Add autopilot panel and retry system

9 files changed, 607 insertions, 95 deletions

diff --git a/makima/frontend/src/components/contracts/AutopilotPanel.tsx b/makima/frontend/src/components/contracts/AutopilotPanel.tsx
new file mode 100644
index 0000000..a8a8e2e
--- /dev/null
+++ b/makima/frontend/src/components/contracts/AutopilotPanel.tsx
@@ -0,0 +1,208 @@
+import { useState, useCallback } from "react";
+import type { ContractWithRelations } from "../../lib/api";
+import {
+  getSupervisorStatus,
+  startSupervisor,
+  stopSupervisor,
+  resumeSupervisor,
+  type SupervisorStatus,
+} from "../../lib/api";
+
+interface AutopilotPanelProps {
+  contract: ContractWithRelations;
+  onUpdate: () => void;
+}
+
+const statusConfig: Record<
+  SupervisorStatus["status"],
+  { label: string; color: string; bgColor: string }
+> = {
+  not_configured: {
+    label: "Not Configured",
+    color: "text-[#555]",
+    bgColor: "bg-[#555]/10",
+  },
+  pending: {
+    label: "Ready",
+    color: "text-yellow-400",
+    bgColor: "bg-yellow-400/10",
+  },
+  starting: {
+    label: "Starting...",
+    color: "text-blue-400",
+    bgColor: "bg-blue-400/10",
+  },
+  running: {
+    label: "Running",
+    color: "text-green-400",
+    bgColor: "bg-green-400/10",
+  },
+  paused: {
+    label: "Paused",
+    color: "text-orange-400",
+    bgColor: "bg-orange-400/10",
+  },
+  done: {
+    label: "Completed",
+    color: "text-blue-400",
+    bgColor: "bg-blue-400/10",
+  },
+  failed: {
+    label: "Failed",
+    color: "text-red-400",
+    bgColor: "bg-red-400/10",
+  },
+};
+
+export function AutopilotPanel({ contract, onUpdate }: AutopilotPanelProps) {
+  const [loading, setLoading] = useState(false);
+  const [error, setError] = useState<string | null>(null);
+
+  const supervisorStatus = getSupervisorStatus(contract);
+  const config = statusConfig[supervisorStatus.status];
+
+  const handleStart = useCallback(async () => {
+    if (!supervisorStatus.supervisorTaskId) return;
+
+    setLoading(true);
+    setError(null);
+
+    try {
+      await startSupervisor(supervisorStatus.supervisorTaskId);
+      onUpdate();
+    } catch (e) {
+      setError(e instanceof Error ? e.message : "Failed to start autopilot");
+    } finally {
+      setLoading(false);
+    }
+  }, [supervisorStatus.supervisorTaskId, onUpdate]);
+
+  const handleStop = useCallback(async () => {
+    if (!supervisorStatus.supervisorTaskId) return;
+
+    setLoading(true);
+    setError(null);
+
+    try {
+      await stopSupervisor(supervisorStatus.supervisorTaskId);
+      onUpdate();
+    } catch (e) {
+      setError(e instanceof Error ? e.message : "Failed to stop autopilot");
+    } finally {
+      setLoading(false);
+    }
+  }, [supervisorStatus.supervisorTaskId, onUpdate]);
+
+  const handleResume = useCallback(async () => {
+    setLoading(true);
+    setError(null);
+
+    try {
+      await resumeSupervisor(contract.id, { resumeMode: "continue" });
+      // After resuming, we need to start the task
+      if (supervisorStatus.supervisorTaskId) {
+        await startSupervisor(supervisorStatus.supervisorTaskId);
+      }
+      onUpdate();
+    } catch (e) {
+      setError(e instanceof Error ? e.message : "Failed to resume autopilot");
+    } finally {
+      setLoading(false);
+    }
+  }, [contract.id, supervisorStatus.supervisorTaskId, onUpdate]);
+
+  // Don't show panel for task-type contracts (they don't have supervisors)
+  if (contract.contractType === "task") {
+    return null;
+  }
+
+  return (
+    <div className="space-y-3">
+      <div className="flex items-center justify-between">
+        <h3 className="font-mono text-xs text-[#75aafc] uppercase">
+          Autopilot Mode
+        </h3>
+        <div
+          className={`px-2 py-1 rounded font-mono text-xs ${config.color} ${config.bgColor}`}
+        >
+          {config.label}
+        </div>
+      </div>
+
+      <p className="font-mono text-xs text-[#555]">
+        {supervisorStatus.status === "not_configured" ? (
+          "This contract does not have an autopilot supervisor configured."
+        ) : supervisorStatus.status === "running" ? (
+          "Autopilot is actively working on this contract, spawning tasks and managing progress."
+        ) : supervisorStatus.status === "pending" ? (
+          "Autopilot is ready to start. Click 'Enable' to begin autonomous work."
+        ) : supervisorStatus.status === "paused" ? (
+          "Autopilot is paused. Click 'Resume' to continue work."
+        ) : supervisorStatus.status === "failed" ? (
+          "Autopilot encountered an error. You can resume to retry."
+        ) : supervisorStatus.status === "done" ? (
+          "Autopilot has completed its work on this contract."
+        ) : (
+          "Autopilot is initializing..."
+        )}
+      </p>
+
+      {error && (
+        <div className="px-3 py-2 bg-red-500/10 border border-red-400/30 font-mono text-xs text-red-400">
+          {error}
+        </div>
+      )}
+
+      <div className="flex gap-2">
+        {supervisorStatus.canStart && (
+          <button
+            onClick={handleStart}
+            disabled={loading}
+            className="px-4 py-2 font-mono text-xs text-[#dbe7ff] bg-green-600/20 border border-green-400/50 hover:bg-green-600/30 transition-colors disabled:opacity-50 disabled:cursor-not-allowed"
+          >
+            {loading ? "Starting..." : "Enable Autopilot"}
+          </button>
+        )}
+
+        {supervisorStatus.canResume && (
+          <button
+            onClick={handleResume}
+            disabled={loading}
+            className="px-4 py-2 font-mono text-xs text-[#dbe7ff] bg-blue-600/20 border border-blue-400/50 hover:bg-blue-600/30 transition-colors disabled:opacity-50 disabled:cursor-not-allowed"
+          >
+            {loading ? "Resuming..." : "Resume Autopilot"}
+          </button>
+        )}
+
+        {supervisorStatus.canStop && (
+          <button
+            onClick={handleStop}
+            disabled={loading}
+            className="px-4 py-2 font-mono text-xs text-[#dbe7ff] bg-orange-600/20 border border-orange-400/50 hover:bg-orange-600/30 transition-colors disabled:opacity-50 disabled:cursor-not-allowed"
+          >
+            {loading ? "Stopping..." : "Pause Autopilot"}
+          </button>
+        )}
+      </div>
+
+      {/* Show running indicator when active */}
+      {supervisorStatus.status === "running" && (
+        <div className="flex items-center gap-2 pt-2 border-t border-dashed border-[rgba(117,170,252,0.2)]">
+          <div className="w-2 h-2 rounded-full bg-green-400 animate-pulse" />
+          <span className="font-mono text-xs text-green-400">
+            Autopilot is actively working
+          </span>
+        </div>
+      )}
+
+      {supervisorStatus.status === "starting" && (
+        <div className="flex items-center gap-2 pt-2 border-t border-dashed border-[rgba(117,170,252,0.2)]">
+          <div className="w-2 h-2 rounded-full bg-blue-400 animate-pulse" />
+          <span className="font-mono text-xs text-blue-400">
+            Initializing autopilot...
+          </span>
+        </div>
+      )}
+    </div>
+  );
+}
diff --git a/makima/frontend/src/components/contracts/ContractDetail.tsx b/makima/frontend/src/components/contracts/ContractDetail.tsx
index cf5f8f2..f93097a 100644
--- a/makima/frontend/src/components/contracts/ContractDetail.tsx
+++ b/makima/frontend/src/components/contracts/ContractDetail.tsx
@@ -18,6 +18,7 @@ import { PhaseHint } from "./PhaseHint";
 import { RepositoryPanel } from "./RepositoryPanel";
 import { ContractCliInput } from "./ContractCliInput";
 import { PhaseDeliverablesPanel } from "./PhaseDeliverablesPanel";
+import { AutopilotPanel } from "./AutopilotPanel";
 import { TaskTree } from "../mesh/TaskTree";
 
