diff --git a/apps/api/v2/src/ee/calendars/services/apple-calendar.service.ts b/apps/api/v2/src/ee/calendars/services/apple-calendar.service.ts
index e04ee36b7f..d54f4b0df5 100644
--- a/apps/api/v2/src/ee/calendars/services/apple-calendar.service.ts
+++ b/apps/api/v2/src/ee/calendars/services/apple-calendar.service.ts
@@ -5,7 +5,8 @@ import { BadRequestException, UnauthorizedException } from "@nestjs/common";
 import { Injectable } from "@nestjs/common";
 
 import { SUCCESS_STATUS, APPLE_CALENDAR_TYPE, APPLE_CALENDAR_ID } from "@calcom/platform-constants";
-import { symmetricEncrypt, CalendarService } from "@calcom/platform-libraries";
+import { symmetricEncrypt, CalendarService, symmetricDecrypt } from "@calcom/platform-libraries";
+import { Credential } from "@calcom/prisma/client";
 
 @Injectable()
 export class AppleCalendarService implements CredentialSyncCalendarApp {
@@ -61,26 +62,70 @@ export class AppleCalendarService implements CredentialSyncCalendarApp {
     if (username.length <= 1 || password.length <= 1)
       throw new BadRequestException(`Username or password cannot be empty`);
 
-    const data = {
-      type: APPLE_CALENDAR_TYPE,
-      key: symmetricEncrypt(
-        JSON.stringify({ username, password }),
-        process.env.CALENDSO_ENCRYPTION_KEY || ""
-      ),
-      userId: userId,
-      teamId: null,
-      appId: APPLE_CALENDAR_ID,
-      invalid: false,
-    };
+    const existingAppleCalendarCredentials = await this.credentialRepository.getAllUserCredentialsByTypeAndId(
+      APPLE_CALENDAR_TYPE,
+      userId
+    );
+
+    let hasMatchingUsernameAndPassword = false;
+
+    if (existingAppleCalendarCredentials.length > 0) {
+      const hasCalendarWithGivenCredentials = existingAppleCalendarCredentials.find(
+        (calendarCredential: Credential) => {
+          const decryptedKey = JSON.parse(
+            symmetricDecrypt(calendarCredential.key as string, process.env.CALENDSO_ENCRYPTION_KEY || "")
+          );
+
+          if (decryptedKey.username === username) {
+            if (decryptedKey.password === password) {
+              hasMatchingUsernameAndPassword = true;
+            }
+
+            return true;
+          }
+        }
+      );
+
+      if (!!hasCalendarWithGivenCredentials && hasMatchingUsernameAndPassword) {
+        return {
+          status: SUCCESS_STATUS,
+        };
+      }
+
+      if (!!hasCalendarWithGivenCredentials && !hasMatchingUsernameAndPassword) {
+        await this.credentialRepository.upsertAppCredential(
+          APPLE_CALENDAR_TYPE,
+          symmetricEncrypt(JSON.stringify({ username, password }), process.env.CALENDSO_ENCRYPTION_KEY || ""),
+          userId,
+          hasCalendarWithGivenCredentials.id
+        );
+
+        return {
+          status: SUCCESS_STATUS,
+        };
+      }
+    }
 
     try {
+      const data = {
+        type: APPLE_CALENDAR_TYPE,
+        key: symmetricEncrypt(
+          JSON.stringify({ username, password }),
+          process.env.CALENDSO_ENCRYPTION_KEY || ""
+        ),
+        userId: userId,
+        teamId: null,
+        appId: APPLE_CALENDAR_ID,
+        invalid: false,
+      };
+
       const dav = new CalendarService({
         id: 0,
         ...data,
         user: { email: userEmail },
       });
       await dav?.listCalendars();
-      await this.credentialRepository.createAppCredential(APPLE_CALENDAR_TYPE, data.key, userId);
+      await this.credentialRepository.upsertAppCredential(APPLE_CALENDAR_TYPE, data.key, userId);
     } catch (reason) {
       throw new BadRequestException(`Could not add this apple calendar account: ${reason}`);
     }
diff --git a/apps/api/v2/src/ee/calendars/services/calendars.service.ts b/apps/api/v2/src/ee/calendars/services/calendars.service.ts
index 4f509f1935..ba2ce7b2a8 100644
--- a/apps/api/v2/src/ee/calendars/services/calendars.service.ts
+++ b/apps/api/v2/src/ee/calendars/services/calendars.service.ts
@@ -6,6 +6,7 @@ import {
 } from "@/modules/credentials/credentials.repository";
 import { PrismaReadService } from "@/modules/prisma/prisma-read.service";
 import { PrismaWriteService } from "@/modules/prisma/prisma-write.service";
+import { SelectedCalendarsRepository } from "@/modules/selected-calendars/selected-calendars.repository";
 import { UsersRepository } from "@/modules/users/users.repository";
 import {
   Injectable,
@@ -15,9 +16,11 @@ import {
 } from "@nestjs/common";
 import { ConfigService } from "@nestjs/config";
 import { User } from "@prisma/client";
+import { Prisma } from "@prisma/client";
 import { DateTime } from "luxon";
 import { z } from "zod";
 
