, 'Unknown') FROM entries WHERE parent_id=@id AND status=0",
+                new { id = folderOrArchiveId }).ConfigureAwait(false)).ToList();
+            if (children.Count == 0)
+            {
+                return;
+            }
+
+            var cats = children.Select(EntryCategoryAssigner.ParseCategory).ToList();
+            EntryCategoryAssigner.ApplyAutomatic(entry, childCategories: cats);
+            await SqliteExec.ExecuteAsync(conn, """
+                UPDATE entries SET
+                  category=@Category, category_reason=@CategoryReason,
+                  category_confidence=@CategoryConfidence, category_source=@CategorySource,
+                  category_utc=@CategoryUtc
+                WHERE id=@Id
+                """, ToArgs(entry)).ConfigureAwait(false);
+        }, cancellationToken);
+
+    public Task SetUserCategoryAsync(long entryId, FileCategory category, string? reason = null, CancellationToken cancellationToken = default)
+        => _store.WriteAsync(async conn =>
+        {
+            var row = await conn.QuerySingleOrDefaultAsync<EntryRow>(
+                "SELECT * FROM entries WHERE id=@id", new { id = entryId }).ConfigureAwait(false);
+            if (row is null)
+            {
+                return;
+            }
+
+            var entry = row.ToModel();
+            EntryCategoryAssigner.ApplyUser(entry, category, reason);
+            await SqliteExec.ExecuteAsync(conn, """
+                UPDATE entries SET
+                  category=@Category, category_reason=@CategoryReason,
+                  category_confidence=@CategoryConfidence, category_source=@CategorySource,
+                  category_utc=@CategoryUtc
+                WHERE id=@Id
+                """, ToArgs(entry)).ConfigureAwait(false);
+        }, cancellationToken);
+
+    public Task<int> BackfillCheapCategoriesAsync(int take, CancellationToken cancellationToken = default)
+        => _store.WriteAsync(async conn =>
+        {
+            take = Math.Clamp(take, 1, 500);
+            var rows = (await conn.QueryAsync<EntryRow>(new CommandDefinition("""
+                SELECT * FROM entries
+                WHERE status=0 AND ifnull(category_source, 'none') IN ('none', '')
+                  AND category_utc IS NULL
+                ORDER BY id
+                LIMIT @take
+                """, new { take }, cancellationToken: cancellationToken)).ConfigureAwait(false)).ToList();
+            foreach (var row in rows)
+            {
+                var entry = row.ToModel();
+                EntryCategoryAssigner.ApplyAutomatic(entry);
+                await SqliteExec.ExecuteAsync(conn, """
+                    UPDATE entries SET
+                      category=@Category, category_reason=@CategoryReason,
+                      category_confidence=@CategoryConfidence, category_source=@CategorySource,
+                      category_utc=@CategoryUtc
+                    WHERE id=@Id
+                    """, ToArgs(entry)).ConfigureAwait(false);
+            }
+
+            return rows.Count;
+        }, cancellationToken);
+
+    public async Task<IReadOnlyList<long>> GetArchiveIdsNeedingContentClassifyAsync(int take, CancellationToken cancellationToken = default)
+    {
+        take = Math.Clamp(take, 1, 100);
+        await using var conn = await _store.OpenReadAsync(cancellationToken).ConfigureAwait(false);
+        var ids = await conn.QueryAsync<long>(new CommandDefinition("""
+            SELECT a.id
+            FROM entries a
+            WHERE a.status=0 AND a.is_dir=0 AND a.category='Archive'
+              AND ifnull(a.category_source, 'none') IN ('extension', 'none')
+              AND EXISTS (
+                SELECT 1 FROM entries c WHERE c.parent_id=a.id AND c.status=0 LIMIT 1)
+            ORDER BY a.id
+            LIMIT @take
+            """, new { take }, cancellationToken: cancellationToken)).ConfigureAwait(false);
+        return ids.ToList();
+    }
+
+    public async Task<IReadOnlyList<IndexEntry>> GetUnknownFilesForSignatureAsync(int take, CancellationToken cancellationToken = default)
+    {
+        take = Math.Clamp(take, 1, 50);
+        await using var conn = await _store.OpenReadAsync(cancellationToken).ConfigureAwait(false);
+        var rows = await conn.QueryAsync<EntryRow>(new CommandDefinition("""
+            SELECT * FROM entries
+            WHERE status=0 AND is_dir=0 AND category='Unknown'
+              AND ifnull(category_source, 'none') IN ('none', '')
+              AND ifnull(cloud_availability, 0) != 1
+            ORDER BY id
+            LIMIT @take
+            """, new { take }, cancellationToken: cancellationToken)).ConfigureAwait(false);
+        return rows.Select(r => r.ToModel()).ToList();
+    }
+
     private static string EscapeLike(string? value)
     {
         if (string.IsNullOrEmpty(value))
@@ -302,7 +455,12 @@ internal sealed class EntryStore : IEntryStore
         HashState = (int)e.HashState,
         e.ScanGeneration,
         e.AllocatedSizeBytes,
-        CloudAvailability = e.CloudAvailability is { } a ? (int?)a : null
+        CloudAvailability = e.CloudAvailability is { } a ? (int?)a : null,
+        Category = e.Category.ToString(),
+        e.CategoryReason,
+        e.CategoryConfidence,
+        e.CategorySource,
+        CategoryUtc = e.CategoryUtc?.ToString("O")
     };
 }
 
