diff --git a/packages/app-store/googlecalendar/api/callback.ts b/packages/app-store/googlecalendar/api/callback.ts
index 1aec90fbe0..cebf818d61 100644
--- a/packages/app-store/googlecalendar/api/callback.ts
+++ b/packages/app-store/googlecalendar/api/callback.ts
@@ -2,6 +2,7 @@ import type { Auth } from "googleapis";
 import { google } from "googleapis";
 import type { NextApiRequest, NextApiResponse } from "next";
 
+import { renewSelectedCalendarCredentialId } from "@calcom/lib/connectedCalendar";
 import { WEBAPP_URL_FOR_OAUTH, WEBAPP_URL } from "@calcom/lib/constants";
 import { getSafeRedirectUrl } from "@calcom/lib/getSafeRedirectUrl";
 import { HttpError } from "@calcom/lib/http-error";
@@ -105,23 +106,38 @@ async function getHandler(req: NextApiRequest, res: NextApiResponse) {
         appId: "google-calendar",
       },
     });
+
+    const selectedCalendarWhereUnique = {
+      userId: req.session.user.id,
+      externalId: primaryCal.id,
+      integration: "google_calendar",
+    };
+
     // Wrapping in a try/catch to reduce chance of race conditions-
     // also this improves performance for most of the happy-paths.
     try {
       await prisma.selectedCalendar.create({
         data: {
-          userId: req.session.user.id,
-          externalId: primaryCal.id,
           credentialId: credential.id,
-          integration: "google_calendar",
+          ...selectedCalendarWhereUnique,
         },
       });
     } catch (error) {
-      await prisma.credential.delete({ where: { id: credential.id } });
       let errorMessage = "something_went_wrong";
       if (error instanceof Prisma.PrismaClientKnownRequestError && error.code === "P2002") {
+        // it is possible a selectedCalendar was orphaned, in this situation-
+        // we want to recover by connecting the existing selectedCalendar to the new Credential.
+        if (await renewSelectedCalendarCredentialId(selectedCalendarWhereUnique, credential.id)) {
+          res.redirect(
+            getSafeRedirectUrl(state?.returnTo) ??
+              getInstalledAppPath({ variant: "calendar", slug: "google-calendar" })
+          );
+          return;
+        }
+        // else
         errorMessage = "account_already_linked";
       }
+      await prisma.credential.delete({ where: { id: credential.id } });
       res.redirect(
         `${
           getSafeRedirectUrl(state?.onErrorReturnTo) ??
diff --git a/packages/app-store/office365calendar/api/callback.ts b/packages/app-store/office365calendar/api/callback.ts
index 05d283af70..6877144053 100644
--- a/packages/app-store/office365calendar/api/callback.ts
+++ b/packages/app-store/office365calendar/api/callback.ts
@@ -1,6 +1,7 @@
 import type { Calendar as OfficeCalendar } from "@microsoft/microsoft-graph-types-beta";
 import type { NextApiRequest, NextApiResponse } from "next";
 
+import { renewSelectedCalendarCredentialId } from "@calcom/lib/connectedCalendar";
 import { WEBAPP_URL } from "@calcom/lib/constants";
 import { handleErrorsJson } from "@calcom/lib/errors";
 import { getSafeRedirectUrl } from "@calcom/lib/getSafeRedirectUrl";
@@ -119,23 +120,36 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
         appId: "office365-calendar",
       },
     });
+    const selectedCalendarWhereUnique = {
+      userId: req.session?.user.id,
+      integration: "office365_calendar",
+      externalId: defaultCalendar.id,
+    };
     // Wrapping in a try/catch to reduce chance of race conditions-
     // also this improves performance for most of the happy-paths.
     try {
       await prisma.selectedCalendar.create({
         data: {
-          userId: req.session?.user.id,
-          integration: "office365_calendar",
-          externalId: defaultCalendar.id,
+          ...selectedCalendarWhereUnique,
           credentialId: credential.id,
         },
       });
     } catch (error) {
-      await prisma.credential.delete({ where: { id: credential.id } });
       let errorMessage = "something_went_wrong";
       if (error instanceof Prisma.PrismaClientKnownRequestError && error.code === "P2002") {
+        // it is possible a selectedCalendar was orphaned, in this situation-
+        // we want to recover by connecting the existing selectedCalendar to the new Credential.
+        if (await renewSelectedCalendarCredentialId(selectedCalendarWhereUnique, credential.id)) {
+          res.redirect(
+            getSafeRedirectUrl(state?.returnTo) ??
+              getInstalledAppPath({ variant: "calendar", slug: "office365-calendar" })
+          );
+          return;
+        }
+        // else
         errorMessage = "account_already_linked";
       }
+      await prisma.credential.delete({ where: { id: credential.id } });
       res.redirect(
         `${
           getSafeRedirectUrl(state?.onErrorReturnTo) ??
@@ -146,8 +160,9 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
     }
   }
 
