diff --git a/packages/server/src/api/controllers/Banking/BankTransactionsMatchingController.ts b/packages/server/src/api/controllers/Banking/BankTransactionsMatchingController.ts
index 23c392e46..a1db1faf6 100644
--- a/packages/server/src/api/controllers/Banking/BankTransactionsMatchingController.ts
+++ b/packages/server/src/api/controllers/Banking/BankTransactionsMatchingController.ts
@@ -1,12 +1,8 @@
 import { Inject, Service } from 'typedi';
+import { body, param } from 'express-validator';
 import { NextFunction, Request, Response, Router } from 'express';
 import BaseController from '@/api/controllers/BaseController';
 import { MatchBankTransactionsApplication } from '@/services/Banking/Matching/MatchBankTransactionsApplication';
-import { body, param } from 'express-validator';
-import {
-  GetMatchedTransactionsFilter,
-  IMatchTransactionsDTO,
-} from '@/services/Banking/Matching/types';
 
 @Service()
 export class BankTransactionsMatchingController extends BaseController {
@@ -20,9 +16,17 @@ export class BankTransactionsMatchingController extends BaseController {
     const router = Router();
 
     router.post(
-      '/:transactionId',
+      '/unmatch/:transactionId',
+      [param('transactionId').exists()],
+      this.validationResult,
+      this.unmatchMatchedBankTransaction.bind(this)
+    );
+    router.post(
+      '/match',
       [
-        param('transactionId').exists(),
+        body('uncategorizedTransactions').exists().isArray({ min: 1 }),
+        body('uncategorizedTransactions.*').isNumeric().toInt(),
+
         body('matchedTransactions').isArray({ min: 1 }),
         body('matchedTransactions.*.reference_type').exists(),
         body('matchedTransactions.*.reference_id').isNumeric().toInt(),
@@ -30,12 +34,6 @@ export class BankTransactionsMatchingController extends BaseController {
       this.validationResult,
       this.matchBankTransaction.bind(this)
     );
-    router.post(
-      '/unmatch/:transactionId',
-      [param('transactionId').exists()],
-      this.validationResult,
-      this.unmatchMatchedBankTransaction.bind(this)
-    );
     return router;
   }
 
@@ -50,21 +48,21 @@ export class BankTransactionsMatchingController extends BaseController {
     req: Request<{ transactionId: number }>,
     res: Response,
     next: NextFunction
-  ) {
+  ): Promise<Response | null> {
     const { tenantId } = req;
-    const { transactionId } = req.params;
-    const matchTransactionDTO = this.matchedBodyData(
-      req
-    ) as IMatchTransactionsDTO;
+    const bodyData = this.matchedBodyData(req);
+
+    const uncategorizedTransactions = bodyData?.uncategorizedTransactions;
+    const matchedTransactions = bodyData?.matchedTransactions;
 
     try {
       await this.bankTransactionsMatchingApp.matchTransaction(
         tenantId,
-        transactionId,
-        matchTransactionDTO
+        uncategorizedTransactions,
+        matchedTransactions
       );
       return res.status(200).send({
-        id: transactionId,
+        ids: uncategorizedTransactions,
         message: 'The bank transaction has been matched.',
       });
     } catch (error) {
diff --git a/packages/server/src/api/controllers/Cashflow/NewCashflowTransaction.ts b/packages/server/src/api/controllers/Cashflow/NewCashflowTransaction.ts
index a1af70c15..df6c86bcf 100644
--- a/packages/server/src/api/controllers/Cashflow/NewCashflowTransaction.ts
+++ b/packages/server/src/api/controllers/Cashflow/NewCashflowTransaction.ts
@@ -1,10 +1,15 @@
 import { Service, Inject } from 'typedi';
 import { ValidationChain, check, param, query } from 'express-validator';
 import { Router, Request, Response, NextFunction } from 'express';
+import { omit } from 'lodash';
 import BaseController from '../BaseController';
 import { ServiceError } from '@/exceptions';
 import CheckPolicies from '@/api/middleware/CheckPolicies';
-import { AbilitySubject, CashflowAction } from '@/interfaces';
+import {
+  AbilitySubject,
+  CashflowAction,
+  ICategorizeCashflowTransactioDTO,
+} from '@/interfaces';
 import { CashflowApplication } from '@/services/Cashflow/CashflowApplication';
 
 @Service()
@@ -44,7 +49,7 @@ export default class NewCashflowTransactionController extends BaseController {
       this.catchServiceErrors
     );
     router.post(
-      '/transactions/:id/categorize',
+      '/transactions/categorize',
       this.categorizeCashflowTransactionValidationSchema,
       this.validationResult,
       this.categorizeCashflowTransaction,
@@ -89,6 +94,7 @@ export default class NewCashflowTransactionController extends BaseController {
    */
   public get categorizeCashflowTransactionValidationSchema() {
     return [
+      check('uncategorized_transaction_ids').exists().isArray({ min: 1 }),
       check('date').exists().isISO8601().toDate(),
       check('credit_account_id').exists().isInt().toInt(),
       check('transaction_number').optional(),
@@ -191,14 +197,18 @@ export default class NewCashflowTransactionController extends BaseController {
     next: NextFunction
   ) => {
     const { tenantId } = req;
-    const { id: cashflowTransactionId } = req.params;
-    const cashflowTransaction = this.matchedBodyData(req);
+    const matchedObject = this.matchedBodyData(req);
+    const categorizeDTO = omit(matchedObject, [
+      'uncategorizedTransactionIds',
+    ]) as ICategorizeCashflowTransactioDTO;
+    const uncategorizedTransactionIds =
+      matchedObject.uncategorizedTransactionIds;
 