+import { APPS_TYPE_ID_MAPPING } from "@calcom/platform-constants";
 import { getConnectedDestinationCalendars, getBusyCalendarTimes } from "@calcom/platform-libraries";
 import { Calendar } from "@calcom/platform-types";
 import { PrismaClient } from "@calcom/prisma";
@@ -33,7 +36,8 @@ export class CalendarsService {
     private readonly calendarsRepository: CalendarsRepository,
     private readonly dbRead: PrismaReadService,
     private readonly dbWrite: PrismaWriteService,
-    private readonly config: ConfigService
+    private readonly config: ConfigService,
+    private readonly selectedCalendarsRepository: SelectedCalendarsRepository
   ) {}
 
   async getCalendars(userId: number) {
@@ -145,4 +149,32 @@ export class CalendarsService {
       throw new NotFoundException("Calendar credentials not found");
     }
   }
+
+  async createAndLinkCalendarEntry(
+    userId: number,
+    externalId: string,
+    key: Prisma.InputJsonValue,
+    calendarType: keyof typeof APPS_TYPE_ID_MAPPING,
+    credentialId?: number | null
+  ) {
+    const credential = await this.credentialsRepository.upsertAppCredential(
+      calendarType,
+      key,
+      userId,
+      credentialId
+    );
+
+    await this.selectedCalendarsRepository.upsertSelectedCalendar(
+      externalId,
+      credential.id,
+      userId,
+      calendarType
+    );
+  }
+
+  async checkCalendarCredentialValidity(userId: number, credentialId: number, type: string) {
+    const credential = await this.credentialsRepository.getUserCredentialById(userId, credentialId, type);
+
+    return !credential?.invalid;
+  }
 }
diff --git a/apps/api/v2/src/ee/calendars/services/gcal.service.ts b/apps/api/v2/src/ee/calendars/services/gcal.service.ts
index 9f0d25471c..ea1d220d41 100644
--- a/apps/api/v2/src/ee/calendars/services/gcal.service.ts
+++ b/apps/api/v2/src/ee/calendars/services/gcal.service.ts
@@ -131,11 +131,6 @@ export class GoogleCalendarService implements OAuthCalendarApp {
     const token = await oAuth2Client.getToken(parsedCode);
     // Google oAuth Credentials are stored in token.tokens
     const key = token.tokens;
-    const credential = await this.credentialRepository.createAppCredential(
-      GOOGLE_CALENDAR_TYPE,
-      key as Prisma.InputJsonValue,
-      ownerId
-    );
 
     oAuth2Client.setCredentials(key);
 
@@ -149,10 +144,39 @@ export class GoogleCalendarService implements OAuthCalendarApp {
     const primaryCal = cals.data.items?.find((cal) => cal.primary);
 
     if (primaryCal?.id) {
-      await this.selectedCalendarsRepository.createSelectedCalendar(
-        primaryCal.id,
-        credential.id,
+      const alreadyExistingSelectedCalendar = await this.selectedCalendarsRepository.getUserSelectedCalendar(
         ownerId,
+        GOOGLE_CALENDAR_TYPE,
+        primaryCal.id
+      );
+
+      if (alreadyExistingSelectedCalendar) {
+        const isCredentialValid = await this.calendarsService.checkCalendarCredentialValidity(
+          ownerId,
+          alreadyExistingSelectedCalendar.credentialId ?? 0,
+          GOOGLE_CALENDAR_TYPE
+        );
+
+        // user credential probably got expired in this case
+        if (!isCredentialValid) {
+          await this.calendarsService.createAndLinkCalendarEntry(
+            ownerId,
+            alreadyExistingSelectedCalendar.externalId,
+            key as Prisma.InputJsonValue,
+            GOOGLE_CALENDAR_TYPE,
+            alreadyExistingSelectedCalendar.credentialId
+          );
+        }
+
+        return {
+          url: redir || origin,
+        };
+      }
+
+      await this.calendarsService.createAndLinkCalendarEntry(
+        ownerId,
+        primaryCal.id,
+        key as Prisma.InputJsonValue,
         GOOGLE_CALENDAR_TYPE
       );
     }
diff --git a/apps/api/v2/src/ee/calendars/services/outlook.service.ts b/apps/api/v2/src/ee/calendars/services/outlook.service.ts
index 060427fdce..eeab3027e1 100644
--- a/apps/api/v2/src/ee/calendars/services/outlook.service.ts
+++ b/apps/api/v2/src/ee/calendars/services/outlook.service.ts
@@ -168,16 +168,39 @@ export class OutlookService implements OAuthCalendarApp {
     const defaultCalendar = await this.getDefaultCalendar(office365OAuthCredentials.access_token);
 
