diff --git a/src/server/config-schema.ts b/src/server/config-schema.ts
index 0c2f111..daf0b03 100644
--- a/src/server/config-schema.ts
+++ b/src/server/config-schema.ts
@@ -125,6 +125,14 @@ export function getConfigSchema(): AdapterConfigSchema {
         hint: "Skip cleanup on completion for debugging",
         group: "Kubernetes",
       },
+      {
+        key: "reattachOrphanedJobs",
+        label: "Reattach Orphaned Jobs",
+        type: "toggle",
+        default: false,
+        hint: "When a running Job for the same task is found after a server restart, reattach (stream logs and await completion) instead of blocking",
+        group: "Kubernetes",
+      },
 
       // Operational fields (timeoutSec and graceSec are provided by the platform)
     ],
diff --git a/src/server/job-manifest.test.ts b/src/server/job-manifest.test.ts
index 79c986d..cdc2460 100644
--- a/src/server/job-manifest.test.ts
+++ b/src/server/job-manifest.test.ts
@@ -70,6 +70,48 @@ describe("buildJobManifest", () => {
     expect(result.job.metadata?.labels?.["paperclip.io/run-id"]).toBe("run123456");
   });
 
+  it("sets paperclip.io/task-id label when context.taskId is present", () => {
+    const ctx = {
+      ...mockCtx,
+      context: { ...mockCtx.context, taskId: "7e0829c0-cbf7-4652-9554-4d777ce84bff" },
+    };
+    const result = buildJobManifest({ ctx, selfPod: mockSelfPod });
+
+    expect(result.job.metadata?.labels?.["paperclip.io/task-id"]).toBe("7e0829c0-cbf7-4652-9554-4d777ce84bff");
+  });
+
+  it("falls back to context.issueId for paperclip.io/task-id when taskId is null", () => {
+    const ctx = {
+      ...mockCtx,
+      context: { ...mockCtx.context, taskId: null, issueId: "issue-uuid-xyz" },
+    };
+    const result = buildJobManifest({ ctx, selfPod: mockSelfPod });
+
+    expect(result.job.metadata?.labels?.["paperclip.io/task-id"]).toBe("issue-uuid-xyz");
+  });
+
+  it("omits paperclip.io/task-id label when context.taskId and issueId are both null", () => {
+    const result = buildJobManifest({ ctx: mockCtx, selfPod: mockSelfPod });
+
+    expect(result.job.metadata?.labels?.["paperclip.io/task-id"]).toBeUndefined();
+  });
+
+  it("sets paperclip.io/session-id label when runtime.sessionParams.sessionId is present", () => {
+    const ctx = {
+      ...mockCtx,
+      runtime: { ...mockCtx.runtime, sessionParams: { sessionId: "ses_abc123" } },
+    };
+    const result = buildJobManifest({ ctx, selfPod: mockSelfPod });
+
+    expect(result.job.metadata?.labels?.["paperclip.io/session-id"]).toBe("ses_abc123");
+  });
+
+  it("omits paperclip.io/session-id label when no session exists", () => {
+    const result = buildJobManifest({ ctx: mockCtx, selfPod: mockSelfPod });
+
+    expect(result.job.metadata?.labels?.["paperclip.io/session-id"]).toBeUndefined();
+  });
+
   it("creates init container for prompt", () => {
     const result = buildJobManifest({ ctx: mockCtx, selfPod: mockSelfPod });
 
diff --git a/src/server/job-manifest.ts b/src/server/job-manifest.ts
index b43a2fe..bfea102 100644
--- a/src/server/job-manifest.ts
+++ b/src/server/job-manifest.ts
@@ -320,6 +320,9 @@ export function buildJobManifest(input: JobBuildInput): JobBuildResult {
     "paperclip.io/company-id": sanitizeLabelValue(agent.companyId, warnLabel),
     "paperclip.io/adapter-type": "opencode_k8s",
   };
+  const taskId = asString(context.taskId ?? context.issueId, "").trim();
+  if (taskId) labels["paperclip.io/task-id"] = sanitizeLabelValue(taskId, warnLabel);
+  if (runtimeSessionId) labels["paperclip.io/session-id"] = sanitizeLabelValue(runtimeSessionId, warnLabel);
   for (const [key, value] of Object.entries(extraLabels)) {
     if (typeof value === "string") labels[key] = sanitizeLabelValue(value, warnLabel);
   }