feat(worker): AskUser MCP tool so a running task can ask the user mid-run

A running task can call mcp__claudedo_run__AskUser(question) to block (up to 3
min) on a human answer. PendingQuestionRegistry holds the pending question +
TaskCompletionSource; the tool broadcasts TaskQuestionAsked, awaits the answer
(WorkerHub.AnswerTaskQuestion resolves it), and returns it as the tool result —
or a 'proceed on your judgment' fallback on timeout. The run stays Running
throughout (no status/schema change). ClaudeProcess raises MCP_TOOL_TIMEOUT so
the 60s HTTP-MCP cap doesn't kill the wait; the run MCP is now wired for every
task, not just standalone ones. System prompt updated to reconcile 'unattended'.

src/ClaudeDo.Data/PromptFiles.cs

@@ -105,9 +105,12 @@ public static class PromptFiles
         - Don't introduce injection/XSS/secret-leak issues. Never commit credentials.
 
         ## You are running unattended
-        You run autonomously with no human watching. There is no one to answer mid-task
-        questions, so never stop to ask — make the most reasonable decision, note the
-        assumption, and continue.
+        You run autonomously, usually with no one watching. Default to making the most
+        reasonable decision yourself, noting the assumption, and continuing — do not stop
+        for routine choices. The one exception: at a genuine fork where a wrong guess
+        would be costly or hard to undo (an irreversible action, contradictory
+        requirements), you may call AskUser(question) to ask the user and wait briefly for
+        an answer. If no one responds in time, proceed on your best judgment.
 
         ## When you are blocked
         If something genuinely prevents you from completing part of the task (missing

src/ClaudeDo.Worker/Hub/HubBroadcaster.cs

@@ -26,6 +26,12 @@ public sealed class HubBroadcaster : IPrimeBroadcaster, IRefineBroadcaster
     public Task TaskUpdated(string taskId) =>
         _hub.Clients.All.SendAsync("TaskUpdated", taskId);
 
+    public Task TaskQuestionAsked(string taskId, string questionId, string question) =>
+        _hub.Clients.All.SendAsync("TaskQuestionAsked", taskId, questionId, question);
+
+    public Task TaskQuestionResolved(string taskId, string questionId) =>
+        _hub.Clients.All.SendAsync("TaskQuestionResolved", taskId, questionId);
+
     public Task ListUpdated(string listId) =>
         _hub.Clients.All.SendAsync("ListUpdated", listId);
 

src/ClaudeDo.Worker/Hub/WorkerHub.cs

@@ -56,6 +56,7 @@ public record WorktreeOverviewDto(
     bool PathExistsOnDisk);
 
 public record ForceRemoveResultDto(bool Removed, string? Reason);
+public record PendingQuestionDto(string TaskId, string QuestionId, string Question);
 public record MergeResultDto(string Status, IReadOnlyList<string> ConflictFiles, string? ErrorMessage);
 public record MergePreviewDto(string Status, IReadOnlyList<string> ConflictFiles, int ChangedFileCount);
 public record MergeTargetsDto(string DefaultBranch, IReadOnlyList<string> LocalBranches);
@@ -114,6 +115,7 @@ public sealed class WorkerHub : Microsoft.AspNetCore.SignalR.Hub
     private readonly WorkerConfig _cfg;
     private readonly OnlineInboxConfig _onlineInboxConfig;
     private readonly OnlineTokenStore _onlineTokenStore;
+    private readonly Runner.PendingQuestionRegistry _pendingQuestions;
     private readonly LogRingBuffer? _logBuffer;
 
     public WorkerHub(
@@ -139,6 +141,7 @@ public sealed class WorkerHub : Microsoft.AspNetCore.SignalR.Hub
         WorkerConfig cfg,
         OnlineInboxConfig onlineInboxConfig,
         OnlineTokenStore onlineTokenStore,
+        Runner.PendingQuestionRegistry pendingQuestions,
         LogRingBuffer? logBuffer = null)
     {
         _queue = queue;
@@ -163,9 +166,22 @@ public sealed class WorkerHub : Microsoft.AspNetCore.SignalR.Hub
         _cfg = cfg;
         _onlineInboxConfig = onlineInboxConfig;
         _onlineTokenStore = onlineTokenStore;
+        _pendingQuestions = pendingQuestions;
         _logBuffer = logBuffer;
     }
 
+    /// <summary>Deliver the user's answer to a question a running task raised via AskUser.
+    /// Returns false if no matching question is still pending (already answered or timed out).</summary>
+    public bool AnswerTaskQuestion(string taskId, string questionId, string answer) =>
+        _pendingQuestions.TryAnswer(taskId, questionId, answer ?? string.Empty);
+
+    /// <summary>The question a running task is currently blocked on, if any (for UI re-attach).</summary>
+    public PendingQuestionDto? GetPendingQuestion(string taskId)
+    {
+        var q = _pendingQuestions.Get(taskId);
+        return q is null ? null : new PendingQuestionDto(q.TaskId, q.QuestionId, q.Question);
+    }
+
     /// <summary>Recent worker log records (last 30 min, all levels) for the Log Visualizer overlay.</summary>
     public IReadOnlyList<WorkerLogRecord> GetRecentLogs() =>
         _logBuffer?.Snapshot() ?? Array.Empty<WorkerLogRecord>();