     try {
       await this.cashflowApplication.categorizeTransaction(
         tenantId,
-        cashflowTransactionId,
-        cashflowTransaction
+        uncategorizedTransactionIds,
+        categorizeDTO
       );
       return res.status(200).send({
         message: 'The cashflow transaction has been created successfully.',
diff --git a/packages/server/src/interfaces/CashFlow.ts b/packages/server/src/interfaces/CashFlow.ts
index e6838711c..4fe1e90c1 100644
--- a/packages/server/src/interfaces/CashFlow.ts
+++ b/packages/server/src/interfaces/CashFlow.ts
@@ -236,6 +236,7 @@ export interface ICashflowTransactionSchema {
 export interface ICashflowTransactionInput extends ICashflowTransactionSchema {}
 
 export interface ICategorizeCashflowTransactioDTO {
+  date: Date;
   creditAccountId: number;
   referenceNo: string;
   transactionNumber: string;
diff --git a/packages/server/src/interfaces/CashflowService.ts b/packages/server/src/interfaces/CashflowService.ts
index 99977c31d..66b258406 100644
--- a/packages/server/src/interfaces/CashflowService.ts
+++ b/packages/server/src/interfaces/CashflowService.ts
@@ -130,14 +130,15 @@ export interface ICommandCashflowDeletedPayload {
 
 export interface ICashflowTransactionCategorizedPayload {
   tenantId: number;
-  uncategorizedTransaction: any;
+  uncategorizedTransactions: any;
   cashflowTransaction: ICashflowTransaction;
+  oldUncategorizedTransactions: Array<IUncategorizedCashflowTransaction>;
   categorizeDTO: any;
   trx: Knex.Transaction;
 }
 export interface ICashflowTransactionUncategorizingPayload {
   tenantId: number;
-  uncategorizedTransaction: IUncategorizedCashflowTransaction;
+  oldUncategorizedTransactions: Array<IUncategorizedCashflowTransaction>;
   trx: Knex.Transaction;
 }
 export interface ICashflowTransactionUncategorizedPayload {
diff --git a/packages/server/src/services/Banking/Matching/GetMatchedTransactionsByType.ts b/packages/server/src/services/Banking/Matching/GetMatchedTransactionsByType.ts
index ad036fa98..df35a9d9b 100644
--- a/packages/server/src/services/Banking/Matching/GetMatchedTransactionsByType.ts
+++ b/packages/server/src/services/Banking/Matching/GetMatchedTransactionsByType.ts
@@ -7,6 +7,7 @@ import {
   MatchedTransactionsPOJO,
 } from './types';
 import { Inject, Service } from 'typedi';
+import PromisePool from '@supercharge/promise-pool';
 
 export abstract class GetMatchedTransactionsByType {
   @Inject()
@@ -45,22 +46,26 @@ export abstract class GetMatchedTransactionsByType {
   /**
    *
    * @param {number} tenantId
-   * @param {number} uncategorizedTransactionId
+   * @param {Array<number>} uncategorizedTransactionIds
    * @param {IMatchTransactionDTO} matchTransactionDTO
    * @param {Knex.Transaction} trx
    */
   public async createMatchedTransaction(
     tenantId: number,
-    uncategorizedTransactionId: number,
+    uncategorizedTransactionIds: Array<number>,
     matchTransactionDTO: IMatchTransactionDTO,
     trx?: Knex.Transaction
   ) {
     const { MatchedBankTransaction } = this.tenancy.models(tenantId);
 
-    await MatchedBankTransaction.query(trx).insert({
-      uncategorizedTransactionId,
-      referenceType: matchTransactionDTO.referenceType,
-      referenceId: matchTransactionDTO.referenceId,
-    });
+    await PromisePool.withConcurrency(2)
+      .for(uncategorizedTransactionIds)
+      .process(async (uncategorizedTransactionId) => {
+        await MatchedBankTransaction.query(trx).insert({
+          uncategorizedTransactionId,
+          referenceType: matchTransactionDTO.referenceType,
+          referenceId: matchTransactionDTO.referenceId,
+        });
+      });
   }
 }
diff --git a/packages/server/src/services/Banking/Matching/MatchBankTransactionsApplication.ts b/packages/server/src/services/Banking/Matching/MatchBankTransactionsApplication.ts
index 61884190f..39702c4bb 100644
--- a/packages/server/src/services/Banking/Matching/MatchBankTransactionsApplication.ts
+++ b/packages/server/src/services/Banking/Matching/MatchBankTransactionsApplication.ts
@@ -2,7 +2,7 @@ import { Inject, Service } from 'typedi';
 import { GetMatchedTransactions } from './GetMatchedTransactions';
 import { MatchBankTransactions } from './MatchTransactions';
 import { UnmatchMatchedBankTransaction } from './UnmatchMatchedTransaction';
-import { GetMatchedTransactionsFilter, IMatchTransactionsDTO } from './types';
+import { GetMatchedTransactionsFilter, IMatchTransactionDTO } from './types';
 
