diff --git a/packages/adapter-utils/src/server-utils.ts b/packages/adapter-utils/src/server-utils.ts
index 3e24155fb87..8538a710687 100644
--- a/packages/adapter-utils/src/server-utils.ts
+++ b/packages/adapter-utils/src/server-utils.ts
@@ -2477,6 +2477,9 @@ function renderPaperclipWakePromptBody(
       : [];
   const wakeSummaryLines = [
     `- reason: ${normalized.reason ?? "unknown"}`,
+    ...(normalized.executionContinuation?.trigger?.retriedReason
+      ? [`- retried wake: ${normalized.executionContinuation.trigger.retriedReason} (this Retry re-delivers the wake the failed run did not finish; handle it as that wake)`]
+      : []),
     `- issue: ${normalized.issue?.identifier ?? normalized.issue?.id ?? "unknown"}${normalized.issue?.title ? ` ${normalized.issue.title}` : ""}`,
     ...(hasWakeCommentBatch
       ? [
diff --git a/packages/shared/src/types/execution-continuation.ts b/packages/shared/src/types/execution-continuation.ts
index 545998e33ab..5afe62afd22 100644
--- a/packages/shared/src/types/execution-continuation.ts
+++ b/packages/shared/src/types/execution-continuation.ts
@@ -7,6 +7,7 @@ export interface ExecutionContinuationEnvelope {
     reason: string;
     interactionId: string | null;
     sourceRunId: string | null;
+    retriedReason?: string;
   };
   originCommentIds: string[];
   objective: string;
diff --git a/server/src/services/execution-continuation.test.ts b/server/src/services/execution-continuation.test.ts
index 1c81337f4ce..24e108e18ac 100644
--- a/server/src/services/execution-continuation.test.ts
+++ b/server/src/services/execution-continuation.test.ts
@@ -366,6 +366,36 @@ const support = externalUrl ? { supported: true } : await getEmbeddedPostgresTes
       }
     });
 
+    it("carries the failed run's wake reason into a Retry so a monitor check is not lost", async () => {
+      const [source] = await db.select().from(heartbeatRuns).where(eq(heartbeatRuns.id, runId));
+      const retryRunId = randomUUID();
+      await db.update(heartbeatRuns).set({ status: "failed", errorCode: "native_session_interrupted",
+        contextSnapshot: { issueId, wakeReason: "issue_monitor_due", monitorNotes: "Phase 2 check" } })
+        .where(eq(heartbeatRuns.id, runId));
+      try {
+        const envelope = await buildExecutionContinuation({ db, companyId, issueId, agentId,
+          context: { retryOfRunId: runId, wakeReason: "task_retry" }, summary: null, exposeLowTrustRaw: false });
+        expect(envelope.trigger).toMatchObject({ reason: "task_retry", sourceRunId: runId, retriedReason: "issue_monitor_due" });
+        await db.insert(heartbeatRuns).values({ id: retryRunId, companyId, agentId, status: "failed",
+          contextSnapshot: { issueId, wakeReason: "task_retry", executionContinuation: envelope } });
+        const chained = await buildExecutionContinuation({ db, companyId, issueId, agentId,
+          context: { retryOfRunId: retryRunId, wakeReason: "task_retry" }, summary: null, exposeLowTrustRaw: false });
+        expect(chained.trigger).toMatchObject({ sourceRunId: retryRunId, retriedReason: "issue_monitor_due" });
+        for (const resumedSession of [false, true]) {
+          const prompt = renderPaperclipWakePrompt({ reason: "task_retry", executionContinuation: envelope }, { resumedSession });
+          expect(prompt).toContain("- reason: task_retry");
+          expect(prompt).toContain("- retried wake: issue_monitor_due");
+        }
+        const fresh = await buildExecutionContinuation({ db, companyId, issueId, agentId,
+          context: { wakeReason: "issue_assigned" }, summary: null, exposeLowTrustRaw: false });