@@ -335,6 +493,11 @@ internal sealed class EntryRow
     public long scan_generation { get; set; }
     public long? allocated_size { get; set; }
     public int? cloud_availability { get; set; }
+    public string? category { get; set; }
+    public string? category_reason { get; set; }
+    public int category_confidence { get; set; }
+    public string? category_source { get; set; }
+    public string? category_utc { get; set; }
 
     public IndexEntry ToModel() => new()
     {
@@ -364,7 +527,12 @@ internal sealed class EntryRow
         HashState = (HashState)hash_state,
         ScanGeneration = scan_generation,
         AllocatedSizeBytes = allocated_size,
-        CloudAvailability = cloud_availability is { } a ? (CloudAvailability)a : null
+        CloudAvailability = cloud_availability is { } a ? (CloudAvailability)a : null,
+        Category = EntryCategoryAssigner.ParseCategory(category),
+        CategoryReason = category_reason,
+        CategoryConfidence = category_confidence,
+        CategorySource = string.IsNullOrWhiteSpace(category_source) ? CategorySources.None : category_source,
+        CategoryUtc = Parse(category_utc)
     };
 
     private static DateTimeOffset? Parse(string? v)

src/Explorer.Storage.Sqlite/SchemaScript.cs

@@ -63,11 +63,17 @@ internal static class SchemaScript
           hash_state INTEGER NOT NULL DEFAULT 0,
           scan_generation INTEGER NOT NULL DEFAULT 0,
           allocated_size INTEGER,
-          cloud_availability INTEGER
+          cloud_availability INTEGER,
+          category TEXT NOT NULL DEFAULT 'Unknown',
+          category_reason TEXT,
+          category_confidence INTEGER NOT NULL DEFAULT 0,
+          category_source TEXT NOT NULL DEFAULT 'none',
+          category_utc TEXT
         )
         """,
         "CREATE UNIQUE INDEX ix_entries_identity ON entries(source_id, ifnull(parent_id, -1), name_norm)",
         "CREATE INDEX ix_entries_parent ON entries(source_id, parent_id, status)",
+        "CREATE INDEX IF NOT EXISTS ix_entries_category ON entries(source_id, category) WHERE status = 0",
         "CREATE INDEX ix_entries_ext_size ON entries(source_id, extension, size_bytes) WHERE is_dir = 0",
         "CREATE INDEX ix_entries_size ON entries(source_id, size_bytes) WHERE is_dir = 0 AND status = 0",
         "CREATE INDEX ix_entries_modified ON entries(source_id, modified_utc)",

src/Explorer.Storage.Sqlite/SearchStore.cs

@@ -63,6 +63,12 @@ internal sealed class SearchStore : ISearchStore
             args.Add("Ext", NameNormalizer.Normalize(request.Extension.TrimStart('.')));
         }
 
+        if (request.Category is { } category)
+        {
+            sql.Append(" AND e.category = @Category");
+            args.Add("Category", category.ToString());
+        }
+
         if (request.MinSize is not null)
         {
             sql.Append(" AND e.size_bytes >= @MinSize");

src/Explorer.Storage.Sqlite/SqliteIndexStore.cs

@@ -606,6 +606,25 @@ public sealed class SqliteIndexStore : IIndexStore, IAsyncDisposable
 
             SetUserVersion(conn, 10);
             _logger.LogInformation("Migrated SQLite schema to v10 (hash queue state index)");
+            version = 10;
+        }
+
+        if (version < 11)
+        {
+            EnsureColumn(conn, "entries", "category", "TEXT NOT NULL DEFAULT 'Unknown'");
+            EnsureColumn(conn, "entries", "category_reason", "TEXT");
+            EnsureColumn(conn, "entries", "category_confidence", "INTEGER NOT NULL DEFAULT 0");
+            EnsureColumn(conn, "entries", "category_source", "TEXT NOT NULL DEFAULT 'none'");
+            EnsureColumn(conn, "entries", "category_utc", "TEXT");
+            using (var idx = conn.CreateCommand())
+            {
+                idx.CommandText =
+                    "CREATE INDEX IF NOT EXISTS ix_entries_category ON entries(source_id, category) WHERE status = 0";
+                idx.ExecuteNonQuery();
+            }
+
+            SetUserVersion(conn, 11);
+            _logger.LogInformation("Migrated SQLite schema to v11 (entry categories)");
         }
     }
 