 @Service()
 export class MatchBankTransactionsApplication {
@@ -42,13 +42,13 @@ export class MatchBankTransactionsApplication {
    */
   public matchTransaction(
     tenantId: number,
-    uncategorizedTransactionId: number,
-    matchTransactionsDTO: IMatchTransactionsDTO
+    uncategorizedTransactionId: number | Array<number>,
+    matchedTransactions: Array<IMatchTransactionDTO>
   ): Promise<void> {
     return this.matchTransactionService.matchTransaction(
       tenantId,
       uncategorizedTransactionId,
-      matchTransactionsDTO
+      matchedTransactions
     );
   }
 
diff --git a/packages/server/src/services/Banking/Matching/MatchTransactions.ts b/packages/server/src/services/Banking/Matching/MatchTransactions.ts
index a85fb6a98..9ec128831 100644
--- a/packages/server/src/services/Banking/Matching/MatchTransactions.ts
+++ b/packages/server/src/services/Banking/Matching/MatchTransactions.ts
@@ -1,4 +1,4 @@
-import { isEmpty } from 'lodash';
+import { castArray } from 'lodash';
 import { Knex } from 'knex';
 import { Inject, Service } from 'typedi';
 import { PromisePool } from '@supercharge/promise-pool';
@@ -10,11 +10,15 @@ import {
   ERRORS,
   IBankTransactionMatchedEventPayload,
   IBankTransactionMatchingEventPayload,
-  IMatchTransactionsDTO,
+  IMatchTransactionDTO,
 } from './types';
 import { MatchTransactionsTypes } from './MatchTransactionsTypes';
 import { ServiceError } from '@/exceptions';
-import { sumMatchTranasctions } from './_utils';
+import {
+  sumMatchTranasctions,
+  validateUncategorizedTransactionsExcluded,
+  validateUncategorizedTransactionsNotMatched,
+} from './_utils';
 
 @Service()
 export class MatchBankTransactions {
@@ -39,27 +43,24 @@ export class MatchBankTransactions {
    */
   async validate(
     tenantId: number,
-    uncategorizedTransactionId: number,
-    matchTransactionsDTO: IMatchTransactionsDTO
+    uncategorizedTransactionId: number | Array<number>,
+    matchedTransactions: Array<IMatchTransactionDTO>
   ) {
     const { UncategorizedCashflowTransaction } = this.tenancy.models(tenantId);
-    const { matchedTransactions } = matchTransactionsDTO;
+    const uncategorizedTransactionIds = castArray(uncategorizedTransactionId);
 
     // Validates the uncategorized transaction existance.
-    const uncategorizedTransaction =
+    const uncategorizedTransactions =
       await UncategorizedCashflowTransaction.query()
-        .findById(uncategorizedTransactionId)
-        .withGraphFetched('matchedBankTransactions')
-        .throwIfNotFound();
+        .whereIn('id', uncategorizedTransactionIds)
+        .withGraphFetched('matchedBankTransactions');
 
     // Validates the uncategorized transaction is not already matched.
-    if (!isEmpty(uncategorizedTransaction.matchedBankTransactions)) {
-      throw new ServiceError(ERRORS.TRANSACTION_ALREADY_MATCHED);
-    }
+    validateUncategorizedTransactionsNotMatched(uncategorizedTransactions);
+
     // Validate the uncategorized transaction is not excluded.
-    if (uncategorizedTransaction.excluded) {
-      throw new ServiceError(ERRORS.CANNOT_MATCH_EXCLUDED_TRANSACTION);
-    }
+    validateUncategorizedTransactionsExcluded(uncategorizedTransactions);
+
     // Validates the given matched transaction.
     const validateMatchedTransaction = async (matchedTransaction) => {
       const getMatchedTransactionsService =
@@ -96,9 +97,9 @@ export class MatchBankTransactions {
     );
     // Validates the total given matching transcations whether is not equal
     // uncategorized transaction amount.
-    if (totalMatchedTranasctions !== uncategorizedTransaction.amount) {
-      throw new ServiceError(ERRORS.TOTAL_MATCHING_TRANSACTIONS_INVALID);
-    }
+    // if (totalMatchedTranasctions !== uncategorizedTransaction.amount) {
+    //   throw new ServiceError(ERRORS.TOTAL_MATCHING_TRANSACTIONS_INVALID);
+    // }
   }
 
   /**
@@ -109,23 +110,23 @@ export class MatchBankTransactions {
    */
   public async matchTransaction(
     tenantId: number,
-    uncategorizedTransactionId: number,
-    matchTransactionsDTO: IMatchTransactionsDTO
+    uncategorizedTransactionId: number | Array<number>,
+    matchedTransactions: Array<IMatchTransactionDTO>
   ): Promise<void> {
-    const { matchedTransactions } = matchTransactionsDTO;
+    const uncategorizedTransactionIds = castArray(uncategorizedTransactionId);
 
     // Validates the given matching transactions DTO.
     await this.validate(
       tenantId,
-      uncategorizedTransactionId,
-      matchTransactionsDTO
+      uncategorizedTransactionIds,
+      matchedTransactions
     );
     return this.uow.withTransaction(tenantId, async (trx: Knex.Transaction) => {
       // Triggers the event `onBankTransactionMatching`.
       await this.eventPublisher.emitAsync(events.bankMatch.onMatching, {
         tenantId,
-        uncategorizedTransactionId,
-        matchTransactionsDTO,
+        uncategorizedTransactionIds,
+        matchedTransactions,
         trx,
       } as IBankTransactionMatchingEventPayload);
 
