diff --git a/packages/webapp/src/containers/CashFlow/AccountTransactions/AccountTransactionsActionsBar.tsx b/packages/webapp/src/containers/CashFlow/AccountTransactions/AccountTransactionsActionsBar.tsx
index 7ca9abc37..d94b67544 100644
--- a/packages/webapp/src/containers/CashFlow/AccountTransactions/AccountTransactionsActionsBar.tsx
+++ b/packages/webapp/src/containers/CashFlow/AccountTransactions/AccountTransactionsActionsBar.tsx
@@ -12,6 +12,8 @@ import {
   PopoverInteractionKind,
   Position,
   Intent,
+  Switch,
+  Tooltip,
 } from '@blueprintjs/core';
 import { useHistory } from 'react-router-dom';
 import {
@@ -39,9 +41,9 @@ import { withBanking } from '../withBanking';
 import { isEmpty } from 'lodash';
 import {
   useExcludeUncategorizedTransactions,
-  useUnexcludeUncategorizedTransaction,
   useUnexcludeUncategorizedTransactions,
 } from '@/hooks/query/bank-rules';
+import { withBankingActions } from '../withBankingActions';
 
 function AccountTransactionsActionsBar({
   // #withDialogActions
@@ -56,6 +58,9 @@ function AccountTransactionsActionsBar({
   // #withBanking
   uncategorizedTransationsIdsSelected,
   excludedTransactionsIdsSelected,
+
+  // #withBankingActions
+  enableMultipleCategorization,
 }) {
   const history = useHistory();
   const { accountId } = useAccountTransactionsContext();
@@ -148,6 +153,10 @@ function AccountTransactionsActionsBar({
       });
   };
 
+  const handleMultipleCategorizingSwitch = (event) => {
+    enableMultipleCategorization(event.currentTarget.checked);
+  };
+
   return (
     <DashboardActionsBar>
       <NavbarGroup>
@@ -201,7 +210,6 @@ function AccountTransactionsActionsBar({
             disable={isExcludingLoading}
           />
         )}
-
         {!isEmpty(excludedTransactionsIdsSelected) && (
           <Button
             icon={<Icon icon="disable" iconSize={16} />}
@@ -215,6 +223,20 @@ function AccountTransactionsActionsBar({
       </NavbarGroup>
 
       <NavbarGroup align={Alignment.RIGHT}>
+        <Tooltip
+          content={
+            'Enables to categorize or matching multiple bank transactions into one transaction.'
+          }
+          position={Position.BOTTOM}
+          minimal
+        >
+          <Switch
+            label={'Multi Select'}
+            inline
+            onChange={handleMultipleCategorizingSwitch}
+          />
+        </Tooltip>
+        <NavbarDivider />
         <Popover
           minimal={true}
           interactionKind={PopoverInteractionKind.CLICK}
@@ -256,4 +278,5 @@ export default compose(
       excludedTransactionsIdsSelected,
     }),
   ),
+  withBankingActions,
 )(AccountTransactionsActionsBar);
diff --git a/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/AccountTransactionsUncategorizedTable.module.scss b/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/AccountTransactionsUncategorizedTable.module.scss
new file mode 100644
index 000000000..875ab6a14
--- /dev/null
+++ b/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/AccountTransactionsUncategorizedTable.module.scss
@@ -0,0 +1,15 @@
+
+
+.table :global .td.categorize_include,
+.table :global .th.categorize_include {
+  display: none;  
+}
+
+.table.showCategorizeColumn :global .td.categorize_include,
+.table.showCategorizeColumn :global .th.categorize_include {
+  display: flex;
+}
+
+.categorizeCheckbox:global(.bp4-checkbox) :global .bp4-control-indicator {
+  border-radius: 20px;
+}
\ No newline at end of file
diff --git a/packages/webapp/src/containers/CashFlow/AccountTransactions/AccountTransactionsUncategorizedTable.tsx b/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/AccountTransactionsUncategorizedTable.tsx
similarity index 85%
rename from packages/webapp/src/containers/CashFlow/AccountTransactions/AccountTransactionsUncategorizedTable.tsx
rename to packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/AccountTransactionsUncategorizedTable.tsx
index 0d36596d3..715ec1296 100644
--- a/packages/webapp/src/containers/CashFlow/AccountTransactions/AccountTransactionsUncategorizedTable.tsx
+++ b/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/AccountTransactionsUncategorizedTable.tsx
@@ -1,5 +1,6 @@
 // @ts-nocheck
 import React from 'react';
+import clsx from 'classnames';
 import styled from 'styled-components';
 import { Intent } from '@blueprintjs/core';
 import {
@@ -12,17 +13,19 @@ import {
   AppToaster,
 } from '@/components';
 import { TABLES } from '@/constants/tables';
-import { ActionsMenu } from './UncategorizedTransactions/components';
+import { ActionsMenu } from './components';
 
