diff --git a/apps/web/app/api/v1/approvals/route.ts b/apps/web/app/api/v1/approvals/route.ts
index 91e8824..e3bf84f 100644
--- a/apps/web/app/api/v1/approvals/route.ts
+++ b/apps/web/app/api/v1/approvals/route.ts
@@ -5,7 +5,10 @@ export async function GET(request: Request) {
   const traceId = requestTraceId(request);
   try {
     return Response.json({
-      data: await new ApprovalDomainService().list(await apiSubject(request)),
+      data: await new ApprovalDomainService().list(
+        await apiSubject(request),
+        traceId,
+      ),
       traceId,
     });
   } catch (error) {
diff --git a/apps/web/features/approvals/governance-inbox.tsx b/apps/web/features/approvals/governance-inbox.tsx
index 8d0fd92..8b2c505 100644
--- a/apps/web/features/approvals/governance-inbox.tsx
+++ b/apps/web/features/approvals/governance-inbox.tsx
@@ -209,7 +209,14 @@ function ApprovalDetail({
 }) {
   const severity = riskSeverity(approval.riskSummary);
   const highImpact = severity === "critical";
-  const pending = approval.status === "pending";
+  // A row can still read as pending until the next inbox load expires it, so
+  // trust the deadline rather than the stored status for what is offerable.
+  const overdue = new Date(approval.expiresAt) <= new Date();
+  const pending = approval.status === "pending" && !overdue;
+  // Includes rows already stored as `expired` by the inbox's lazy sweep, not
+  // just ones that are still nominally pending.
+  const closable =
+    approval.status === "expired" || (approval.status === "pending" && overdue);
 
   return (
     <div>
@@ -277,9 +284,15 @@ function ApprovalDetail({
           </div>
         </dl>
 
-        {pending ? (
+        {pending || closable ? (
           <div className="space-y-3 rounded-md border border-border bg-[var(--color-paper)] p-3">
-            <label className="block text-xs font-semibold" htmlFor="decision-reason">
+            {closable ? (
+              <p className="rounded-md border border-[var(--color-warning)]/40 bg-[var(--color-warning-soft)] p-2 text-sm text-[var(--color-warning)]">
+                This request passed its deadline, so it can no longer be
+                approved. Reject it to close it out with a recorded reason.
+              </p>
+            ) : null}
+            <label className="block text-sm font-semibold" htmlFor="decision-reason">
               Decision reason (required)
             </label>
             <textarea
@@ -308,28 +321,28 @@ function ApprovalDetail({
               </label>
             ) : null}
             <div className="flex flex-wrap gap-2">
+              {closable ? null : (
+                <Button type="button" disabled={busy} onClick={onApprove}>
+                  <Check className="size-4" />
+                  Approve
+                </Button>
+              )}
               <Button
                 type="button"
-                disabled={busy}
-                onClick={onApprove}
-              >
-                <Check className="size-4" />
-                Approve
-              </Button>
-              <Button
-                type="button"
-                variant="outline"
+                variant={closable ? "default" : "outline"}
                 disabled={busy}
                 onClick={onReject}
               >
                 <X className="size-4" />
-                Reject
+                {closable ? "Reject and close" : "Reject"}
               </Button>
             </div>
           </div>
         ) : (
           <p className="text-sm text-muted-foreground">
-            This approval is no longer pending.
+            {approval.status === "expired"
+              ? "This approval expired without a decision. Nothing was executed."
+              : "This approval is no longer pending."}
             {approval.reason ? ` Reason: ${approval.reason}` : ""}
           </p>
         )}
diff --git a/apps/web/features/operations/operations-view.test.ts b/apps/web/features/operations/operations-view.test.ts
index 9441069..aa1da75 100644
--- a/apps/web/features/operations/operations-view.test.ts
+++ b/apps/web/features/operations/operations-view.test.ts
@@ -29,7 +29,7 @@ describe("Operations board", () => {
     expect(view).toContain("dispatchBlockedReason");
     // Every refusal path returns operator-readable text.
     expect(view).toContain("Assign this task to an agent to dispatch it.");
-    expect(view).toContain("already has an active agent run");
+    expect(view).toContain("A run is already in flight.");
     expect(view).toContain("assigneeReadinessReason");
   });
 
