diff --git a/CHANGES.md b/CHANGES.md
index cbd35507d8..5173ea7910 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -37,6 +37,7 @@
 - Fix hovering over templates [Taiga #10545](https://tree.taiga.io/project/penpot/issue/10545)
 - Fix problem with default shadows value in plugins [Plugins #191](https://github.com/penpot/penpot-plugins/issues/191)
 - Fix problem with constraints when creating group [Taiga #10455](https://tree.taiga.io/project/penpot/issue/10455)
+- Fix opening pen with shortcut multiple times breaks toolbar [Taiga #10566](https://tree.taiga.io/project/penpot/issue/10566)
 
 ## 2.5.4
 
diff --git a/frontend/src/app/main/data/workspace/path/drawing.cljs b/frontend/src/app/main/data/workspace/path/drawing.cljs
index 631c28d323..be1bbfd2ff 100644
--- a/frontend/src/app/main/data/workspace/path/drawing.cljs
+++ b/frontend/src/app/main/data/workspace/path/drawing.cljs
@@ -324,7 +324,9 @@
       (let [id      (dm/get-in state [:workspace-local :edition])
             objects (dsh/lookup-page-objects state)
             content (dm/get-in objects [id :content])]
-        (update-in state [:workspace-local :edit-path id] assoc :old-content content)))
+        (if content
+          (update-in state [:workspace-local :edit-path id] assoc :old-content content)
+          state)))
 
     ptk/WatchEvent
     (watch [_ state stream]