diff --git a/packages/cli/src/commands/spawn.ts b/packages/cli/src/commands/spawn.ts
index 62f30c0cb..e6713758f 100644
--- a/packages/cli/src/commands/spawn.ts
+++ b/packages/cli/src/commands/spawn.ts
@@ -132,8 +132,8 @@ async function spawnSession(
     if (claimedPrUrl) console.log(`  PR:       ${chalk.dim(claimedPrUrl)}`);
 
     // Warn if prompt delivery failed (for post-launch agents like Claude Code)
-    const promptDelivered = session.metadata?.promptDelivered === "true";
-    if (!promptDelivered) {
+    const promptDelivered = session.metadata?.promptDelivered;
+    if (promptDelivered === "false") {
       console.log();
       console.warn(
         chalk.yellow(
diff --git a/packages/core/src/session-manager.ts b/packages/core/src/session-manager.ts
index 2c2680cc6..d23333cc4 100644
--- a/packages/core/src/session-manager.ts
+++ b/packages/core/src/session-manager.ts
@@ -1210,6 +1210,12 @@ export function createSessionManager(deps: SessionManagerDeps): OpenCodeSessionM
       }
 
       session.metadata["promptDelivered"] = String(promptDelivered);
+    } else if (agentLaunchConfig.prompt) {
+      session.metadata["promptDelivered"] = "true";
+    }
+
+    if (session.metadata["promptDelivered"]) {
+      updateMetadata(sessionsDir, sessionId, session.metadata);
     }
 
     return session;