tests/Explorer.Analysis.Tests/AnalysisTests.cs

@@ -39,6 +39,8 @@ public class AnalysisTests
         Assert.Equal("a.mkv", files[0].Name);
         var types = await analysis.UsageByExtensionAsync(source.Id, null);
         Assert.Contains(types, t => t.Extension == "mkv" && t.TotalSize == 200);
+        var cats = await analysis.UsageByCategoryAsync(source.Id, null);
+        Assert.Contains(cats, c => c.Category == "Video" && c.TotalSize == 200);
         var drill = await analysis.DrilldownAsync(root.Id);
         Assert.Contains(drill, e => e.Name == "Movies");
         Assert.Equal("Movies", dirs[0].PathRel);

tests/Explorer.Application.Tests/EntryClassificationServiceTests.cs

@@ -0,0 +1,160 @@
+using Explorer.Application;
+using Explorer.Domain;
+using Explorer.Domain.Abstractions;
+using Explorer.Storage.Sqlite;
+using Microsoft.Extensions.Logging.Abstractions;
+
+namespace Explorer.Application.Tests;
+
+public class EntryClassificationServiceTests
+{
+    [Fact]
+    public async Task Archive_children_override_zip_as_photos()
+    {
+        await using var store = await OpenStore();
+        var source = await AddSource(store, @"C:\media");
+        var zip = await Upsert(store, new IndexEntry
+        {
+            SourceId = source.Id,
+            Name = "photos.zip",
+            NameNorm = "photos.zip",
+            Extension = "zip",
+            PathRel = "photos.zip",
+            LastSeenUtc = DateTimeOffset.UtcNow
+        });
+        await Upsert(store, Child(source.Id, zip.Id, "a.jpg", "jpg"));
+        await Upsert(store, Child(source.Id, zip.Id, "b.jpg", "jpg"));
+        await Upsert(store, Child(source.Id, zip.Id, "c.jpg", "jpg"));
+
+        var service = Create(store, new MemoryEnumerator());
+        service.Resume();
+        Assert.True(await service.ProcessPendingAsync());
+        var loaded = await store.Entries.GetAsync(zip.Id);
+        Assert.Equal(FileCategory.Photos, loaded!.Category);
+        Assert.Equal(CategorySources.ArchiveContents, loaded.CategorySource);
+        Assert.False(await service.ProcessPendingAsync());
+    }
+
+    [Fact]
+    public async Task Signature_classifies_jpeg_without_extension()
+    {
+        var root = Path.Combine(Path.GetTempPath(), "ew-classify", Guid.NewGuid().ToString("N"));
+        Directory.CreateDirectory(root);
+        var file = Path.Combine(root, "pic.bin");
+        File.WriteAllBytes(file, [0xFF, 0xD8, 0xFF, 0xE0, 0x00, 0x10, 0x4A, 0x46, 0x49, 0x46, 0x00, 0x01]);
+        await using var store = await OpenStore();
+        var source = await AddSource(store, root);
+        var entry = await Upsert(store, new IndexEntry
+        {
+            SourceId = source.Id,
+            Name = "pic.bin",
+            NameNorm = "pic.bin",
+            Extension = "bin",
+            PathRel = "pic.bin",
+            LastSeenUtc = DateTimeOffset.UtcNow
+        });
+        Assert.Equal(FileCategory.Unknown, entry.Category);
+
+        var enumerator = new MemoryEnumerator();
+        enumerator.Add(new FileSystemItem { FullPath = file, Name = "pic.bin" });
+        var service = Create(store, enumerator);
+        service.Resume();
+        Assert.True(await service.ProcessPendingAsync());
+        var loaded = await store.Entries.GetAsync(entry.Id);
+        Assert.Equal(FileCategory.Photos, loaded!.Category);
+        Assert.Equal(CategorySources.Mime, loaded.CategorySource);
+    }
+
+    [Fact]
+    public async Task Pause_skips_work()
+    {
+        await using var store = await OpenStore();
+        var source = await AddSource(store, @"C:\media");
+        var zip = await Upsert(store, new IndexEntry
+        {
+            SourceId = source.Id,
+            Name = "photos.zip",
+            NameNorm = "photos.zip",
+            Extension = "zip",
+            PathRel = "photos.zip",
+            LastSeenUtc = DateTimeOffset.UtcNow
+        });
+        await Upsert(store, Child(source.Id, zip.Id, "a.jpg", "jpg"));
+        var service = Create(store, new MemoryEnumerator());
+        Assert.True(service.IsPaused);
+        Assert.False(await service.ProcessPendingAsync());
+        var loaded = await store.Entries.GetAsync(zip.Id);
+        Assert.Equal(FileCategory.Archive, loaded!.Category);
+    }
+
+    private static EntryClassificationService Create(IIndexStore store, IFileSystemEnumerator enumerator)
+        => new(
+            store,
+            enumerator,
+            new NeverHydrate(),
+            NullLogger<EntryClassificationService>.Instance);
+
+    private static async Task<SqliteIndexStore> OpenStore()
+    {
+        var db = Path.Combine(Path.GetTempPath(), "ew-classify", Guid.NewGuid().ToString("N"), "index.db");
+        var store = new SqliteIndexStore(db, NullLogger<SqliteIndexStore>.Instance);
+        await store.OpenAsync();
+        return store;
+    }
+
+    private static async Task<Source> AddSource(IIndexStore store, string root)
+    {
+        var source = new Source
+        {
+            StableKey = Guid.NewGuid().ToString("N"),
+            Kind = SourceKind.NtfsLocal,
+            DisplayName = "Test",
+            LastRootPath = root,
+            Status = SourceStatus.Online
+        };
+        source.Id = await store.Sources.UpsertAsync(source);
+        return source;
+    }
+
+    private static async Task<IndexEntry> Upsert(IIndexStore store, IndexEntry entry)
+    {
+        entry.Id = await store.Entries.UpsertAsync(entry);
+        return (await store.Entries.GetAsync(entry.Id))!;
+    }
+
+    private static IndexEntry Child(long sourceId, long parentId, string name, string ext)
+        => new()
+        {
+            SourceId = sourceId,
+            ParentId = parentId,
+            Name = name,
+            NameNorm = name,
+            Extension = ext,
+            PathRel = name,
+            LastSeenUtc = DateTimeOffset.UtcNow
+        };
+
+    private sealed class NeverHydrate : IHydrationGuard
+    {
+        public bool WouldHydrateOnRead(FileSystemItem item) => false;
+        public bool WouldHydrateOnRead(int attributes, CloudAvailability? availability) => false;
+        public Task<bool> WouldHydrateOnReadAsync(string path, CancellationToken cancellationToken = default)
+            => Task.FromResult(false);
+    }
+
+    private sealed class MemoryEnumerator : IFileSystemEnumerator
+    {
+        private readonly Dictionary<string, FileSystemItem> _items = new(StringComparer.OrdinalIgnoreCase);
+
+        public void Add(FileSystemItem item) => _items[item.FullPath] = item;
+
+        public IEnumerable<FileSystemItem> EnumerateChildren(string directoryPath) => [];
+        public FileSystemItem? GetItem(string path)
+            => _items.TryGetValue(path, out var item) ? item : null;
+        public IReadOnlyList<FileSystemItem> EnumerateChildrenSafe(string directoryPath, out string? error)
+        {
+            error = null;
+            return [];
+        }
+    }
+}

