diff --git a/tests/tools/test_cron_not_interactive.py b/tests/tools/test_cron_not_interactive.py
index e00579bf43..0228c4ea48 100644
--- a/tests/tools/test_cron_not_interactive.py
+++ b/tests/tools/test_cron_not_interactive.py
@@ -1,9 +1,10 @@
 """Unattended approval contexts never resolve as interactive (#110932).
 
 A gateway sets HERMES_EXEC_ASK=1 at startup and hands its environ to every external cron
-worker; interactive launches export HERMES_INTERACTIVE=1. Inside cron (or a programmatic
-platform session) nobody can answer the card, so ``_presence()`` must clear the trio and let
-the gate resolve from ``approvals.cron_mode`` / ``approvals.unattended_mode``.
+worker; interactive launches export HERMES_INTERACTIVE=1. Inside cron nobody can answer the
+card, so ``_presence()`` must clear the trio and let the gate resolve from
+``approvals.cron_mode``. Unattended platforms are NOT cleared: api_server answers via the
+``/v1/runs`` approval bridge, which needs ``is_ask`` intact.
 """
 
 import pytest
@@ -21,14 +22,8 @@ def leaked_presence(monkeypatch):
     monkeypatch.delenv("HERMES_SESSION_PLATFORM", raising=False)
 
 
-@pytest.mark.parametrize(
-    "unattended_env",
-    [{"HERMES_CRON_SESSION": "1"}, {"HERMES_SESSION_PLATFORM": "webhook"}],
-    ids=["cron", "webhook"],
-)
-def test_unattended_context_clears_leaked_presence(monkeypatch, leaked_presence, unattended_env):
-    for key, value in unattended_env.items():
-        monkeypatch.setenv(key, value)
+def test_cron_context_clears_leaked_presence(monkeypatch, leaked_presence):
+    monkeypatch.setenv("HERMES_CRON_SESSION", "1")
     _, is_cli, is_gateway, is_ask = approval_mod._presence()
     assert (is_cli, is_gateway, is_ask) == (False, False, False)
 
@@ -36,3 +31,11 @@ def test_unattended_context_clears_leaked_presence(monkeypatch, leaked_presence,
 def test_interactive_session_keeps_presence(monkeypatch, leaked_presence):
     _, is_cli, is_gateway, is_ask = approval_mod._presence()
     assert (is_cli, is_gateway, is_ask) == (True, True, True)
+
+
+def test_api_server_platform_keeps_exec_ask_for_runs_approval_bridge(monkeypatch, leaked_presence):
+    """api_server resolves approvals via ``approval.request`` → ``POST /v1/runs/{id}/approval``;
+    clearing ``is_ask`` there would turn every dangerous command into an instant BLOCK."""
+    monkeypatch.setenv("HERMES_SESSION_PLATFORM", "api_server")
+    _, _, _, is_ask = approval_mod._presence()
+    assert is_ask is True
diff --git a/tests/tools/test_cronjob_tools.py b/tests/tools/test_cronjob_tools.py
index 32dc66a37b..b80dd0e7e5 100644
--- a/tests/tools/test_cronjob_tools.py
+++ b/tests/tools/test_cronjob_tools.py
@@ -207,6 +207,15 @@ class TestCronjobRequirements:
         assert check_cronjob_requirements() is True
 
 
+    def test_accepts_external_cron_worker_with_presence_vars_stripped(self, monkeypatch):
+        """``_launch_external_cron_worker`` strips the presence trio from the worker env; the
+        cron session marker alone must keep ``cron.allow_agent_scheduling: true`` effective."""
+        for v in ("HERMES_INTERACTIVE", "HERMES_GATEWAY_SESSION", "HERMES_EXEC_ASK"):
+            monkeypatch.delenv(v, raising=False)
+        monkeypatch.setenv("HERMES_CRON_SESSION", "1")
+
+        assert check_cronjob_requirements() is True
+
     @pytest.mark.parametrize(
         "var_name",
         ["HERMES_INTERACTIVE", "HERMES_GATEWAY_SESSION", "HERMES_EXEC_ASK"],
diff --git a/tools/approval.py b/tools/approval.py
index 3a3761be6c..f5082238d9 100644
--- a/tools/approval.py
+++ b/tools/approval.py
@@ -869,16 +869,16 @@ def _human_decision(spec: _GateSpec, *, command: str, description: str,
 def _presence(approval_callback=None) -> tuple:
     """``(approval_callback, is_cli, is_gateway, is_ask)`` for the current context.
 
-    Every unattended context (single-query ``-q``, cron, programmatic platforms) clears the
-    presence trio: ``hermes chat -q`` exports HERMES_INTERACTIVE=1 for sudo prompts, a gateway
-    sets HERMES_EXEC_ASK=1 at startup and passes its environ to every external cron worker
-    (#110932), and a webhook session inherits that same HERMES_EXEC_ASK — in none of them can a
-    human answer the card, so the gate must resolve from ``approvals.<ctx>_mode`` instead of
-    parking on a pending approval."""
+    Single-query ``-q`` and cron clear the presence trio: ``hermes chat -q`` exports
+    HERMES_INTERACTIVE=1 for sudo prompts, and a gateway sets HERMES_EXEC_ASK=1 at startup and
+    passes its environ to every external cron worker (#110932) — in neither can a human answer
+    the card, so the gate must resolve from ``approvals.<ctx>_mode`` instead of parking on a
+    pending approval. Unattended *platforms* keep ``is_ask``: api_server relies on it for the
+    ``/v1/runs`` approval bridge (``approval.request`` → ``POST /v1/runs/{id}/approval``)."""
     approval_callback = _resolve_cli_approval_callback(approval_callback)
     is_cli, is_gateway = _is_interactive_cli(), _is_gateway_approval_context()
     is_ask = env_var_enabled("HERMES_EXEC_ASK")
-    if _unattended_contexts():
+    if _is_single_query_approval_context() or _is_cron_approval_context():
         is_cli = is_gateway = is_ask = False
     return approval_callback, is_cli, is_gateway, is_ask
 
diff --git a/tools/cronjob_tools.py b/tools/cronjob_tools.py
index 79048541b8..d9073638b5 100644
--- a/tools/cronjob_tools.py
+++ b/tools/cronjob_tools.py
@@ -1094,13 +1094,17 @@ Jobs run in a fresh session with no current-chat context, so prompts must be sel
 
 
 def check_cronjob_requirements() -> bool:
-    """Available in interactive CLI mode and gateway/messaging platforms (the scheduler is
-    internal; no crontab needed). Flags must be explicitly truthy via ``env_var_enabled``."""
-    from utils import env_var_enabled
+    """Available in interactive CLI mode, gateway/messaging platforms, and cron runs (the
+    scheduler is internal; no crontab needed). Flags must be explicitly truthy via
+    ``env_var_enabled``. An external cron worker has the presence vars stripped from its env, so
+    the cron session marker keeps ``cron.allow_agent_scheduling`` meaningful there."""
+    from gateway.session_context import get_session_env
+    from utils import env_var_enabled, is_truthy_value
     return (
         env_var_enabled("HERMES_INTERACTIVE")
         or env_var_enabled("HERMES_GATEWAY_SESSION")
         or env_var_enabled("HERMES_EXEC_ASK")
+        or is_truthy_value(get_session_env("HERMES_CRON_SESSION", ""))
     )