diff --git a/server/src/__tests__/heartbeat-workspace-session.test.ts b/server/src/__tests__/heartbeat-workspace-session.test.ts
index 404b777d..30921283 100644
--- a/server/src/__tests__/heartbeat-workspace-session.test.ts
+++ b/server/src/__tests__/heartbeat-workspace-session.test.ts
@@ -18,6 +18,7 @@ import {
   resolveNextSessionState,
   resolveWorkspaceAfterLowTrustPreflight,
   resolveRuntimeSessionParamsForWorkspace,
+  shouldDeferFollowupWakeForSameIssue,
   stripHostWorkspaceProvisionForLowTrustSandbox,
   stripWorkspaceRuntimeFromExecutionRunConfig,
   shouldResetTaskSessionForWake,
@@ -879,6 +880,52 @@ describe("shouldResetTaskSessionForWake", () => {
   });
 });
 
+describe("shouldDeferFollowupWakeForSameIssue", () => {
+  it("defers a same-agent follow-up for mention-style comment wakes while a run is active", () => {
+    expect(
+      shouldDeferFollowupWakeForSameIssue({
+        activeRunStatus: "running",
+        isSameExecutionAgent: true,
+        wakeCommentId: "comment-1",
+        forceFreshSession: false,
+      }),
+    ).toBe(true);
+  });
+
+  it("defers a same-agent follow-up when a fresh session is explicitly requested", () => {
+    expect(
+      shouldDeferFollowupWakeForSameIssue({
+        activeRunStatus: "running",
+        isSameExecutionAgent: true,
+        wakeCommentId: null,
+        forceFreshSession: true,
+      }),
+    ).toBe(true);
+  });
+
+  it("does not defer when the existing run is only queued", () => {
+    expect(
+      shouldDeferFollowupWakeForSameIssue({
+        activeRunStatus: "queued",
+        isSameExecutionAgent: true,
+        wakeCommentId: null,
+        forceFreshSession: true,
+      }),
+    ).toBe(false);
+  });
+
+  it("does not defer normal same-agent wakes without a comment or fresh-session request", () => {
+    expect(
+      shouldDeferFollowupWakeForSameIssue({
+        activeRunStatus: "running",
+        isSameExecutionAgent: true,
+        wakeCommentId: null,
+        forceFreshSession: false,
+      }),
+    ).toBe(false);
+  });
+});
+
 describe("deriveTaskKeyWithHeartbeatFallback", () => {
   it("returns explicit taskKey when present", () => {
     expect(deriveTaskKeyWithHeartbeatFallback({ taskKey: "issue-123" }, null)).toBe("issue-123");
@@ -931,6 +978,21 @@ describe("comment wake batching", () => {
     expect(merged.wakeCommentId).toBe("comment-2");
     expect(merged.paperclipWake).toBeUndefined();
   });
+
+  it("keeps forceFreshSession sticky once any coalesced wake requests it", () => {
+    const merged = mergeCoalescedContextSnapshot(
+      {
+        issueId: "issue-1",
+        forceFreshSession: true,
+      },
+      {
+        issueId: "issue-1",
+        forceFreshSession: false,
+      },
+    );
+
+    expect(merged.forceFreshSession).toBe(true);
+  });
 });
 
 describe("buildExplicitResumeSessionOverride", () => {
diff --git a/server/src/services/heartbeat.ts b/server/src/services/heartbeat.ts
index 4b0a0c00..a74369ef 100644
--- a/server/src/services/heartbeat.ts
+++ b/server/src/services/heartbeat.ts
@@ -2117,6 +2117,20 @@ export function describeSessionResetReason(
   return null;
 }
 
+export function shouldDeferFollowupWakeForSameIssue(input: {
+  activeRunStatus: string | null | undefined;
+  isSameExecutionAgent: boolean;
+  wakeCommentId: string | null | undefined;
+  forceFreshSession: boolean;
+}) {
+  // A comment follow-up or explicit fresh-session wake needs a new run boundary.
+  if (!input.isSameExecutionAgent) return false;
+  if (input.activeRunStatus !== "running") return false;
+  if (input.wakeCommentId) return true;
+  if (input.forceFreshSession) return true;
+  return false;
+}
+
 function shouldAutoCheckoutIssueForWake(input: {
   contextSnapshot: Record<string, unknown> | null | undefined;
   issueStatus: string | null;
@@ -2366,6 +2380,9 @@ export function mergeCoalescedContextSnapshot(
     ...existing,
     ...incoming,
   };
+  if (existing.forceFreshSession === true || incoming.forceFreshSession === true) {
+    merged.forceFreshSession = true;
+  }
   const mergedCommentIds = mergeWakeCommentIds(existing, incoming);
   if (mergedCommentIds.length > 0) {
     const latestCommentId = mergedCommentIds[mergedCommentIds.length - 1];
@@ -10238,12 +10255,18 @@ export function heartbeatService(db: Db, options: HeartbeatServiceOptions = {})
             normalizeAgentNameKey(executionAgent?.name);
           const isSameExecutionAgent =
             Boolean(executionAgentNameKey) && executionAgentNameKey === agentNameKey;
+          const shouldDeferFollowupWake = shouldDeferFollowupWakeForSameIssue({
+            activeRunStatus: activeExecutionRun.status,
+            isSameExecutionAgent,
+            wakeCommentId,
+            forceFreshSession: enrichedContextSnapshot.forceFreshSession === true,
+          });
           const shouldQueueFollowupForRunningWake =
             shouldQueueFollowupForRunningIssueWake({ contextSnapshot: enrichedContextSnapshot, wakeCommentId }) &&
             activeExecutionRun.status === "running" &&
             isSameExecutionAgent;
 
-          if (isSameExecutionAgent && !shouldQueueFollowupForRunningWake) {
+          if (isSameExecutionAgent && !shouldDeferFollowupWake && !shouldQueueFollowupForRunningWake) {
             const mergedContextSnapshot = mergeCoalescedContextSnapshot(
               activeExecutionRun.contextSnapshot,
               enrichedContextSnapshot,