     if (defaultCalendar?.id) {
-      const credential = await this.credentialRepository.createAppCredential(
+      const alreadyExistingSelectedCalendar = await this.selectedCalendarsRepository.getUserSelectedCalendar(
+        ownerId,
         OFFICE_365_CALENDAR_TYPE,
-        office365OAuthCredentials,
-        ownerId
+        defaultCalendar.id
       );
 
-      await this.selectedCalendarsRepository.createSelectedCalendar(
-        defaultCalendar.id,
-        credential.id,
+      if (alreadyExistingSelectedCalendar) {
+        const isCredentialValid = await this.calendarsService.checkCalendarCredentialValidity(
+          ownerId,
+          alreadyExistingSelectedCalendar.credentialId ?? 0,
+          OFFICE_365_CALENDAR_TYPE
+        );
+
+        // user credential probably got expired in this case
+        if (!isCredentialValid) {
+          await this.calendarsService.createAndLinkCalendarEntry(
+            ownerId,
+            alreadyExistingSelectedCalendar.externalId,
+            office365OAuthCredentials,
+            OFFICE_365_CALENDAR_TYPE,
+            alreadyExistingSelectedCalendar.credentialId
+          );
+        }
+
+        return {
+          url: redir || origin,
+        };
+      }
+
+      await this.calendarsService.createAndLinkCalendarEntry(
         ownerId,
+        defaultCalendar.id,
+        office365OAuthCredentials,
         OFFICE_365_CALENDAR_TYPE
       );
     }
diff --git a/apps/api/v2/src/modules/credentials/credentials.repository.ts b/apps/api/v2/src/modules/credentials/credentials.repository.ts
index 5a496cc85f..3ae5dd5798 100644
--- a/apps/api/v2/src/modules/credentials/credentials.repository.ts
+++ b/apps/api/v2/src/modules/credentials/credentials.repository.ts
@@ -9,12 +9,12 @@ import { APPS_TYPE_ID_MAPPING } from "@calcom/platform-constants";
 export class CredentialsRepository {
   constructor(private readonly dbRead: PrismaReadService, private readonly dbWrite: PrismaWriteService) {}
 
-  async createAppCredential(
+  async upsertAppCredential(
     type: keyof typeof APPS_TYPE_ID_MAPPING,
     key: Prisma.InputJsonValue,
-    userId: number
+    userId: number,
+    credentialId?: number | null
   ) {
-    const credential = await this.getByTypeAndUserId(type, userId);
     return this.dbWrite.prisma.credential.upsert({
       create: {
         type,
@@ -27,7 +27,7 @@ export class CredentialsRepository {
         invalid: false,
       },
       where: {
-        id: credential?.id ?? 0,
+        id: credentialId ?? 0,
       },
     });
   }
@@ -36,6 +36,10 @@ export class CredentialsRepository {
     return this.dbWrite.prisma.credential.findFirst({ where: { type, userId } });
   }
 