@@ -139,17 +140,16 @@ export class MatchBankTransactions {
             );
           await getMatchedTransactionsService.createMatchedTransaction(
             tenantId,
-            uncategorizedTransactionId,
+            uncategorizedTransactionIds,
             matchedTransaction,
             trx
           );
         });
-
       // Triggers the event `onBankTransactionMatched`.
       await this.eventPublisher.emitAsync(events.bankMatch.onMatched, {
         tenantId,
-        uncategorizedTransactionId,
-        matchTransactionsDTO,
+        uncategorizedTransactionIds,
+        matchedTransactions,
         trx,
       } as IBankTransactionMatchedEventPayload);
     });
diff --git a/packages/server/src/services/Banking/Matching/_utils.ts b/packages/server/src/services/Banking/Matching/_utils.ts
index 67e7b0042..b78045904 100644
--- a/packages/server/src/services/Banking/Matching/_utils.ts
+++ b/packages/server/src/services/Banking/Matching/_utils.ts
@@ -1,7 +1,9 @@
 import moment from 'moment';
 import * as R from 'ramda';
 import UncategorizedCashflowTransaction from '@/models/UncategorizedCashflowTransaction';
-import { MatchedTransactionPOJO } from './types';
+import { ERRORS, MatchedTransactionPOJO } from './types';
+import { isEmpty } from 'lodash';
+import { ServiceError } from '@/exceptions';
 
 export const sortClosestMatchTransactions = (
   uncategorizedTransaction: UncategorizedCashflowTransaction,
@@ -29,3 +31,26 @@ export const sumMatchTranasctions = (transactions: Array<any>) => {
     0
   );
 };
+
+export const validateUncategorizedTransactionsNotMatched = (
+  uncategorizedTransactions: any
+) => {
+  const isMatchedTransactions = uncategorizedTransactions.filter(
+    (trans) => !isEmpty(trans.matchedBankTransactions)
+  );
+  //
+  if (isMatchedTransactions.length > 0) {
+    throw new ServiceError(ERRORS.TRANSACTION_ALREADY_MATCHED);
+  }
+};
+
+export const validateUncategorizedTransactionsExcluded = (
+  uncategorizedTransactions: any
+) => {
+  const excludedTransactions = uncategorizedTransactions.filter(
+    (trans) => trans.excluded
+  );
+  if (excludedTransactions.length > 0) {
+    throw new ServiceError(ERRORS.CANNOT_MATCH_EXCLUDED_TRANSACTION);
+  }
+};
diff --git a/packages/server/src/services/Banking/Matching/events/DecrementUncategorizedTransactionsOnMatch.ts b/packages/server/src/services/Banking/Matching/events/DecrementUncategorizedTransactionsOnMatch.ts
index 8cd291f18..8acda3d4d 100644
--- a/packages/server/src/services/Banking/Matching/events/DecrementUncategorizedTransactionsOnMatch.ts
+++ b/packages/server/src/services/Banking/Matching/events/DecrementUncategorizedTransactionsOnMatch.ts
@@ -5,6 +5,7 @@ import {
   IBankTransactionUnmatchedEventPayload,
 } from '../types';
 import HasTenancyService from '@/services/Tenancy/TenancyService';
+import PromisePool from '@supercharge/promise-pool';
 
 @Service()
 export class DecrementUncategorizedTransactionOnMatching {
@@ -30,18 +31,23 @@ export class DecrementUncategorizedTransactionOnMatching {
    */
   public async decrementUnCategorizedTransactionsOnMatching({
     tenantId,
-    uncategorizedTransactionId,
+    uncategorizedTransactionIds,
     trx,
   }: IBankTransactionMatchedEventPayload) {
     const { UncategorizedCashflowTransaction, Account } =
       this.tenancy.models(tenantId);
 
-    const transaction = await UncategorizedCashflowTransaction.query().findById(
-      uncategorizedTransactionId
+    const transactions = await UncategorizedCashflowTransaction.query().whereIn(
+      'id',
+      uncategorizedTransactionIds
     );
-    await Account.query(trx)
-      .findById(transaction.accountId)
-      .decrement('uncategorizedTransactions', 1);
+    await PromisePool.withConcurrency(1)
+      .for(transactions)
+      .process(async (transaction) => {
+        await Account.query(trx)
+          .findById(transaction.accountId)
+          .decrement('uncategorizedTransactions', 1);
+      });
   }
 
   /**
diff --git a/packages/server/src/services/Banking/Matching/types.ts b/packages/server/src/services/Banking/Matching/types.ts
index d415b6478..ff295bd9d 100644
--- a/packages/server/src/services/Banking/Matching/types.ts
+++ b/packages/server/src/services/Banking/Matching/types.ts
@@ -2,15 +2,15 @@ import { Knex } from 'knex';
 
 export interface IBankTransactionMatchingEventPayload {
   tenantId: number;
-  uncategorizedTransactionId: number;
-  matchTransactionsDTO: IMatchTransactionsDTO;
+  uncategorizedTransactionIds: Array<number>;
+  matchedTransactions: Array<IMatchTransactionDTO>;
   trx?: Knex.Transaction;
 }
 
 export interface IBankTransactionMatchedEventPayload {
   tenantId: number;
-  uncategorizedTransactionId: number;
-  matchTransactionsDTO: IMatchTransactionsDTO;
+  uncategorizedTransactionIds: Array<number>;
+  matchedTransactions: Array<IMatchTransactionDTO>;
   trx?: Knex.Transaction;
 }
 