 type Tab = "overview" | "repos" | "files" | "tasks";
@@ -225,6 +226,7 @@ export function ContractDetail({
             onStatusChange={onStatusChange}
             onPhaseChange={onPhaseChange}
             onCreateFile={onCreateFileFromTemplate}
+            onRefresh={onRefresh}
           />
         )}
 
@@ -276,14 +278,19 @@ function OverviewTab({
   onStatusChange,
   onPhaseChange,
   onCreateFile,
+  onRefresh,
 }: {
   contract: ContractWithRelations;
   onStatusChange: (status: ContractStatus) => void;
   onPhaseChange: (phase: ContractPhase) => void;
   onCreateFile?: (templateId: string, suggestedName: string) => void;
+  onRefresh: () => void;
 }) {
   return (
     <div className="space-y-6">
+      {/* Autopilot controls */}
+      <AutopilotPanel contract={contract} onUpdate={onRefresh} />
+
       {/* Phase deliverables checklist */}
       <PhaseDeliverablesPanel
         contract={contract}
diff --git a/makima/frontend/src/lib/api.ts b/makima/frontend/src/lib/api.ts
index 9c56f6b..ee04935 100644
--- a/makima/frontend/src/lib/api.ts
+++ b/makima/frontend/src/lib/api.ts
@@ -2492,3 +2492,117 @@ export async function resumeFromCheckpoint(
   }
   return res.json();
 }
+
+// =============================================================================
+// Supervisor/Autopilot Control Functions
+// =============================================================================
+
+/**
+ * Start a contract's supervisor task (enable autopilot mode).
+ * This is a convenience wrapper around startTask.
+ */
+export async function startSupervisor(supervisorTaskId: string): Promise<Task> {
+  return startTask(supervisorTaskId);
+}
+
+/**
+ * Stop a contract's supervisor task (pause autopilot mode).
+ * This is a convenience wrapper around stopTask.
+ */
+export async function stopSupervisor(supervisorTaskId: string): Promise<Task> {
+  return stopTask(supervisorTaskId);
+}
+
+/** Status of the supervisor/autopilot for a contract */
+export interface SupervisorStatus {
+  supervisorTaskId: string | null;
+  status: "not_configured" | "pending" | "starting" | "running" | "paused" | "done" | "failed";
+  daemonId: string | null;
+  canStart: boolean;
+  canStop: boolean;
+  canResume: boolean;
+}
+
+/**
+ * Get the supervisor status for a contract.
+ */
+export function getSupervisorStatus(
+  contract: ContractWithRelations
+): SupervisorStatus {
+  const supervisorTaskId = contract.supervisorTaskId;
+
+  if (!supervisorTaskId) {
+    return {
+      supervisorTaskId: null,
+      status: "not_configured",
+      daemonId: null,
+      canStart: false,
+      canStop: false,
+      canResume: false,
+    };
+  }
+
+  // Find the supervisor task in the contract's tasks
+  const supervisorTask = contract.tasks.find(
+    (t) => t.id === supervisorTaskId && t.isSupervisor
+  );
+
+  if (!supervisorTask) {
+    return {
+      supervisorTaskId,
+      status: "pending",
+      daemonId: null,
+      canStart: true,
+      canStop: false,
+      canResume: false,
+    };
+  }
+
+  // Map task status to supervisor status
+  let status: SupervisorStatus["status"];
+  let canStart = false;
+  let canStop = false;
+  let canResume = false;
+
+  switch (supervisorTask.status) {
+    case "pending":
+      status = "pending";
+      canStart = true;
+      break;
+    case "initializing":
+    case "starting":
+      status = "starting";
+      canStop = true;
+      break;
+    case "running":
+      status = "running";
+      canStop = true;
+      break;
+    case "paused":
+    case "blocked":
+      status = "paused";
+      canResume = true;
+      canStop = true;
+      break;
+    case "done":
+    case "merged":
+      status = "done";
+      break;
+    case "failed":
+      status = "failed";
+      canResume = true;
+      break;
+    default:
+      status = "pending";
+      canStart = true;
+  }
+
+  return {
+    supervisorTaskId,
+    status,
+    daemonId: null, // Task summary doesn't have daemon_id, would need full task
+    canStart,
+    canStop,
+    canResume,
+  };
+}
diff --git a/makima/frontend/tsconfig.tsbuildinfo b/makima/frontend/tsconfig.tsbuildinfo
index 33deafa..a3ef773 100644
--- a/makima/frontend/tsconfig.tsbuildinfo
+++ b/makima/frontend/tsconfig.tsbuildinfo
@@ -1 +1 @@
