Merge claudedo/1f4f59b14e4d481d97e843b6b2014af5

src/ClaudeDo.Worker/Runner/InteractiveLaunchSpecService.cs

@@ -104,12 +104,30 @@ public sealed class InteractiveLaunchSpecService : IInteractiveLaunchSpecService
         // The model itself is deliberately NOT forced here — the user can still switch it in the TUI.
         var effort = EffortFor(globalSettings, task.Model ?? listConfig?.Model);
 
-        // Resume an existing session as-is; for a fresh session, seed the interactive TUI with
-        // the task's brief (title + description) via a file, never as a positional CLI argument --
-        // see BuildFreshTaskArgsAsync for why.
-        var args = run?.SessionId is { Length: > 0 } sessionId
-            ? WithEffort(WindowsTerminalLauncher.BuildResumeArgs(sessionId), effort)
-            : await BuildFreshTaskArgsAsync(task, effort, ct);
+        // Resume this task's own last interactive conversation when it has one -- it takes
+        // precedence over the latest autonomous run's session, since an interactive session is a
+        // distinct conversation from an autonomous run even against the same worktree. Fall back
+        // to the autonomous run's session so opening a task interactively for the first time still
+        // picks up prior context. Neither survives a freshly (re)created worktree (isFreshWorktree
+        // already forced `run` to null above).
+        var resumeSessionId = isFreshWorktree ? null : task.InteractiveSessionId ?? run?.SessionId;
+
+        // For a fresh session, seed the interactive TUI with the task's brief (title +
+        // description) via a file, never as a positional CLI argument -- see
+        // BuildFreshTaskArgsAsync for why. The session id claude will run under is generated and
+        // persisted HERE, before launch, so a closed/aborted session -- even one that never got
+        // past startup -- still leaves an id the next open can resume.
+        IReadOnlyList<string> args;
+        if (resumeSessionId is { Length: > 0 })
+        {
+            args = WithEffort(WindowsTerminalLauncher.BuildResumeArgs(resumeSessionId), effort);
+        }
+        else
+        {
+            var sessionId = Guid.NewGuid().ToString();
+            await new TaskRepository(ctx).SetInteractiveSessionIdAsync(taskId, sessionId, ct);
+            args = await BuildFreshTaskArgsAsync(task, effort, sessionId, ct);
+        }
 
         // Same run environment variable ClaudeProcess sets for every headless run: the
         // AskUser MCP tool call and wait_for_task_change cap at 60s unless raised, and lifting
@@ -445,11 +463,15 @@ public sealed class InteractiveLaunchSpecService : IInteractiveLaunchSpecService
     // Read; --effort (single-value) must sit directly before the positional kickoff so the
     // preceding variadic --add-dir doesn't swallow the kickoff as another directory.
     // No brief (task has neither a title nor a description) -> no positional arg at all.
-    private static async Task<IReadOnlyList<string>> BuildFreshTaskArgsAsync(TaskEntity task, string effort, CancellationToken ct)
+    // `--session-id` pre-assigns the claude session id the caller already persisted (see
+    // BuildForTaskAsync) so this fresh conversation is resumable from its very first turn --
+    // it's a single-value flag, so it may sit directly before the positional kickoff.
+    private static async Task<IReadOnlyList<string>> BuildFreshTaskArgsAsync(
+        TaskEntity task, string effort, string sessionId, CancellationToken ct)
     {
         var brief = BuildTaskBrief(task);
         if (string.IsNullOrEmpty(brief))
-            return new[] { "--effort", effort };
+            return new[] { "--effort", effort, "--session-id", sessionId };
 
         var sessionDir = Path.Combine(Paths.AppDataRoot(), "task-sessions", task.Id);
         Directory.CreateDirectory(sessionDir);
@@ -460,6 +482,7 @@ public sealed class InteractiveLaunchSpecService : IInteractiveLaunchSpecService
         {
             "--add-dir", sessionDir,
             "--effort", effort,
+            "--session-id", sessionId,
             $"Read the file {briefPath} first. It contains the task you must work on. " +
             "After reading it, begin the session as your instructions describe.",
         };

src/ClaudeDo.Worker/Runner/Interfaces/IInteractiveLaunchSpecService.cs

@@ -17,9 +17,12 @@ public interface IInteractiveLaunchSpecService
     /// Throws KeyNotFoundException if the task doesn't exist, InvalidOperationException
     /// if it's Running/Queued. If the task has no usable worktree yet, one is created on
     /// demand (same mechanism as an autonomous run) provided the task's list has a working
-    /// directory pointing at a git repo -- otherwise throws InvalidOperationException. A task
-    /// that has never run, or whose worktree was just created fresh, gets a fresh-start spec
-    /// (no --resume); an existing worktree with a persisted SessionId gets --resume.</summary>
+    /// directory pointing at a git repo -- otherwise throws InvalidOperationException. Resumes
+    /// (--resume) this task's own last interactive session (TaskEntity.InteractiveSessionId) if
+    /// it has one, else the latest autonomous run's session; a task that has never run either
+    /// way, or whose worktree was just created fresh, gets a fresh-start spec instead -- pre-
+    /// assigned a new session id via --session-id and persisted to InteractiveSessionId before
+    /// launch, so a closed/aborted session can be resumed next time.</summary>
     Task<LaunchSpec> BuildForTaskAsync(string taskId, CancellationToken ct);
 
     /// <summary>Builds a LaunchSpec for an ad-hoc interactive session in an arbitrary directory --