tests/Explorer.Application.Tests/ReorganizePlannerTests.cs

@@ -132,6 +132,40 @@ public class ReorganizePlannerTests
         Assert.Null(fs.GetItem(@"C:\Pictures\photo.jpg"));
     }
 
+    [Fact]
+    public void Prefers_indexed_archive_contents_over_extension()
+    {
+        var fs = Tree()
+            .Dir(@"C:\Downloads")
+            .File(@"C:\Downloads\photos.zip", 4, T0)
+            .Dir(@"C:\Pictures")
+            .Dir(@"C:\Archive");
+
+        var indexed = new Dictionary<string, IndexEntry>(StringComparer.OrdinalIgnoreCase)
+        {
+            ["photos.zip"] = new IndexEntry
+            {
+                Name = "photos.zip",
+                NameNorm = "photos.zip",
+                PathRel = "photos.zip",
+                Category = FileCategory.Photos,
+                CategorySource = CategorySources.ArchiveContents,
+                CategoryReason = "Archive contents are mostly photos."
+            }
+        };
+        var plan = new ReorganizePlanner().Build(
+            @"C:\Downloads",
+            Map(),
+            fs,
+            _ => true,
+            _ => false,
+            now: T0,
+            pathExists: _ => false,
+            indexedByName: indexed);
+        Assert.Contains(plan.Operations, o => o.SourcePath.EndsWith("photos.zip") && o.DestinationPath == @"C:\Pictures\photos.zip");
+        Assert.DoesNotContain(plan.Operations, o => o.DestinationPath == @"C:\Archive\photos.zip");
+    }
+
     private static OperationPlan Build(
         IFileSystemEnumerator fs,
         Action<OrganizeDestinations>? configure = null,

tests/Explorer.Domain.Tests/DomainTests.cs

@@ -484,6 +484,108 @@ public class FileClassifierTests
         => FileClassifier.Classify(name, @"C:\Downloads\" + name, isDirectory, isDirectory ? AttributeFlags.Directory : 0, isRepoRoot).Category;
 }
 