 import withSettings from '@/containers/Settings/withSettings';
-import { withBankingActions } from '../withBankingActions';
+import { withBankingActions } from '../../withBankingActions';
 
 import { useMemorizedColumnsWidths } from '@/hooks';
-import { useAccountUncategorizedTransactionsColumns } from './components';
-import { useAccountUncategorizedTransactionsContext } from './AllTransactionsUncategorizedBoot';
+import { useAccountUncategorizedTransactionsContext } from '../AllTransactionsUncategorizedBoot';
 import { useExcludeUncategorizedTransaction } from '@/hooks/query/bank-rules';
+import { useAccountUncategorizedTransactionsColumns } from './hooks';
 
 import { compose } from '@/utils';
+import { withBanking } from '../../withBanking';
+import styles from './AccountTransactionsUncategorizedTable.module.scss';
 
 /**
  * Account transactions data table.
@@ -31,6 +34,9 @@ function AccountTransactionsDataTable({
   // #withSettings
   cashflowTansactionsTableSize,
 
+  // #withBanking
+  openMatchingTransactionAside,
+
   // #withBankingActions
   setUncategorizedTransactionIdForMatching,
   setUncategorizedTransactionsSelected,
@@ -66,7 +72,7 @@ function AccountTransactionsDataTable({
           message: 'The bank transaction has been excluded successfully.',
         });
       })
-      .catch((error) => {
+      .catch(() => {
         AppToaster.show({
           intent: Intent.DANGER,
           message: 'Something went wrong.',
@@ -106,12 +112,14 @@ function AccountTransactionsDataTable({
       noResults={
         'There is no uncategorized transactions in the current account.'
       }
-      className="table-constrant"
       onSelectedRowsChange={handleSelectedRowsChange}
       payload={{
         onExclude: handleExcludeTransaction,
         onCategorize: handleCategorizeBtnClick,
       }}
+      className={clsx('table-constrant', styles.table, {
+        [styles.showCategorizeColumn]: openMatchingTransactionAside,
+      })}
     />
   );
 }
@@ -121,6 +129,9 @@ export default compose(
     cashflowTansactionsTableSize: cashflowTransactionsSettings?.tableSize,
   })),
   withBankingActions,
+  withBanking(({ openMatchingTransactionAside }) => ({
+    openMatchingTransactionAside,
+  })),
 )(AccountTransactionsDataTable);
 