-{"root":["./src/main.tsx","./src/vite-env.d.ts","./src/components/gridoverlay.tsx","./src/components/japanesehovertext.tsx","./src/components/logo.tsx","./src/components/masthead.tsx","./src/components/navstrip.tsx","./src/components/protectedroute.tsx","./src/components/rewritelink.tsx","./src/components/simplemarkdown.tsx","./src/components/supervisorquestionnotification.tsx","./src/components/charts/chartrenderer.tsx","./src/components/contracts/contractcliinput.tsx","./src/components/contracts/contractdetail.tsx","./src/components/contracts/contractlist.tsx","./src/components/contracts/phasebadge.tsx","./src/components/contracts/phasedeliverablespanel.tsx","./src/components/contracts/phasehint.tsx","./src/components/contracts/phaseprogressbar.tsx","./src/components/contracts/quickactionbuttons.tsx","./src/components/contracts/repositorypanel.tsx","./src/components/contracts/taskderivationpreview.tsx","./src/components/files/bodyrenderer.tsx","./src/components/files/cliinput.tsx","./src/components/files/conflictnotification.tsx","./src/components/files/elementcontextmenu.tsx","./src/components/files/filedetail.tsx","./src/components/files/filelist.tsx","./src/components/files/reposyncindicator.tsx","./src/components/files/updatenotification.tsx","./src/components/files/versionhistorydropdown.tsx","./src/components/history/checkpointcard.tsx","./src/components/history/checkpointlist.tsx","./src/components/history/conversationmessage.tsx","./src/components/history/conversationview.tsx","./src/components/history/historyfilters.tsx","./src/components/history/resumecontrols.tsx","./src/components/history/timelineeventcard.tsx","./src/components/history/timelinelist.tsx","./src/components/history/index.ts","./src/components/listen/contractpickermodal.tsx","./src/components/listen/controlpanel.tsx","./src/components/listen/speakerpanel.tsx","./src/components/listen/transcriptanalysispanel.tsx","./src/components/listen/transcriptpanel.tsx","./src/components/mesh/directoryinput.tsx","./src/components/mesh/inlinesubtaskeditor.tsx","./src/components/mesh/mergeconflictresolver.tsx","./src/components/mesh/overlaydiffviewer.tsx","./src/components/mesh/prpreview.tsx","./src/components/mesh/subtasktree.tsx","./src/components/mesh/taskdetail.tsx","./src/components/mesh/tasklist.tsx","./src/components/mesh/taskoutput.tsx","./src/components/mesh/tasktree.tsx","./src/components/mesh/unifiedmeshchatinput.tsx","./src/components/workflow/phasecolumn.tsx","./src/components/workflow/workflowboard.tsx","./src/components/workflow/workflowcontractcard.tsx","./src/contexts/authcontext.tsx","./src/contexts/supervisorquestionscontext.tsx","./src/hooks/usecontracts.ts","./src/hooks/usefilesubscription.ts","./src/hooks/usefiles.ts","./src/hooks/usemeshchathistory.ts","./src/hooks/usemicrophone.ts","./src/hooks/usetasksubscription.ts","./src/hooks/usetasks.ts","./src/hooks/usetextscramble.ts","./src/hooks/useversionhistory.ts","./src/hooks/usewebsocket.ts","./src/lib/api.ts","./src/lib/listenapi.ts","./src/lib/markdown.ts","./src/lib/supabase.ts","./src/routes/_index.tsx","./src/routes/contracts.tsx","./src/routes/files.tsx","./src/routes/history.tsx","./src/routes/listen.tsx","./src/routes/login.tsx","./src/routes/mesh.tsx","./src/routes/settings.tsx","./src/routes/workflow.tsx","./src/types/messages.ts"],"version":"5.9.3"}
\ No newline at end of file
+{"root":["./src/main.tsx","./src/vite-env.d.ts","./src/components/gridoverlay.tsx","./src/components/japanesehovertext.tsx","./src/components/logo.tsx","./src/components/masthead.tsx","./src/components/navstrip.tsx","./src/components/protectedroute.tsx","./src/components/rewritelink.tsx","./src/components/simplemarkdown.tsx","./src/components/supervisorquestionnotification.tsx","./src/components/charts/chartrenderer.tsx","./src/components/contracts/autopilotpanel.tsx","./src/components/contracts/contractcliinput.tsx","./src/components/contracts/contractdetail.tsx","./src/components/contracts/contractlist.tsx","./src/components/contracts/phasebadge.tsx","./src/components/contracts/phasedeliverablespanel.tsx","./src/components/contracts/phasehint.tsx","./src/components/contracts/phaseprogressbar.tsx","./src/components/contracts/quickactionbuttons.tsx","./src/components/contracts/repositorypanel.tsx","./src/components/contracts/taskderivationpreview.tsx","./src/components/files/bodyrenderer.tsx","./src/components/files/cliinput.tsx","./src/components/files/conflictnotification.tsx","./src/components/files/elementcontextmenu.tsx","./src/components/files/filedetail.tsx","./src/components/files/filelist.tsx","./src/components/files/reposyncindicator.tsx","./src/components/files/updatenotification.tsx","./src/components/files/versionhistorydropdown.tsx","./src/components/history/checkpointcard.tsx","./src/components/history/checkpointlist.tsx","./src/components/history/conversationmessage.tsx","./src/components/history/conversationview.tsx","./src/components/history/historyfilters.tsx","./src/components/history/resumecontrols.tsx","./src/components/history/timelineeventcard.tsx","./src/components/history/timelinelist.tsx","./src/components/history/index.ts","./src/components/listen/contractpickermodal.tsx","./src/components/listen/controlpanel.tsx","./src/components/listen/speakerpanel.tsx","./src/components/listen/transcriptanalysispanel.tsx","./src/components/listen/transcriptpanel.tsx","./src/components/mesh/directoryinput.tsx","./src/components/mesh/inlinesubtaskeditor.tsx","./src/components/mesh/mergeconflictresolver.tsx","./src/components/mesh/overlaydiffviewer.tsx","./src/components/mesh/prpreview.tsx","./src/components/mesh/subtasktree.tsx","./src/components/mesh/taskdetail.tsx","./src/components/mesh/tasklist.tsx","./src/components/mesh/taskoutput.tsx","./src/components/mesh/tasktree.tsx","./src/components/mesh/unifiedmeshchatinput.tsx","./src/components/workflow/phasecolumn.tsx","./src/components/workflow/workflowboard.tsx","./src/components/workflow/workflowcontractcard.tsx","./src/contexts/authcontext.tsx","./src/contexts/supervisorquestionscontext.tsx","./src/hooks/usecontracts.ts","./src/hooks/usefilesubscription.ts","./src/hooks/usefiles.ts","./src/hooks/usemeshchathistory.ts","./src/hooks/usemicrophone.ts","./src/hooks/usetasksubscription.ts","./src/hooks/usetasks.ts","./src/hooks/usetextscramble.ts","./src/hooks/useversionhistory.ts","./src/hooks/usewebsocket.ts","./src/lib/api.ts","./src/lib/listenapi.ts","./src/lib/markdown.ts","./src/lib/supabase.ts","./src/routes/_index.tsx","./src/routes/contracts.tsx","./src/routes/files.tsx","./src/routes/history.tsx","./src/routes/listen.tsx","./src/routes/login.tsx","./src/routes/mesh.tsx","./src/routes/settings.tsx","./src/routes/workflow.tsx","./src/types/messages.ts"],"version":"5.9.3"}
\ No newline at end of file
diff --git a/makima/migrations/20250119000000_add_task_retry_tracking.sql b/makima/migrations/20250119000000_add_task_retry_tracking.sql
new file mode 100644
index 0000000..4d8eea6
--- /dev/null
+++ b/makima/migrations/20250119000000_add_task_retry_tracking.sql
@@ -0,0 +1,22 @@
+-- Add retry tracking columns to tasks table for daemon failover
+
+-- Number of times this task has been retried after daemon failure
+ALTER TABLE tasks ADD COLUMN IF NOT EXISTS retry_count INTEGER NOT NULL DEFAULT 0;
+
+-- Maximum retry attempts before marking as permanently failed
+ALTER TABLE tasks ADD COLUMN IF NOT EXISTS max_retries INTEGER NOT NULL DEFAULT 3;
+
+-- Array of daemon IDs that have failed this task (excluded from retry selection)
+ALTER TABLE tasks ADD COLUMN IF NOT EXISTS failed_daemon_ids UUID[] DEFAULT '{}';
+
+-- When the task was last interrupted due to daemon disconnect
+ALTER TABLE tasks ADD COLUMN IF NOT EXISTS interrupted_at TIMESTAMPTZ;
+
+-- Index for efficient pending task queries with retry consideration
+CREATE INDEX IF NOT EXISTS idx_tasks_status_retry ON tasks(status, retry_count)
+  WHERE status = 'pending';
+
+COMMENT ON COLUMN tasks.retry_count IS 'Number of times this task has been retried after daemon failure';
+COMMENT ON COLUMN tasks.max_retries IS 'Maximum retry attempts before marking as permanently failed';
+COMMENT ON COLUMN tasks.failed_daemon_ids IS 'Array of daemon IDs that have failed this task (excluded from retry)';
+COMMENT ON COLUMN tasks.interrupted_at IS 'When the task was last interrupted due to daemon disconnect';
diff --git a/makima/src/db/models.rs b/makima/src/db/models.rs
index 0e1303c..72ba6f2 100644
--- a/makima/src/db/models.rs
+++ b/makima/src/db/models.rs
@@ -6,6 +6,11 @@ use sqlx::FromRow;
 use utoipa::ToSchema;
 use uuid::Uuid;
 
