fix(worker): stop sibling worktrees from landing inside the repo tree

Path.GetDirectoryName returned workingDir itself instead of its parent
whenever list.WorkingDir ended in a directory separator, placing
.claudedo-worktrees inside the target repo's own working tree. Add
WorktreeRootResolver to normalize the trailing separator before deriving
the sibling root and to guard that the resulting worktree path never
lands inside workingDir, used by both WorktreeManager and
PlanningSessionManager. Add a startup sweep (LegacyWorktreeFolderRecovery)
that warns when a list's working dir already contains a leftover
.claudedo-worktrees folder from before the fix.

src/ClaudeDo.Worker/Git/WorktreeRootResolver.cs

@@ -0,0 +1,36 @@
+namespace ClaudeDo.Worker.Git;
+
+/// <summary>
+/// Resolves the "sibling" worktree root and guards against a worktree landing inside the
+/// repository it was created from. A <c>list.WorkingDir</c> ending in a directory separator
+/// makes <see cref="Path.GetDirectoryName(string)"/> return the same directory instead of its
+/// parent, which used to place <c>.claudedo-worktrees</c> inside the target repo's own tree.
+/// </summary>
+public static class WorktreeRootResolver
+{
+    /// <summary>The parent directory of <paramref name="workingDir"/>, trailing-separator safe.</summary>
+    public static string ResolveSiblingRoot(string workingDir)
+    {
+        var full = Path.TrimEndingDirectorySeparator(Path.GetFullPath(workingDir));
+        var parent = Path.GetDirectoryName(full);
+        if (string.IsNullOrEmpty(parent))
+            throw new InvalidOperationException(
+                $"Cannot place a sibling worktree next to '{workingDir}': it has no parent directory.");
+        return parent;
+    }
+
+    /// <summary>Throws if <paramref name="worktreePath"/> is <paramref name="workingDir"/> or lies beneath it.</summary>
+    public static void EnsureOutsideWorkingDir(string worktreePath, string workingDir)
+    {
+        var comparison = OperatingSystem.IsWindows() ? StringComparison.OrdinalIgnoreCase : StringComparison.Ordinal;
+        var worktreeFull = Path.GetFullPath(worktreePath);
+        var workingDirFull = Path.TrimEndingDirectorySeparator(Path.GetFullPath(workingDir));
+
+        var isInside = worktreeFull.Equals(workingDirFull, comparison)
+            || worktreeFull.StartsWith(workingDirFull + Path.DirectorySeparatorChar, comparison);
+        if (isInside)
+            throw new InvalidOperationException(
+                $"Refusing to create worktree '{worktreeFull}' inside the target repository's working " +
+                $"tree '{workingDirFull}'. Check list.WorkingDir for a trailing separator or a misconfigured worktree root.");
+    }
+}

src/ClaudeDo.Worker/Lifecycle/LegacyWorktreeFolderRecovery.cs

@@ -0,0 +1,54 @@
+using ClaudeDo.Data;
+using ClaudeDo.Data.Models;
+using ClaudeDo.Data.Repositories;
+using Microsoft.EntityFrameworkCore;
+
+namespace ClaudeDo.Worker.Lifecycle;
+
+/// <summary>
+/// Startup-only sweep: warns when a list's working directory already contains a
+/// <c>.claudedo-worktrees</c> folder inside its own tree — the symptom of the sibling-worktree
+/// path bug (see <see cref="ClaudeDo.Worker.Git.WorktreeRootResolver"/>) from before it was
+/// fixed. Detection only; moving or ignoring existing folders is left to the user.
+/// </summary>
+public sealed class LegacyWorktreeFolderRecovery : IHostedService
+{
+    private const string LegacyFolderName = ".claudedo-worktrees";
+
+    private readonly IDbContextFactory<ClaudeDoDbContext> _dbFactory;
+    private readonly ILogger<LegacyWorktreeFolderRecovery> _logger;
+
+    public LegacyWorktreeFolderRecovery(
+        IDbContextFactory<ClaudeDoDbContext> dbFactory,
+        ILogger<LegacyWorktreeFolderRecovery> logger)
+    {
+        _dbFactory = dbFactory;
+        _logger = logger;
+    }
+
+    public async Task StartAsync(CancellationToken cancellationToken)
+    {
+        await using var ctx = await _dbFactory.CreateDbContextAsync(cancellationToken);
+        var lists = await new ListRepository(ctx).GetAllAsync(cancellationToken);
+
+        var affected = FindAffectedListNames(lists);
+
+        if (affected.Count > 0)
+            _logger.LogWarning(
+                "Legacy worktree folder recovery: found '{Folder}' inside the working tree of {Count} list(s): {Lists}. " +
+                "This was previously caused by a trailing separator on the list's working directory; existing worktrees were not moved.",
+                LegacyFolderName, affected.Count, string.Join(", ", affected));
+        else
+            _logger.LogInformation("Legacy worktree folder recovery: no lists affected");
+    }
+
+    public Task StopAsync(CancellationToken cancellationToken) => Task.CompletedTask;
+
+    /// <summary>Names of lists whose working dir already contains a <c>.claudedo-worktrees</c> folder.</summary>
+    public static List<string> FindAffectedListNames(IEnumerable<ListEntity> lists) =>
+        lists
+            .Where(l => !string.IsNullOrWhiteSpace(l.WorkingDir))
+            .Where(l => Directory.Exists(Path.Combine(l.WorkingDir!, LegacyFolderName)))
+            .Select(l => l.Name)
+            .ToList();
+}