src/ClaudeDo.Worker/Program.cs

@@ -72,6 +72,7 @@ builder.Services.AddSingleton<GitService>();
 builder.Services.AddSingleton<WorktreeManager>();
 builder.Services.AddSingleton<ClaudeArgsBuilder>();
 builder.Services.AddSingleton<TaskRunTokenRegistry>();
+builder.Services.AddSingleton<PendingQuestionRegistry>();
 builder.Services.AddSingleton<TaskRunner>();
 builder.Services.AddSingleton<WorktreeMaintenanceService>();
 builder.Services.AddSingleton<TaskResetService>();

src/ClaudeDo.Worker/Runner/ClaudeProcess.cs

@@ -39,6 +39,11 @@ public sealed class ClaudeProcess : IClaudeProcess
         foreach (var arg in arguments)
             psi.ArgumentList.Add(arg);
 
+        // Claude Code caps HTTP MCP tool calls at 60 s unless MCP_TOOL_TIMEOUT is raised.
+        // The in-task AskUser tool blocks up to 3 min waiting for the user, so lift the cap
+        // (with margin) or that wait would be killed early. Harmless for every other tool.
+        psi.Environment["MCP_TOOL_TIMEOUT"] = "200000";
+
         using var process = new Process { StartInfo = psi };
         process.Start();
 

src/ClaudeDo.Worker/Runner/PendingQuestionRegistry.cs

@@ -0,0 +1,51 @@
+using System.Collections.Concurrent;
+
+namespace ClaudeDo.Worker.Runner;
+
+public sealed record PendingQuestion(string TaskId, string QuestionId, string Question);
+
+// In-memory store of questions a running task has raised via the AskUser MCP tool and is
+// blocking on. One pending question per task (the run's process is blocked mid-tool-call,
+// so it cannot ask twice at once). Kept out of the DB on purpose: a question that outlives
+// a Worker restart is already dead (StaleTaskRecovery flips the run to Failed). Singleton.
+public sealed class PendingQuestionRegistry
+{
+    private readonly ConcurrentDictionary<string, Entry> _byTask = new();
+
+    private sealed record Entry(string QuestionId, string Question, TaskCompletionSource<string> Answer);
+
+    // Registers a question for the task and returns its id plus the awaitable answer.
+    // A second register for the same task replaces any stale entry.
+    public (string QuestionId, Task<string> Answer) Register(string taskId, string question)
+    {
+        var questionId = Guid.NewGuid().ToString("N");
+        var tcs = new TaskCompletionSource<string>(TaskCreationOptions.RunContinuationsAsynchronously);
+        _byTask[taskId] = new Entry(questionId, question, tcs);
+        return (questionId, tcs.Task);
+    }
+
+    // Delivers the answer to a waiting question. Returns false if no matching question is
+    // pending (already answered, timed out, or stale id).
+    public bool TryAnswer(string taskId, string questionId, string answer)
+    {
+        if (_byTask.TryGetValue(taskId, out var entry)
+            && entry.QuestionId == questionId
+            && _byTask.TryRemove(taskId, out _))
+        {
+            return entry.Answer.TrySetResult(answer ?? string.Empty);
+        }
+        return false;
+    }
+
+    public PendingQuestion? Get(string taskId) =>
+        _byTask.TryGetValue(taskId, out var entry)
+            ? new PendingQuestion(taskId, entry.QuestionId, entry.Question)
+            : null;
+
+    // Drops a pending question without delivering an answer (timeout/cancel cleanup).
+    public void Remove(string taskId, string questionId)
+    {
+        if (_byTask.TryGetValue(taskId, out var entry) && entry.QuestionId == questionId)
+            _byTask.TryRemove(taskId, out _);
+    }
+}

src/ClaudeDo.Worker/Runner/TaskRunMcpService.cs

@@ -13,12 +13,28 @@ public sealed class TaskRunMcpService
     private readonly TaskRepository _tasks;
     private readonly TaskRunMcpContextAccessor _ctx;
     private readonly HubBroadcaster _broadcaster;
+    private readonly PendingQuestionRegistry _pending;
 
-    public TaskRunMcpService(TaskRepository tasks, TaskRunMcpContextAccessor ctx, HubBroadcaster broadcaster)
+    // How long a running task blocks waiting for the user to answer an AskUser question
+    // before it gives up and proceeds autonomously. NOTE: the spawned claude process must
+    // run with MCP_TOOL_TIMEOUT raised above this (ClaudeProcess sets it) — Claude Code
+    // otherwise caps HTTP MCP tool calls at 60 s and would kill the call early.
+    internal static readonly TimeSpan QuestionWindow = TimeSpan.FromMinutes(3);
+
+    internal const string TimeoutFallback =
+        "No response received within 3 minutes — proceed using your best judgment, "
+        + "note the assumption you made, and continue.";
+
+    public TaskRunMcpService(
+        TaskRepository tasks,
+        TaskRunMcpContextAccessor ctx,
+        HubBroadcaster broadcaster,
+        PendingQuestionRegistry pending)
     {
         _tasks = tasks;
         _ctx = ctx;
         _broadcaster = broadcaster;
+        _pending = pending;
     }
 