+public class EntryCategoryAssignerTests
+{
+    [Fact]
+    public void ApplyAutomatic_sets_extension_category_on_files()
+    {
+        var entry = new IndexEntry
+        {
+            Name = "clip.mkv",
+            NameNorm = "clip.mkv",
+            PathRel = "clip.mkv",
+            Extension = "mkv"
+        };
+        EntryCategoryAssigner.ApplyAutomatic(entry);
+        Assert.Equal(FileCategory.Video, entry.Category);
+        Assert.Equal(CategorySources.Extension, entry.CategorySource);
+        Assert.True(entry.CategoryConfidence >= 80);
+    }
+
+    [Fact]
+    public void User_category_is_not_overwritten()
+    {
+        var entry = new IndexEntry
+        {
+            Name = "clip.mkv",
+            NameNorm = "clip.mkv",
+            PathRel = "clip.mkv",
+            Extension = "mkv"
+        };
+        EntryCategoryAssigner.ApplyUser(entry, FileCategory.Documents, "Manual");
+        EntryCategoryAssigner.ApplyAutomatic(entry);
+        Assert.Equal(FileCategory.Documents, entry.Category);
+        Assert.Equal(CategorySources.User, entry.CategorySource);
+    }
+
+    [Fact]
+    public void Children_majority_sets_folder_or_archive_source()
+    {
+        var folder = new IndexEntry
+        {
+            Name = "Vacation",
+            NameNorm = "vacation",
+            PathRel = "Vacation",
+            IsDirectory = true,
+            Attributes = AttributeFlags.Directory
+        };
+        EntryCategoryAssigner.ApplyAutomatic(
+            folder,
+            childCategories: [FileCategory.Photos, FileCategory.Photos, FileCategory.Photos, FileCategory.Documents]);
+        Assert.Equal(FileCategory.Photos, folder.Category);
+        Assert.Equal(CategorySources.Children, folder.CategorySource);
+
+        var zip = new IndexEntry
+        {
+            Name = "photos.zip",
+            NameNorm = "photos.zip",
+            PathRel = "photos.zip",
+            Extension = "zip"
+        };
+        EntryCategoryAssigner.ApplyAutomatic(
+            zip,
+            childCategories: [FileCategory.Photos, FileCategory.Photos, FileCategory.Photos]);
+        Assert.Equal(FileCategory.Photos, zip.Category);
+        Assert.Equal(CategorySources.ArchiveContents, zip.CategorySource);
+    }
+}
+
+public class OrganizeDestinationsTests
+{
+    [Fact]
+    public void Parses_category_aliases()
+    {
+        Assert.True(OrganizeDestinations.TryParse("photos", out var photos));
+        Assert.Equal(FileCategory.Photos, photos);
+        Assert.True(OrganizeDestinations.TryParse("zip", out var zip));
+        Assert.Equal(FileCategory.Archive, zip);
+        Assert.True(OrganizeDestinations.TryParse("unknown", out var unknown));
+        Assert.Equal(FileCategory.Unknown, unknown);
+        Assert.False(OrganizeDestinations.TryParse("not-a-category", out _));
+    }
+}
+
+public class FileSignatureClassifierTests
+{
+    [Fact]
+    public void Recognizes_common_headers()
+    {
+        Assert.Equal(FileCategory.Photos, Hit([0xFF, 0xD8, 0xFF, 0xE0]));
+        Assert.Equal(FileCategory.Photos, Hit([0x89, 0x50, 0x4E, 0x47, 0x0D, 0x0A, 0x1A, 0x0A]));
+        Assert.Equal(FileCategory.Documents, Hit([0x25, 0x50, 0x44, 0x46]));
+        Assert.Equal(FileCategory.Archive, Hit([0x50, 0x4B, 0x03, 0x04]));
+        Assert.Equal(FileCategory.Archive, Hit([0x37, 0x7A, 0xBC, 0xAF]));
+        Assert.Equal(FileCategory.Installer, Hit([0x4D, 0x5A, 0x90, 0x00]));
+        Assert.Equal(FileCategory.Audio, Hit("RIFF....WAVE"u8.ToArray()));
+        Assert.Equal(FileCategory.Video, Hit("RIFF....AVI "u8.ToArray()));
+        Assert.Null(FileSignatureClassifier.TryClassify([0x00, 0x01, 0x02, 0x03]));
+        Assert.Null(FileSignatureClassifier.TryClassify([0xFF, 0xD8]));
+    }
+
+    private static FileCategory Hit(byte[] header)
+        => FileSignatureClassifier.TryClassify(header)!.Category;
+}
+
 public class GitChangeTests
 {
     [Fact]

tests/Explorer.Hosting.Tests/BackgroundMaintenanceCoordinatorTests.cs

@@ -149,6 +149,44 @@ public class BackgroundMaintenanceCoordinatorTests
         Assert.Empty(indexing.IdleScans);
     }
 
