diff --git a/apps/server/src/keybindings.test.ts b/apps/server/src/keybindings.test.ts
index b674688f0410..aec04b467d28 100644
--- a/apps/server/src/keybindings.test.ts
+++ b/apps/server/src/keybindings.test.ts
@@ -436,6 +436,29 @@ it.layer(NodeServices.layer)("keybindings", (it) => {
     }).pipe(Effect.provide(makeKeybindingsLayer())),
   );
 
+  it.effect("replaces a rule whose stored key uses an alias spelling", () =>
+    Effect.gen(function* () {
+      const { keybindingsConfigPath } = yield* ServerConfig.ServerConfig;
+      yield* writeKeybindingsConfig(keybindingsConfigPath, [
+        { key: "escape", command: "script.run-tests.run" },
+      ]);
+      yield* Effect.gen(function* () {
+        const keybindings = yield* Keybindings.Keybindings;
+        // The settings UI renders a stored "escape" rule as "esc", so the
+        // replace target arrives spelled differently than it was persisted.
+        return yield* keybindings.upsertKeybindingRule({
+          key: "mod+m",
+          command: "script.run-tests.run",
+          replace: { key: "esc", command: "script.run-tests.run" },
+        });
+      });
+
+      const persisted = yield* readKeybindingsConfig(keybindingsConfigPath);
+      const persistedView = persisted.map(({ key, command }) => ({ key, command }));
+      assert.deepEqual(persistedView, [{ key: "mod+m", command: "script.run-tests.run" }]);
+    }).pipe(Effect.provide(makeKeybindingsLayer())),
+  );
+
   it.effect("removes only the targeted custom keybinding", () =>
     Effect.gen(function* () {
       const { keybindingsConfigPath } = yield* ServerConfig.ServerConfig;
diff --git a/apps/server/src/keybindings.ts b/apps/server/src/keybindings.ts
index 10d98bf64290..e48280e4071f 100644
--- a/apps/server/src/keybindings.ts
+++ b/apps/server/src/keybindings.ts
@@ -101,11 +101,21 @@ export const ResolvedKeybindingsFromConfig = Schema.Array(ResolvedKeybindingFrom
 );
 
 function isSameKeybindingRule(left: KeybindingRule, right: KeybindingRule): boolean {
-  return (
-    left.command === right.command &&
-    left.key === right.key &&
-    (left.when ?? undefined) === (right.when ?? undefined)
-  );
+  if (left.command !== right.command) return false;
+  if ((left.when ?? undefined) !== (right.when ?? undefined)) return false;
+  if (left.key === right.key) return true;
+  // A key can be spelled more than one way ("esc"/"escape", "space"/" "), and
+  // the settings UI renders a stored rule back as the alias. Comparing raw
+  // strings would then fail to match a rule against itself, so replacing that
+  // rule would leave the original behind instead of updating it.
+  const leftKey = canonicalKeybindingKey(left);
+  return leftKey !== null && leftKey === canonicalKeybindingKey(right);
+}
+
+function canonicalKeybindingKey(rule: KeybindingRule): string | null {
+  const parsed = parseKeybindingShortcut(rule.key);
+  if (!parsed) return null;
+  return encodeShortcut(parsed);
 }
 
 function keybindingShortcutContext(rule: KeybindingRule): string | null {