diff --git a/apps/api/v2/src/modules/ooo/guards/is-user-ooo.ts b/apps/api/v2/src/modules/ooo/guards/is-user-ooo.ts
new file mode 100644
index 0000000000..05ed3c78bc
--- /dev/null
+++ b/apps/api/v2/src/modules/ooo/guards/is-user-ooo.ts
@@ -0,0 +1,30 @@
+import { UserOOORepository } from "@/modules/ooo/repositories/ooo.repository";
+import { Injectable, CanActivate, ExecutionContext, ForbiddenException } from "@nestjs/common";
+import { Request } from "express";
+
+@Injectable()
+export class IsUserOOO implements CanActivate {
+  constructor(private oooRepo: UserOOORepository) {}
+
+  async canActivate(context: ExecutionContext): Promise<boolean> {
+    const request = context.switchToHttp().getRequest<Request>();
+    const oooId: string = request.params.oooId;
+    const userId: string = request.params.userId;
+
+    if (!userId) {
+      throw new ForbiddenException("No user id found in request params.");
+    }
+
+    if (!oooId) {
+      throw new ForbiddenException("No ooo entry id found in request params.");
+    }
+
+    const ooo = await this.oooRepo.getUserOOOByIdAndUserId(Number(oooId), Number(userId));
+
+    if (ooo) {
+      return true;
+    }
+
+    throw new ForbiddenException("This OOO entry does not belong to this user.");
+  }
+}
diff --git a/apps/api/v2/src/modules/ooo/inputs/ooo.input.ts b/apps/api/v2/src/modules/ooo/inputs/ooo.input.ts
new file mode 100644
index 0000000000..1e67a9bb50
--- /dev/null
+++ b/apps/api/v2/src/modules/ooo/inputs/ooo.input.ts
@@ -0,0 +1,81 @@
+import { BadRequestException } from "@nestjs/common";
+import { ApiProperty, ApiPropertyOptional, PartialType } from "@nestjs/swagger";
+import { Transform } from "class-transformer";
+import { IsDate, IsInt, IsOptional, IsString, IsEnum, isDate } from "class-validator";
+
+export enum OutOfOfficeReason {
+  UNSPECIFIED = "unspecified",
+  VACATION = "vacation",
+  TRAVEL = "travel",
+  SICK_LEAVE = "sick",
+  PUBLIC_HOLIDAY = "public_holiday",
+}
+
+export type OutOfOfficeReasonType = `${OutOfOfficeReason}`;
+
+const isDateString = (dateString: string) => {
+  try {
+    const isoDateRegex = /^(\d{4})-(\d{2})-(\d{2})T(\d{2}):(\d{2}):(\d{2})(\.\d{3})?Z$/;
+    return isoDateRegex.test(dateString);
+  } catch {
+    throw new BadRequestException("Invalid Date.");
+  }
+};
+
+export class CreateOutOfOfficeEntryDto {
+  @Transform(({ value }: { value: string }) => {
+    if (isDateString(value)) {
+      const date = new Date(value);
+      date.setUTCHours(0, 0, 0, 0);
+      return date;
+    }
+    throw new BadRequestException("Invalid Date.");
+  })
+  @IsDate()
+  @ApiProperty({
+    description: "The start date and time of the out of office period in ISO 8601 format in UTC timezone.",
+    example: "2023-05-01T00:00:00.000Z",
+  })
+  start!: Date;
+
+  @Transform(({ value }: { value: string }) => {
+    if (isDateString(value)) {
+      const date = new Date(value);
+      date.setUTCHours(23, 59, 59, 999);
+      return date;
+    }
+    throw new BadRequestException("Invalid Date.");
+  })
+  @IsDate()
+  @ApiProperty({
+    description: "The end date and time of the out of office period in ISO 8601 format in UTC timezone.",
+    example: "2023-05-10T23:59:59.999Z",
+  })
+  end!: Date;
+
+  @IsString()
+  @IsOptional()
+  @ApiPropertyOptional({
+    description: "Optional notes for the out of office entry.",
+    example: "Vacation in Hawaii",
+  })
+  notes?: string;
+
+  @IsInt()
+  @IsOptional()
+  @ApiPropertyOptional({
+    description: "The ID of the user covering for the out of office period, if applicable.",
+    example: 2,
+  })
+  toUserId?: number;
+
+  @IsEnum(OutOfOfficeReason)
+  @IsOptional()
+  @ApiPropertyOptional({
+    description: "the reason for the out of office entry, if applicable",
+    example: "vacation",
+  })
+  reason?: OutOfOfficeReasonType;
+}
+
+export class UpdateOutOfOfficeEntryDto extends PartialType(CreateOutOfOfficeEntryDto) {}
diff --git a/apps/api/v2/src/modules/ooo/outputs/ooo.output.ts b/apps/api/v2/src/modules/ooo/outputs/ooo.output.ts
new file mode 100644
index 0000000000..48a62e4001
--- /dev/null
+++ b/apps/api/v2/src/modules/ooo/outputs/ooo.output.ts
@@ -0,0 +1,99 @@
+import { OutOfOfficeReason } from "@/modules/ooo/inputs/ooo.input";
+import { ApiProperty, ApiPropertyOptional } from "@nestjs/swagger";
+import { Expose, Type } from "class-transformer";
+import { IsInt, IsEnum, ValidateNested, IsString, IsDateString, IsOptional } from "class-validator";
+
+import { SUCCESS_STATUS, ERROR_STATUS } from "@calcom/platform-constants";
+
+export class UserOooOutputDto {
+  @IsInt()
+  @Expose()
+  @ApiProperty({
+    description: "The ID of the user.",
+    example: 2,
+  })
+  readonly userId!: number;
+
+  @IsInt()
+  @IsOptional()
+  @ApiPropertyOptional({
+    description: "The ID of the user covering for the out of office period, if applicable.",
+    example: 2,
+  })
+  @Expose()
+  readonly toUserId?: number;
+
+  @IsInt()
+  @Expose()
+  @ApiProperty({
+    description: "The ID of the ooo entry.",
+    example: 2,
+  })
+  readonly id!: number;
+
+  @IsString()
+  @Expose()
+  @ApiProperty({
+    description: "The UUID of the ooo entry.",
+    example: 2,
+  })
+  readonly uuid!: string;
+
+  @IsDateString()
+  @ApiProperty({
+    description: "The start date and time of the out of office period in ISO 8601 format in UTC timezone.",
+    example: "2023-05-01T00:00:00.000Z",
+  })
+  @Expose()
+  start!: Date;
+
+  @IsDateString()
+  @ApiProperty({
+    description: "The end date and time of the out of office period in ISO 8601 format in UTC timezone.",
+    example: "2023-05-10T23:59:59.999Z",
+  })
+  @Expose()
+  end!: Date;
+
+  @IsString()
+  @IsOptional()
+  @ApiPropertyOptional({
+    description: "Optional notes for the out of office entry.",
+    example: "Vacation in Hawaii",
+  })
+  @Expose()
+  notes?: string;
+
+  @IsEnum(OutOfOfficeReason)
+  @IsOptional()
+  @ApiPropertyOptional({
+    description: "the reason for the out of office entry, if applicable",
+    example: "vacation",
+  })
+  @Expose()
+  reason?: OutOfOfficeReason;
+}
+
+export class UserOooOutputResponseDto {
+  @Expose()
+  @ApiProperty({ example: SUCCESS_STATUS, enum: [SUCCESS_STATUS, ERROR_STATUS] })
+  @IsEnum([SUCCESS_STATUS, ERROR_STATUS])
+  status!: typeof SUCCESS_STATUS | typeof ERROR_STATUS;
+
+  @Expose()
+  @ValidateNested()
+  @Type(() => UserOooOutputDto)
+  data!: UserOooOutputDto;