src/ClaudeDo.Worker/Planning/PlanningSessionManager.cs

@@ -5,6 +5,7 @@ using ClaudeDo.Data.Git;
 using ClaudeDo.Data.Models;
 using ClaudeDo.Data.Repositories;
 using ClaudeDo.Worker.Config;
+using ClaudeDo.Worker.Git;
 using ClaudeDo.Worker.State;
 using Microsoft.EntityFrameworkCore;
 using TaskStatus = ClaudeDo.Data.Models.TaskStatus;
@@ -366,9 +367,11 @@ public sealed class PlanningSessionManager
 
         var raw = strategy.Equals("central", StringComparison.OrdinalIgnoreCase)
             ? Path.Combine(centralRoot, "planning", taskId)
-            : Path.Combine(Path.GetDirectoryName(listWorkingDir)!, ".claudedo-worktrees", "planning", taskId);
+            : Path.Combine(WorktreeRootResolver.ResolveSiblingRoot(listWorkingDir), ".claudedo-worktrees", "planning", taskId);
 
-        return Path.GetFullPath(raw);
+        var worktreePath = Path.GetFullPath(raw);
+        WorktreeRootResolver.EnsureOutsideWorkingDir(worktreePath, listWorkingDir);
+        return worktreePath;
     }
 
     private static string TokenFilePathFor(string sessionDir) =>

src/ClaudeDo.Worker/Program.cs

@@ -69,6 +69,7 @@ builder.Services.AddHostedService<StaleTaskRecovery>();
 builder.Services.AddHostedService<OrphanRecovery>();
 builder.Services.AddHostedService<AttachmentOrphanRecovery>();
 builder.Services.AddHostedService<PromptFileRecovery>();
+builder.Services.AddHostedService<LegacyWorktreeFolderRecovery>();
 builder.Services.AddSignalR().AddJsonProtocol(options =>
 {
     options.PayloadSerializerOptions.Converters.Add(new System.Text.Json.Serialization.JsonStringEnumConverter());

src/ClaudeDo.Worker/Runner/WorktreeManager.cs

@@ -3,6 +3,7 @@ using ClaudeDo.Data.Git;
 using ClaudeDo.Data.Models;
 using ClaudeDo.Data.Repositories;
 using ClaudeDo.Worker.Config;
+using ClaudeDo.Worker.Git;
 using Microsoft.EntityFrameworkCore;
 
 namespace ClaudeDo.Worker.Runner;
@@ -52,9 +53,10 @@ public sealed class WorktreeManager
 
         var worktreePath = strategy.Equals("central", StringComparison.OrdinalIgnoreCase)
             ? Path.Combine(centralRoot ?? _cfg.CentralWorktreeRoot, slug, task.Id)
-            : Path.Combine(Path.GetDirectoryName(workingDir)!, ".claudedo-worktrees", slug, task.Id);
+            : Path.Combine(WorktreeRootResolver.ResolveSiblingRoot(workingDir), ".claudedo-worktrees", slug, task.Id);
 
         worktreePath = Path.GetFullPath(worktreePath);
+        WorktreeRootResolver.EnsureOutsideWorkingDir(worktreePath, workingDir);
 
         // Ensure parent directory exists.
         Directory.CreateDirectory(Path.GetDirectoryName(worktreePath)!);

