diff --git a/erpnext/venue/doctype/item_booking/item_booking.py b/erpnext/venue/doctype/item_booking/item_booking.py
index 15d17f61015c9551eaaac4ceadf491cdf540fe8e..42ba68c87e1fac53b6065871a08a9855ec953066 100644
--- a/erpnext/venue/doctype/item_booking/item_booking.py
+++ b/erpnext/venue/doctype/item_booking/item_booking.py
@@ -1984,16 +1984,44 @@ def move_booking_with_event(doc, method):
 	doc_before_save = doc.get_doc_before_save()
 	if doc_before_save and getdate(doc_before_save.starts_on) != getdate(doc.starts_on):
 		days = date_diff(doc.starts_on, doc_before_save.starts_on)
-		bookings = frappe.get_all(
-			"Item Booking", filters={"event": doc.name}, fields=["name", "starts_on", "ends_on"]
+		frappe.msgprint(
+			msg=_("Would you like to move the associated item bookings from {0} days ?").format(days),
+			title=_("Associated bookings"),
+			primary_action={
+				"server_action": "erpnext.venue.doctype.item_booking.item_booking.offset_linked_bookings",
+				"args": {"event": doc.name, "offset": days},
+				"hide_on_success": True,
+				"label": _("Offset bookings")
+			}
 		)
 
-		for booking in bookings:
-			doc = frappe.get_doc("Item Booking", booking.name)
-			doc.starts_on = add_days(booking.starts_on, days)
-			doc.ends_on = add_days(booking.ends_on, days)
+@frappe.whitelist()
+def offset_linked_bookings(args):
+	parsed_args: dict = frappe.parse_json(args) # type: ignore
+	event = parsed_args.get("event")
+	offset = parsed_args.get("offset") or 0
+
+	if not event:
+		return
+
+	bookings = frappe.get_all(
+		"Item Booking", filters={"event": event}, fields=["name", "starts_on", "ends_on"]
+	)
+
+	for booking in bookings:
+		try:
+			doc: ItemBooking = frappe.get_doc("Item Booking", booking.name) # type: ignore
+			doc.starts_on = add_to_date(booking.starts_on, days=offset, as_datetime=True)
+			doc.ends_on = add_to_date(booking.ends_on, days=offset, as_datetime=True)
 			doc.flags.ignore_permissions = True
 			doc.save()
+		except ExceptionTooManyBookings:
+			frappe.msgprint(
+				msg=_("Booking for {0} ({1}) could not be offset because it overlaps with existing bookings on the same slot").format(doc.booking_resource, doc.name),
+				alert=True,
+				indicator="red",
+				realtime=True
+			)
 
 
 @frappe.whitelist()