+}
+
+export class UserOoosOutputResponseDto {
+  @Expose()
+  @ApiProperty({ example: SUCCESS_STATUS, enum: [SUCCESS_STATUS, ERROR_STATUS] })
+  @IsEnum([SUCCESS_STATUS, ERROR_STATUS])
+  status!: typeof SUCCESS_STATUS | typeof ERROR_STATUS;
+
+  @Expose()
+  @ValidateNested()
+  @Type(() => UserOooOutputDto)
+  data!: UserOooOutputDto[];
+}
diff --git a/apps/api/v2/src/modules/ooo/repositories/ooo.repository.ts b/apps/api/v2/src/modules/ooo/repositories/ooo.repository.ts
new file mode 100644
index 0000000000..c2363ccded
--- /dev/null
+++ b/apps/api/v2/src/modules/ooo/repositories/ooo.repository.ts
@@ -0,0 +1,100 @@
+import { PrismaReadService } from "@/modules/prisma/prisma-read.service";
+import { Injectable } from "@nestjs/common";
+import { v4 as uuidv4 } from "uuid";
+
+import { Prisma } from "@calcom/prisma/client";
+
+import { PrismaWriteService } from "../../prisma/prisma-write.service";
+
+type OOOInputData = Omit<Prisma.OutOfOfficeEntryCreateInput, "user" | "toUser" | "reason" | "uuid"> & {
+  toUserId?: number;
+  userId: number;
+  reasonId?: number;
+};
+
+@Injectable()
+export class UserOOORepository {
+  constructor(private readonly dbRead: PrismaReadService, private readonly dbWrite: PrismaWriteService) {}
+
+  async createUserOOO(data: OOOInputData) {
+    const uuid = uuidv4();
+    return this.dbWrite.prisma.outOfOfficeEntry.create({
+      data: { ...data, uuid },
+      include: { reason: true },
+    });
+  }
+
+  async updateUserOOO(oooId: number, data: Partial<OOOInputData>) {
+    return this.dbWrite.prisma.outOfOfficeEntry.update({
+      where: { id: oooId },
+      data,
+      include: { reason: true },
+    });
+  }
+
+  async getUserOOOById(oooId: number) {
+    return this.dbRead.prisma.outOfOfficeEntry.findFirst({
+      where: { id: oooId },
+      include: { reason: true },
+    });
+  }
+
+  async getUserOOOByIdAndUserId(oooId: number, userId: number) {
+    return this.dbRead.prisma.outOfOfficeEntry.findFirst({
+      where: { id: oooId, userId },
+      include: { reason: true },
+    });
+  }
+
+  async getUserOOOPaginated(userId: number, skip: number, take: number) {
+    return this.dbRead.prisma.outOfOfficeEntry.findMany({
+      where: { userId },
+      skip,
+      take,
+      include: { reason: true },
+    });
+  }
+
+  async deleteUserOOO(oooId: number) {
+    return this.dbWrite.prisma.outOfOfficeEntry.delete({
+      where: { id: oooId },
+      include: { reason: true },
+    });
+  }
+
+  async findExistingOooRedirect(userId: number, start: Date, end: Date, toUserId?: number) {
+    const existingOutOfOfficeEntry = await this.dbRead.prisma.outOfOfficeEntry.findFirst({
+      select: {
+        userId: true,
+        toUserId: true,
+      },
+      where: {
+        ...(toUserId && { userId: toUserId }),
+        toUserId: userId,
+        // Check for time overlap or collision
+        OR: [
+          // Outside of range
+          {
+            AND: [{ start: { lte: end } }, { end: { gte: start } }],
+          },
+          // Inside of range
+          {
+            AND: [{ start: { gte: start } }, { end: { lte: end } }],
+          },
+        ],
+      },
+    });
+
+    return existingOutOfOfficeEntry;
+  }
+
+  async getOooByUserIdAndTime(userId: number, start: Date, end: Date) {
+    return await this.dbRead.prisma.outOfOfficeEntry.findFirst({
+      where: {
+        userId,
+        start,
+        end,
+      },
+    });
+  }
+}
diff --git a/apps/api/v2/src/modules/ooo/services/ooo.service.ts b/apps/api/v2/src/modules/ooo/services/ooo.service.ts
new file mode 100644
index 0000000000..8905065bda
--- /dev/null
+++ b/apps/api/v2/src/modules/ooo/services/ooo.service.ts
@@ -0,0 +1,135 @@
+import {
+  CreateOutOfOfficeEntryDto,
+  UpdateOutOfOfficeEntryDto,
+  OutOfOfficeReason,
+} from "@/modules/ooo/inputs/ooo.input";
+import { UserOOORepository } from "@/modules/ooo/repositories/ooo.repository";
+import { UsersRepository } from "@/modules/users/users.repository";
+import { BadRequestException, ConflictException, Injectable } from "@nestjs/common";
+
+import { OutOfOfficeEntry } from "@calcom/prisma/client";
+
+const OOO_REASON_ID_TO_REASON = {
+  1: OutOfOfficeReason["UNSPECIFIED"],
+  2: OutOfOfficeReason["VACATION"],
+  3: OutOfOfficeReason["TRAVEL"],
+  4: OutOfOfficeReason["SICK_LEAVE"],
+  5: OutOfOfficeReason["PUBLIC_HOLIDAY"],
+};
+
+const OOO_REASON_TO_REASON_ID = {
+  [OutOfOfficeReason["UNSPECIFIED"]]: 1,
+  [OutOfOfficeReason["VACATION"]]: 2,
+  [OutOfOfficeReason["TRAVEL"]]: 3,
+  [OutOfOfficeReason["SICK_LEAVE"]]: 4,
+  [OutOfOfficeReason["PUBLIC_HOLIDAY"]]: 5,
+};
+
+@Injectable()
+export class UserOOOService {
+  constructor(
+    private readonly oooRepository: UserOOORepository,
+    private readonly usersRepository: UsersRepository
+  ) {}
+
+  formatOooReason(ooo: OutOfOfficeEntry) {
+    return {
+      ...ooo,
+      reason: ooo.reasonId
+        ? OOO_REASON_ID_TO_REASON[ooo.reasonId as keyof typeof OOO_REASON_ID_TO_REASON]
+        : OOO_REASON_ID_TO_REASON[1],
+    };
+  }
+
+  isStartBeforeEnd(start?: Date, end?: Date) {
+    if ((end && !start) || (start && !end)) {
+      throw new BadRequestException("Please specify both ooo start and end time.");
+    }
+
+    if (start && end) {
+      if (start.getTime() > end.getTime()) {
+        throw new BadRequestException("Start date must be before end date.");
+      }
+    }
+    return true;
+  }
+
+  async checkUserEligibleForRedirect(userId: number, toUserId?: number) {
+    if (toUserId) {
+      const user = await this.usersRepository.findUserOOORedirectEligible(userId, toUserId);
+      if (!user) {
+        throw new BadRequestException("Cannot redirect to this user.");
+      }
+    }
+  }
+
+  async checkExistingOooRedirect(userId: number, start?: Date, end?: Date, toUserId?: number) {
+    if (start && end) {
+      const existingOooRedirect = await this.oooRepository.findExistingOooRedirect(
+        userId,
+        start,
+        end,
+        toUserId
+      );
+
+      if (existingOooRedirect) {
+        throw new BadRequestException("Booking redirect infinite not allowed.");
+      }
+    }
+  }
+
+  async checkDuplicateOOOEntry(userId: number, start?: Date, end?: Date) {
+    if (start && end) {
+      const duplicateEntry = await this.oooRepository.getOooByUserIdAndTime(userId, start, end);
+
+      if (duplicateEntry) {