tests/ClaudeDo.Worker.Tests/Git/WorktreeRootResolverTests.cs

@@ -0,0 +1,83 @@
+using ClaudeDo.Worker.Git;
+
+namespace ClaudeDo.Worker.Tests.Git;
+
+public class WorktreeRootResolverTests
+{
+    [Fact]
+    public void ResolveSiblingRoot_NoTrailingSeparator_ReturnsParent()
+    {
+        var workingDir = Path.Combine(Path.GetTempPath(), "cd_repo_no_sep");
+
+        var root = WorktreeRootResolver.ResolveSiblingRoot(workingDir);
+
+        Assert.Equal(Path.GetFullPath(Path.GetTempPath()).TrimEnd(Path.DirectorySeparatorChar), root);
+    }
+
+    [Fact]
+    public void ResolveSiblingRoot_WithTrailingSeparator_StillReturnsParent()
+    {
+        var workingDir = Path.Combine(Path.GetTempPath(), "cd_repo_with_sep") + Path.DirectorySeparatorChar;
+
+        var root = WorktreeRootResolver.ResolveSiblingRoot(workingDir);
+
+        Assert.Equal(Path.GetFullPath(Path.GetTempPath()).TrimEnd(Path.DirectorySeparatorChar), root);
+    }
+
+    [Fact]
+    public void ResolveSiblingRoot_WithTrailingAltSeparator_StillReturnsParent()
+    {
+        var workingDir = Path.Combine(Path.GetTempPath(), "cd_repo_with_alt_sep") + "/";
+
+        var root = WorktreeRootResolver.ResolveSiblingRoot(workingDir);
+
+        Assert.Equal(Path.GetFullPath(Path.GetTempPath()).TrimEnd(Path.DirectorySeparatorChar), root);
+    }
+
+    [Fact]
+    public void ResolveSiblingRoot_DriveRoot_Throws()
+    {
+        var driveRoot = Path.GetPathRoot(Path.GetTempPath())!;
+
+        Assert.Throws<InvalidOperationException>(() => WorktreeRootResolver.ResolveSiblingRoot(driveRoot));
+    }
+
+    [Fact]
+    public void EnsureOutsideWorkingDir_PathOutside_DoesNotThrow()
+    {
+        var workingDir = Path.Combine(Path.GetTempPath(), "cd_repo");
+        var worktreePath = Path.Combine(Path.GetTempPath(), ".claudedo-worktrees", "slug", "task1");
+
+        WorktreeRootResolver.EnsureOutsideWorkingDir(worktreePath, workingDir);
+    }
+
+    [Fact]
+    public void EnsureOutsideWorkingDir_PathInsideWorkingDir_Throws()
+    {
+        var workingDir = Path.Combine(Path.GetTempPath(), "cd_repo");
+        var worktreePath = Path.Combine(workingDir, ".claudedo-worktrees", "slug", "task1");
+
+        Assert.Throws<InvalidOperationException>(
+            () => WorktreeRootResolver.EnsureOutsideWorkingDir(worktreePath, workingDir));
+    }
+
+    [Fact]
+    public void EnsureOutsideWorkingDir_PathEqualsWorkingDir_Throws()
+    {
+        var workingDir = Path.Combine(Path.GetTempPath(), "cd_repo");
+
+        Assert.Throws<InvalidOperationException>(
+            () => WorktreeRootResolver.EnsureOutsideWorkingDir(workingDir, workingDir));
+    }
+
+    [Fact]
+    public void EnsureOutsideWorkingDir_SiblingWithSharedPrefix_DoesNotThrow()
+    {
+        // "cd_repo-other" is NOT under "cd_repo" even though it shares a string prefix;
+        // a naive StartsWith(workingDir) check would incorrectly reject this.
+        var workingDir = Path.Combine(Path.GetTempPath(), "cd_repo");
+        var worktreePath = Path.Combine(Path.GetTempPath(), "cd_repo-other", "task1");
+
+        WorktreeRootResolver.EnsureOutsideWorkingDir(worktreePath, workingDir);
+    }
+}

