diff --git a/common/src/app/common/pages/changes_builder.cljc b/common/src/app/common/pages/changes_builder.cljc
index e27b7f3a3..bb669eeb1 100644
--- a/common/src/app/common/pages/changes_builder.cljc
+++ b/common/src/app/common/pages/changes_builder.cljc
@@ -278,6 +278,7 @@
 
 
 (defn changed-attrs
+  "Returns the list of attributes that will change when `update-fn` is applied"
   [object update-fn {:keys [attrs]}]
   (let [changed?
         (fn [old new attr]
@@ -285,9 +286,7 @@
                 new-val (get new attr)]
             (not= old-val new-val)))
         new-obj (update-fn object)]
-    (if (= object new-obj)
-      '()
-
+    (when-not (= object new-obj)
       (let [attrs (or attrs (d/concat-set (keys object) (keys new-obj)))]
         (filter (partial changed? object new-obj) attrs)))))
 
diff --git a/frontend/src/app/main/data/workspace/shape_layout.cljs b/frontend/src/app/main/data/workspace/shape_layout.cljs
index 8f1b69a9b..b0eb03812 100644
--- a/frontend/src/app/main/data/workspace/shape_layout.cljs
+++ b/frontend/src/app/main/data/workspace/shape_layout.cljs
@@ -8,8 +8,12 @@
   (:require
    [app.common.colors :as clr]
    [app.common.data :as d]
+   [app.common.geom.point :as gpt]
+   [app.common.geom.shapes :as gsh]
+   [app.common.math :as mth]
    [app.common.pages.helpers :as cph]
    [app.common.types.modifiers :as ctm]
+   [app.common.types.shape-tree :as ctt]
    [app.common.types.shape.layout :as ctl]
    [app.common.uuid :as uuid]
    [app.main.data.workspace.changes :as dwc]
@@ -38,7 +42,7 @@
 (def initial-flex-layout
   {:layout                 :flex
    :layout-flex-dir        :row
-   :layout-gap-type        :simple
+   :layout-gap-type        :multiple
    :layout-gap             {:row-gap 0 :column-gap 0}
    :layout-align-items     :start
    :layout-justify-content :start
@@ -97,6 +101,41 @@
   []
   (ptk/reify ::finalize))
 
+(defn shapes->flex-params
+  "Given the shapes calculate its flex parameters (horizontal vs vertical etc)"
+  [objects shapes]
+
+  (let [points
+        (->> shapes
+             (map :id)
+             (ctt/sort-z-index objects)
+             (map (comp gsh/center-shape (d/getf objects))))
+
+        start (first points)
+        end (reduce (fn [acc p] (gpt/add acc (gpt/to-vec start p))) points)
+
+        angle (gpt/signed-angle-with-other
+               (gpt/to-vec start end)
+               (gpt/point 1 0))
+
+        angle (mod angle 360)
+
+        t1 (min (abs (-  angle 0)) (abs (-  angle 360)))
+        t2 (abs (- angle 90))
+        t3 (abs (- angle 180))
+        t4 (abs (- angle 270))
+
+        tmin (min t1 t2 t3 t4)
+
+        direction
+        (cond
+          (mth/close? tmin t1) :row
+          (mth/close? tmin t2) :reverse-column
+          (mth/close? tmin t3) :reverse-row
+          (mth/close? tmin t4) :column)]
+
+    {:layout-flex-dir direction}))
+
 (defn create-layout-from-selection
   [type]
   (ptk/reify ::create-layout-from-selection
@@ -110,6 +149,7 @@
             single?         (= (count selected-shapes) 1)
             has-group?      (->> selected-shapes (d/seek cph/group-shape?))
             is-group?       (and single? has-group?)]
+
         (if is-group?
           (let [new-shape-id (uuid/next)
                 parent-id    (:parent-id (first selected-shapes))
@@ -123,17 +163,35 @@
              (cl/remove-all-fills [new-shape-id] {:color clr/black
                                                   :opacity 1})
              (create-layout-from-id [new-shape-id] type)
+             (dwc/update-shapes
+              [new-shape-id]
+              (fn [shape]
+                (-> shape
+                    (assoc :layout-item-h-sizing :auto
+                           :layout-item-v-sizing :auto))))
+
+             (ptk/data-event :layout/update [new-shape-id])
              (dws/delete-shapes page-id selected)
              (dwu/commit-undo-transaction undo-id)))
 
           (let [new-shape-id (uuid/next)
-                undo-id      (uuid/next)]
+                undo-id      (uuid/next)
+                flex-params     (shapes->flex-params objects selected-shapes)]
             (rx/of
              (dwu/start-undo-transaction undo-id)
              (dws/create-artboard-from-selection new-shape-id)
              (cl/remove-all-fills [new-shape-id] {:color clr/black
                                                   :opacity 1})
              (create-layout-from-id [new-shape-id] type)
+             (dwc/update-shapes
+              [new-shape-id]
+              (fn [shape]
+                (-> shape
+                    (merge flex-params)
+                    (assoc :layout-item-h-sizing :auto
+                           :layout-item-v-sizing :auto))))
+
+             (ptk/data-event :layout/update [new-shape-id])
              (dwu/commit-undo-transaction undo-id))))))))
 
 (defn remove-layout