@@ -32,6 +32,7 @@ export interface IMatchTransactionDTO {
 }
 
 export interface IMatchTransactionsDTO {
+  uncategorizedTransactionIds: Array<number>;
   matchedTransactions: Array<IMatchTransactionDTO>;
 }
 
diff --git a/packages/server/src/services/Cashflow/CashflowApplication.ts b/packages/server/src/services/Cashflow/CashflowApplication.ts
index f534e706e..f54935db7 100644
--- a/packages/server/src/services/Cashflow/CashflowApplication.ts
+++ b/packages/server/src/services/Cashflow/CashflowApplication.ts
@@ -164,12 +164,12 @@ export class CashflowApplication {
    */
   public categorizeTransaction(
     tenantId: number,
-    cashflowTransactionId: number,
+    uncategorizeTransactionIds: Array<number>,
     categorizeDTO: ICategorizeCashflowTransactioDTO
   ) {
     return this.categorizeTransactionService.categorize(
       tenantId,
-      cashflowTransactionId,
+      uncategorizeTransactionIds,
       categorizeDTO
     );
   }
diff --git a/packages/server/src/services/Cashflow/CategorizeCashflowTransaction.ts b/packages/server/src/services/Cashflow/CategorizeCashflowTransaction.ts
index 43ddfe603..3a4977f48 100644
--- a/packages/server/src/services/Cashflow/CategorizeCashflowTransaction.ts
+++ b/packages/server/src/services/Cashflow/CategorizeCashflowTransaction.ts
@@ -1,4 +1,6 @@
 import { Inject, Service } from 'typedi';
+import { castArray } from 'lodash';
+import { Knex } from 'knex';
 import HasTenancyService from '../Tenancy/TenancyService';
 import events from '@/subscribers/events';
 import { EventPublisher } from '@/lib/EventPublisher/EventPublisher';
@@ -8,12 +10,12 @@ import {
   ICashflowTransactionUncategorizingPayload,
   ICategorizeCashflowTransactioDTO,
 } from '@/interfaces';
-import { Knex } from 'knex';
-import { transformCategorizeTransToCashflow } from './utils';
+import {
+  transformCategorizeTransToCashflow,
+  validateUncategorizedTransactionsNotExcluded,
+} from './utils';
 import { CommandCashflowValidator } from './CommandCasflowValidator';
 import NewCashflowTransactionService from './NewCashflowTransactionService';
-import { ServiceError } from '@/exceptions';
-import { ERRORS } from './constants';
 
 @Service()
 export class CategorizeCashflowTransaction {
@@ -39,29 +41,31 @@ export class CategorizeCashflowTransaction {
    */
   public async categorize(
     tenantId: number,
-    uncategorizedTransactionId: number,
+    uncategorizedTransactionId: number | Array<number>,
     categorizeDTO: ICategorizeCashflowTransactioDTO
   ) {
     const { UncategorizedCashflowTransaction } = this.tenancy.models(tenantId);
+    const uncategorizedTransactionIds = castArray(uncategorizedTransactionId);
 
     // Retrieves the uncategorized transaction or throw an error.
-    const transaction = await UncategorizedCashflowTransaction.query()
-      .findById(uncategorizedTransactionId)
-      .throwIfNotFound();
+    const oldUncategorizedTransactions =
+      await UncategorizedCashflowTransaction.query()
+        .whereIn('id', uncategorizedTransactionIds)
+        .throwIfNotFound();
 
     // Validate cannot categorize excluded transaction.
-    if (transaction.excluded) {
-      throw new ServiceError(ERRORS.CANNOT_CATEGORIZE_EXCLUDED_TRANSACTION);
-    }
-    // Validates the transaction shouldn't be categorized before.
-    this.commandValidators.validateTransactionShouldNotCategorized(transaction);
+    validateUncategorizedTransactionsNotExcluded(oldUncategorizedTransactions);
 
+    // Validates the transaction shouldn't be categorized before.
+    this.commandValidators.validateTransactionsShouldNotCategorized(
+      oldIncategorizedTransactions
+    );
     // Validate the uncateogirzed transaction if it's deposit the transaction direction
     // should `IN` and the same thing if it's withdrawal the direction should be OUT.
-    this.commandValidators.validateUncategorizeTransactionType(
-      transaction,
-      categorizeDTO.transactionType
-    );
+    // this.commandValidators.validateUncategorizeTransactionType(
+    //   uncategorizedTransactions,
+    //   categorizeDTO.transactionType
+    // );
     // Edits the cashflow transaction under UOW env.
     return this.uow.withTransaction(tenantId, async (trx: Knex.Transaction) => {
       // Triggers `onTransactionCategorizing` event.
@@ -69,12 +73,13 @@ export class CategorizeCashflowTransaction {
         events.cashflow.onTransactionCategorizing,
         {
           tenantId,
+          oldUncategorizedTransactions,
           trx,
         } as ICashflowTransactionUncategorizingPayload
       );
       // Transformes the categorize DTO to the cashflow transaction.
       const cashflowTransactionDTO = transformCategorizeTransToCashflow(
-        transaction,
+        oldUncategorizedTransactions,
         categorizeDTO
       );
       // Creates a new cashflow transaction.
@@ -84,22 +89,28 @@ export class CategorizeCashflowTransaction {
           cashflowTransactionDTO
         );
       // Updates the uncategorized transaction as categorized.
-      const uncategorizedTransaction =
-        await UncategorizedCashflowTransaction.query(trx).patchAndFetchById(
-          uncategorizedTransactionId,
-          {
-            categorized: true,
-            categorizeRefType: 'CashflowTransaction',
-            categorizeRefId: cashflowTransaction.id,
-          }
+      await UncategorizedCashflowTransaction.query(trx)
+        .whereIn('id', uncategorizedTransactionIds)
+        .patch({
+          categorized: true,
+          categorizeRefType: 'CashflowTransaction',
+          categorizeRefId: cashflowTransaction.id,
+        });
+      // Fetch the new updated uncategorized transactions.
+      const uncategorizedTransactions =
+        await UncategorizedCashflowTransaction.query(trx).whereIn(
+          'id',
+          uncategorizedTransactionIds
         );
+
       // Triggers `onCashflowTransactionCategorized` event.
       await this.eventPublisher.emitAsync(
         events.cashflow.onTransactionCategorized,
         {
           tenantId,
           cashflowTransaction,
-          uncategorizedTransaction,
+          uncategorizedTransactions,
+          oldUncategorizedTransactions,
           categorizeDTO,
           trx,
         } as ICashflowTransactionCategorizedPayload
diff --git a/packages/server/src/services/Cashflow/CommandCasflowValidator.ts b/packages/server/src/services/Cashflow/CommandCasflowValidator.ts
index 7a6c5c973..cec6ac4ca 100644
--- a/packages/server/src/services/Cashflow/CommandCasflowValidator.ts
+++ b/packages/server/src/services/Cashflow/CommandCasflowValidator.ts
@@ -68,10 +68,12 @@ export class CommandCashflowValidator {
    * Validate the given transcation shouldn't be categorized.
    * @param {CashflowTransaction} cashflowTransaction
    */
-  public validateTransactionShouldNotCategorized(
-    cashflowTransaction: CashflowTransaction
+  public validateTransactionsShouldNotCategorized(
+    cashflowTransactions: Array<IUncategorizedCashflowTransaction>
   ) {
-    if (cashflowTransaction.uncategorize) {
+    const categorized = cashflowTransactions.filter((t) => t.categorized);
+
+    if (categorized?.length > 0) {
       throw new ServiceError(ERRORS.TRANSACTION_ALREADY_CATEGORIZED);
     }
   }
@@ -87,7 +89,7 @@ export class CommandCashflowValidator {
     transactionType: string
   ) {
     const type = getCashflowTransactionType(
-      upperFirst(camelCase(transactionType)) as CASHFLOW_TRANSACTION_TYPE
+      transactionType as CASHFLOW_TRANSACTION_TYPE
     );
     if (
       (type.direction === CASHFLOW_DIRECTION.IN &&
diff --git a/packages/server/src/services/Cashflow/utils.ts b/packages/server/src/services/Cashflow/utils.ts
index 8258abb28..2cc80c041 100644
--- a/packages/server/src/services/Cashflow/utils.ts
+++ b/packages/server/src/services/Cashflow/utils.ts
@@ -1,7 +1,9 @@
-import { upperFirst, camelCase } from 'lodash';
+import { upperFirst, camelCase, first, sum, sumBy } from 'lodash';
 import {
+  CASHFLOW_DIRECTION,
   CASHFLOW_TRANSACTION_TYPE,
   CASHFLOW_TRANSACTION_TYPE_META,
+  ERRORS,
   ICashflowTransactionTypeMeta,
 } from './constants';
 import {
@@ -9,6 +11,8 @@ import {
   ICategorizeCashflowTransactioDTO,
   IUncategorizedCashflowTransaction,
 } from '@/interfaces';
+import { UncategorizeCashflowTransaction } from './UncategorizeCashflowTransaction';
+import { ServiceError } from '@/exceptions';
 
 /**
  * Ensures the given transaction type to transformed to appropriate format.
@@ -27,7 +31,9 @@ export const transformCashflowTransactionType = (type) => {
 export function getCashflowTransactionType(
   transactionType: CASHFLOW_TRANSACTION_TYPE
 ): ICashflowTransactionTypeMeta {
-  return CASHFLOW_TRANSACTION_TYPE_META[transactionType];
+  const _transactionType = transformCashflowTransactionType(transactionType);
+
+  return CASHFLOW_TRANSACTION_TYPE_META[_transactionType];
 }
 
