diff --git a/frontend/src/app/main/data/workspace.cljs b/frontend/src/app/main/data/workspace.cljs
index 449bc5956..23629fb39 100644
--- a/frontend/src/app/main/data/workspace.cljs
+++ b/frontend/src/app/main/data/workspace.cljs
@@ -1324,10 +1324,33 @@
   (ptk/reify ::show-context-menu
     ptk/UpdateEvent
     (update [_ state]
-      (let [mdata (cond-> params
-                    (some? shape)
-                    (assoc :selected
-                           (wsh/lookup-selected state)))]
+      (let [selected (wsh/lookup-selected state)
+            objects (wsh/lookup-page-objects state)
+
+            selected-with-children
+            (into []
+                  (mapcat #(cp/get-object-with-children % objects))
+                  selected)
+
+            head (get objects (first selected))
+
+            first-not-group-like?
+            (and (= (count selected) 1)
+                 (not (contains? #{:group :bool} (:type head))))
+
+            has-invalid-shapes? (->> selected-with-children
+                                     (some (comp #{:frame :text} :type)))
+
+            disable-booleans? (or (empty? selected) has-invalid-shapes? first-not-group-like?)
+            disable-flatten? (or (empty? selected) has-invalid-shapes?)
+
+            mdata
+            (-> params
+                (assoc :disable-booleans? disable-booleans?)
+                (assoc :disable-flatten? disable-flatten?)
+                (cond-> (some? shape)
+                  (assoc :selected selected)))]
+
         (assoc-in state [:workspace-local :context-menu] mdata)))))
 
 (defn show-shape-context-menu
diff --git a/frontend/src/app/main/ui/workspace/context_menu.cljs b/frontend/src/app/main/ui/workspace/context_menu.cljs
index 6833c4070..9cdae0466 100644
--- a/frontend/src/app/main/ui/workspace/context_menu.cljs
+++ b/frontend/src/app/main/ui/workspace/context_menu.cljs
@@ -87,15 +87,15 @@
 
 (mf/defc shape-context-menu
   [{:keys [mdata] :as props}]
-  (let [{:keys [id] :as shape} (:shape mdata)
-        selected (:selected mdata)
+  (let [{:keys [shape selected disable-booleans? disable-flatten?]} mdata
+        {:keys [id type]} shape
 
         single? (= (count selected) 1)
         multiple? (> (count selected) 1)
-        editable-shape? (#{:group :text :path} (:type shape))
+        editable-shape? (#{:group :text :path} type)
 
-        is-group? (and (some? shape) (= :group (:type shape)))
-        is-bool?  (and (some? shape) (= :bool (:type shape)))
+        is-group? (and (some? shape) (= :group type))
+        is-bool?  (and (some? shape) (= :bool type))
 
         options (mf/deref refs/workspace-page-options)
         flows   (:flows options)
@@ -235,10 +235,12 @@
                        :shortcut (sc/get-tooltip :start-editing)
                        :on-click do-start-editing}])
 
-     [:& menu-entry {:title (tr "workspace.shape.menu.transform-to-path")
-                     :on-click do-transform-to-path}]
+     (when-not disable-flatten?
+       [:& menu-entry {:title (tr "workspace.shape.menu.transform-to-path")
+                       :on-click do-transform-to-path}])
 
-     (when (or multiple? (and single? (or is-group? is-bool?)))
+     (when (and (not disable-booleans?)
+                (or multiple? (and single? (or is-group? is-bool?))))
        [:& menu-entry {:title (tr "workspace.shape.menu.path")}
         [:& menu-entry {:title (tr "workspace.shape.menu.union")
                         :shortcut (sc/get-tooltip :boolean-union)
@@ -253,7 +255,7 @@
                         :shortcut (sc/get-tooltip :boolean-exclude)
                         :on-click (set-bool :exclude)}]
 
-        (when (and single? is-bool?)
+        (when (and single? is-bool? (not disable-flatten?))
           [:*
            [:& menu-separator]
            [:& menu-entry {:title (tr "workspace.shape.menu.flatten")
diff --git a/frontend/src/app/main/ui/workspace/sidebar/options/menus/booleans.cljs b/frontend/src/app/main/ui/workspace/sidebar/options/menus/booleans.cljs
index 64b287417..80b2be852 100644
--- a/frontend/src/app/main/ui/workspace/sidebar/options/menus/booleans.cljs
+++ b/frontend/src/app/main/ui/workspace/sidebar/options/menus/booleans.cljs
@@ -17,19 +17,22 @@
 (mf/defc booleans-options
   []
   (let [selected (mf/deref refs/selected-objects)
+        selected-with-children (mf/deref refs/selected-objects-with-children)
 
-        disabled-bool-btns
-        (or (empty? selected)
-            (and (<= (count selected) 1)
-                 (not (contains? #{:group :bool} (:type (first selected))))))
+        has-invalid-shapes? (->> selected-with-children
+                                 (some (comp #{:frame :text} :type)))
 
-        disabled-flatten
-        (empty? selected)
+        first-not-group-like?
+        (and (= (count selected) 1)
+             (not (contains? #{:group :bool} (:type (first selected)))))
+
+        disabled-bool-btns (or (empty? selected) has-invalid-shapes? first-not-group-like?)
+        disabled-flatten (or (empty? selected) has-invalid-shapes?)
 
         head (first selected)
         is-group? (and (some? head) (= :group (:type head)))
         is-bool?  (and (some? head) (= :bool (:type head)))
-        head-bool-type (and (some? head) (:bool-type head))
+        head-bool-type (and (some? head) is-bool? (:bool-type head))
 
         set-bool
         (fn [bool-type]