@@ -103,3 +103,29 @@ describe("Task composer", () => {
     expect(composer).not.toMatch(/[0-9a-f]{8}-[0-9a-f]{4}-[0-9a-f]{4}-/);
   });
 });
+
+describe("Stuck and failed agent work", () => {
+  it("offers cancel while a run is in flight", async () => {
+    const view = await source("./operations-view.tsx");
+    expect(view).toContain("useCancelTaskRun");
+    expect(view).toContain("Cancel run");
+    // Every status the server treats as in-flight must be escapable, not just
+    // queued/running — awaiting_approval wedges a task just as hard.
+    expect(view).toContain('"awaiting_approval"');
+    expect(view).toContain('"waiting_sources"');
+  });
+
+  it("labels a re-dispatch as a retry and says why", async () => {
+    const view = await source("./operations-view.tsx");
+    expect(view).toContain("function isRetry");
+    expect(view).toContain("Retry dispatch");
+    expect(view).toContain("Previous run");
+  });
+
+  it("points a blocked dispatch at the way out", async () => {
+    const view = await source("./operations-view.tsx");
+    expect(view).toContain(
+      "A run is already in flight. Cancel it before dispatching again.",
+    );
+  });
+});
diff --git a/apps/web/features/operations/operations-view.tsx b/apps/web/features/operations/operations-view.tsx
index 5bdc61a..bb52b07 100644
--- a/apps/web/features/operations/operations-view.tsx
+++ b/apps/web/features/operations/operations-view.tsx
@@ -26,6 +26,7 @@ import {
   type ComposerSeed,
 } from "@/features/operations/task-composer";
 import {
+  useCancelTaskRun,
   useDelegateTask,
   useTasks,
   useUpdateTask,
@@ -162,12 +163,24 @@ function taskToBoardItem(task: RawTask): BoardItem {
   };
 }
 
-/** A run that is already queued or running must not be dispatched again. */
+/** Statuses the server treats as an in-flight run; cancel is the only exit. */
+const ACTIVE_RUN_STATUSES = [
+  "queued",
+  "running",
+  "awaiting_approval",
+  "waiting_sources",
+];
+
+function hasActiveRun(item: BoardItem): boolean {
+  return ACTIVE_RUN_STATUSES.includes(item.agentRunStatus ?? "");
+}
+
+/** A run already in flight must not be dispatched again. */
 function dispatchBlockedReason(item: BoardItem): string | null {
   if (!item.assigneeIsAgent)
     return "Assign this task to an agent to dispatch it.";
-  if (item.agentRunStatus === "queued" || item.agentRunStatus === "running")
-    return "This task already has an active agent run.";
+  if (hasActiveRun(item))
+    return "A run is already in flight. Cancel it before dispatching again.";
   if (item.assigneeReadiness !== "ready")
     return (
       item.assigneeReadinessReason ?? "Assigned agent is not ready for work."
@@ -175,6 +188,13 @@ function dispatchBlockedReason(item: BoardItem): string | null {
   return null;
 }
 
+/** A settled run can be handed back to the agent; label it as a retry. */
+function isRetry(item: BoardItem): boolean {
+  return (
+    item.agentRunStatus === "failed" || item.agentRunStatus === "cancelled"
+  );
+}
+
 export function OperationsView() {
   const tasks = useTasks();
   const updateTask = useUpdateTask();
@@ -473,6 +493,7 @@ export function OperationsView() {
 
 function DetailDrawer({ item }: { item: BoardItem | null }) {
   const delegateTask = useDelegateTask();
+  const cancelRun = useCancelTaskRun();
   const [error, setError] = useState<string | null>(null);
   const [notice, setNotice] = useState<string | null>(null);
 
@@ -501,6 +522,20 @@ function DetailDrawer({ item }: { item: BoardItem | null }) {
     }
   }
 