+        throw new ConflictException("Ooo entry already exists.");
+      }
+    }
+  }
+
+  checkRedirectToSelf(userId: number, toUserId?: number) {
+    if (toUserId && toUserId === userId) {
+      throw new BadRequestException("Cannot redirect to self.");
+    }
+  }
+
+  async checkIsValidOOO(userId: number, ooo: CreateOutOfOfficeEntryDto | UpdateOutOfOfficeEntryDto) {
+    this.isStartBeforeEnd(ooo.start, ooo.end);
+    await this.checkExistingOooRedirect(userId, ooo.start, ooo.end, ooo.toUserId);
+    await this.checkDuplicateOOOEntry(userId, ooo.start, ooo.end);
+    await this.checkRedirectToSelf(userId, ooo.toUserId);
+    await this.checkUserEligibleForRedirect(userId, ooo.toUserId);
+  }
+
+  async createUserOOO(userId: number, body: CreateOutOfOfficeEntryDto) {
+    await this.checkIsValidOOO(userId, body);
+    const { reason, ...rest } = body;
+    const ooo = await this.oooRepository.createUserOOO({
+      ...rest,
+      userId,
+      reasonId: OOO_REASON_TO_REASON_ID[reason ?? OutOfOfficeReason["UNSPECIFIED"]],
+    });
+    return this.formatOooReason(ooo);
+  }
+
+  async updateUserOOO(userId: number, oooId: number, body: UpdateOutOfOfficeEntryDto) {
+    await this.checkIsValidOOO(userId, body);
+    const { reason, ...rest } = body;
+    const data = reason
+      ? { ...rest, reasonId: OOO_REASON_TO_REASON_ID[reason ?? OutOfOfficeReason["UNSPECIFIED"]] }
+      : rest;
+    const ooo = await this.oooRepository.updateUserOOO(oooId, data);
+    return this.formatOooReason(ooo);
+  }
+
+  async deleteUserOOO(oooId: number) {
+    const ooo = await this.oooRepository.deleteUserOOO(oooId);
+    return this.formatOooReason(ooo);
+  }
+
+  async getUserOOOPaginated(userId: number, skip: number, take: number) {
+    const ooos = await this.oooRepository.getUserOOOPaginated(userId, skip, take);
+    return ooos.map((ooo) => this.formatOooReason(ooo));
+  }
+}
diff --git a/apps/api/v2/src/modules/organizations/controllers/users/ooo/organizations-users-ooo-controller.ts b/apps/api/v2/src/modules/organizations/controllers/users/ooo/organizations-users-ooo-controller.ts
new file mode 100644
index 0000000000..90f6f604d6
--- /dev/null
+++ b/apps/api/v2/src/modules/organizations/controllers/users/ooo/organizations-users-ooo-controller.ts
@@ -0,0 +1,114 @@
+import { API_VERSIONS_VALUES } from "@/lib/api-versions";
+import { PlatformPlan } from "@/modules/auth/decorators/billing/platform-plan.decorator";
+import { Roles } from "@/modules/auth/decorators/roles/roles.decorator";
+import { ApiAuthGuard } from "@/modules/auth/guards/api-auth/api-auth.guard";
+import { PlatformPlanGuard } from "@/modules/auth/guards/billing/platform-plan.guard";
+import { IsAdminAPIEnabledGuard } from "@/modules/auth/guards/organizations/is-admin-api-enabled.guard";
+import { IsOrgGuard } from "@/modules/auth/guards/organizations/is-org.guard";
+import { RolesGuard } from "@/modules/auth/guards/roles/roles.guard";
+import { IsUserInOrg } from "@/modules/auth/guards/users/is-user-in-org.guard";
+import { IsUserOOO } from "@/modules/ooo/guards/is-user-ooo";
+import { CreateOutOfOfficeEntryDto, UpdateOutOfOfficeEntryDto } from "@/modules/ooo/inputs/ooo.input";
+import {
+  UserOooOutputDto,
+  UserOooOutputResponseDto,
+  UserOoosOutputResponseDto,
+} from "@/modules/ooo/outputs/ooo.output";
+import { UserOOOService } from "@/modules/ooo/services/ooo.service";
+import {
+  Controller,
+  UseGuards,
+  Get,
+  Post,
+  Patch,
+  Delete,
+  Param,
+  ParseIntPipe,
+  Body,
+  UseInterceptors,
+  Query,
+} from "@nestjs/common";
+import { ClassSerializerInterceptor } from "@nestjs/common";
+import { ApiOperation, ApiTags as DocsTags } from "@nestjs/swagger";
+import { plainToInstance } from "class-transformer";
+
+import { SUCCESS_STATUS } from "@calcom/platform-constants";
+import { SkipTakePagination } from "@calcom/platform-types";
+
+@Controller({
+  path: "/v2/organizations/:orgId/users/:userId/ooo",
+  version: API_VERSIONS_VALUES,
+})
+@UseInterceptors(ClassSerializerInterceptor)
+@UseGuards(ApiAuthGuard, IsOrgGuard, RolesGuard, PlatformPlanGuard, IsAdminAPIEnabledGuard)
+@UseGuards(IsOrgGuard)
+@DocsTags("Orgs / Users / OOO")
+export class OrganizationsUsersOOOController {
+  constructor(private readonly userOOOService: UserOOOService) {}
+
+  @Get()
+  @Roles("ORG_ADMIN")
+  @PlatformPlan("ESSENTIALS")
+  @UseGuards(IsUserInOrg)
+  @ApiOperation({ summary: "Get all ooo entries of a user" })
+  async getOrganizationUserOOO(
+    @Param("userId", ParseIntPipe) userId: number,
+    @Query() query: SkipTakePagination
+  ): Promise<UserOoosOutputResponseDto> {
+    const ooos = await this.userOOOService.getUserOOOPaginated(userId, query.skip ?? 0, query.take ?? 250);
+
+    return {
+      status: SUCCESS_STATUS,
+      data: ooos.map((ooo) => plainToInstance(UserOooOutputDto, ooo, { strategy: "excludeAll" })),
+    };
+  }
+
+  @Post()
+  @Roles("ORG_ADMIN")
+  @PlatformPlan("ESSENTIALS")
+  @UseGuards(IsUserInOrg)
+  @ApiOperation({ summary: "Create an ooo entry for user" })
+  async createOrganizationUserOOO(
+    @Param("userId", ParseIntPipe) userId: number,
+    @Body() input: CreateOutOfOfficeEntryDto
+  ): Promise<UserOooOutputResponseDto> {
+    const ooo = await this.userOOOService.createUserOOO(userId, input);
+    return {
+      status: SUCCESS_STATUS,
+      data: plainToInstance(UserOooOutputDto, ooo, { strategy: "excludeAll" }),
+    };
+  }
+
+  @Patch("/:oooId")
+  @Roles("ORG_ADMIN")
+  @PlatformPlan("ESSENTIALS")
+  @UseGuards(IsUserInOrg, IsUserOOO)
+  @ApiOperation({ summary: "Update ooo entry of a user" })
+  async updateOrganizationUserOOO(
+    @Param("userId", ParseIntPipe) userId: number,
+    @Param("oooId", ParseIntPipe) oooId: number,
+
+    @Body() input: UpdateOutOfOfficeEntryDto
+  ): Promise<UserOooOutputResponseDto> {
+    const ooo = await this.userOOOService.updateUserOOO(userId, oooId, input);
+    return {
+      status: SUCCESS_STATUS,
+      data: plainToInstance(UserOooOutputDto, ooo, { strategy: "excludeAll" }),
+    };
+  }
+
+  @Delete("/:oooId")
+  @Roles("ORG_ADMIN")
+  @PlatformPlan("ESSENTIALS")
+  @UseGuards(IsUserInOrg, IsUserOOO)
+  @ApiOperation({ summary: "Delete ooo entry of a user" })
+  async deleteOrganizationUserOOO(
+    @Param("oooId", ParseIntPipe) oooId: number
+  ): Promise<UserOooOutputResponseDto> {
+    const ooo = await this.userOOOService.deleteUserOOO(oooId);
+    return {
+      status: SUCCESS_STATUS,