+/// Default max retries for task daemon failover (3 attempts)
+fn default_max_retries() -> i32 {
+    3
+}
+
 /// Flexible datetime deserialization module.
 /// Accepts both date-only ("2026-01-15") and full ISO 8601 datetime ("2026-01-15T00:00:00Z") formats.
 pub mod flexible_datetime {
@@ -500,6 +505,20 @@ pub struct Task {
     /// Files to copy from parent task's worktree when starting.
     #[serde(skip_serializing_if = "Option::is_none")]
     pub copy_files: Option<serde_json::Value>,
+
+    // Retry tracking for daemon failover
+    /// Number of times this task has been retried after daemon failure
+    #[serde(default)]
+    pub retry_count: i32,
+    /// Maximum retry attempts before marking as permanently failed
+    #[serde(default = "default_max_retries")]
+    pub max_retries: i32,
+    /// Array of daemon IDs that have failed this task (excluded from retry)
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub failed_daemon_ids: Option<Vec<Uuid>>,
+    /// When the task was last interrupted due to daemon disconnect
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub interrupted_at: Option<DateTime<Utc>>,
 }
 
 impl Task {
diff --git a/makima/src/db/repository.rs b/makima/src/db/repository.rs
index 2b069d5..43b8e3a 100644
--- a/makima/src/db/repository.rs
+++ b/makima/src/db/repository.rs
@@ -790,6 +790,8 @@ pub async fn list_tasks_by_contract(
 }
 
 /// Get pending tasks for a contract (non-supervisor tasks only).
+/// Includes tasks that were interrupted (retry candidates).
+/// Prioritizes interrupted tasks and excludes those that exceeded max_retries.
 pub async fn get_pending_tasks_for_contract(
     pool: &PgPool,
     contract_id: Uuid,
@@ -801,7 +803,11 @@ pub async fn get_pending_tasks_for_contract(
         WHERE contract_id = $1 AND owner_id = $2
           AND status = 'pending'
           AND is_supervisor = false
-        ORDER BY priority DESC, created_at ASC
+          AND retry_count < max_retries
+        ORDER BY
+          interrupted_at DESC NULLS LAST,
+          priority DESC,
+          created_at ASC
         "#,
     )
     .bind(contract_id)
@@ -810,6 +816,61 @@ pub async fn get_pending_tasks_for_contract(
     .await
 }
 
