diff --git a/src/element/resizeElements.ts b/src/element/resizeElements.ts
index ff7956f38..8ab611069 100644
--- a/src/element/resizeElements.ts
+++ b/src/element/resizeElements.ts
@@ -20,6 +20,7 @@ import {
   getCommonBoundingBox,
 } from "./bounds";
 import {
+  isBoundToContainer,
   isFreeDrawElement,
   isLinearElement,
   isTextElement,
@@ -39,9 +40,11 @@ import {
   getApproxMinLineWidth,
   getBoundTextElement,
   getBoundTextElementId,
+  getContainerElement,
   handleBindTextResize,
   measureText,
 } from "./textElement";
+import { getMaxContainerWidth } from "./newElement";
 
 export const normalizeAngle = (angle: number): number => {
   if (angle >= 2 * Math.PI) {
@@ -182,14 +185,21 @@ const measureFontSizeFromWH = (
   nextHeight: number,
 ): { size: number; baseline: number } | null => {
   // We only use width to scale font on resize
-  const nextFontSize = element.fontSize * (nextWidth / element.width);
+  let width = element.width;
+
+  const hasContainer = isBoundToContainer(element);
+  if (hasContainer) {
+    const container = getContainerElement(element)!;
+    width = getMaxContainerWidth(container);
+  }
+  const nextFontSize = element.fontSize * (nextWidth / width);
   if (nextFontSize < MIN_FONT_SIZE) {
     return null;
   }
   const metrics = measureText(
     element.text,
     getFontString({ fontSize: nextFontSize, fontFamily: element.fontFamily }),
-    element.containerId ? element.width : null,
+    hasContainer ? width : null,
   );
   return {
     size: nextFontSize,
diff --git a/src/element/textWysiwyg.test.tsx b/src/element/textWysiwyg.test.tsx
index c900ba62f..6456781d5 100644
--- a/src/element/textWysiwyg.test.tsx
+++ b/src/element/textWysiwyg.test.tsx
@@ -1099,5 +1099,27 @@ describe("textWysiwyg", () => {
         { id: text.id, type: "text" },
       ]);
     });
+
+    it("should scale font size correctly when resizing using shift", async () => {
+      Keyboard.keyPress(KEYS.ENTER);
+
+      const editor = document.querySelector(
+        ".excalidraw-textEditorContainer > textarea",
+      ) as HTMLTextAreaElement;
+      await new Promise((r) => setTimeout(r, 0));
+      fireEvent.change(editor, { target: { value: "Hello" } });
+      editor.blur();
+      const textElement = h.elements[1] as ExcalidrawTextElement;
+      expect(rectangle.width).toBe(90);
+      expect(rectangle.height).toBe(75);
+      expect(textElement.fontSize).toBe(20);
+
+      resize(rectangle, "ne", [rectangle.x + 100, rectangle.y - 50], {
+        shift: true,
+      });
+      expect(rectangle.width).toBe(200);
+      expect(rectangle.height).toBe(166.66666666666669);
+      expect(textElement.fontSize).toBe(47.5);
+    });
   });
 });
diff --git a/src/element/typeChecks.ts b/src/element/typeChecks.ts
index fdebca875..053b31ccb 100644
--- a/src/element/typeChecks.ts
+++ b/src/element/typeChecks.ts
@@ -139,6 +139,9 @@ export const isBoundToContainer = (
   element: ExcalidrawElement | null,
 ): element is ExcalidrawTextElementWithContainer => {
   return (
-    element !== null && isTextElement(element) && element.containerId !== null
+    element !== null &&
+    "containerId" in element &&
+    element.containerId !== null &&
+    isTextElement(element)
   );
 };