+      data: plainToInstance(UserOooOutputDto, ooo, { strategy: "excludeAll" }),
+    };
+  }
+}
diff --git a/apps/api/v2/src/modules/organizations/controllers/users/ooo/organizations-users-ooo.e2e-spec.ts b/apps/api/v2/src/modules/organizations/controllers/users/ooo/organizations-users-ooo.e2e-spec.ts
new file mode 100644
index 0000000000..ab8252b703
--- /dev/null
+++ b/apps/api/v2/src/modules/organizations/controllers/users/ooo/organizations-users-ooo.e2e-spec.ts
@@ -0,0 +1,421 @@
+import { bootstrap } from "@/app";
+import { AppModule } from "@/app.module";
+import { UserOooOutputDto } from "@/modules/ooo/outputs/ooo.output";
+import { PrismaModule } from "@/modules/prisma/prisma.module";
+import { TokensModule } from "@/modules/tokens/tokens.module";
+import { UsersModule } from "@/modules/users/users.module";
+import { INestApplication } from "@nestjs/common";
+import { NestExpressApplication } from "@nestjs/platform-express";
+import { Test } from "@nestjs/testing";
+import { User } from "@prisma/client";
+import * as request from "supertest";
+import { MembershipRepositoryFixture } from "test/fixtures/repository/membership.repository.fixture";
+import { OrganizationRepositoryFixture } from "test/fixtures/repository/organization.repository.fixture";
+import { ProfileRepositoryFixture } from "test/fixtures/repository/profiles.repository.fixture";
+import { TeamRepositoryFixture } from "test/fixtures/repository/team.repository.fixture";
+import { UserRepositoryFixture } from "test/fixtures/repository/users.repository.fixture";
+import { withApiAuth } from "test/utils/withApiAuth";
+
+import { SUCCESS_STATUS } from "@calcom/platform-constants";
+import { Team } from "@calcom/prisma/client";
+
+describe("Organizations User OOO Endpoints", () => {
+  describe("User Authentication - User is Org Admin", () => {
+    let app: INestApplication;
+    let oooCreatedViaApiId: number;
+    let userRepositoryFixture: UserRepositoryFixture;
+    let organizationsRepositoryFixture: OrganizationRepositoryFixture;
+    let teamsRepositoryFixture: TeamRepositoryFixture;
+    let membershipsRepositoryFixture: MembershipRepositoryFixture;
+    let profileRepositoryFixture: ProfileRepositoryFixture;
+
+    let org: Team;
+    let team: Team;
+    let falseTestOrg: Team;
+    let falseTestTeam: Team;
+
+    const userEmail = "org-admin-ooo-controller-e222e@api.com";
+    let userAdmin: User;
+
+    const teammate1Email = "teammate111ooo@team.com";
+    const teammate2Email = "teammate221ooo@team.com";
+    const falseTestUserEmail = "false-user-ooo@false-team.com";
+    let teammate1: User;
+    let teammate2: User;
+    let falseTestUser: User;
+
+    beforeAll(async () => {
+      const moduleRef = await withApiAuth(
+        userEmail,
+        Test.createTestingModule({
+          imports: [AppModule, PrismaModule, UsersModule, TokensModule],
+        })
+      ).compile();
+
+      userRepositoryFixture = new UserRepositoryFixture(moduleRef);
+      organizationsRepositoryFixture = new OrganizationRepositoryFixture(moduleRef);
+      teamsRepositoryFixture = new TeamRepositoryFixture(moduleRef);
+      membershipsRepositoryFixture = new MembershipRepositoryFixture(moduleRef);
+      profileRepositoryFixture = new ProfileRepositoryFixture(moduleRef);
+
+      userAdmin = await userRepositoryFixture.create({
+        email: userEmail,
+        username: userEmail,
+        role: "ADMIN",
+      });
+
+      teammate1 = await userRepositoryFixture.create({
+        email: teammate1Email,
+        username: teammate1Email,
+      });
+
+      teammate2 = await userRepositoryFixture.create({
+        email: teammate2Email,
+        username: teammate2Email,
+      });
+
+      falseTestUser = await userRepositoryFixture.create({
+        email: falseTestUserEmail,
+        username: falseTestUserEmail,
+      });
+
+      org = await organizationsRepositoryFixture.create({
+        name: "Test Organization ooo",
+        isOrganization: true,
+      });
+
+      falseTestOrg = await organizationsRepositoryFixture.create({
+        name: "False test org ooo",
+        isOrganization: true,
+      });
+
+      team = await teamsRepositoryFixture.create({
+        name: "Test org team ooo",
+        isOrganization: false,
+        parent: { connect: { id: org.id } },
+      });
+
+      falseTestTeam = await teamsRepositoryFixture.create({
+        name: "Outside org team ooo",
+        isOrganization: false,
+        parent: { connect: { id: falseTestOrg.id } },
+      });
+
+      await profileRepositoryFixture.create({
+        uid: `usr-${userAdmin.id}`,
+        username: userEmail,
+        organization: {
+          connect: {
+            id: org.id,
+          },
+        },
+        user: {
+          connect: {
+            id: userAdmin.id,
+          },
+        },
+      });
+
+      await profileRepositoryFixture.create({
+        uid: `usr-${teammate1.id}`,
+        username: teammate1Email,
+        organization: {
+          connect: {
+            id: org.id,
+          },
+        },
+        user: {
+          connect: {
+            id: teammate1.id,
+          },
+        },
+      });
+
+      await membershipsRepositoryFixture.create({
+        role: "ADMIN",
+        user: { connect: { id: userAdmin.id } },
+        team: { connect: { id: org.id } },
+        accepted: true,
+      });
+
+      await membershipsRepositoryFixture.create({
+        role: "MEMBER",
+        user: { connect: { id: teammate1.id } },
+        team: { connect: { id: team.id } },
+        accepted: true,
+      });
+
+      await membershipsRepositoryFixture.create({
+        role: "MEMBER",
+        user: { connect: { id: teammate2.id } },
+        team: { connect: { id: team.id } },
+        accepted: true,
+      });
+
+      await membershipsRepositoryFixture.create({
+        role: "MEMBER",
+        user: { connect: { id: falseTestUser.id } },
+        team: { connect: { id: falseTestTeam.id } },
+        accepted: true,
+      });
+
+      app = moduleRef.createNestApplication();
+      bootstrap(app as NestExpressApplication);
+
+      await app.init();
+    });
+
+    it("should be defined", () => {
+      expect(userRepositoryFixture).toBeDefined();
+      expect(organizationsRepositoryFixture).toBeDefined();
+      expect(userAdmin).toBeDefined();
+      expect(org).toBeDefined();
+    });
+