+/// Mark a task as pending for retry after daemon failure.
+/// Increments retry count and adds the failed daemon to exclusion list.
+pub async fn mark_task_for_retry(
+    pool: &PgPool,
+    task_id: Uuid,
+    failed_daemon_id: Uuid,
+) -> Result<Option<Task>, sqlx::Error> {
+    sqlx::query_as::<_, Task>(
+        r#"
+        UPDATE tasks
+        SET status = 'pending',
+            daemon_id = NULL,
+            retry_count = retry_count + 1,
+            failed_daemon_ids = array_append(COALESCE(failed_daemon_ids, '{}'), $2),
+            last_active_daemon_id = $2,
+            interrupted_at = NOW(),
+            error_message = 'Daemon disconnected, awaiting retry',
+            updated_at = NOW()
+        WHERE id = $1
+          AND retry_count < max_retries
+        RETURNING *
+        "#,
+    )
+    .bind(task_id)
+    .bind(failed_daemon_id)
+    .fetch_optional(pool)
+    .await
+}
+
+/// Mark a task as permanently failed (exceeded retry limit).
+pub async fn mark_task_permanently_failed(
+    pool: &PgPool,
+    task_id: Uuid,
+    failed_daemon_id: Uuid,
+) -> Result<(), sqlx::Error> {
+    sqlx::query(
+        r#"
+        UPDATE tasks
+        SET status = 'failed',
+            daemon_id = NULL,
+            retry_count = retry_count + 1,
+            failed_daemon_ids = array_append(COALESCE(failed_daemon_ids, '{}'), $2),
+            last_active_daemon_id = $2,
+            error_message = 'Task failed: exceeded maximum retry attempts',
+            updated_at = NOW()
+        WHERE id = $1
+        "#,
+    )
+    .bind(task_id)
+    .bind(failed_daemon_id)
+    .execute(pool)
+    .await?;
+    Ok(())
+}
+
 /// Update a task by ID with optimistic locking.
 pub async fn update_task(
     pool: &PgPool,
@@ -3008,6 +3069,35 @@ pub async fn get_available_daemons(
     .await
 }
 
+/// Get daemons with capacity info for selection, excluding specified daemon IDs.
+/// Used for task retry to avoid reassigning to daemons that have already failed.
+pub async fn get_available_daemons_excluding(
+    pool: &PgPool,
+    owner_id: Uuid,
+    exclude_daemon_ids: &[Uuid],
+) -> Result<Vec<DaemonWithCapacity>, sqlx::Error> {
+    sqlx::query_as::<_, DaemonWithCapacity>(
+        r#"
+        SELECT id, owner_id, connection_id, hostname, machine_id,
+               max_concurrent_tasks, current_task_count,
+               capacity_score, task_queue_length, supports_migration,
+               status, last_heartbeat_at, connected_at
+        FROM daemons
+        WHERE owner_id = $1
+          AND status = 'connected'
+          AND id != ALL($2)
+        ORDER BY
+            COALESCE(capacity_score, 100) DESC,
+            (max_concurrent_tasks - current_task_count) DESC,
+            COALESCE(task_queue_length, 0) ASC
+        "#,
+    )
+    .bind(owner_id)
+    .bind(exclude_daemon_ids)
+    .fetch_all(pool)
+    .await
+}
+
 /// Create a daemon task assignment.
 pub async fn create_daemon_task_assignment(
     pool: &PgPool,
diff --git a/makima/src/server/handlers/mesh_daemon.rs b/makima/src/server/handlers/mesh_daemon.rs
index 4bcb5cd..beb676e 100644
--- a/makima/src/server/handlers/mesh_daemon.rs
+++ b/makima/src/server/handlers/mesh_daemon.rs
@@ -20,6 +20,7 @@ use sqlx::Row;
 use tokio::sync::mpsc;
 use uuid::Uuid;
 
+use crate::db::models::Task;
 use crate::db::repository;
 use crate::server::auth::{hash_api_key, API_KEY_HEADER};
 use crate::server::messages::ApiError;
@@ -1334,42 +1335,86 @@ async fn handle_daemon_connection(socket: WebSocket, state: SharedState, auth_re
                 );
             }
 
-            // Find tasks assigned to this daemon that are still active
-            if let Err(e) = clear_daemon_from_tasks(&pool, daemon_uuid).await {
+            // Find tasks assigned to this daemon and mark for retry or fail permanently
+            if let Err(e) = handle_daemon_disconnect_tasks(&pool, daemon_uuid).await {
                 tracing::error!(
                     daemon_id = %daemon_uuid,
                     error = %e,
-                    "Failed to clear daemon from tasks on disconnect"
+                    "Failed to handle daemon disconnect for tasks"
                 );
             }
         });
     }
 }
 
-/// Clear daemon_id from tasks when daemon disconnects
-async fn clear_daemon_from_tasks(pool: &sqlx::PgPool, daemon_id: Uuid) -> Result<(), sqlx::Error> {
-    // Update tasks that were running on this daemon to failed state
-    let result = sqlx::query(
+/// Handle tasks when daemon disconnects - mark for retry or fail permanently.
+async fn handle_daemon_disconnect_tasks(pool: &sqlx::PgPool, daemon_id: Uuid) -> Result<(), sqlx::Error> {
+    // Get all active tasks on this daemon
+    let active_tasks: Vec<Task> = sqlx::query_as(
         r#"
-        UPDATE tasks
-        SET daemon_id = NULL,
-            status = 'failed',
-            error_message = 'Daemon disconnected',
-            updated_at = NOW()
+        SELECT * FROM tasks
         WHERE daemon_id = $1
           AND status IN ('starting', 'running', 'initializing')
         "#,
     )
     .bind(daemon_id)
-    .execute(pool)
+    .fetch_all(pool)
     .await?;
 
