diff --git a/hermes_cli/_early_recovery.py b/hermes_cli/_early_recovery.py
index 1eb0d21ed1..e049fb7253 100644
--- a/hermes_cli/_early_recovery.py
+++ b/hermes_cli/_early_recovery.py
@@ -96,8 +96,17 @@ _UPDATE_RETRY_RECOVERED = False
 
 
 def _should_skip_external_secret_sources() -> bool:
-    """Whether this updater already completed its deferred native install."""
-    return _UPDATE_RETRY_RECOVERED
+    """True inside any ``hermes update`` process (and its import probes).
+
+    Every dotenv load in the process — ``hermes_cli.main``, ``run_agent``, ``cli`` — consults
+    this, so the updater never resolves external secret sources: on Windows they map
+    ``cryptography._rust.pyd`` into the process replacing that venv, and everywhere a slow
+    ``op``/``bws``/command helper (up to 120s per source) would run inside the updater's
+    120s critical-module import probe and be reported as an import-health timeout.
+    Profile flags are stripped before ``hermes_cli.main`` loads dotenv, so ``argv[1]`` is
+    the authoritative subcommand.
+    """
+    return _UPDATE_RETRY_RECOVERED or sys.argv[1:2] == ["update"]
 
 
 def _project_root() -> Path:
diff --git a/hermes_cli/main.py b/hermes_cli/main.py
index 535580b596..70182df53d 100644
--- a/hermes_cli/main.py
+++ b/hermes_cli/main.py
@@ -586,17 +586,10 @@ if sys.platform == "win32":
 from hermes_cli.config import get_hermes_home
 from hermes_cli.env_loader import load_hermes_dotenv
 
-# ``update`` must not import optional secret-manager libs before ``uv``
-# replaces the environment: on Windows Bitwarden's cryptography import maps
-# ``_rust.pyd`` and the parent updater then blocks its own child installer.
-# Profile flags are already stripped, so argv[1] is the authoritative subcommand.
-# Profile flags have already been stripped above, so the first remaining argument is the authoritative
-# argparse subcommand. Dotenv/managed config still loads; only external secret fetches are unnecessary for
-# installation maintenance. See #73381.
-load_hermes_dotenv(
-    project_env=PROJECT_ROOT / ".env",
-    load_external_secrets=sys.argv[1:2] != ["update"],
-)
+# ``update`` must not resolve external secret sources (Windows self-lock via cryptography, slow
+# helpers inside the import probe) — ``_early_recovery._should_skip_external_secret_sources``
+# owns that argv check for every dotenv load in the process. See #73381.
+load_hermes_dotenv(project_env=PROJECT_ROOT / ".env")
 
