diff --git a/apps/web/components/DestinationCalendarSelector.tsx b/apps/web/components/DestinationCalendarSelector.tsx
index fb515ea99b..7f6933bd28 100644
--- a/apps/web/components/DestinationCalendarSelector.tsx
+++ b/apps/web/components/DestinationCalendarSelector.tsx
@@ -25,20 +25,18 @@ const DestinationCalendarSelector = ({
   const [selectedOption, setSelectedOption] = useState<{ value: string; label: string } | null>(null);
 
   useEffect(() => {
-    if (!selectedOption) {
-      const selected = query.data?.connectedCalendars
-        .map((connected) => connected.calendars ?? [])
-        .flat()
-        .find((cal) => cal.externalId === value);
+    const selected = query.data?.connectedCalendars
+      .map((connected) => connected.calendars ?? [])
+      .flat()
+      .find((cal) => cal.externalId === value);
 
-      if (selected) {
-        setSelectedOption({
-          value: `${selected.integration}:${selected.externalId}`,
-          label: selected.name || "",
-        });
-      }
+    if (selected) {
+      setSelectedOption({
+        value: `${selected.integration}:${selected.externalId}`,
+        label: selected.name || "",
+      });
     }
-  }, [query.data?.connectedCalendars, selectedOption, value]);
+  }, [query.data?.connectedCalendars, value]);
 
   if (!query.data?.connectedCalendars.length) {
     return null;
diff --git a/apps/web/server/routers/viewer.tsx b/apps/web/server/routers/viewer.tsx
index 4ed8e024f4..58b97ff114 100644
--- a/apps/web/server/routers/viewer.tsx
+++ b/apps/web/server/routers/viewer.tsx
@@ -429,6 +429,50 @@ const loggedInViewerRouter = createProtectedRouter()
       // get all the connected integrations' calendars (from third party)
       const connectedCalendars = await getConnectedCalendars(calendarCredentials, user.selectedCalendars);
 
+      if (connectedCalendars.length === 0) {
+        /* As there are no connected calendars, delete the destination calendar if it exists */
+        if (user.destinationCalendar) {
+          await ctx.prisma.destinationCalendar.delete({
+            where: { userId: user.id },
+          });
+          user.destinationCalendar = null;
+        }
+      } else if (!user.destinationCalendar) {
+        /*
+        There are connected calendars, but no destination calendar
+        So create a default destination calendar with the first primary connected calendar
+        */
+        const { integration = "", externalId = "" } = connectedCalendars[0].primary ?? {};
+        user.destinationCalendar = await ctx.prisma.destinationCalendar.create({
+          data: {
+            userId: user.id,
+            integration,
+            externalId,
+          },
+        });
+      } else {
+        /* There are connected calendars and a destination calendar */
+
+        // Check if destinationCalendar exists in connectedCalendars
+        const allCals = connectedCalendars.map((cal) => cal.calendars ?? []).flat();
+        const destinationCal = allCals.find(
+          (cal) =>
+            cal.externalId === user.destinationCalendar?.externalId &&
+            cal.integration === user.destinationCalendar?.integration
+        );
+        if (!destinationCal) {
+          // If destinationCalendar is out of date, update it with the first primary connected calendar
+          const { integration = "", externalId = "" } = connectedCalendars[0].primary ?? {};
+          user.destinationCalendar = await ctx.prisma.destinationCalendar.update({
+            where: { userId: user.id },
+            data: {
+              integration,
+              externalId,
+            },
+          });
+        }
+      }
+
       return {
         connectedCalendars,
         destinationCalendar: user.destinationCalendar,