 /**
@@ -46,22 +52,35 @@ export const getCashflowAccountTransactionsTypes = () => {
  * @returns {ICashflowNewCommandDTO}
  */
 export const transformCategorizeTransToCashflow = (
-  uncategorizeModel: IUncategorizedCashflowTransaction,
+  uncategorizeTransactions: Array<IUncategorizedCashflowTransaction>,
   categorizeDTO: ICategorizeCashflowTransactioDTO
 ): ICashflowNewCommandDTO => {
+  const uncategorizeTransaction = first(uncategorizeTransactions);
+  const amount = sumBy(uncategorizeTransactions, 'amount');
+  const amountAbs = Math.abs(amount);
+
   return {
-    date: uncategorizeModel.date,
-    referenceNo: categorizeDTO.referenceNo || uncategorizeModel.referenceNo,
-    description: categorizeDTO.description || uncategorizeModel.description,
-    cashflowAccountId: uncategorizeModel.accountId,
+    date: categorizeDTO.date,
+    referenceNo: categorizeDTO.referenceNo,
+    description: categorizeDTO.description,
+    cashflowAccountId: uncategorizeTransaction.accountId,
     creditAccountId: categorizeDTO.creditAccountId,
     exchangeRate: categorizeDTO.exchangeRate || 1,
-    currencyCode: uncategorizeModel.currencyCode,
-    amount: uncategorizeModel.amount,
+    currencyCode: categorizeDTO.currencyCode,
+    amount: amountAbs,
     transactionNumber: categorizeDTO.transactionNumber,
     transactionType: categorizeDTO.transactionType,
-    uncategorizedTransactionId: uncategorizeModel.id,
     branchId: categorizeDTO?.branchId,
     publish: true,
   };
 };
+
+export const validateUncategorizedTransactionsNotExcluded = (
+  transactions: Array<UncategorizeCashflowTransaction>
+) => {
+  const excluded = transactions.filter((tran) => tran.excluded);
+
+  if (excluded?.length > 0) {
+    throw new ServiceError(ERRORS.CANNOT_CATEGORIZE_EXCLUDED_TRANSACTION);
+  }
+};
diff --git a/packages/webapp/src/containers/CashFlow/AccountTransactions/components.tsx b/packages/webapp/src/containers/CashFlow/AccountTransactions/components.tsx
index 2edf0c423..00981d38e 100644
--- a/packages/webapp/src/containers/CashFlow/AccountTransactions/components.tsx
+++ b/packages/webapp/src/containers/CashFlow/AccountTransactions/components.tsx
@@ -9,10 +9,15 @@ import {
   PopoverInteractionKind,
   Position,
   Tooltip,
+  Checkbox,
 } from '@blueprintjs/core';
 import { Box, FormatDateCell, Icon, MaterialProgressBar } from '@/components';
 import { useAccountTransactionsContext } from './AccountTransactionsProvider';
 import { safeCallback } from '@/utils';
+import {
+  useAddTransactionsToCategorizeSelected,
+  useRemoveTransactionsToCategorizeSelected,
+} from '@/hooks/state/banking';
 
 export function ActionsMenu({
   payload: { onUncategorize, onUnmatch },
@@ -183,6 +188,20 @@ function statusAccessor(transaction) {
  * Retrieve account uncategorized transctions table columns.
  */
 export function useAccountUncategorizedTransactionsColumns() {
+  const addTransactionsToCategorizeSelected =
+    useAddTransactionsToCategorizeSelected();
+
+  const removeTransactionsToCategorizeSelected =
+    useRemoveTransactionsToCategorizeSelected();
+
+  const handleChange = (value) => (event) => {
+    if (event.currentTarget.checked) {
+      addTransactionsToCategorizeSelected(value.id);
+    } else {
+      removeTransactionsToCategorizeSelected(value.id);
+    }
+  };
+
   return React.useMemo(
     () => [
       {
@@ -242,6 +261,15 @@ export function useAccountUncategorizedTransactionsColumns() {
         align: 'right',
         clickable: true,
       },
+      {
+        id: 'categorize_include',
+        Header: 'Include',
+        accessor: (value) => <Checkbox large onChange={handleChange(value)} />,
+        width: 10,
+        minWidth: 10,
+        maxWidth: 10,
+        align: 'right',
+      },
     ],
     [],
   );
diff --git a/packages/webapp/src/containers/CashFlow/withBankingActions.ts b/packages/webapp/src/containers/CashFlow/withBankingActions.ts
index 4cb4e281e..b8fb49e31 100644
--- a/packages/webapp/src/containers/CashFlow/withBankingActions.ts
+++ b/packages/webapp/src/containers/CashFlow/withBankingActions.ts
@@ -8,6 +8,8 @@ import {
   resetUncategorizedTransactionsSelected,
   resetExcludedTransactionsSelected,
   setExcludedTransactionsSelected,
+  resetTransactionsToCategorizeSelected,
+  setTransactionsToCategorizeSelected,
 } from '@/store/banking/banking.reducer';
 
 export interface WithBankingActionsProps {
@@ -23,6 +25,9 @@ export interface WithBankingActionsProps {
 
   setExcludedTransactionsSelected: (ids: Array<string | number>) => void;
   resetExcludedTransactionsSelected: () => void;
+
+  setTransactionsToCategorizeSelected: (ids: Array<string | number>) => void;
+  resetTransactionsToCategorizeSelected: () => void;
 }
 
 const mapDipatchToProps = (dispatch: any): WithBankingActionsProps => ({
@@ -56,6 +61,11 @@ const mapDipatchToProps = (dispatch: any): WithBankingActionsProps => ({
     ),
   resetExcludedTransactionsSelected: () =>
     dispatch(resetExcludedTransactionsSelected()),
+
+  setTransactionsToCategorizeSelected: (ids: Array<string | number>) =>
+    dispatch(setTransactionsToCategorizeSelected({ ids })),
+  resetTransactionsToCategorizeSelected: () =>
+    dispatch(resetTransactionsToCategorizeSelected()),
 });
 