+    it("should create a ooo entry without redirect", async () => {
+      const body = {
+        start: "2025-05-01T01:00:00.000Z",
+        end: "2025-05-10T13:59:59.999Z",
+        notes: "ooo numero uno",
+      };
+
+      return request(app.getHttpServer())
+        .post(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo`)
+        .send(body)
+        .expect(201)
+        .then((response) => {
+          const responseBody = response.body;
+          expect(responseBody.status).toEqual(SUCCESS_STATUS);
+
+          const data = responseBody.data as UserOooOutputDto;
+          expect(data.reason).toEqual("unspecified");
+          expect(data.userId).toEqual(teammate1.id);
+          expect(data.start).toEqual("2025-05-01T00:00:00.000Z");
+          expect(data.end).toEqual("2025-05-10T23:59:59.999Z");
+          oooCreatedViaApiId = data.id;
+        });
+    });
+
+    it("should create a ooo entry with redirect", async () => {
+      const body = {
+        start: "2025-08-01T01:00:00.000Z",
+        end: "2025-10-10T13:59:59.999Z",
+        notes: "ooo numero dos with redirect",
+        toUserId: teammate2.id,
+      };
+
+      return request(app.getHttpServer())
+        .post(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo`)
+        .send(body)
+        .expect(201)
+        .then((response) => {
+          const responseBody = response.body;
+          expect(responseBody.status).toEqual(SUCCESS_STATUS);
+          const data = responseBody.data as UserOooOutputDto;
+          expect(data.reason).toEqual("unspecified");
+          expect(data.userId).toEqual(teammate1.id);
+          expect(data.start).toEqual("2025-08-01T00:00:00.000Z");
+          expect(data.end).toEqual("2025-10-10T23:59:59.999Z");
+          expect(data.toUserId).toEqual(teammate2.id);
+        });
+    });
+
+    it("should fail to create a ooo entry with start after end", async () => {
+      const body = {
+        start: "2025-07-01T00:00:00.000Z",
+        end: "2025-05-10T23:59:59.999Z",
+        notes: "ooo numero uno duplicate",
+      };
+
+      return request(app.getHttpServer())
+        .post(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo`)
+        .send(body)
+        .expect(400);
+    });
+
+    it("should fail to create a duplicate ooo entry", async () => {
+      const body = {
+        start: "2025-05-01T00:00:00.000Z",
+        end: "2025-05-10T23:59:59.999Z",
+        notes: "ooo numero uno duplicate",
+      };
+
+      return request(app.getHttpServer())
+        .post(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo`)
+        .send(body)
+        .expect(409);
+    });
+
+    it("should fail to create an ooo entry that redirects to self", async () => {
+      const body = {
+        start: "2025-05-02T00:00:00.000Z",
+        end: "2025-05-03T23:59:59.999Z",
+        notes: "ooo infinite redirect",
+        toUserId: teammate1.id,
+      };
+
+      return request(app.getHttpServer())
+        .post(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo`)
+        .send(body)
+        .expect(400);
+    });
+
+    it("should fail to create an ooo entry that redirects to member outside of org", async () => {
+      const body = {
+        start: "2025-05-02T00:00:00.000Z",
+        end: "2025-05-03T23:59:59.999Z",
+        notes: "ooo invalid redirect",
+        toUserId: falseTestUser.id,
+      };
+
+      return request(app.getHttpServer())
+        .post(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo`)
+        .send(body)
+        .expect(400);
+    });
+
+    it("should update a ooo entry without redirect", async () => {
+      const body = {
+        start: "2025-06-01T01:00:00.000Z",
+        end: "2025-06-10T13:59:59.999Z",
+        notes: "ooo numero uno",
+        reason: "vacation",
+      };
+
+      return request(app.getHttpServer())
+        .patch(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo/${oooCreatedViaApiId}`)
+        .send(body)
+        .expect(200)
+        .then((response) => {
+          const responseBody = response.body;
+          expect(responseBody.status).toEqual(SUCCESS_STATUS);
+
+          const data = responseBody.data as UserOooOutputDto;
+          expect(data.reason).toEqual("vacation");
+          expect(data.userId).toEqual(teammate1.id);
+          expect(data.start).toEqual("2025-06-01T00:00:00.000Z");
+          expect(data.end).toEqual("2025-06-10T23:59:59.999Z");
+        });
+    });
+
+    it("should fail to update a ooo entry with redirect outside of org", async () => {
+      const body = {
+        toUserId: falseTestUser.id,
+      };
+
+      return request(app.getHttpServer())
+        .patch(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo/${oooCreatedViaApiId}`)
+        .send(body)
+        .expect(400);
+    });
+
+    it("should fail to update a ooo entry with start after end ", async () => {
+      const body = {
+        start: "2025-07-01T00:00:00.000Z",
+        end: "2025-05-10T23:59:59.999Z",
+      };
+
+      return request(app.getHttpServer())
+        .patch(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo/${oooCreatedViaApiId}`)
+        .send(body)
+        .expect(400);
+    });
+
+    it("should fail to update a ooo entry with redirect to self ", async () => {
+      const body = {
+        toUserId: teammate1.id,
+      };
+
+      return request(app.getHttpServer())
+        .patch(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo/${oooCreatedViaApiId}`)
+        .send(body)
+        .expect(400);
+    });
+
+    it("should fail to update a ooo entry with duplicate time", async () => {
+      const body = {
+        start: "2025-06-01T01:00:00.000Z",
+        end: "2025-06-10T13:59:59.999Z",
+      };
+
+      return request(app.getHttpServer())
+        .patch(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo/${oooCreatedViaApiId}`)
+        .send(body)
+        .expect(409);
+    });
+
+    it("should update a ooo entry without redirect", async () => {
+      const body = {
+        toUserId: teammate2.id,
+      };
+
+      return request(app.getHttpServer())
+        .patch(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo/${oooCreatedViaApiId}`)
+        .send(body)
+        .expect(200)
+        .then((response) => {
+          const responseBody = response.body;
+          expect(responseBody.status).toEqual(SUCCESS_STATUS);
+
+          const data = responseBody.data as UserOooOutputDto;
+          expect(data.reason).toEqual("vacation");
+          expect(data.toUserId).toEqual(teammate2.id);
+          expect(data.userId).toEqual(teammate1.id);
+          expect(data.start).toEqual("2025-06-01T00:00:00.000Z");
+          expect(data.end).toEqual("2025-06-10T23:59:59.999Z");
+        });
+    });
+
+    it("should get 2 ooo entries", async () => {
+      return request(app.getHttpServer())
+        .get(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo`)
+        .expect(200)
+        .then((response) => {
+          const responseBody = response.body;
+          expect(responseBody.status).toEqual(SUCCESS_STATUS);
+
+          const data = responseBody.data as UserOooOutputDto[];
+          expect(data.length).toEqual(2);
+          const oooUno = data.find((ooo) => ooo.id === oooCreatedViaApiId);
+          expect(oooUno).toBeDefined();
+          if (oooUno) {
+            expect(oooUno.reason).toEqual("vacation");
+            expect(oooUno.toUserId).toEqual(teammate2.id);
+            expect(oooUno.userId).toEqual(teammate1.id);
+            expect(oooUno.start).toEqual("2025-06-01T00:00:00.000Z");
+            expect(oooUno.end).toEqual("2025-06-10T23:59:59.999Z");
+          }
+        });
+    });
+
+    it("should delete ooo entry", async () => {
+      return request(app.getHttpServer())
+        .delete(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo/${oooCreatedViaApiId}`)
+        .expect(200);
+    });
+
+    it("user should have 1 ooo entries", async () => {
+      return request(app.getHttpServer())
+        .get(`/v2/organizations/${org.id}/users/${teammate1.id}/ooo`)
+        .expect(200)
+        .then((response) => {
+          const responseBody = response.body;
+          expect(responseBody.status).toEqual(SUCCESS_STATUS);
+          const data = responseBody.data as UserOooOutputDto[];
+          expect(data.length).toEqual(1);
+        });
+    });
+
+    afterAll(async () => {
+      await userRepositoryFixture.deleteByEmail(userAdmin.email);
+      await userRepositoryFixture.deleteByEmail(teammate1.email);
+      await userRepositoryFixture.deleteByEmail(teammate2.email);
+      await userRepositoryFixture.deleteByEmail(falseTestUser.email);
+      await teamsRepositoryFixture.delete(team.id);
+      await teamsRepositoryFixture.delete(falseTestTeam.id);
+      await organizationsRepositoryFixture.delete(org.id);
+      await organizationsRepositoryFixture.delete(falseTestOrg.id);
+      await app.close();
+    });
+  });
+});
diff --git a/apps/api/v2/src/modules/organizations/organizations.module.ts b/apps/api/v2/src/modules/organizations/organizations.module.ts
index 3a708a0d71..d741a89866 100644
--- a/apps/api/v2/src/modules/organizations/organizations.module.ts
+++ b/apps/api/v2/src/modules/organizations/organizations.module.ts
@@ -3,6 +3,8 @@ import { SchedulesModule_2024_06_11 } from "@/ee/schedules/schedules_2024_06_11/
 import { EmailModule } from "@/modules/email/email.module";
 import { EmailService } from "@/modules/email/email.service";
 import { MembershipsRepository } from "@/modules/memberships/memberships.repository";
+import { UserOOORepository } from "@/modules/ooo/repositories/ooo.repository";
+import { UserOOOService } from "@/modules/ooo/services/ooo.service";
 import { OrganizationsOptionsAttributesController } from "@/modules/organizations/controllers/attributes/organizations-attributes-options.controller";
 import { OrganizationsAttributesController } from "@/modules/organizations/controllers/attributes/organizations-attributes.controller";
 import { OrganizationsEventTypesController } from "@/modules/organizations/controllers/event-types/organizations-event-types.controller";
@@ -12,6 +14,7 @@ import { OrganizationsSchedulesController } from "@/modules/organizations/contro
 import { OrganizationsTeamsMembershipsController } from "@/modules/organizations/controllers/teams/memberships/organizations-teams-memberships.controller";
 import { OrganizationsTeamsController } from "@/modules/organizations/controllers/teams/organizations-teams.controller";
 import { OrganizationsTeamsSchedulesController } from "@/modules/organizations/controllers/teams/schedules/organizations-teams-schedules.controller";
+import { OrganizationsUsersOOOController } from "@/modules/organizations/controllers/users/ooo/organizations-users-ooo-controller";
 import { OrganizationsUsersController } from "@/modules/organizations/controllers/users/organizations-users.controller";
 import { OrganizationsWebhooksController } from "@/modules/organizations/controllers/webhooks/organizations-webhooks.controller";
 import { OrganizationsRepository } from "@/modules/organizations/organizations.repository";
@@ -86,6 +89,8 @@ import { Module } from "@nestjs/common";
     WebhooksRepository,
     WebhooksService,
     OutputTeamEventTypesResponsePipe,
+    UserOOOService,
+    UserOOORepository,
   ],
   exports: [
     OrganizationsService,
@@ -118,6 +123,7 @@ import { Module } from "@nestjs/common";
     OrganizationsOptionsAttributesController,
     OrganizationsWebhooksController,
     OrganizationsTeamsSchedulesController,
+    OrganizationsUsersOOOController,
   ],
 })
 export class OrganizationsModule {}
diff --git a/apps/api/v2/src/modules/users/users.repository.ts b/apps/api/v2/src/modules/users/users.repository.ts
index 2a8cc0331b..f113708d3d 100644
--- a/apps/api/v2/src/modules/users/users.repository.ts
+++ b/apps/api/v2/src/modules/users/users.repository.ts
@@ -265,4 +265,27 @@ export class UsersRepository {
       where: { id: userId },
     });
   }
+
+  async findUserOOORedirectEligible(userId: number, toTeamUserId: number) {
+    return await this.dbRead.prisma.user.findUnique({
+      where: {
+        id: toTeamUserId,
+        teams: {
+          some: {
+            team: {
+              members: {
+                some: {
+                  userId: userId,
+                  accepted: true,
+                },
+              },
+            },
+          },
+        },
+      },
+      select: {
+        id: true,
+      },
+    });
+  }
 }
diff --git a/apps/api/v2/swagger/documentation.json b/apps/api/v2/swagger/documentation.json
index e1c631dd3b..f04d0a9cc8 100644
--- a/apps/api/v2/swagger/documentation.json
+++ b/apps/api/v2/swagger/documentation.json
@@ -2684,6 +2684,146 @@
         ]
       }
     },