+  async function cancel() {
+    if (!item) return;
+    setError(null);
+    setNotice(null);
+    try {
+      await cancelRun.mutateAsync(item.id);
+      setNotice("Run cancelled. You can dispatch it again.");
+    } catch (caught) {
+      setError(
+        caught instanceof Error ? caught.message : "Could not cancel the run.",
+      );
+    }
+  }
+
   return (
     <aside className="rounded-md border border-border bg-card p-4">
       <h2 className="text-sm font-semibold">{item.title}</h2>
@@ -518,19 +553,38 @@ function DetailDrawer({ item }: { item: BoardItem | null }) {
             )}
             {item.ownerName ?? "Unassigned"}
           </p>
-          <Button
-            type="button"
-            size="sm"
-            disabled={Boolean(blocked) || delegateTask.isPending}
-            title={blocked ?? undefined}
-            onClick={() => void dispatch()}
-          >
-            {delegateTask.isPending ? "Dispatching…" : "Dispatch to agent"}
-          </Button>
+          <div className="flex flex-wrap gap-2">
+            {hasActiveRun(item) ? (
+              <Button
+                type="button"
+                size="sm"
+                variant="outline"
+                disabled={cancelRun.isPending}
+                onClick={() => void cancel()}
+              >
+                {cancelRun.isPending ? "Cancelling…" : "Cancel run"}
+              </Button>
+            ) : null}
+            <Button
+              type="button"
+              size="sm"
+              disabled={Boolean(blocked) || delegateTask.isPending}
+              title={blocked ?? undefined}
+              onClick={() => void dispatch()}
+            >
+              {delegateTask.isPending
+                ? "Dispatching…"
+                : isRetry(item)
+                  ? "Retry dispatch"
+                  : "Dispatch to agent"}
+            </Button>
+          </div>
         </div>
-        <p className="mt-1.5 text-xs text-muted-foreground">
+        <p className="mt-1.5 text-sm text-muted-foreground">
           {blocked ??
-            "Runs under the agent's governed capability envelope. External writes stay approval-gated."}
+            (isRetry(item)
+              ? `Previous run ${item.agentRunStatus}. Dispatching again starts a fresh run under the agent's governed capability envelope.`
+              : "Runs under the agent's governed capability envelope. External writes stay approval-gated.")}
         </p>
         {error ? (
           <p role="alert" className="mt-1.5 text-xs text-[var(--color-error)]">
diff --git a/apps/web/lib/approval-expiry.test.ts b/apps/web/lib/approval-expiry.test.ts
new file mode 100644
index 0000000..9053166
--- /dev/null
+++ b/apps/web/lib/approval-expiry.test.ts
@@ -0,0 +1,76 @@
+import { readFile } from "node:fs/promises";
+import { describe, expect, it } from "vitest";
+
+async function source(name: string) {
+  return readFile(new URL(name, import.meta.url), "utf8");
+}
+
+/**
+ * An expired approval used to be a permanent dead row: `decide` refused both
+ * verdicts, and nothing ever moved it out of `pending`.
+ */
+describe("approval expiry", () => {
+  it("refuses approval past the deadline but allows rejection", async () => {
+    const domain = await source("./integration-action-domain.ts");
+    expect(domain).toContain(
+      'approval.expiresAt <= new Date() && decision.status !== "rejected"',
+    );
+    expect(domain).toContain("Reject it to close it out.");
+  });
+
+  it("transitions overdue rows to expired with an audit event", async () => {
+    const domain = await source("./integration-action-domain.ts");
+    expect(domain).toContain("async expireOverdue(");
+    expect(domain).toContain('set({ status: "expired"');
+    expect(domain).toContain("lte(schema.approvals.expiresAt, new Date())");
