diff --git a/bot_bottle/cli/start.py b/bot_bottle/cli/start.py
index afe78a8..27bcf3a 100644
--- a/bot_bottle/cli/start.py
+++ b/bot_bottle/cli/start.py
@@ -14,6 +14,7 @@ the private orchestrator `_launch_bottle`.
 from __future__ import annotations
 
 import argparse
+import io
 import os
 import shutil
 import sys
@@ -195,7 +196,11 @@ def _start_headless(
     path, so the agent still execs on the inherited stdio/PTY — an
     orchestrator allocates that PTY and relays it to its
     desktop/mobile clients."""
-    if not os.isatty(sys.stdin.fileno()):
+    try:
+        stdin_fd = sys.stdin.fileno()
+    except io.UnsupportedOperation:
+        stdin_fd = -1
+    if not os.isatty(stdin_fd):
         die(
             "--headless requires a PTY on stdin; run via:\n"
             "  script -q /dev/null ./cli.py start ..."
diff --git a/tests/unit/test_cli_start_headless.py b/tests/unit/test_cli_start_headless.py
index 48bc274..092b26c 100644
--- a/tests/unit/test_cli_start_headless.py
+++ b/tests/unit/test_cli_start_headless.py
@@ -69,6 +69,9 @@ class TestCmdStartHeadless(unittest.TestCase):
         self._modal = patch.object(tui_mod, "name_color_modal").start()
         patch.dict(os.environ, {}, clear=False).start()
         os.environ.pop("BOT_BOTTLE_BACKEND", None)
+        # PTY check uses os.isatty(sys.stdin.fileno()); stub both so
+        # headless unit tests aren't blocked on a real TTY.
+        patch("bot_bottle.cli.start.os.isatty", return_value=True).start()
         self.addCleanup(patch.stopall)
 
     def _spec(self):