     [McpServerTool, Description(
@@ -47,4 +63,57 @@ public sealed class TaskRunMcpService
         await _broadcaster.TaskUpdated(callerId);
         return new SuggestedImprovementDto(child.Id);
     }
+
+    [McpServerTool, Description(
+        "Ask the user a question and wait up to 3 minutes for their answer. Use this ONLY "
+        + "when you genuinely need a human decision to proceed correctly and a wrong guess "
+        + "would be costly or hard to undo (an irreversible action, contradictory "
+        + "requirements, or a real fork where both options have meaningful consequences). "
+        + "Do NOT use it for routine choices you can reasonably make yourself — for those, "
+        + "pick the most sensible option and continue. The returned string is the user's "
+        + "answer; if no one responds in time it tells you to proceed on your own judgment.")]
+    public Task<string> AskUser(string question, CancellationToken cancellationToken)
+    {
+        var callerId = _ctx.Current.CallerTaskId;
+        return AwaitAnswerAsync(
+            _pending, callerId, question ?? string.Empty,
+            (questionId, q) => _broadcaster.TaskQuestionAsked(callerId, questionId, q),
+            questionId => _broadcaster.TaskQuestionResolved(callerId, questionId),
+            QuestionWindow, cancellationToken);
+    }
+
+    // Registers the question, signals it, and blocks until the user answers, the window
+    // elapses (returns the fallback), or the run is cancelled (rethrows). Pure except for
+    // the two broadcast callbacks, so it is unit-testable without a real hub or DbContext.
+    internal static async Task<string> AwaitAnswerAsync(
+        PendingQuestionRegistry pending,
+        string taskId,
+        string question,
+        Func<string, string, Task> onAsked,
+        Func<string, Task> onResolved,
+        TimeSpan timeout,
+        CancellationToken ct)
+    {
+        var (questionId, answer) = pending.Register(taskId, question);
+        await onAsked(questionId, question);
+        try
+        {
+            using var timeoutCts = CancellationTokenSource.CreateLinkedTokenSource(ct);
+            timeoutCts.CancelAfter(timeout);
+            try
+            {
+                return await answer.WaitAsync(timeoutCts.Token);
+            }
+            catch (OperationCanceledException) when (!ct.IsCancellationRequested)
+            {
+                // The window elapsed (not a run cancellation) — let the agent carry on.
+                return TimeoutFallback;
+            }
+        }
+        finally
+        {
+            pending.Remove(taskId, questionId);
+            await onResolved(questionId);
+        }
+    }
 }

src/ClaudeDo.Worker/Runner/TaskRunner.cs

@@ -90,21 +90,23 @@ public sealed class TaskRunner
 
             var resolvedConfig = await ResolveConfigAsync(task, listConfig, null, ct);
 
-            // Improvement-eligible runs get a per-run MCP identity so the agent can file
-            // out-of-scope follow-ups via SuggestImprovement. Children and planning runs do not.
-            if (task.ParentTaskId is null && task.PlanningPhase == PlanningPhase.None)
+            // Every run gets a per-run MCP identity so the agent can ask the user a
+            // mid-run question via AskUser. Improvement-eligible (standalone top-level)
+            // runs additionally get SuggestImprovement for filing out-of-scope follow-ups.
+            mcpToken = TaskRunTokenRegistry.GenerateToken();
+            _tokens.Register(mcpToken, task.Id);
+            Directory.CreateDirectory(_cfg.LogRoot);
+            mcpConfigPath = Path.Combine(_cfg.LogRoot, $"{task.Id}_mcp.json");
+            await File.WriteAllTextAsync(mcpConfigPath, BuildRunMcpConfigJson(mcpToken), ct);
+
+            var improvementEligible = task.ParentTaskId is null && task.PlanningPhase == PlanningPhase.None;
+            resolvedConfig = resolvedConfig with
             {
-                mcpToken = TaskRunTokenRegistry.GenerateToken();
-                _tokens.Register(mcpToken, task.Id);
-                Directory.CreateDirectory(_cfg.LogRoot);
-                mcpConfigPath = Path.Combine(_cfg.LogRoot, $"{task.Id}_mcp.json");
-                await File.WriteAllTextAsync(mcpConfigPath, BuildRunMcpConfigJson(mcpToken), ct);
-                resolvedConfig = resolvedConfig with
-                {
-                    McpConfigPath = mcpConfigPath,
-                    AllowedTools = "mcp__claudedo_run__SuggestImprovement",
-                };
-            }
+                McpConfigPath = mcpConfigPath,
+                AllowedTools = improvementEligible
+                    ? "mcp__claudedo_run__AskUser,mcp__claudedo_run__SuggestImprovement"
+                    : "mcp__claudedo_run__AskUser",
+            };
 
             var now = DateTime.UtcNow;
             // The queue picker claims Queued→Running atomically (incl. StartedAt) before