-    if result.rows_affected() > 0 {
-        tracing::warn!(
-            daemon_id = %daemon_id,
-            tasks_affected = result.rows_affected(),
-            "Marked tasks as failed due to daemon disconnect"
-        );
+    if active_tasks.is_empty() {
+        return Ok(());
+    }
+
+    tracing::info!(
+        daemon_id = %daemon_id,
+        task_count = active_tasks.len(),
+        "Processing tasks for disconnected daemon"
+    );
+
+    for task in active_tasks {
+        if task.retry_count < task.max_retries {
+            // Mark for retry
+            match repository::mark_task_for_retry(pool, task.id, daemon_id).await {
+                Ok(Some(updated_task)) => {
+                    tracing::info!(
+                        task_id = %task.id,
+                        task_name = %task.name,
+                        retry_count = updated_task.retry_count,
+                        max_retries = updated_task.max_retries,
+                        "Task marked for retry after daemon disconnect"
+                    );
+                }
+                Ok(None) => {
+                    tracing::warn!(
+                        task_id = %task.id,
+                        "Task not found or already at max retries"
+                    );
+                }
+                Err(e) => {
+                    tracing::error!(
+                        task_id = %task.id,
+                        error = %e,
+                        "Failed to mark task for retry"
+                    );
+                }
+            }
+        } else {
+            // Exceeded retries, mark as permanently failed
+            if let Err(e) = repository::mark_task_permanently_failed(pool, task.id, daemon_id).await {
+                tracing::error!(
+                    task_id = %task.id,
+                    error = %e,
+                    "Failed to mark task as permanently failed"
+                );
+            } else {
+                tracing::warn!(
+                    task_id = %task.id,
+                    task_name = %task.name,
+                    retry_count = task.retry_count + 1,
+                    "Task permanently failed: exceeded maximum retries"
+                );
+            }
+        }
     }
 
     Ok(())
diff --git a/makima/src/server/handlers/mesh_supervisor.rs b/makima/src/server/handlers/mesh_supervisor.rs
index 1014fdc..754d086 100644
--- a/makima/src/server/handlers/mesh_supervisor.rs
+++ b/makima/src/server/handlers/mesh_supervisor.rs
@@ -256,6 +256,7 @@ async fn verify_supervisor_auth(
 
 /// Try to start a pending task on an available daemon.
 /// Returns Ok(Some(task)) if a task was started, Ok(None) if no tasks could be started.
+/// For retried tasks, excludes daemons that previously failed the task.
 async fn try_start_pending_task(
     state: &SharedState,
     contract_id: Uuid,
@@ -263,7 +264,7 @@ async fn try_start_pending_task(
 ) -> Result<Option<Task>, String> {
     let pool = state.db_pool.as_ref().ok_or("Database not configured")?;
 
-    // Get pending tasks for this contract
+    // Get pending tasks for this contract (includes interrupted tasks awaiting retry)
     let pending_tasks = repository::get_pending_tasks_for_contract(pool, contract_id, owner_id)
         .await
         .map_err(|e| format!("Failed to get pending tasks: {}", e))?;
@@ -272,89 +273,95 @@ async fn try_start_pending_task(
         return Ok(None);
     }
 
-    // Get available daemons with capacity
-    let daemons = repository::get_available_daemons(pool, owner_id)
-        .await
-        .map_err(|e| format!("Failed to get available daemons: {}", e))?;
-
-    // Find a daemon with capacity
-    let available_daemon = daemons.iter().find(|d| {
-        d.current_task_count < d.max_concurrent_tasks
-            && state.daemon_connections.contains_key(&d.connection_id)
-    });
+    // Try each pending task until we find one we can start
+    for task in &pending_tasks {
+        // Get excluded daemon IDs for this task (daemons that have already failed it)
+        let exclude_ids: Vec<Uuid> = task.failed_daemon_ids.clone().unwrap_or_default();
 
-    let daemon = match available_daemon {
-        Some(d) => d,
-        None => return Ok(None), // No daemon with capacity
-    };
+        // Get available daemons excluding failed ones for this task
+        let daemons = repository::get_available_daemons_excluding(pool, owner_id, &exclude_ids)
+            .await
+            .map_err(|e| format!("Failed to get available daemons: {}", e))?;
 
-    // Try to start the first pending task
-    let task = &pending_tasks[0];
+        // Find a daemon with capacity
+        let available_daemon = daemons.iter().find(|d| {
+            d.current_task_count < d.max_concurrent_tasks
+                && state.daemon_connections.contains_key(&d.connection_id)
+        });
 