 # Bridge security.redact_secrets → HERMES_REDACT_SECRETS BEFORE hermes_logging
 # imports agent.redact, which snapshots the flag exactly once at import. A
diff --git a/hermes_cli/update_cmd_deps.py b/hermes_cli/update_cmd_deps.py
index 7e3362f3ad..5b2cd19d0c 100644
--- a/hermes_cli/update_cmd_deps.py
+++ b/hermes_cli/update_cmd_deps.py
@@ -58,6 +58,10 @@ def _critical_module_import_failures(
     marker = f"__HERMES_IMPORT_HEALTH_{secrets.token_hex(16)}__"
     probe = (
         "import importlib, json, sys\n"
+        # Importing hermes_cli.main runs the startup dotenv load, which pulls external secret
+        # sources (op/bws/command helpers, up to 120s each) unless argv says ``update``. The
+        # probe only checks importability, so it inherits the updater's own argv contract.
+        "sys.argv = ['hermes', 'update']\n"
         "failures = []\n"
         "for name in %r:\n"
         "    try:\n"
diff --git a/tests/hermes_cli/test_update_secret_import_lock.py b/tests/hermes_cli/test_update_secret_import_lock.py
index 3dd95042d5..5bcf976b12 100644
--- a/tests/hermes_cli/test_update_secret_import_lock.py
+++ b/tests/hermes_cli/test_update_secret_import_lock.py
@@ -117,3 +117,27 @@ def test_dotenv_loading_is_preserved_when_external_secrets_are_skipped(
     assert loaded == [env_file]
     assert os.environ["UPDATE_TEST_VALUE"] == "from-dotenv"
     assert applied == ([home] if external_secrets else [])
+
+
+@pytest.mark.skipif(sys.platform == "win32", reason="the 'command' secret source is POSIX-only")
+def test_update_probe_children_skip_external_secret_sources(tmp_path):
+    """The critical-module import probe imports ``run_agent``, whose dotenv load must not run a
+    configured secret helper: a slow helper (op/bws/command, 120s budget) inside the 120s probe
+    surfaced as ``timed out before reporting import health`` on a healthy install (#110823)."""
+    home = tmp_path / "hermes-home"
+    home.mkdir()
+    hit = tmp_path / "helper_hit"
+    (home / "config.yaml").write_text(
+        f"secrets:\n  command:\n    enabled: true\n    command: 'touch {hit}'\n", encoding="utf-8",
+    )
+    result = subprocess.run(
+        [sys.executable, "-c",
+         "import sys; sys.argv = ['hermes', 'update']\n"
+         "from hermes_cli.update_cmd_deps import _validate_critical_modules_import\n"
+         "print('PROBE=' + repr(_validate_critical_modules_import(__import__('os').getcwd())))"],
+        capture_output=True, text=True, timeout=180, cwd=REPO_ROOT,
+        env={**os.environ, "HERMES_HOME": str(home)},
+    )
+    assert result.returncode == 0, result.stderr
+    assert "PROBE=(True, None, None)" in result.stdout, result.stdout + result.stderr
+    assert not hit.exists(), "the import probe resolved external secret sources"
diff --git a/tests/test_hermes_logging.py b/tests/test_hermes_logging.py
index 9e2129fd05..6a2073ea8b 100644
--- a/tests/test_hermes_logging.py
+++ b/tests/test_hermes_logging.py
@@ -604,19 +604,37 @@ class TestExternalRotationRecovery:
         assert "AFTER rotation" not in rotated.read_text()
 
 
-def test_eio_from_file_handler_is_suppressed(tmp_path, capsys):
-    """An unavailable log destination must not print a traceback per record."""
-    handler = hermes_logging._ManagedRotatingFileHandler(
-        str(tmp_path / "agent.log"), maxBytes=1024, backupCount=1, encoding="utf-8",
-    )
-    record = logging.LogRecord("test.eio", logging.INFO, __file__, 0, "message", (), None)
-    try:
-        try:
-            raise OSError(5, "Input/output error")
-        except OSError:
-            handler.handleError(record)
+def test_eio_from_file_handler_names_the_path_once_then_recovers(tmp_path, capsys):
+    """A failing log destination is named once (no per-record traceback) and writes resume
+    once the file is reachable again."""
+    import io
 
-        assert "--- Logging error ---" not in capsys.readouterr().err
+    class _SickStream(io.TextIOBase):
+        def writable(self):
+            return True
+
+        def write(self, _s):
+            raise OSError(5, "Input/output error")
+
+        seek = tell = flush = write
+
+    path = tmp_path / "agent.log"
+    handler = hermes_logging._ManagedRotatingFileHandler(
+        str(path), maxBytes=1024, backupCount=1, encoding="utf-8",
+    )
+    handler.setFormatter(logging.Formatter("%(message)s"))
+    try:
+        handler.stream.close()
+        handler.stream = _SickStream()
+        for i in range(5):
+            handler.handle(logging.LogRecord("t", logging.INFO, __file__, 0, f"sick {i}", (), None))
+        err = capsys.readouterr().err
+        assert "--- Logging error ---" not in err
+        assert err.count(str(path)) == 1 and "Input/output error" in err
+
+        # Stream dropped, so the next emit reopens the real file and logging resumes.
+        handler.handle(logging.LogRecord("t", logging.INFO, __file__, 0, "recovered", (), None))
+        assert "recovered" in path.read_text(encoding="utf-8")
     finally:
         handler.close()