diff --git a/hermes_cli/main.py b/hermes_cli/main.py
index ddaa3ee3198..f4356f2c62a 100644
--- a/hermes_cli/main.py
+++ b/hermes_cli/main.py
@@ -2358,7 +2358,11 @@ def cmd_chat(args):
     except Exception:
         pass
 
-    # --yolo: bypass all dangerous command approvals
+    # --yolo: bypass all dangerous command approvals.
+    # Also set in main() before _prepare_agent_startup() — that is the
+    # authoritative site because it runs before tool imports freeze
+    # _YOLO_MODE_FROZEN.  This redundant set is a safety net for callers
+    # that invoke cmd_chat directly (e.g. subcommand dispatch).
     if getattr(args, "yolo", False):
         os.environ["HERMES_YOLO_MODE"] = "1"
 
@@ -14627,6 +14631,15 @@ def main():
         cmd_version(args)
         return
 
+    # --yolo: set HERMES_YOLO_MODE *before* plugin discovery.  The call to
+    # _prepare_agent_startup() below triggers discover_plugins() → tool
+    # imports, and tools.approval freezes _YOLO_MODE_FROZEN at module
+    # import time (PR #7994, security hardening against prompt-injection).
+    # If the env var is set only later (e.g. inside cmd_chat), the frozen
+    # value is already False and --yolo silently does nothing.
+    if getattr(args, "yolo", False):
+        os.environ["HERMES_YOLO_MODE"] = "1"
+
     # Discover Python plugins and register shell hooks once, before any
     # command that can fire lifecycle hooks.  Both are idempotent; gated
     # so introspection/management commands (hermes hooks list, cron
diff --git a/tests/hermes_cli/test_yolo_startup_order.py b/tests/hermes_cli/test_yolo_startup_order.py
new file mode 100644
index 00000000000..6d30b776fbd
--- /dev/null
+++ b/tests/hermes_cli/test_yolo_startup_order.py
@@ -0,0 +1,77 @@
+"""Regression tests for #60328: --yolo must set HERMES_YOLO_MODE in
+main() before _prepare_agent_startup() triggers tool imports.
+
+The freeze mechanism in tools.approval (_YOLO_MODE_FROZEN) is correct
+by design (PR #7994). The bug was that main() set the env var inside
+cmd_chat(), which runs *after* _prepare_agent_startup() has already
+imported tools.approval and frozen the constant to False.
+
+These tests verify the ordering in main() itself: the env var must
+already be set at the moment _prepare_agent_startup() is called.
+If someone moves the assignment back into cmd_chat(), these tests
+fail — catching the exact #60328 regression.
+"""
+
+import os
+import sys
+
+
+def _run_main_and_capture_yolo_at_startup(monkeypatch, argv):
+    """Run main() with *argv*, capturing HERMES_YOLO_MODE at the
+    moment _prepare_agent_startup is called.
+
+    Returns the captured env var value (or None if unset).
+    """
+    yolo_at_startup = {}
+
+    def spy_prepare_startup(args):
+        yolo_at_startup["value"] = os.environ.get("HERMES_YOLO_MODE")
+
+    monkeypatch.setattr(
+        "hermes_cli.main._prepare_agent_startup", spy_prepare_startup
+    )
+    # Stub cmd_chat so main() returns cleanly without entering chat.
+    monkeypatch.setattr("hermes_cli.main.cmd_chat", lambda args: None)
+    monkeypatch.delenv("HERMES_YOLO_MODE", raising=False)
+    monkeypatch.setattr(sys, "argv", argv)
+
+    from hermes_cli.main import main as cli_main
+
+    cli_main()
+
+    return yolo_at_startup.get("value")
+
+
+def test_top_level_yolo_flag_sets_env_before_startup(monkeypatch):
+    """hermes --yolo must set HERMES_YOLO_MODE before
+    _prepare_agent_startup imports tools.approval."""
+    result = _run_main_and_capture_yolo_at_startup(
+        monkeypatch, ["hermes", "--yolo"]
+    )
+    assert result == "1", (
+        "HERMES_YOLO_MODE was not '1' when _prepare_agent_startup was "
+        "called from main() with --yolo. This is the #60328 regression: "
+        "the env var is set too late (inside cmd_chat, after tool imports)."
+    )
+
+
+def test_chat_subcommand_yolo_flag_sets_env_before_startup(monkeypatch):
+    """hermes chat --yolo must also set HERMES_YOLO_MODE before
+    _prepare_agent_startup."""
+    result = _run_main_and_capture_yolo_at_startup(
+        monkeypatch, ["hermes", "chat", "--yolo"]
+    )
+    assert result == "1", (
+        "HERMES_YOLO_MODE was not '1' when _prepare_agent_startup was "
+        "called from main() with 'chat --yolo'."
+    )
+
+
+def test_no_yolo_flag_leaves_env_unset_at_startup(monkeypatch):
+    """Without --yolo, HERMES_YOLO_MODE must not be set at startup."""
+    result = _run_main_and_capture_yolo_at_startup(
+        monkeypatch, ["hermes"]
+    )
+    assert result is None, (
+        "HERMES_YOLO_MODE was unexpectedly set at startup without --yolo."
+    )