+    [Fact]
+    public async Task Idle_classifies_before_hashing()
+    {
+        var hash = new FakeHash { Pending = true };
+        var indexing = new FakeIndexing();
+        var classify = new FakeClassify { Work = true };
+        var coordinator = Create(hash, indexing, idle: TimeSpan.FromMinutes(20), classify: classify);
+        await coordinator.TickAsync(CancellationToken.None);
+        Assert.Equal(1, classify.Calls);
+        Assert.True(hash.IsPaused);
+        Assert.Contains("classifying", coordinator.Snapshot.Message, StringComparison.OrdinalIgnoreCase);
+    }
+
+    [Fact]
+    public async Task Idle_hashes_when_classify_is_idle()
+    {
+        var hash = new FakeHash { Pending = true };
+        var indexing = new FakeIndexing();
+        var classify = new FakeClassify();
+        var coordinator = Create(hash, indexing, idle: TimeSpan.FromMinutes(20), classify: classify);
+        await coordinator.TickAsync(CancellationToken.None);
+        Assert.Equal(1, classify.Calls);
+        Assert.False(hash.IsPaused);
+        Assert.Contains("hashing", coordinator.Snapshot.Message, StringComparison.OrdinalIgnoreCase);
+    }
+
+    [Fact]
+    public async Task Activity_pauses_classify()
+    {
+        var hash = new FakeHash();
+        var indexing = new FakeIndexing();
+        var classify = new FakeClassify { Paused = false };
+        var coordinator = Create(hash, indexing, idle: TimeSpan.Zero, classify: classify);
+        await coordinator.TickAsync(CancellationToken.None);
+        Assert.True(classify.IsPaused);
+        Assert.Equal(0, classify.Calls);
+    }
+
     private static Source StaleLocal()
         => new()
         {
@@ -168,8 +206,9 @@ public class BackgroundMaintenanceCoordinatorTests
         bool enabled = true,
         bool ac = true,
         bool foreground = false,
-        IReadOnlyList<Source>? sources = null)
+        IReadOnlyList<Source>? sources = null,
-        => Create(hash, indexing, new FakeIdle(idle), enabled, ac, foreground, sources);
+        FakeClassify? classify = null)
+        => Create(hash, indexing, new FakeIdle(idle), enabled, ac, foreground, sources, classify);
 
     private static BackgroundMaintenanceCoordinator Create(
         FakeHash hash,
@@ -178,7 +217,8 @@ public class BackgroundMaintenanceCoordinatorTests
         bool enabled = true,
         bool ac = true,
         bool foreground = false,
-        IReadOnlyList<Source>? sources = null)
+        IReadOnlyList<Source>? sources = null,
+        FakeClassify? classify = null)
     {
         var dir = Path.Combine(Path.GetTempPath(), "ew-maint", Guid.NewGuid().ToString("N"));
         Directory.CreateDirectory(dir);
@@ -199,7 +239,8 @@ public class BackgroundMaintenanceCoordinatorTests
             new FakeHistory(),
             new FakeStore(sources ?? []),
             new FakeVolumes(),
-            NullLogger<BackgroundMaintenanceCoordinator>.Instance);
+            NullLogger<BackgroundMaintenanceCoordinator>.Instance,
+            classify: classify);
     }
 
     private sealed class FakeIdle(TimeSpan idle) : IUserIdleMonitor
@@ -233,14 +274,31 @@ public class BackgroundMaintenanceCoordinatorTests
 
     private sealed class FakeHash : IIdleHashWork
     {
+        public bool Pending { get; set; }
         public bool Paused { get; set; } = true;
         public bool IsPaused => Paused;
         public string? CurrentPath => null;
         public void Pause() => Paused = true;
         public void Resume() => Paused = false;
         public void BeginUserRequested() { }
-        public Task<bool> HasPendingAsync(CancellationToken cancellationToken = default) => Task.FromResult(false);
+        public Task<bool> HasPendingAsync(CancellationToken cancellationToken = default) => Task.FromResult(Pending);
-        public Task<long> CountPendingAsync(CancellationToken cancellationToken = default) => Task.FromResult(0L);
+        public Task<long> CountPendingAsync(CancellationToken cancellationToken = default) => Task.FromResult(Pending ? 1L : 0L);
+    }
+
+    private sealed class FakeClassify : IIdleClassifyWork
+    {
+        public bool Work { get; set; }
+        public int Calls { get; private set; }
+        public bool Paused { get; set; } = true;
+        public bool IsPaused => Paused;
+        public string? CurrentPath => null;
+        public void Pause() => Paused = true;
+        public void Resume() => Paused = false;
+        public Task<bool> ProcessPendingAsync(CancellationToken cancellationToken = default)
+        {
+            Calls++;
+            return Task.FromResult(Work);
+        }
     }
 