+        expect(fresh.trigger).not.toHaveProperty("retriedReason");
+      } finally {
+        await db.delete(heartbeatRuns).where(eq(heartbeatRuns.id, retryRunId));
+        await db.update(heartbeatRuns).set({ status: "failed", errorCode: null, contextSnapshot: source.contextSnapshot })
+          .where(eq(heartbeatRuns.id, runId));
+      }
+    });
+
     it("keeps Local CLI run-authored comments as history without promoting them to human direction", async () => {
       const id = randomUUID();
       await db.insert(issueComments).values({ id, companyId, issueId, authorType: "user",
diff --git a/server/src/services/execution-continuation.ts b/server/src/services/execution-continuation.ts
index 29a44f2e316..5e2dc7aa6c8 100644
--- a/server/src/services/execution-continuation.ts
+++ b/server/src/services/execution-continuation.ts
@@ -20,6 +20,8 @@ import { isCompletedOnboardingHandoffWake } from "./chat-completion-delivery.js"
 import { githubRecoveryReceipts } from "./chat-channels/github/recovery-receipts.js";
 import { readTaskRetryIntent } from "./task-retry.js";
 
+const retryWakeReasons = new Set(["task_retry", "retry_failed_run"]);
+
 const savedRecordOperations = new Set([
   "PUT /api/issues/{id}/documents/{key}",
   "POST /api/issues/{id}/comments",
@@ -534,6 +536,12 @@ export async function buildExecutionContinuation(input: {
     (hasConversationContinuationPolicy(lastTerminal.result) ||
       lastTerminal.status === "interrupted" || lastTerminal.errorCode === "process_lost")
     ? lastTerminal.id : undefined);
+  const triggerReason = string(input.context.wakeReason) ?? "task_execution";
+  const sourceContext = object(sourceRun?.context);
+  const retriedCandidate = retryWakeReasons.has(triggerReason) && sourceRun
+    ? string(object(object(sourceContext.executionContinuation).trigger).retriedReason) ?? string(sourceContext.wakeReason)
+    : null;
+  const retriedReason = retriedCandidate && !retryWakeReasons.has(retriedCandidate) ? retriedCandidate : null;
   return {
     ...(interruptedRunId ? { interruptedRunId } : {}),
     ...(resumeDelta ? { resumeDelta } : {}),
@@ -547,9 +555,10 @@ export async function buildExecutionContinuation(input: {
     companyId,
     issueId,
     trigger: {
-      reason: string(input.context.wakeReason) ?? "task_execution",
+      reason: triggerReason,
       interactionId: triggerInteraction?.id ?? null,
       sourceRunId,
+      ...(retriedReason ? { retriedReason } : {}),
     },
     originCommentIds,
     objective: latestRequest?.body ?? issue.description ?? issue.title,
diff --git a/tests/runner-e2e/source-sdk-public-inputs.json b/tests/runner-e2e/source-sdk-public-inputs.json
index 28b9b17be8c..b438afbecc3 100644
--- a/tests/runner-e2e/source-sdk-public-inputs.json
+++ b/tests/runner-e2e/source-sdk-public-inputs.json
@@ -387,7 +387,7 @@
     "packages/shared/src/types/document-annotation.ts": "7769a42f1ccd707a2259774e7fe6aa536b5d183f",
     "packages/shared/src/types/email.ts": "556ff6a0dcefa01eb704d6d00d3b191de81ff4dc",
     "packages/shared/src/types/environment.ts": "a380b9ce9d2d1763011e9adaa58615a3ef1e56c5",
-    "packages/shared/src/types/execution-continuation.ts": "545998e33ab18d38268558d1a367f4aa12c2d5d3",
+    "packages/shared/src/types/execution-continuation.ts": "5afe62afd227efa03ff847d8f73291c14707ab5b",
     "packages/shared/src/types/execution-projection.ts": "e72e641602b296f6d3e16d07700629df3039a7b1",
     "packages/shared/src/types/external-object.ts": "7a225e0f5a6777d449019a30530c858b753eb4c1",
     "packages/shared/src/types/feedback.ts": "c5eb31545c7f67c04ad9afd9db45a6b4774bcb35",