+    expect(domain).toContain('action: "workflow.approval.expired"');
+    // Expiry must run before the inbox is read, or the UI keeps offering
+    // Approve on a request that can no longer be approved.
+    expect(domain).toContain("await this.expireOverdue(subject.organisationId");
+  });
+
+  it("never counts an overdue approval as actionable on Command", async () => {
+    const summary = await source("./command-summary-domain.ts");
+    expect(summary).toContain("gt(schema.approvals.expiresAt, new Date())");
+  });
+});
+
+describe("approval inbox controls", () => {
+  it("drops Approve and offers a closing Reject once overdue", async () => {
+    const view = await source("../features/approvals/governance-inbox.tsx");
+    expect(view).toContain("const overdue = new Date(approval.expiresAt)");
+    expect(view).toContain('(approval.status === "pending" && overdue)');
+    expect(view).toContain("{closable ? null : (");
+    expect(view).toContain('{closable ? "Reject and close" : "Reject"}');
+    expect(view).toContain("can no longer be");
+  });
+
+  it("explains an expired outcome rather than saying only 'not pending'", async () => {
+    const view = await source("../features/approvals/governance-inbox.tsx");
+    expect(view).toContain('approval.status === "expired"');
+    expect(view).toContain("Nothing was executed.");
+  });
+});
+
+/**
+ * The lazy sweep and the decision path have to agree. If listing the inbox
+ * moves a row to `expired` and `decide` then treats `expired` as terminal,
+ * opening Approvals is what destroys the only way to close the row.
+ */
+describe("expired rows stay closable after the lazy sweep", () => {
+  it("does not short-circuit a rejection on a stored expired row", async () => {
+    const domain = await source("./integration-action-domain.ts");
+    expect(domain).toContain("const closingExpired =");
+    expect(domain).toContain(
+      'approval.status === "expired" && decision.status === "rejected"',
+    );
+    expect(domain).toContain(
+      'if (approval.status !== "pending" && !closingExpired)',
+    );
+  });
+
+  it("still offers the closing control once the row reads expired", async () => {
+    const view = await source("../features/approvals/governance-inbox.tsx");
+    expect(view).toContain('approval.status === "expired" ||');
+  });
+});
diff --git a/apps/web/lib/command-summary-domain.ts b/apps/web/lib/command-summary-domain.ts
index 96a0348..7d276b6 100644
--- a/apps/web/lib/command-summary-domain.ts
+++ b/apps/web/lib/command-summary-domain.ts
@@ -1,4 +1,4 @@
-import { and, desc, eq, inArray, isNull } from "drizzle-orm";
+import { and, desc, eq, gt, inArray, isNull } from "drizzle-orm";
 import {
   hasCapability,
   type AuthorisationSubject,
@@ -74,6 +74,9 @@ export async function getCommandSummary(
           and(
             eq(schema.approvals.organisationId, subject.organisationId),
             eq(schema.approvals.status, "pending"),
+            // An overdue row is still stored as pending until something reads
+            // the inbox and expires it. Never count it as actionable here.
+            gt(schema.approvals.expiresAt, new Date()),
           ),
         )
         .orderBy(desc(schema.approvals.requestedAt))
diff --git a/apps/web/lib/integration-action-domain.ts b/apps/web/lib/integration-action-domain.ts
index 805f438..2a54535 100644
--- a/apps/web/lib/integration-action-domain.ts
+++ b/apps/web/lib/integration-action-domain.ts
@@ -18,7 +18,7 @@ import {
   IntegrationActionRequestSchema,
   type IntegrationActionRequest,
 } from "@muster/integrations";
-import { and, desc, eq, inArray } from "drizzle-orm";
+import { and, desc, eq, inArray, lte } from "drizzle-orm";
 import { z } from "zod";
 import { ApiProblem } from "./api-context.ts";
 
