diff --git a/src/vs/workbench/contrib/customEditor/browser/customEditorInput.ts b/src/vs/workbench/contrib/customEditor/browser/customEditorInput.ts
index 964a6a0443b..55bb2295d65 100644
--- a/src/vs/workbench/contrib/customEditor/browser/customEditorInput.ts
+++ b/src/vs/workbench/contrib/customEditor/browser/customEditorInput.ts
@@ -152,6 +152,11 @@ export class CustomEditorInput extends LazilyResolvedWebviewEditorInput {
 
 		if (this.resource.scheme === Schemas.untitled) {
 			capabilities |= EditorInputCapabilities.Untitled;
+			capabilities |= EditorInputCapabilities.AuxWindowUnsupported;
+		}
+
+		if (this.isDirty()) {
+			capabilities |= EditorInputCapabilities.AuxWindowUnsupported;
 		}
 
 		return capabilities;
diff --git a/src/vs/workbench/contrib/webview/browser/overlayWebview.ts b/src/vs/workbench/contrib/webview/browser/overlayWebview.ts
index a5cfe2c7e89..c47093f3967 100644
--- a/src/vs/workbench/contrib/webview/browser/overlayWebview.ts
+++ b/src/vs/workbench/contrib/webview/browser/overlayWebview.ts
@@ -123,6 +123,9 @@ export class OverlayWebview extends Disposable implements IOverlayWebview {
 		if (this._windowId !== targetWindow.vscodeWindowId) {
 			// moving to a new window
 			this.release(oldOwner);
+			// since we are moving to a new window, we need to dispose the webview and recreate
+			this._webview.clear();
+			this._webviewEvents.clear();
 			this._container?.domNode.remove();
 			this._container = undefined;
 		}