+    "/v2/organizations/{orgId}/users/{userId}/ooo": {
+      "get": {
+        "operationId": "OrganizationsUsersOOOController_getOrganizationUserOOO",
+        "summary": "Get all ooo entries of a user",
+        "parameters": [
+          {
+            "name": "userId",
+            "required": true,
+            "in": "path",
+            "schema": {
+              "type": "number"
+            }
+          },
+          {
+            "name": "take",
+            "required": false,
+            "in": "query",
+            "description": "The number of items to return",
+            "example": 10,
+            "schema": {
+              "type": "number"
+            }
+          },
+          {
+            "name": "skip",
+            "required": false,
+            "in": "query",
+            "description": "The number of items to skip",
+            "example": 0,
+            "schema": {
+              "type": "number"
+            }
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": ""
+          }
+        },
+        "tags": [
+          "Orgs / Users / OOO"
+        ]
+      },
+      "post": {
+        "operationId": "OrganizationsUsersOOOController_createOrganizationUserOOO",
+        "summary": "Create an ooo entry for user",
+        "parameters": [
+          {
+            "name": "userId",
+            "required": true,
+            "in": "path",
+            "schema": {
+              "type": "number"
+            }
+          }
+        ],
+        "requestBody": {
+          "required": true,
+          "content": {
+            "application/json": {
+              "schema": {
+                "$ref": "#/components/schemas/CreateOutOfOfficeEntryDto"
+              }
+            }
+          }
+        },
+        "responses": {
+          "201": {
+            "description": ""
+          }
+        },
+        "tags": [
+          "Orgs / Users / OOO"
+        ]
+      }
+    },
+    "/v2/organizations/{orgId}/users/{userId}/ooo/{oooId}": {
+      "patch": {
+        "operationId": "OrganizationsUsersOOOController_updateOrganizationUserOOO",
+        "summary": "Update ooo entry of a user",
+        "parameters": [
+          {
+            "name": "userId",
+            "required": true,
+            "in": "path",
+            "schema": {
+              "type": "number"
+            }
+          },
+          {
+            "name": "oooId",
+            "required": true,
+            "in": "path",
+            "schema": {
+              "type": "number"
+            }
+          }
+        ],
+        "requestBody": {
+          "required": true,
+          "content": {
+            "application/json": {
+              "schema": {
+                "$ref": "#/components/schemas/UpdateOutOfOfficeEntryDto"
+              }
+            }
+          }
+        },
+        "responses": {
+          "200": {
+            "description": ""
+          }
+        },
+        "tags": [
+          "Orgs / Users / OOO"
+        ]
+      },
+      "delete": {
+        "operationId": "OrganizationsUsersOOOController_deleteOrganizationUserOOO",
+        "summary": "Delete ooo entry of a user",
+        "parameters": [
+          {
+            "name": "oooId",
+            "required": true,
+            "in": "path",
+            "schema": {
+              "type": "number"
+            }
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": ""
+          }
+        },
+        "tags": [
+          "Orgs / Users / OOO"
+        ]
+      }
+    },
     "/v2/organizations/{orgId}/webhooks": {
       "get": {
         "operationId": "OrganizationsWebhooksController_getAllOrganizationWebhooks",
@@ -13454,6 +13594,74 @@
           }
         }
       },
+      "CreateOutOfOfficeEntryDto": {
+        "type": "object",
+        "properties": {
+          "start": {
+            "format": "date-time",
+            "type": "string",
+            "description": "The start date and time of the out of office period in ISO 8601 format in UTC timezone.",
+            "example": "2023-05-01T00:00:00.000Z"
+          },
+          "end": {
+            "format": "date-time",
+            "type": "string",
+            "description": "The end date and time of the out of office period in ISO 8601 format in UTC timezone.",
+            "example": "2023-05-10T23:59:59.999Z"
+          },
+          "notes": {
+            "type": "string",
+            "description": "Optional notes for the out of office entry.",
+            "example": "Vacation in Hawaii"
+          },
+          "toUserId": {
+            "type": "number",
+            "description": "The ID of the user covering for the out of office period, if applicable.",
+            "example": 2
+          },
+          "reason": {
+            "type": "object",
+            "description": "the reason for the out of office entry, if applicable",
+            "example": "vacation"
+          }
+        },
+        "required": [
+          "start",
+          "end"
+        ]
+      },
+      "UpdateOutOfOfficeEntryDto": {
+        "type": "object",
+        "properties": {
+          "start": {
+            "format": "date-time",
+            "type": "string",
+            "description": "The start date and time of the out of office period in ISO 8601 format in UTC timezone.",
+            "example": "2023-05-01T00:00:00.000Z"
+          },
+          "end": {
+            "format": "date-time",
+            "type": "string",
+            "description": "The end date and time of the out of office period in ISO 8601 format in UTC timezone.",
+            "example": "2023-05-10T23:59:59.999Z"
+          },
+          "notes": {
+            "type": "string",
+            "description": "Optional notes for the out of office entry.",
+            "example": "Vacation in Hawaii"
+          },
+          "toUserId": {
+            "type": "number",
+            "description": "The ID of the user covering for the out of office period, if applicable.",
+            "example": 2
+          },
+          "reason": {
+            "type": "object",
+            "description": "the reason for the out of office entry, if applicable",
+            "example": "vacation"
+          }
+        }
+      },
       "StripConnectOutputDto": {
         "type": "object",
         "properties": {
diff --git a/docs/api-reference/v2/openapi.json b/docs/api-reference/v2/openapi.json
index e7a70411a0..dc0446dd31 100644