tests/ClaudeDo.Worker.Tests/Lifecycle/LegacyWorktreeFolderRecoveryTests.cs

@@ -0,0 +1,71 @@
+using ClaudeDo.Data.Models;
+using ClaudeDo.Worker.Lifecycle;
+using ClaudeDo.Worker.Tests.Infrastructure;
+using Microsoft.Extensions.Logging.Abstractions;
+
+namespace ClaudeDo.Worker.Tests.Lifecycle;
+
+public sealed class LegacyWorktreeFolderRecoveryTests : IDisposable
+{
+    private readonly DbFixture _db = new();
+    private readonly List<string> _tempDirs = new();
+
+    public void Dispose()
+    {
+        _db.Dispose();
+        foreach (var d in _tempDirs)
+        {
+            try { Directory.Delete(d, recursive: true); } catch { }
+        }
+    }
+
+    private string MakeWorkingDir()
+    {
+        var dir = Path.Combine(Path.GetTempPath(), $"claudedo_legacy_wt_{Guid.NewGuid():N}");
+        Directory.CreateDirectory(dir);
+        _tempDirs.Add(dir);
+        return dir;
+    }
+
+    [Fact]
+    public void FindAffectedListNames_FolderInsideWorkingDir_ReturnsListName()
+    {
+        var wd = MakeWorkingDir();
+        Directory.CreateDirectory(Path.Combine(wd, ".claudedo-worktrees"));
+        var list = new ListEntity { Id = "1", Name = "Bandel.Hub", WorkingDir = wd, CreatedAt = DateTime.UtcNow };
+
+        var affected = LegacyWorktreeFolderRecovery.FindAffectedListNames(new[] { list });
+
+        Assert.Equal(new[] { "Bandel.Hub" }, affected);
+    }
+
+    [Fact]
+    public void FindAffectedListNames_NoLegacyFolder_ReturnsEmpty()
+    {
+        var wd = MakeWorkingDir();
+        var list = new ListEntity { Id = "1", Name = "Clean", WorkingDir = wd, CreatedAt = DateTime.UtcNow };
+
+        var affected = LegacyWorktreeFolderRecovery.FindAffectedListNames(new[] { list });
+
+        Assert.Empty(affected);
+    }
+
+    [Fact]
+    public void FindAffectedListNames_NullWorkingDir_IsSkipped()
+    {
+        var list = new ListEntity { Id = "1", Name = "NoRepo", WorkingDir = null, CreatedAt = DateTime.UtcNow };
+
+        var affected = LegacyWorktreeFolderRecovery.FindAffectedListNames(new[] { list });
+
+        Assert.Empty(affected);
+    }
+
+    [Fact]
+    public async Task StartAsync_NoLists_DoesNotThrow()
+    {
+        var sut = new LegacyWorktreeFolderRecovery(_db.CreateFactory(), NullLogger<LegacyWorktreeFolderRecovery>.Instance);
+
+        await sut.StartAsync(CancellationToken.None);
+        await sut.StopAsync(CancellationToken.None);
+    }
+}

tests/ClaudeDo.Worker.Tests/Planning/PlanningSessionManagerTests.cs

@@ -123,6 +123,30 @@ public sealed class PlanningSessionManagerTests : IDisposable
         Assert.NotNull(loaded.PlanningSessionToken);
     }
 
+    [Fact]
+    public async Task StartAsync_TrailingSeparatorOnWorkingDir_PlacesWorktreeOutsideRepo()
+    {
+        var listId = Guid.NewGuid().ToString();
+        var wd = Path.Combine(Path.GetTempPath(), $"cd_wd_{Guid.NewGuid():N}");
+        GitRepoFixture.InitRepoWithInitialCommit(wd);
+        await _lists.AddAsync(new ListEntity
+        {
+            Id = listId,
+            Name = "Test",
+            WorkingDir = wd + Path.DirectorySeparatorChar,
+            CreatedAt = DateTime.UtcNow,
+        });
+        var parent = await SeedManualTaskAsync(listId);
+
+        var ctx = await _sut.StartAsync(parent.Id, CancellationToken.None);
+
+        var wdFull = Path.GetFullPath(wd);
+        Assert.False(
+            ctx.WorktreePath.StartsWith(wdFull + Path.DirectorySeparatorChar, StringComparison.OrdinalIgnoreCase),
+            $"worktree path {ctx.WorktreePath} should not be nested inside the repo dir {wdFull}");
+        Assert.True(Directory.Exists(ctx.WorktreePath));
+    }
+
     [Fact]
     public async Task StartAsync_TaskNotManual_Throws()
     {

tests/ClaudeDo.Worker.Tests/Runner/WorktreeManagerTests.cs

@@ -189,6 +189,26 @@ public class WorktreeManagerTests : IDisposable
         Assert.DoesNotContain(task.Id, worktreeList);
     }
 
+    [Fact]
+    public async Task CreateAsync_TrailingSeparatorOnWorkingDir_PlacesWorktreeOutsideRepo()
+    {
+        if (!GitAvailable) { Assert.True(true, "git not available -- skipping"); return; }
+
+        var repo = CreateRepo();
+        var workingDirWithSeparator = repo.RepoDir + Path.DirectorySeparatorChar;
+        var (task, list) = MakeEntities(workingDirWithSeparator);
+        var (mgr, db) = await CreateManagerAsync(task, list);
+
+        var ctx = await mgr.CreateAsync(task, list, CancellationToken.None);
+        _worktreeCleanups.Add((repo.RepoDir, ctx.WorktreePath));
+
+        var repoDirFull = Path.GetFullPath(repo.RepoDir);
+        Assert.False(
+            ctx.WorktreePath.StartsWith(repoDirFull + Path.DirectorySeparatorChar, StringComparison.OrdinalIgnoreCase),
+            $"worktree path {ctx.WorktreePath} should not be nested inside the repo dir {repoDirFull}");
+        Assert.True(Directory.Exists(ctx.WorktreePath));
+    }
+
     private static (TaskEntity task, ListEntity list) MakeEntities(string workingDir)
     {
         var listId = Guid.NewGuid().ToString();