-  return res.redirect(
+  res.redirect(
     getSafeRedirectUrl(state?.returnTo) ??
       getInstalledAppPath({ variant: "calendar", slug: "office365-calendar" })
   );
+  return;
 }
diff --git a/packages/app-store/zohocalendar/api/callback.ts b/packages/app-store/zohocalendar/api/callback.ts
index fcc01265fc..2ffa8373cd 100644
--- a/packages/app-store/zohocalendar/api/callback.ts
+++ b/packages/app-store/zohocalendar/api/callback.ts
@@ -1,6 +1,7 @@
 import type { NextApiRequest, NextApiResponse } from "next";
 import { stringify } from "querystring";
 
+import { renewSelectedCalendarCredentialId } from "@calcom/lib/connectedCalendar";
 import { WEBAPP_URL } from "@calcom/lib/constants";
 import { getSafeRedirectUrl } from "@calcom/lib/getSafeRedirectUrl";
 import logger from "@calcom/lib/logger";
@@ -86,23 +87,36 @@ async function getHandler(req: NextApiRequest, res: NextApiResponse) {
         appId: config.slug,
       },
     });
+    const selectedCalendarWhereUnique = {
+      userId: req.session?.user.id,
+      integration: config.type,
+      externalId: primaryCalendar.uid,
+    };
     // Wrapping in a try/catch to reduce chance of race conditions-
     // also this improves performance for most of the happy-paths.
     try {
       await prisma.selectedCalendar.create({
         data: {
-          userId: req.session.user.id,
-          integration: config.type,
-          externalId: primaryCalendar.uid,
+          ...selectedCalendarWhereUnique,
           credentialId: credential.id,
         },
       });
     } catch (error) {
-      await prisma.credential.delete({ where: { id: credential.id } });
       let errorMessage = "something_went_wrong";
       if (error instanceof Prisma.PrismaClientKnownRequestError && error.code === "P2002") {
+        // it is possible a selectedCalendar was orphaned, in this situation-
+        // we want to recover by connecting the existing selectedCalendar to the new Credential.
+        if (await renewSelectedCalendarCredentialId(selectedCalendarWhereUnique, credential.id)) {
+          res.redirect(
+            getSafeRedirectUrl(state?.returnTo) ??
+              getInstalledAppPath({ variant: "calendar", slug: config.slug })
+          );
+          return;
+        }
+        // else
         errorMessage = "account_already_linked";
       }
+      await prisma.credential.delete({ where: { id: credential.id } });
       res.redirect(
         `${
           getSafeRedirectUrl(state?.onErrorReturnTo) ??
diff --git a/packages/lib/connectedCalendar.ts b/packages/lib/connectedCalendar.ts
new file mode 100644
index 0000000000..b25c23c544
--- /dev/null
+++ b/packages/lib/connectedCalendar.ts
@@ -0,0 +1,29 @@
+import prisma from "@calcom/prisma";
+
+export async function renewSelectedCalendarCredentialId(
+  selectedCalendarWhereUnique: {
+    userId: number;
+    integration: string;
+    externalId: string;
+  },
+  credentialId: number
+): Promise<boolean> /* True if renewed, false if not */ {
+  const selectedCalendar = await prisma.selectedCalendar.findFirst({
+    where: {
+      ...selectedCalendarWhereUnique,
+      credentialId: null,
+    },
+  });
+  if (selectedCalendar) {
+    await prisma.selectedCalendar.update({
+      where: {
+        userId_integration_externalId: selectedCalendarWhereUnique,
+      },
+      data: {
+        credentialId: credentialId,
+      },
+    });
+    return true;
+  }
+  return false;
+}