diff --git a/src/chat-swarm-runtime.test.ts b/src/chat-swarm-runtime.test.ts
index 316ae907..e1e9fdbb 100644
--- a/src/chat-swarm-runtime.test.ts
+++ b/src/chat-swarm-runtime.test.ts
@@ -323,22 +323,24 @@ test("OpenCLI provisioning fails closed when the authenticated peer probe is mal
   );
 });
 
-test("OpenCLI wake reopens the exact conversation", async () => {
+test("OpenCLI continuation uses send and confirms delivery by exact prompt readback", async () => {
   const driver = openCliDriverForTest();
   const calls: string[][] = [];
+  let sent = false;
   (driver as any).runJson = async (args: string[]) => {
     calls.push(args);
     if (args[1] === "detail") {
       return [
         { Role: "User", Text: "init", Generating: false },
         { Role: "Assistant", Text: "READY_FOR_BOOTSTRAP", Generating: false },
+        ...(sent ? [{ Role: "User", Text: "@devspace wake", Generating: false }] : []),
       ];
     }
-    return [{
-      conversationId: "opencli-managed-02",
-      conversationUrl: "https://chatgpt.com/g/g-p-runtime-test/c/opencli-managed-02",
-      response: "",
-    }];
+    if (args[1] === "send") {
+      sent = true;
+      return [{ Status: "Success", InjectedText: "@devspace wake" }];
+    }
+    throw new Error(`unexpected OpenCLI command: ${args[1]}`);
   };
   const result = await driver.sendPrompt(
     "https://chatgpt.com/g/g-p-runtime-test/c/opencli-managed-02",
@@ -346,13 +348,13 @@ test("OpenCLI wake reopens the exact conversation", async () => {
     new Date(Date.now() + 1_000).toISOString(),
   );
   assert.deepEqual(result, { delivered: true, remoteMayContinue: true });
-  const ask = calls.find((args) => args[1] === "ask")!;
-  assert.equal(ask[ask.indexOf("--conversation") + 1], "opencli-managed-02");
-  assert.equal(ask[ask.indexOf("--wait") + 1], "false");
-  assert.equal(ask[ask.indexOf("--site-session") + 1], "ephemeral");
+  const send = calls.find((args) => args[1] === "send")!;
+  assert.equal(send[send.indexOf("--conversation") + 1], "opencli-managed-02");
+  assert.equal(send.includes("--wait"), false);
+  assert.equal(send[send.indexOf("--site-session") + 1], "ephemeral");
 });
 
-test("OpenCLI wake fails closed when the returned conversation identity drifts", async () => {
+test("OpenCLI continuation fails closed when send acknowledgement has no prompt readback", async () => {
   const driver = openCliDriverForTest();
   (driver as any).runJson = async (args: string[]) => {
     if (args[1] === "detail") {
@@ -361,11 +363,10 @@ test("OpenCLI wake fails closed when the returned conversation identity drifts",
         { Role: "Assistant", Text: "READY_FOR_BOOTSTRAP", Generating: false },
       ];
     }
-    return [{
-      conversationId: "opencli-managed-wrong",
-      conversationUrl: "https://chatgpt.com/g/g-p-runtime-test/c/opencli-managed-wrong",
-      response: "",
-    }];
+    if (args[1] === "send") {
+      return [{ Status: "Success", InjectedText: "@devspace wake" }];
+    }
+    throw new Error(`unexpected OpenCLI command: ${args[1]}`);
   };
   const result = await driver.sendPrompt(
     "https://chatgpt.com/g/g-p-runtime-test/c/opencli-managed-02",
@@ -375,7 +376,7 @@ test("OpenCLI wake fails closed when the returned conversation identity drifts",
   assert.deepEqual(result, {
     delivered: false,
     remoteMayContinue: true,
-    blocker: "OPENCLI_CONVERSATION_IDENTITY_DRIFT",
+    blocker: "OPENCLI_PROMPT_NOT_OBSERVED",
   });
 });
 
diff --git a/src/chat-swarm-runtime.ts b/src/chat-swarm-runtime.ts
index 7d7994d5..99ed0b98 100644
--- a/src/chat-swarm-runtime.ts
+++ b/src/chat-swarm-runtime.ts
@@ -224,6 +224,7 @@ export interface ChatSwarmManagedCarrierAdapter extends ChatSwarmCarrierAdapter
   }): Promise<{
     disposition: "DELIVERED" | "UNKNOWN" | "SETUP_REQUIRED";
     remoteMayContinue: boolean;
+    blocker?: string;
   }>;
   recover(slot: ManagedCarrierSlot): Promise<{ ready: boolean; blocker?: string }>;
   stop(slot: ManagedCarrierSlot): Promise<void>;
@@ -1464,15 +1465,13 @@ export class OpenCliMacWebDriver implements MacWebDriver {
     }
 
     try {
-      const rows = await this.runJson<OpenCliConversationRow[]>(
+      const rows = await this.runJson<Array<{ Status?: string; InjectedText?: string }>>(
         [
           "chatgpt",
-          "ask",
+          "send",
           prompt,
           "--conversation",
           conversationIdFromUrl(conversationUrl),
-          "--wait",
-          "false",
           "--site-session",
           "ephemeral",
           "--keep-tab",
@@ -1482,19 +1481,20 @@ export class OpenCliMacWebDriver implements MacWebDriver {
         ],
         deadlineAt,
       );
-      const observedUrl = rows[0]?.conversationUrl?.trim();
-      if (
-        !observedUrl ||
-        conversationFingerprintFromUrl(observedUrl) !==
-          conversationFingerprintFromUrl(conversationUrl)
-      ) {
-        return {
-          delivered: false,
-          remoteMayContinue: true,
-          blocker: "OPENCLI_CONVERSATION_IDENTITY_DRIFT",
-        };
-      }
-      return { delivered: true, remoteMayContinue: true };
+      const acknowledged =
+        rows[0]?.Status === "Success" && rows[0]?.InjectedText === prompt;
+      const observed = acknowledged
+        ? await this.promptObserved(conversationUrl, prompt, deadlineAt).catch(() => false)
+        : false;
+      return observed
+        ? { delivered: true, remoteMayContinue: true }
+        : {
+            delivered: false,
+            remoteMayContinue: true,
+            blocker: acknowledged
+              ? "OPENCLI_PROMPT_NOT_OBSERVED"
+              : "OPENCLI_SEND_NOT_ACKNOWLEDGED",
+          };
     } catch (error) {
       const observed = await this.promptObserved(
         conversationUrl,
@@ -2061,6 +2061,7 @@ export class MacWebChatCarrierAdapter implements ChatSwarmManagedCarrierAdapter
           ? ("SETUP_REQUIRED" as const)
           : ("UNKNOWN" as const),
         remoteMayContinue: sent.remoteMayContinue,
+        blocker: sent.blocker,
       };
     }
     return { disposition: "DELIVERED" as const, remoteMayContinue: true };
@@ -2369,7 +2370,7 @@ export class ChatSwarmRuntimeManager {
             operation.operationId,
             delivered.disposition === "SETUP_REQUIRED"
               ? "HOST_APP_BINDING_SETUP_REQUIRED"
-              : "BOOTSTRAP_DELIVERY_UNKNOWN",
+              : delivered.blocker ?? "BOOTSTRAP_DELIVERY_UNKNOWN",
           );
         }
         continue;