 export const withBankingActions = connect<
diff --git a/packages/webapp/src/hooks/state/banking.ts b/packages/webapp/src/hooks/state/banking.ts
index 9b6b356ca..a6e007e01 100644
--- a/packages/webapp/src/hooks/state/banking.ts
+++ b/packages/webapp/src/hooks/state/banking.ts
@@ -1,10 +1,15 @@
+import { useDispatch, useSelector } from 'react-redux';
+import { useCallback, useMemo } from 'react';
 import {
   getPlaidToken,
   setPlaidId,
   resetPlaidId,
+  setTransactionsToCategorizeSelected,
+  resetTransactionsToCategorizeSelected,
+  getTransactionsToCategorizeSelected,
+  addTransactionsToCategorizeSelected,
+  removeTransactionsToCategorizeSelected,
 } from '@/store/banking/banking.reducer';
-import { useCallback } from 'react';
-import { useDispatch, useSelector } from 'react-redux';
 
 export const useSetBankingPlaidToken = () => {
   const dispatch = useDispatch();
@@ -30,3 +35,50 @@ export const useResetBankingPlaidToken = () => {
     dispatch(resetPlaidId());
   }, [dispatch]);
 };
+
+export const useGetTransactionsToCategorizeSelected = () => {
+  const selectedTransactions = useSelector(getTransactionsToCategorizeSelected);
+
+  return useMemo(() => selectedTransactions, [selectedTransactions]);
+};
+
+export const useSetTransactionsToCategorizeSelected = () => {
+  const dispatch = useDispatch();
+
+  return useCallback(
+    (ids: Array<string | number>) => {
+      return dispatch(setTransactionsToCategorizeSelected({ ids }));
+    },
+    [dispatch],
+  );
+};
+
+export const useAddTransactionsToCategorizeSelected = () => {
+  const dispatch = useDispatch();
+
+  return useCallback(
+    (id: string | number) => {
+      return dispatch(addTransactionsToCategorizeSelected({ id }));
+    },
+    [dispatch],
+  );
+};
+
+export const useRemoveTransactionsToCategorizeSelected = () => {
+  const dispatch = useDispatch();
+
+  return useCallback(
+    (id: string | number) => {
+      return dispatch(removeTransactionsToCategorizeSelected({ id }));
+    },
+    [dispatch],
+  );
+};
+
+export const useResetTransactionsToCategorizeSelected = () => {
+  const dispatch = useDispatch();
+
+  return useCallback(() => {
+    dispatch(resetTransactionsToCategorizeSelected());
+  }, [dispatch]);
+};
diff --git a/packages/webapp/src/store/banking/banking.reducer.ts b/packages/webapp/src/store/banking/banking.reducer.ts
index d2887076c..1d9720cb0 100644
--- a/packages/webapp/src/store/banking/banking.reducer.ts
+++ b/packages/webapp/src/store/banking/banking.reducer.ts
@@ -1,3 +1,4 @@
+import { uniq } from 'lodash';
 import { PayloadAction, createSlice } from '@reduxjs/toolkit';
 
 interface StorePlaidState {
@@ -8,6 +9,7 @@ interface StorePlaidState {
 
   uncategorizedTransactionsSelected: Array<number | string>;
   excludedTransactionsSelected: Array<number | string>;
+  transactionsToCategorizeSelected: Array<number | string>;
 }
 
 export const PlaidSlice = createSlice({
@@ -22,6 +24,7 @@ export const PlaidSlice = createSlice({
     },
     uncategorizedTransactionsSelected: [],
     excludedTransactionsSelected: [],
+    transactionsToCategorizeSelected: [],
   } as StorePlaidState,
   reducers: {
     setPlaidId: (state: StorePlaidState, action: PayloadAction<string>) => {
@@ -79,6 +82,37 @@ export const PlaidSlice = createSlice({
     resetExcludedTransactionsSelected: (state: StorePlaidState) => {
       state.excludedTransactionsSelected = [];
     },
+
+    setTransactionsToCategorizeSelected: (
+      state: StorePlaidState,
+      action: PayloadAction<{ ids: Array<string | number> }>,
+    ) => {
+      state.transactionsToCategorizeSelected = action.payload.ids;
+    },
+
+    addTransactionsToCategorizeSelected: (
+      state: StorePlaidState,
+      action: PayloadAction<{ id: string | number }>,
+    ) => {
+      state.transactionsToCategorizeSelected = uniq([
+        ...state.transactionsToCategorizeSelected,
+        action.payload.id,
+      ]);
+    },
+
+    removeTransactionsToCategorizeSelected: (
+      state: StorePlaidState,
+      action: PayloadAction<{ id: string | number }>,
+    ) => {
+      state.transactionsToCategorizeSelected =
+        state.transactionsToCategorizeSelected.filter(
+          (t) => t !== action.payload.id,
+        );
+    },
+
+    resetTransactionsToCategorizeSelected: (state: StorePlaidState) => {
+      state.transactionsToCategorizeSelected = [];
+    },
   },
 });
 
@@ -93,6 +127,12 @@ export const {
   resetUncategorizedTransactionsSelected,
   setExcludedTransactionsSelected,
   resetExcludedTransactionsSelected,
+  setTransactionsToCategorizeSelected,
+  addTransactionsToCategorizeSelected,
+  removeTransactionsToCategorizeSelected,
+  resetTransactionsToCategorizeSelected,
 } = PlaidSlice.actions;
 
 export const getPlaidToken = (state: any) => state.plaid.plaidToken;
+export const getTransactionsToCategorizeSelected = (state: any) =>
+  state.plaid.transactionsToCategorizeSelected;