--- a/docs/api-reference/v2/openapi.json
+++ b/docs/api-reference/v2/openapi.json
@@ -2549,6 +2549,138 @@
         "tags": ["Orgs / Users"]
       }
     },
+    "/v2/organizations/{orgId}/users/{userId}/ooo": {
+      "get": {
+        "operationId": "OrganizationsUsersOOOController_getOrganizationUserOOO",
+        "summary": "Get all ooo entries of a user",
+        "parameters": [
+          {
+            "name": "userId",
+            "required": true,
+            "in": "path",
+            "schema": {
+              "type": "number"
+            }
+          },
+          {
+            "name": "take",
+            "required": false,
+            "in": "query",
+            "description": "The number of items to return",
+            "example": 10,
+            "schema": {
+              "type": "number"
+            }
+          },
+          {
+            "name": "skip",
+            "required": false,
+            "in": "query",
+            "description": "The number of items to skip",
+            "example": 0,
+            "schema": {
+              "type": "number"
+            }
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": ""
+          }
+        },
+        "tags": ["Orgs / Users / OOO"]
+      },
+      "post": {
+        "operationId": "OrganizationsUsersOOOController_createOrganizationUserOOO",
+        "summary": "Create an ooo entry for user",
+        "parameters": [
+          {
+            "name": "userId",
+            "required": true,
+            "in": "path",
+            "schema": {
+              "type": "number"
+            }
+          }
+        ],
+        "requestBody": {
+          "required": true,
+          "content": {
+            "application/json": {
+              "schema": {
+                "$ref": "#/components/schemas/CreateOutOfOfficeEntryDto"
+              }
+            }
+          }
+        },
+        "responses": {
+          "201": {
+            "description": ""
+          }
+        },
+        "tags": ["Orgs / Users / OOO"]
+      }
+    },
+    "/v2/organizations/{orgId}/users/{userId}/ooo/{oooId}": {
+      "patch": {
+        "operationId": "OrganizationsUsersOOOController_updateOrganizationUserOOO",
+        "summary": "Update ooo entry of a user",
+        "parameters": [
+          {
+            "name": "userId",
+            "required": true,
+            "in": "path",
+            "schema": {
+              "type": "number"
+            }
+          },
+          {
+            "name": "oooId",
+            "required": true,
+            "in": "path",
+            "schema": {
+              "type": "number"
+            }
+          }
+        ],
+        "requestBody": {
+          "required": true,
+          "content": {
+            "application/json": {
+              "schema": {
+                "$ref": "#/components/schemas/UpdateOutOfOfficeEntryDto"
+              }
+            }
+          }
+        },
+        "responses": {
+          "200": {
+            "description": ""
+          }
+        },
+        "tags": ["Orgs / Users / OOO"]
+      },
+      "delete": {
+        "operationId": "OrganizationsUsersOOOController_deleteOrganizationUserOOO",
+        "summary": "Delete ooo entry of a user",
+        "parameters": [
+          {
+            "name": "oooId",
+            "required": true,
+            "in": "path",
+            "schema": {
+              "type": "number"
+            }
+          }
+        ],
+        "responses": {
+          "200": {
+            "description": ""
+          }
+        },
+        "tags": ["Orgs / Users / OOO"]
+      }
+    },
     "/v2/organizations/{orgId}/webhooks": {
       "get": {
         "operationId": "OrganizationsWebhooksController_getAllOrganizationWebhooks",
@@ -12157,6 +12289,71 @@
           }
         }
       },
+      "CreateOutOfOfficeEntryDto": {
+        "type": "object",
+        "properties": {
+          "start": {
+            "format": "date-time",
+            "type": "string",
+            "description": "The start date and time of the out of office period in ISO 8601 format in UTC timezone.",
+            "example": "2023-05-01T00:00:00.000Z"
+          },
+          "end": {
+            "format": "date-time",
+            "type": "string",
+            "description": "The end date and time of the out of office period in ISO 8601 format in UTC timezone.",
+            "example": "2023-05-10T23:59:59.999Z"
+          },
+          "notes": {
+            "type": "string",
+            "description": "Optional notes for the out of office entry.",
+            "example": "Vacation in Hawaii"
+          },
+          "toUserId": {
+            "type": "number",
+            "description": "The ID of the user covering for the out of office period, if applicable.",
+            "example": 2
+          },
+          "reason": {
+            "type": "object",
+            "description": "the reason for the out of office entry, if applicable",
+            "example": "vacation"
+          }
+        },
+        "required": ["start", "end"]
+      },
+      "UpdateOutOfOfficeEntryDto": {
+        "type": "object",
+        "properties": {
+          "start": {
+            "format": "date-time",
+            "type": "string",
+            "description": "The start date and time of the out of office period in ISO 8601 format in UTC timezone.",
+            "example": "2023-05-01T00:00:00.000Z"
+          },
+          "end": {
+            "format": "date-time",
+            "type": "string",
+            "description": "The end date and time of the out of office period in ISO 8601 format in UTC timezone.",
+            "example": "2023-05-10T23:59:59.999Z"
+          },
+          "notes": {
+            "type": "string",
+            "description": "Optional notes for the out of office entry.",
+            "example": "Vacation in Hawaii"
+          },
+          "toUserId": {
+            "type": "number",
+            "description": "The ID of the user covering for the out of office period, if applicable.",
+            "example": 2
+          },
+          "reason": {
+            "type": "object",
+            "description": "the reason for the out of office entry, if applicable",
+            "example": "vacation"
+          }
+        }
+      },
       "StripConnectOutputDto": {
         "type": "object",
         "properties": {