diff --git a/agent/claude_wrapper.py b/agent/claude_wrapper.py
index 33aa1198..05dd054f 100644
--- a/agent/claude_wrapper.py
+++ b/agent/claude_wrapper.py
@@ -44,8 +44,23 @@ class ClaudeError(RuntimeError):
     """Raised when the claude CLI returns a non-zero exit or unparseable output."""
 
 
+def _session_exists(session_id: str) -> bool:
+    """True if Claude Code has already persisted a JSONL for this session.
+
+    Claude Code stores sessions at ~/.claude/projects/<encoded-cwd>/<uuid>.jsonl
+    where non-alphanumerics in the cwd are replaced with hyphens.
+    """
+    encoded = "".join(c if c.isalnum() else "-" for c in CLAUDE_CWD)
+    path = Path.home() / ".claude" / "projects" / encoded / f"{session_id}.jsonl"
+    return path.is_file()
+
+
 async def ask_claude(message: str, session_id: str) -> ClaudeResult:
-    """Send `message` to `claude -p` resuming session_id; return parsed result.
+    """Send `message` to `claude -p` for `session_id`; return parsed result.
+
+    On the FIRST message of a session uses `--session-id <uuid>` to create it.
+    On subsequent messages uses `--resume <uuid>` because claude rejects
+    `--session-id` on existing sessions ("Session ID ... is already in use").
 
     Raises ClaudeError on subprocess failure, JSON parse failure, or timeout.
     """
@@ -75,10 +90,15 @@ async def ask_claude(message: str, session_id: str) -> ClaudeResult:
         ]
     )
 
+    # Pick --session-id (creates) vs --resume (continues) based on whether
+    # the session JSONL already exists on disk.
+    is_new = not _session_exists(session_id)
+    session_flag = "--session-id" if is_new else "--resume"
+
     args = [
         CLAUDE_BIN,
         "-p",
-        "--session-id",
+        session_flag,
         session_id,
         "--output-format",
         "json",
@@ -90,7 +110,11 @@ async def ask_claude(message: str, session_id: str) -> ClaudeResult:
     ]
 
     logger.info(
-        "claude exec: session=%s msg_len=%d cwd=%s", session_id, len(message), CLAUDE_CWD
+        "claude exec: session=%s mode=%s msg_len=%d cwd=%s",
+        session_id,
+        "new" if is_new else "resume",
+        len(message),
+        CLAUDE_CWD,
     )
 
     proc = await asyncio.create_subprocess_exec(
@@ -114,9 +138,41 @@ async def ask_claude(message: str, session_id: str) -> ClaudeResult:
         raise ClaudeError(f"claude timed out after {CLAUDE_TIMEOUT_S}s")
 
     if proc.returncode != 0:
-        raise ClaudeError(
-            f"claude exited {proc.returncode}: {stderr.decode('utf-8', 'replace')[:500]}"
-        )
+        stderr_text = stderr.decode("utf-8", "replace")
+        # If we picked the wrong flag (e.g. JSONL deleted from disk between
+        # our check and exec, or a never-flushed session), claude prints
+        # "Session ID … is already in use." Re-issue with --resume.
+        if is_new and "already in use" in stderr_text:
+            logger.info("session %s actually exists; retrying with --resume", session_id)
+            args2 = list(args)
+            args2[2] = "--resume"
+            proc2 = await asyncio.create_subprocess_exec(
+                *args2,
+                stdin=asyncio.subprocess.PIPE,
+                stdout=asyncio.subprocess.PIPE,
+                stderr=asyncio.subprocess.PIPE,
+                cwd=CLAUDE_CWD,
+            )
+            try:
+                stdout, stderr = await asyncio.wait_for(
+                    proc2.communicate(input=message.encode("utf-8")),
+                    timeout=CLAUDE_TIMEOUT_S,
+                )
+            except asyncio.TimeoutError:
+                try:
+                    proc2.kill()
+                except ProcessLookupError:
+                    pass
+                raise ClaudeError(f"claude timed out after {CLAUDE_TIMEOUT_S}s")
+            if proc2.returncode != 0:
+                raise ClaudeError(
+                    f"claude exited {proc2.returncode} after retry: "
+                    f"{stderr.decode('utf-8', 'replace')[:500]}"
+                )
+        else:
+            raise ClaudeError(
+                f"claude exited {proc.returncode}: {stderr_text[:500]}"
+            )
 
     raw_text = stdout.decode("utf-8", "replace").strip()
     if not raw_text: