diff --git a/tests/tools/test_approval.py b/tests/tools/test_approval.py
index a36b2e1f8..0cb4c3571 100644
--- a/tests/tools/test_approval.py
+++ b/tests/tools/test_approval.py
@@ -2,12 +2,14 @@
 
 from unittest.mock import patch as mock_patch
 
+import tools.approval as approval_module
 from tools.approval import (
     approve_session,
     clear_session,
     detect_dangerous_command,
     has_pending,
     is_approved,
+    load_permanent,
     pop_pending,
     prompt_dangerous_approval,
     submit_pending,
@@ -368,6 +370,20 @@ class TestPatternKeyUniqueness:
         )
         clear_session(session)
 
+    def test_legacy_find_key_still_approves_find_exec(self):
+        """Old allowlist entry 'find' should keep approving the matching command."""
+        _, key_exec, _ = detect_dangerous_command("find . -exec rm {} \\;")
+        with mock_patch.object(approval_module, "_permanent_approved", set()):
+            load_permanent({"find"})
+            assert is_approved("legacy-find", key_exec) is True
+
+    def test_legacy_find_key_still_approves_find_delete(self):
+        """Old colliding allowlist entry 'find' should remain backwards compatible."""
+        _, key_delete, _ = detect_dangerous_command("find . -name '*.tmp' -delete")
+        with mock_patch.object(approval_module, "_permanent_approved", set()):
+            load_permanent({"find"})
+            assert is_approved("legacy-find", key_delete) is True
+
 
 class TestViewFullCommand:
     """Tests for the 'view full command' option in prompt_dangerous_approval."""
diff --git a/tools/approval.py b/tools/approval.py
index 21baedbd0..7c376f0e9 100644
--- a/tools/approval.py
+++ b/tools/approval.py
@@ -50,6 +50,29 @@ DANGEROUS_PATTERNS = [
 ]
 
 
+def _legacy_pattern_key(pattern: str) -> str:
+    """Reproduce the old regex-derived approval key for backwards compatibility."""
+    return pattern.split(r'\b')[1] if r'\b' in pattern else pattern[:20]
+
+
+_PATTERN_KEY_ALIASES: dict[str, set[str]] = {}
+for _pattern, _description in DANGEROUS_PATTERNS:
+    _legacy_key = _legacy_pattern_key(_pattern)
+    _canonical_key = _description
+    _PATTERN_KEY_ALIASES.setdefault(_canonical_key, set()).update({_canonical_key, _legacy_key})
+    _PATTERN_KEY_ALIASES.setdefault(_legacy_key, set()).update({_legacy_key, _canonical_key})
+
+
+def _approval_key_aliases(pattern_key: str) -> set[str]:
+    """Return all approval keys that should match this pattern.
+
+    New approvals use the human-readable description string, but older
+    command_allowlist entries and session approvals may still contain the
+    historical regex-derived key.
+    """
+    return _PATTERN_KEY_ALIASES.get(pattern_key, {pattern_key})
+
+
 # =========================================================================
 # Detection
 # =========================================================================
@@ -103,11 +126,17 @@ def approve_session(session_key: str, pattern_key: str):
 
 
 def is_approved(session_key: str, pattern_key: str) -> bool:
-    """Check if a pattern is approved (session-scoped or permanent)."""
+    """Check if a pattern is approved (session-scoped or permanent).
+
+    Accept both the current canonical key and the legacy regex-derived key so
+    existing command_allowlist entries continue to work after key migrations.
+    """
+    aliases = _approval_key_aliases(pattern_key)
     with _lock:
-        if pattern_key in _permanent_approved:
+        if any(alias in _permanent_approved for alias in aliases):
             return True
-        return pattern_key in _session_approved.get(session_key, set())
+        session_approvals = _session_approved.get(session_key, set())
+        return any(alias in session_approvals for alias in aliases)
 
 
 def approve_permanent(pattern_key: str):