-    // Get repo URL from task or contract
-    let repo_url = if let Some(url) = &task.repository_url {
-        Some(url.clone())
-    } else {
-        match repository::list_contract_repositories(pool, contract_id).await {
-            Ok(repos) => repos
-                .iter()
-                .find(|r| r.is_primary)
-                .or(repos.first())
-                .and_then(|r| r.repository_url.clone().or_else(|| r.local_path.clone())),
-            Err(_) => None,
-        }
-    };
+        let daemon = match available_daemon {
+            Some(d) => d,
+            None => continue, // Try next task
+        };
 
-    // Update task with daemon assignment
-    let update_req = UpdateTaskRequest {
-        status: Some("starting".to_string()),
-        daemon_id: Some(daemon.id),
-        version: Some(task.version),
-        ..Default::default()
-    };
+        // Get repo URL from task or contract
+        let repo_url = if let Some(url) = &task.repository_url {
+            Some(url.clone())
+        } else {
+            match repository::list_contract_repositories(pool, contract_id).await {
+                Ok(repos) => repos
+                    .iter()
+                    .find(|r| r.is_primary)
+                    .or(repos.first())
+                    .and_then(|r| r.repository_url.clone().or_else(|| r.local_path.clone())),
+                Err(_) => None,
+            }
+        };
 
-    let updated_task = match repository::update_task_for_owner(pool, task.id, owner_id, update_req).await {
-        Ok(Some(t)) => t,
-        Ok(None) => return Ok(None),
-        Err(e) => {
-            tracing::warn!(task_id = %task.id, error = %e, "Failed to update task for daemon assignment");
-            return Ok(None);
-        }
-    };
+        // Update task with daemon assignment
+        let update_req = UpdateTaskRequest {
+            status: Some("starting".to_string()),
+            daemon_id: Some(daemon.id),
+            version: Some(task.version),
+            ..Default::default()
+        };
 
-    // Send spawn command
-    let cmd = DaemonCommand::SpawnTask {
-        task_id: updated_task.id,
-        task_name: updated_task.name.clone(),
-        plan: updated_task.plan.clone(),
-        repo_url,
-        base_branch: updated_task.base_branch.clone(),
-        target_branch: updated_task.target_branch.clone(),
-        parent_task_id: updated_task.parent_task_id,
-        depth: updated_task.depth,
-        is_orchestrator: false,
-        target_repo_path: updated_task.target_repo_path.clone(),
-        completion_action: updated_task.completion_action.clone(),
-        continue_from_task_id: updated_task.continue_from_task_id,
-        copy_files: updated_task.copy_files.as_ref().and_then(|v| serde_json::from_value(v.clone()).ok()),
-        contract_id: updated_task.contract_id,
-        is_supervisor: false,
-    };
+        let updated_task = match repository::update_task_for_owner(pool, task.id, owner_id, update_req).await {
+            Ok(Some(t)) => t,
+            Ok(None) => continue, // Task was modified concurrently, try next
+            Err(e) => {
+                tracing::warn!(task_id = %task.id, error = %e, "Failed to update task for daemon assignment");
+                continue; // Try next task
+            }
+        };
 
-    if let Err(e) = state.send_daemon_command(daemon.id, cmd).await {
-        tracing::warn!(error = %e, daemon_id = %daemon.id, task_id = %task.id, "Failed to send spawn command");
-        // Rollback
-        let rollback_req = UpdateTaskRequest {
-            status: Some("pending".to_string()),
-            clear_daemon_id: true,
-            ..Default::default()
+        // Send spawn command
+        let cmd = DaemonCommand::SpawnTask {
+            task_id: updated_task.id,
+            task_name: updated_task.name.clone(),
+            plan: updated_task.plan.clone(),
+            repo_url,
+            base_branch: updated_task.base_branch.clone(),
+            target_branch: updated_task.target_branch.clone(),
+            parent_task_id: updated_task.parent_task_id,
+            depth: updated_task.depth,
+            is_orchestrator: false,
+            target_repo_path: updated_task.target_repo_path.clone(),
+            completion_action: updated_task.completion_action.clone(),
+            continue_from_task_id: updated_task.continue_from_task_id,
+            copy_files: updated_task.copy_files.as_ref().and_then(|v| serde_json::from_value(v.clone()).ok()),
+            contract_id: updated_task.contract_id,
+            is_supervisor: false,
         };
-        let _ = repository::update_task_for_owner(pool, task.id, owner_id, rollback_req).await;
-        return Ok(None);
+
+        if let Err(e) = state.send_daemon_command(daemon.id, cmd).await {
+            tracing::warn!(error = %e, daemon_id = %daemon.id, task_id = %task.id, "Failed to send spawn command");
+            // Rollback
+            let rollback_req = UpdateTaskRequest {
+                status: Some("pending".to_string()),
+                clear_daemon_id: true,
+                ..Default::default()
+            };
+            let _ = repository::update_task_for_owner(pool, task.id, owner_id, rollback_req).await;
+            continue; // Try next task
+        }
+
+        tracing::info!(task_id = %task.id, daemon_id = %daemon.id, "Started pending task from wait loop");
+        return Ok(Some(updated_task));
     }
 
-    tracing::info!(task_id = %task.id, daemon_id = %daemon.id, "Started pending task from wait loop");
-    Ok(Some(updated_task))
+    // No tasks could be started
+    Ok(None)
 }
 
 // =============================================================================