diff --git a/excalidraw-app/sentry.ts b/excalidraw-app/sentry.ts
index 30b84f3f69..58e34bba53 100644
--- a/excalidraw-app/sentry.ts
+++ b/excalidraw-app/sentry.ts
@@ -1,3 +1,4 @@
+import { getFeatureFlag } from "@excalidraw/common";
 import * as Sentry from "@sentry/browser";
 import callsites from "callsites";
 
@@ -33,6 +34,7 @@ Sentry.init({
     Sentry.captureConsoleIntegration({
       levels: ["error"],
     }),
+    Sentry.featureFlagsIntegration(),
   ],
   beforeSend(event) {
     if (event.request?.url) {
@@ -79,3 +81,14 @@ Sentry.init({
     return event;
   },
 });
+
+const flagsIntegration =
+  Sentry.getClient()?.getIntegrationByName<Sentry.FeatureFlagsIntegration>(
+    "FeatureFlags",
+  );
+if (flagsIntegration) {
+  flagsIntegration.addFeatureFlag(
+    "COMPLEX_BINDINGS",
+    getFeatureFlag("COMPLEX_BINDINGS"),
+  );
+}
diff --git a/packages/element/src/binding.ts b/packages/element/src/binding.ts
index a7a4d7ffb3..ce0d5fada9 100644
--- a/packages/element/src/binding.ts
+++ b/packages/element/src/binding.ts
@@ -631,6 +631,7 @@ const getBindingStrategyForDraggingBindingElementEndpoints_simple = (
     );
   }
 
+  const otherBinding = startDragged ? arrow.endBinding : arrow.startBinding;
   const localPoint = draggingPoints.get(
     startDragged ? startIdx : endIdx,
   )?.point;
@@ -651,8 +652,31 @@ const getBindingStrategyForDraggingBindingElementEndpoints_simple = (
     elementsMap,
     (e) => maxBindingGap_simple(e, e.width, e.height, appState.zoom),
   );
+  const pointInElement = hit && isPointInElement(globalPoint, hit, elementsMap);
+
+  // Handle outside-outside binding with the same element
+  if (otherBinding && otherBinding.elementId === hit?.id && !pointInElement) {
+    const [startFixedPoint, endFixedPoint] = getGlobalFixedPoints(
+      arrow,
+      elementsMap,
+    );
+
+    return {
+      start: {
+        mode: "inside",
+        element: hit,
+        focusPoint: startDragged ? globalPoint : startFixedPoint,
+      },
+      end: {
+        mode: "inside",
+        element: hit,
+        focusPoint: endDragged ? globalPoint : endFixedPoint,
+      },
+    };
+  }
+
   const current: BindingStrategy = hit
-    ? isPointInElement(globalPoint, hit, elementsMap)
+    ? pointInElement
       ? {
           mode: "inside",
           element: hit,
diff --git a/packages/excalidraw/components/Settings/Settings.tsx b/packages/excalidraw/components/Settings/Settings.tsx
index 1b37b9a099..ce12c5d6cb 100644
--- a/packages/excalidraw/components/Settings/Settings.tsx
+++ b/packages/excalidraw/components/Settings/Settings.tsx
@@ -1,6 +1,7 @@
 import { useState } from "react";
 
 import { getFeatureFlag, setFeatureFlag } from "@excalidraw/common";
+import * as Sentry from "@sentry/browser";
 
 import { CheckboxItem } from "../CheckboxItem";
 import { Dialog } from "../Dialog";
@@ -42,7 +43,17 @@ export const Settings = () => {
       category: DEFAULT_SETTINGS_CATEGORIES.experimental,
       flagKey: "COMPLEX_BINDINGS",
       getValue: () => getFeatureFlag("COMPLEX_BINDINGS"),
-      setValue: (value: boolean) => setFeatureFlag("COMPLEX_BINDINGS", value),
+      setValue: (value: boolean) => {
+        const flagsIntegration =
+          Sentry.getClient()?.getIntegrationByName<Sentry.FeatureFlagsIntegration>(
+            "FeatureFlags",
+          );
+        if (flagsIntegration) {
+          flagsIntegration.addFeatureFlag("COMPLEX_BINDINGS", value);
+        }
+
+        setFeatureFlag("COMPLEX_BINDINGS", value);
+      },
     },
   ];