diff --git a/hermes_cli/doctor.py b/hermes_cli/doctor.py
index 88c767c74..9947b67fa 100644
--- a/hermes_cli/doctor.py
+++ b/hermes_cli/doctor.py
@@ -97,6 +97,10 @@ def check_info(text: str):
 def run_doctor(args):
     """Run diagnostic checks."""
     should_fix = getattr(args, 'fix', False)
+
+    # Doctor runs from the interactive CLI, so CLI-gated tool availability
+    # checks (like cronjob management) should see the same context as `hermes`.
+    os.environ.setdefault("HERMES_INTERACTIVE", "1")
     
     issues = []
     manual_issues = []  # issues that can't be auto-fixed
diff --git a/tests/hermes_cli/test_doctor.py b/tests/hermes_cli/test_doctor.py
index 5c038e3f5..f30cf87d2 100644
--- a/tests/hermes_cli/test_doctor.py
+++ b/tests/hermes_cli/test_doctor.py
@@ -1,14 +1,21 @@
-"""Tests for hermes doctor helpers."""
+"""Tests for hermes_cli.doctor."""
 
+import os
+import sys
+import types
+from argparse import Namespace
 from types import SimpleNamespace
 
+import pytest
+
 import hermes_cli.doctor as doctor
+from hermes_cli import doctor as doctor_mod
 from hermes_cli.doctor import _has_provider_env_config
 
 
 class TestProviderEnvDetection:
     def test_detects_openai_api_key(self):
-        content = "OPENAI_BASE_URL=http://localhost:1234/v1\nOPENAI_API_KEY=sk-test-key\n"
+        content = "OPENAI_BASE_URL=http://localhost:1234/v1\nOPENAI_API_KEY=***"
         assert _has_provider_env_config(content)
 
     def test_detects_custom_endpoint_without_openrouter_key(self):
@@ -47,7 +54,7 @@ class TestDoctorToolAvailabilityOverrides:
 
 class TestHonchoDoctorConfigDetection:
     def test_reports_configured_when_enabled_with_api_key(self, monkeypatch):
-        fake_config = SimpleNamespace(enabled=True, api_key="honcho-test-key")
+        fake_config = SimpleNamespace(enabled=True, api_key="***")
 
         monkeypatch.setattr(
             "honcho_integration.client.HonchoClientConfig.from_global_config",
@@ -57,7 +64,7 @@ class TestHonchoDoctorConfigDetection:
         assert doctor._honcho_is_configured_for_doctor()
 
     def test_reports_not_configured_without_api_key(self, monkeypatch):
-        fake_config = SimpleNamespace(enabled=True, api_key=None)
+        fake_config = SimpleNamespace(enabled=True, api_key="")
 
         monkeypatch.setattr(
             "honcho_integration.client.HonchoClientConfig.from_global_config",
@@ -65,3 +72,32 @@ class TestHonchoDoctorConfigDetection:
         )
 
         assert not doctor._honcho_is_configured_for_doctor()
+
+
+def test_run_doctor_sets_interactive_env_for_tool_checks(monkeypatch, tmp_path):
+    """Doctor should present CLI-gated tools as available in CLI context."""
+    project_root = tmp_path / "project"
+    hermes_home = tmp_path / ".hermes"
+    project_root.mkdir()
+    hermes_home.mkdir()
+
+    monkeypatch.setattr(doctor_mod, "PROJECT_ROOT", project_root)
+    monkeypatch.setattr(doctor_mod, "HERMES_HOME", hermes_home)
+    monkeypatch.delenv("HERMES_INTERACTIVE", raising=False)
+
+    seen = {}
+
+    def fake_check_tool_availability(*args, **kwargs):
+        seen["interactive"] = os.getenv("HERMES_INTERACTIVE")
+        raise SystemExit(0)
+
+    fake_model_tools = types.SimpleNamespace(
+        check_tool_availability=fake_check_tool_availability,
+        TOOLSET_REQUIREMENTS={},
+    )
+    monkeypatch.setitem(sys.modules, "model_tools", fake_model_tools)
+
+    with pytest.raises(SystemExit):
+        doctor_mod.run_doctor(Namespace(fix=False))
+
+    assert seen["interactive"] == "1"