     private sealed class FakeHistory : IHistoryMaintenance

tests/Explorer.Hosting.Tests/CoreRegistrationTests.cs

@@ -36,6 +36,7 @@ public class CoreRegistrationTests
             Assert.NotNull(sp.GetService<IBackgroundMaintenance>());
             Assert.NotNull(sp.GetService<IUserIdleMonitor>());
             Assert.NotNull(sp.GetService<IPowerSourceMonitor>());
+            Assert.NotNull(sp.GetService<IIdleClassifyWork>());
             Assert.IsType<StorageProviderRegistry>(sp.GetService<ICloudOverlay>());
         }
         finally

tests/Explorer.Search.Tests/SearchServiceTests.cs

@@ -44,4 +44,37 @@ public class SearchServiceTests
         Assert.Contains(both, e => e.Name == "Folder");
         Assert.Contains(both, e => e.Name == "notes.txt");
     }
+
+    [Fact]
+    public async Task Category_hint_and_filter()
+    {
+        var db = Path.Combine(Path.GetTempPath(), "ew-search", Guid.NewGuid().ToString("N"), "index.db");
+        await using var store = new SqliteIndexStore(db, NullLogger<SqliteIndexStore>.Instance);
+        await store.OpenAsync();
+        var source = new Source { StableKey = "k", DisplayName = "d", Kind = SourceKind.NtfsLocal, LastRootPath = @"C:\d", Status = SourceStatus.Online };
+        source.Id = await store.Sources.UpsertAsync(source);
+        var root = new IndexEntry { SourceId = source.Id, Name = "d", NameNorm = "d", IsDirectory = true, PathRel = "", LastSeenUtc = DateTimeOffset.UtcNow };
+        root.Id = await store.Entries.UpsertAsync(root);
+        await store.Entries.UpsertAsync(new IndexEntry
+        {
+            SourceId = source.Id, ParentId = root.Id, Name = "clip.mkv", NameNorm = "clip.mkv", Extension = "mkv",
+            PathRel = "clip.mkv", LastSeenUtc = DateTimeOffset.UtcNow
+        });
+        await store.Entries.UpsertAsync(new IndexEntry
+        {
+            SourceId = source.Id, ParentId = root.Id, Name = "notes.pdf", NameNorm = "notes.pdf", Extension = "pdf",
+            PathRel = "notes.pdf", LastSeenUtc = DateTimeOffset.UtcNow
+        });
+
+        var search = new SearchService(store);
+        var hinted = await search.SearchAsync(new SearchQuery { Text = "category:video", SourceIds = [source.Id] });
+        Assert.Single(hinted);
+        Assert.Equal("clip.mkv", hinted[0].Name);
+        var filtered = await search.SearchAsync(new SearchQuery { Category = FileCategory.Documents, SourceIds = [source.Id] });
+        Assert.Single(filtered);
+        Assert.Equal("notes.pdf", filtered[0].Name);
+        var split = SearchService.SplitCategoryHint("vacation category:photos");
+        Assert.Equal("vacation", split.Name);
+        Assert.Equal(FileCategory.Photos, split.Category);
+    }
 }

tests/Explorer.Storage.Tests/StorageTests.cs

@@ -114,6 +114,135 @@ public class EntryAndSearchTests
         Assert.Contains(byDate, e => e.Name == "Movie.mkv");
     }
 
