diff --git a/packages/features/bookings/Booker/components/OverlayCalendar/OverlayCalendar.tsx b/packages/features/bookings/Booker/components/OverlayCalendar/OverlayCalendar.tsx
index 93354721db..0236732e0d 100644
--- a/packages/features/bookings/Booker/components/OverlayCalendar/OverlayCalendar.tsx
+++ b/packages/features/bookings/Booker/components/OverlayCalendar/OverlayCalendar.tsx
@@ -1,3 +1,5 @@
+import { useEffect } from "react";
+
 import { useIsPlatform } from "@calcom/atoms/hooks/useIsPlatform";
 
 import type { UseCalendarsReturnType } from "../hooks/useCalendars";
@@ -41,9 +43,16 @@ export const OverlayCalendar = ({
     checkIsCalendarToggled,
   } = useOverlayCalendar({ connectedCalendars, overlayBusyDates, onToggleCalendar });
 
+  // Adding to avoid flickering of continue modal due to stale state
+  useEffect(() => {
+    if (isOverlayCalendarEnabled) {
+      handleCloseContinueModal(false);
+    }
+  }, [isOverlayCalendarEnabled, handleCloseContinueModal]);
+
   // on platform we don't handle connecting to third party calendar via booker yet
   if (isPlatform && connectedCalendars?.length === 0) {
-    return <></>;
+    return null;
   }
 
   return (
@@ -55,7 +64,7 @@ export const OverlayCalendar = ({
       />
       {!isPlatform && (
         <OverlayCalendarContinueModal
-          open={isOpenOverlayContinueModal}
+          open={isOpenOverlayContinueModal && !isOverlayCalendarEnabled}
           onClose={handleCloseContinueModal}
           onContinue={handleClickContinue}
         />
diff --git a/packages/platform/atoms/booker/BookerWebWrapper.tsx b/packages/platform/atoms/booker/BookerWebWrapper.tsx
index db1304331c..49c8fc7041 100644
--- a/packages/platform/atoms/booker/BookerWebWrapper.tsx
+++ b/packages/platform/atoms/booker/BookerWebWrapper.tsx
@@ -209,6 +209,10 @@ export const BookerWebWrapper = (props: BookerWebWrapperAtomProps) => {
       )
   );
 
+  useEffect(() => {
+    if (hasSession) onOverlaySwitchStateChange(true);
+  }, [hasSession]);
+
   return (
     <BookerComponent
       {...props}