+  getAllUserCredentialsByTypeAndId(type: string, userId: number) {
+    return this.dbRead.prisma.credential.findMany({ where: { type, userId } });
+  }
+
   getUserCredentialsByIds(userId: number, credentialIds: number[]) {
     return this.dbRead.prisma.credential.findMany({
       where: {
@@ -60,6 +64,30 @@ export class CredentialsRepository {
       },
     });
   }
+
+  async getUserCredentialById(userId: number, credentialId: number, type: string) {
+    return await this.dbRead.prisma.credential.findUnique({
+      where: {
+        userId,
+        type,
+        id: credentialId,
+      },
+      select: {
+        id: true,
+        type: true,
+        key: true,
+        userId: true,
+        teamId: true,
+        appId: true,
+        invalid: true,
+        user: {
+          select: {
+            email: true,
+          },
+        },
+      },
+    });
+  }
 }
 
 export type CredentialsWithUserEmail = Awaited<
diff --git a/apps/api/v2/src/modules/destination-calendars/destination-calendars.module.ts b/apps/api/v2/src/modules/destination-calendars/destination-calendars.module.ts
index 0c0c29085a..4610749075 100644
--- a/apps/api/v2/src/modules/destination-calendars/destination-calendars.module.ts
+++ b/apps/api/v2/src/modules/destination-calendars/destination-calendars.module.ts
@@ -6,6 +6,7 @@ import { DestinationCalendarsController } from "@/modules/destination-calendars/
 import { DestinationCalendarsRepository } from "@/modules/destination-calendars/destination-calendars.repository";
 import { DestinationCalendarsService } from "@/modules/destination-calendars/services/destination-calendars.service";
 import { PrismaModule } from "@/modules/prisma/prisma.module";
+import { SelectedCalendarsRepository } from "@/modules/selected-calendars/selected-calendars.repository";
 import { UsersRepository } from "@/modules/users/users.repository";
 import { Module } from "@nestjs/common";
 
@@ -19,6 +20,7 @@ import { Module } from "@nestjs/common";
     UsersRepository,
     CredentialsRepository,
     AppsRepository,
+    SelectedCalendarsRepository,
   ],
   controllers: [DestinationCalendarsController],
   exports: [DestinationCalendarsRepository],
diff --git a/apps/api/v2/src/modules/selected-calendars/selected-calendars.repository.ts b/apps/api/v2/src/modules/selected-calendars/selected-calendars.repository.ts
index bdf98d4fce..eb0b8d989e 100644
--- a/apps/api/v2/src/modules/selected-calendars/selected-calendars.repository.ts
+++ b/apps/api/v2/src/modules/selected-calendars/selected-calendars.repository.ts
@@ -6,7 +6,7 @@ import { Injectable } from "@nestjs/common";
 export class SelectedCalendarsRepository {
   constructor(private readonly dbRead: PrismaReadService, private readonly dbWrite: PrismaWriteService) {}
 
-  createSelectedCalendar(externalId: string, credentialId: number, userId: number, integration: string) {
+  upsertSelectedCalendar(externalId: string, credentialId: number, userId: number, integration: string) {
     return this.dbWrite.prisma.selectedCalendar.upsert({
       create: {
         userId,
@@ -38,6 +38,18 @@ export class SelectedCalendarsRepository {
     });
   }
 
+  getUserSelectedCalendar(userId: number, integration: string, externalId: string) {
+    return this.dbRead.prisma.selectedCalendar.findUnique({
+      where: {
+        userId_integration_externalId: {
+          userId,
+          externalId,
+          integration,
+        },
+      },
+    });
+  }
+
   async addUserSelectedCalendar(
     userId: number,
     integration: string,
diff --git a/apps/api/v2/src/modules/users/users.repository.ts b/apps/api/v2/src/modules/users/users.repository.ts
index b6ee18fa74..444b87a173 100644
--- a/apps/api/v2/src/modules/users/users.repository.ts
+++ b/apps/api/v2/src/modules/users/users.repository.ts
@@ -68,7 +68,6 @@ export class UsersRepository {
   }
 
   async findByIdWithProfile(userId: number): Promise<UserWithProfile | null> {
-    console.log("findByIdWithProfile");
     return this.dbRead.prisma.user.findUnique({
       where: {
         id: userId,
diff --git a/packages/platform/atoms/connect/apple/AppleConnect.tsx b/packages/platform/atoms/connect/apple/AppleConnect.tsx
index 128cd97099..83e655f58a 100644
--- a/packages/platform/atoms/connect/apple/AppleConnect.tsx
+++ b/packages/platform/atoms/connect/apple/AppleConnect.tsx
@@ -76,7 +76,7 @@ export const AppleConnect: FC<Partial<Omit<OAuthConnectProps, "redir">>> = ({
       <Dialog open={isDialogOpen}>
         <DialogTrigger>
           <Button
-            StartIcon="calendar"
+            StartIcon="calendar-days"
             color="primary"
             disabled={isDisabled}
             className={cn("", className, isDisabled && "cursor-not-allowed", !isDisabled && "cursor-pointer")}