@@ -348,8 +348,50 @@ export class IntegrationActionDomainService {
 export class ApprovalDomainService {
   constructor(private readonly db = database()) {}
 
-  async list(subject: AuthorisationSubject) {
+  /**
+   * Move overdue pending approvals to `expired` before anyone reads them.
+   *
+   * Nothing else transitions them, so without this they stay `pending`
+   * forever: the inbox keeps offering Approve on a request that can no longer
+   * be approved, and the attention queue keeps counting dead rows. Lazy
+   * expiry runs on read so a workspace self-heals without a scheduler.
+   */
+  async expireOverdue(organisationId: string, traceId: string) {
+    return this.db.transaction(async (tx) => {
+      const overdue = await tx
+        .update(schema.approvals)
+        .set({ status: "expired", decisionAt: new Date() })
+        .where(
+          and(
+            eq(schema.approvals.organisationId, organisationId),
+            eq(schema.approvals.status, "pending"),
+            lte(schema.approvals.expiresAt, new Date()),
+          ),
+        )
+        .returning({
+          id: schema.approvals.id,
+          actionType: schema.approvals.actionType,
+          requestingActorId: schema.approvals.requestingActorId,
+        });
+      for (const approval of overdue) {
+        await appendAuditEvent(tx, {
+          organisationId,
+          actorId: approval.requestingActorId,
+          actorType: "system",
+          action: "workflow.approval.expired",
+          targetType: "approval",
+          targetId: approval.id,
+          metadata: { actionType: approval.actionType },
+          traceId,
+        });
+      }
+      return overdue.length;
+    });
+  }
+
+  async list(subject: AuthorisationSubject, traceId = "approval-list") {
     requireCapability(subject, "workflows.approve");
+    await this.expireOverdue(subject.organisationId, traceId);
     const rows = await this.db
       .select()
       .from(schema.approvals)
@@ -385,10 +427,23 @@ export class ApprovalDomainService {
           "Approval not found",
           "Approval does not exist.",
         );
-      if (approval.status !== "pending")
+      // A row lands on `expired` as soon as anything lists the inbox, so
+      // rejection has to survive that state too — otherwise the very act of
+      // opening Approvals removes the only way to close the row.
+      const closingExpired =
+        approval.status === "expired" && decision.status === "rejected";
+      if (approval.status !== "pending" && !closingExpired)
         return { id: approval.id, status: approval.status, duplicate: true };
-      if (approval.expiresAt <= new Date())
-        throw new ApiProblem(409, "Approval expired", "Approval has expired.");
+      // Approving an expired dangerous action is exactly what expiry exists to
+      // prevent. Rejecting one is strictly de-escalating, so it stays open —
+      // otherwise the row can never be closed and clutters the queue forever.
+      if (approval.expiresAt <= new Date() && decision.status !== "rejected") {
+        throw new ApiProblem(
+          409,
+          "Approval expired",
+          "This approval expired and can no longer be approved. Reject it to close it out.",
+        );
+      }
       if (!capabilities.includes(approval.requiredCapability as Capability))
         throw new Error("Approval requires an unknown capability");
       requireCapability(subject, approval.requiredCapability as Capability);
diff --git a/apps/web/lib/queries/hooks.ts b/apps/web/lib/queries/hooks.ts
index c71a81f..d66d557 100644
--- a/apps/web/lib/queries/hooks.ts
+++ b/apps/web/lib/queries/hooks.ts
@@ -336,6 +336,31 @@ export function useCreateTask() {
   });
 }
 
+/**
+ * Cancel a task's in-flight agent run. Without this a run wedged at
+ * queued/running (gateway crash, expired lease) blocks re-dispatch forever
+ * with no operator escape.
+ */
+export function useCancelTaskRun() {
+  const client = useQueryClient();
+  return useMutation({
+    mutationFn: async (taskId: string) => {
+      const res = await apiPost<{ status?: string }>(
+        `/api/v1/tasks/${taskId}/cancel`,
+        {},
+      );
+      return res.data;
+    },
+    onSuccess: async () => {
+      await Promise.all([
+        client.invalidateQueries({ queryKey: queryKeys.tasks }),
+        client.invalidateQueries({ queryKey: queryKeys.commandSummary }),
+        client.invalidateQueries({ queryKey: ["audit"] }),
+      ]);
+    },
+  });
+}
+
 /**
  * Hand a task to its assigned agent. The server re-checks capability,
  * readiness, and kill switch — this only asks.