diff --git a/src/cli/handlers/session-init.ts b/src/cli/handlers/session-init.ts
index 2e9679bd..095f9497 100644
--- a/src/cli/handlers/session-init.ts
+++ b/src/cli/handlers/session-init.ts
@@ -43,7 +43,9 @@ export const sessionInitHandler: EventHandler = {
     });
 
     if (!initResponse.ok) {
-      throw new Error(`Session initialization failed: ${initResponse.status}`);
+      // Log but don't throw - a worker 500 should not block the user's prompt
+      logger.failure('HOOK', `Session initialization failed: ${initResponse.status}`, { contentSessionId: sessionId, project });
+      return { continue: true, suppressOutput: true, exitCode: HOOK_EXIT_CODES.SUCCESS };
     }
 
     const initResult = await initResponse.json() as {
@@ -86,7 +88,8 @@ export const sessionInitHandler: EventHandler = {
       });
 
       if (!response.ok) {
-        throw new Error(`SDK agent start failed: ${response.status}`);
+        // Log but don't throw - SDK agent failure should not block the user's prompt
+        logger.failure('HOOK', `SDK agent start failed: ${response.status}`, { sessionDbId, promptNumber });
       }
     } else if (input.platform === 'cursor') {
       logger.debug('HOOK', 'session-init: Skipping SDK agent init for Cursor platform', { sessionDbId, promptNumber });
diff --git a/src/cli/handlers/user-message.ts b/src/cli/handlers/user-message.ts
index 061e3dfb..248efb0f 100644
--- a/src/cli/handlers/user-message.ts
+++ b/src/cli/handlers/user-message.ts
@@ -1,8 +1,8 @@
 /**
  * User Message Handler - SessionStart (parallel)
  *
- * Extracted from user-message-hook.ts - displays context info to user via stderr.
- * Uses exit code 3 to show user message without injecting into Claude's context.
+ * Displays context info to user via stderr.
+ * Uses exit code 0 (SUCCESS) - stderr is not shown to Claude with exit 0.
  */
 
 import { basename } from 'path';
@@ -26,21 +26,24 @@ export const userMessageHandler: EventHandler = {
     );
 
     if (!response.ok) {
-      throw new Error(`Failed to fetch context: ${response.status}`);
+      // Don't throw - context fetch failure should not block the user's prompt
+      return { exitCode: HOOK_EXIT_CODES.SUCCESS };
     }
 
     const output = await response.text();
 
-    // Write to stderr for user visibility (Claude Code UI shows stderr)
-    console.error(
-      "\n\n" + String.fromCodePoint(0x1F4DD) + " Claude-Mem Context Loaded\n" +
-      "   " + String.fromCodePoint(0x2139, 0xFE0F) + "  Note: This appears as stderr but is informational only\n\n" +
+    // Write to stderr for user visibility
+    // Note: Using process.stderr.write instead of console.error to avoid
+    // Claude Code treating this as a hook error. The actual hook output
+    // goes to stdout via hook-command.ts JSON serialization.
+    process.stderr.write(
+      "\n\n" + String.fromCodePoint(0x1F4DD) + " Claude-Mem Context Loaded\n\n" +
       output +
-      "\n\n" + String.fromCodePoint(0x1F4A1) + " New! Wrap all or part of any message with <private> ... </private> to prevent storing sensitive information in your observation history.\n" +
+      "\n\n" + String.fromCodePoint(0x1F4A1) + " Wrap any message with <private> ... </private> to prevent storing sensitive information.\n" +
       "\n" + String.fromCodePoint(0x1F4AC) + " Community https://discord.gg/J4wttp9vDu" +
       `\n` + String.fromCodePoint(0x1F4FA) + ` Watch live in browser http://localhost:${port}/\n`
     );
 
-    return { exitCode: HOOK_EXIT_CODES.USER_MESSAGE_ONLY };
+    return { exitCode: HOOK_EXIT_CODES.SUCCESS };
   }
 };