+    [Fact]
+    public async Task Upsert_assigns_and_preserves_categories()
+    {
+        await using var store = await Stores.Open();
+        var source = await store.AddSourceAsync(@"C:\media");
+        var root = new IndexEntry
+        {
+            SourceId = source.Id,
+            Name = "media",
+            NameNorm = "media",
+            IsDirectory = true,
+            PathRel = "",
+            LastSeenUtc = DateTimeOffset.UtcNow
+        };
+        root.Id = await store.Entries.UpsertAsync(root);
+        var photo = new IndexEntry
+        {
+            SourceId = source.Id,
+            ParentId = root.Id,
+            Name = "shot.jpg",
+            NameNorm = "shot.jpg",
+            Extension = "jpg",
+            PathRel = "shot.jpg",
+            LastSeenUtc = DateTimeOffset.UtcNow
+        };
+        photo.Id = await store.Entries.UpsertAsync(photo);
+        var loaded = await store.Entries.GetAsync(photo.Id);
+        Assert.Equal(FileCategory.Photos, loaded!.Category);
+        Assert.Equal(CategorySources.Extension, loaded.CategorySource);
+
+        await store.Entries.SetUserCategoryAsync(photo.Id, FileCategory.Documents, "Manual");
+        photo.SizeBytes = 100;
+        await store.Entries.UpsertAsync(photo);
+        loaded = await store.Entries.GetAsync(photo.Id);
+        Assert.Equal(FileCategory.Documents, loaded!.Category);
+        Assert.Equal(CategorySources.User, loaded.CategorySource);
+
+        var other = new IndexEntry
+        {
+            SourceId = source.Id,
+            ParentId = root.Id,
+            Name = "clip.mkv",
+            NameNorm = "clip.mkv",
+            Extension = "mkv",
+            PathRel = "clip.mkv",
+            LastSeenUtc = DateTimeOffset.UtcNow
+        };
+        other.Id = await store.Entries.UpsertAsync(other);
+        await store.Entries.RefreshCategoryFromChildrenAsync(root.Id);
+        var folder = await store.Entries.GetAsync(root.Id);
+        Assert.Equal(FileCategory.Unknown, folder!.Category);
+    }
+
+    [Fact]
+    public async Task Archive_contents_and_signature_queues()
+    {
+        await using var store = await Stores.Open();
+        var source = await store.AddSourceAsync(@"C:\media");
+        var zip = new IndexEntry
+        {
+            SourceId = source.Id,
+            Name = "photos.zip",
+            NameNorm = "photos.zip",
+            Extension = "zip",
+            PathRel = "photos.zip",
+            LastSeenUtc = DateTimeOffset.UtcNow
+        };
+        zip.Id = await store.Entries.UpsertAsync(zip);
+        Assert.Equal(FileCategory.Archive, (await store.Entries.GetAsync(zip.Id))!.Category);
+
+        for (var i = 0; i < 3; i++)
+        {
+            await store.Entries.UpsertAsync(new IndexEntry
+            {
+                SourceId = source.Id,
+                ParentId = zip.Id,
+                Name = $"shot{i}.jpg",
+                NameNorm = $"shot{i}.jpg",
+                Extension = "jpg",
+                PathRel = $"photos.zip/shot{i}.jpg",
+                LastSeenUtc = DateTimeOffset.UtcNow
+            });
+        }
+
+        var needing = await store.Entries.GetArchiveIdsNeedingContentClassifyAsync(10);
+        Assert.Contains(zip.Id, needing);
+        await store.Entries.RefreshCategoryFromChildrenAsync(zip.Id);
+        var loaded = await store.Entries.GetAsync(zip.Id);
+        Assert.Equal(FileCategory.Photos, loaded!.Category);
+        Assert.Equal(CategorySources.ArchiveContents, loaded.CategorySource);
+        Assert.Empty(await store.Entries.GetArchiveIdsNeedingContentClassifyAsync(10));
+
+        var mystery = new IndexEntry
+        {
+            SourceId = source.Id,
+            Name = "mystery.bin",
+            NameNorm = "mystery.bin",
+            Extension = "bin",
+            PathRel = "mystery.bin",
+            LastSeenUtc = DateTimeOffset.UtcNow
+        };
+        mystery.Id = await store.Entries.UpsertAsync(mystery);
+        var unknowns = await store.Entries.GetUnknownFilesForSignatureAsync(10);
+        Assert.Contains(unknowns, e => e.Id == mystery.Id);
+        Assert.Equal(0, await store.Entries.BackfillCheapCategoriesAsync(50));
+    }
+
+    [Fact]
+    public async Task User_category_by_path_is_preserved()
+    {
+        await using var store = await Stores.Open();
+        var source = await store.AddSourceAsync(@"C:\media");
+        var photo = new IndexEntry
+        {
+            SourceId = source.Id,
+            Name = "shot.jpg",
+            NameNorm = "shot.jpg",
+            Extension = "jpg",
+            PathRel = "shot.jpg",
+            LastSeenUtc = DateTimeOffset.UtcNow
+        };
+        photo.Id = await store.Entries.UpsertAsync(photo);
+        var mutations = new Explorer.Application.LocalIndexMutations(store);
+        await mutations.SetUserCategoryByPathAsync(@"C:\media\shot.jpg", FileCategory.Installer, "Manual");
+        var loaded = await store.Entries.GetAsync(photo.Id);
+        Assert.Equal(FileCategory.Installer, loaded!.Category);
+        Assert.Equal(CategorySources.User, loaded.CategorySource);
+    }
+
     [Fact]
     public async Task Folder_aggregates_and_tombstones()
     {