 const DashboardConstrantTable = styled(DataTable)`
diff --git a/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/AccountUncategorizedTransactionsAll.tsx b/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/AccountUncategorizedTransactionsAll.tsx
index 8a3ce66f9..01c1e2f0d 100644
--- a/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/AccountUncategorizedTransactionsAll.tsx
+++ b/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/AccountUncategorizedTransactionsAll.tsx
@@ -1,6 +1,6 @@
 import * as R from 'ramda';
 import { useEffect } from 'react';
-import AccountTransactionsUncategorizedTable from '../AccountTransactionsUncategorizedTable';
+import AccountTransactionsUncategorizedTable from './AccountTransactionsUncategorizedTable';
 import { AccountUncategorizedTransactionsBoot } from '../AllTransactionsUncategorizedBoot';
 import { AccountTransactionsCard } from './AccountTransactionsCard';
 import {
diff --git a/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/hooks.tsx b/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/hooks.tsx
new file mode 100644
index 000000000..efe3168af
--- /dev/null
+++ b/packages/webapp/src/containers/CashFlow/AccountTransactions/UncategorizedTransactions/hooks.tsx
@@ -0,0 +1,143 @@
+// @ts-nocheck
+import React from 'react';
+import intl from 'react-intl-universal';
+import {
+  Checkbox,
+  Intent,
+  PopoverInteractionKind,
+  Position,
+  Tag,
+  Tooltip,
+} from '@blueprintjs/core';
+import {
+  useAddTransactionsToCategorizeSelected,
+  useRemoveTransactionsToCategorizeSelected,
+} from '@/hooks/state/banking';
+import { Box, Icon } from '@/components';
+import styles from './AccountTransactionsUncategorizedTable.module.scss';
+
+function statusAccessor(transaction) {
+  return transaction.is_recognized ? (
+    <Tooltip
+      // compact
+      interactionKind={PopoverInteractionKind.HOVER}
+      position={Position.RIGHT}
+      content={
+        <Box>
+          <span>{transaction.assigned_category_formatted}</span>
+          <Icon
+            icon={'arrowRight'}
+            color={'#8F99A8'}
+            iconSize={12}
+            style={{ marginLeft: 8, marginRight: 8 }}
+          />
+          <span>{transaction.assigned_account_name}</span>
+        </Box>
+      }
+    >
+      <Box>
+        <Tag intent={Intent.SUCCESS} interactive>
+          Recognized
+        </Tag>
+      </Box>
+    </Tooltip>
+  ) : null;
+}
+
+/**
+ * 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(
+    () => [
+      {
+        id: 'date',
+        Header: intl.get('date'),
+        accessor: 'formatted_date',
+        width: 40,
+        clickable: true,
+        textOverview: true,
+      },
+      {
+        id: 'description',
+        Header: 'Description',
+        accessor: 'description',
+        width: 160,
+        textOverview: true,
+        clickable: true,
+      },
+      {
+        id: 'payee',
+        Header: 'Payee',
+        accessor: 'payee',
+        width: 60,
+        clickable: true,
+        textOverview: true,
+      },
+      {
+        id: 'reference_number',
+        Header: 'Ref.#',
+        accessor: 'reference_no',
+        width: 50,
+        clickable: true,
+        textOverview: true,
+      },
+      {
+        id: 'status',
+        Header: 'Status',
+        accessor: statusAccessor,
+      },
+      {
+        id: 'deposit',
+        Header: intl.get('cash_flow.label.deposit'),
+        accessor: 'formatted_deposit_amount',
+        width: 40,
+        className: 'deposit',
+        textOverview: true,
+        align: 'right',
+        clickable: true,
+      },
+      {
+        id: 'withdrawal',
+        Header: intl.get('cash_flow.label.withdrawal'),
+        accessor: 'formatted_withdrawal_amount',
+        className: 'withdrawal',
+        width: 40,
+        textOverview: true,
+        align: 'right',
+        clickable: true,
+      },
+      {
+        id: 'categorize_include',
+        Header: '',
+        accessor: (value) => (
+          <Checkbox
+            large
+            onChange={handleChange(value)}
+            className={styles.categorizeCheckbox}
+          />
+        ),
+        width: 10,
+        minWidth: 10,
+        maxWidth: 10,
+        align: 'right',
+        className: 'categorize_include',
+      },
+    ],
+    [],
+  );
+}
diff --git a/packages/webapp/src/containers/CashFlow/AccountTransactions/components.tsx b/packages/webapp/src/containers/CashFlow/AccountTransactions/components.tsx
index 00981d38e..715ee0b33 100644
--- a/packages/webapp/src/containers/CashFlow/AccountTransactions/components.tsx
+++ b/packages/webapp/src/containers/CashFlow/AccountTransactions/components.tsx
@@ -9,15 +9,10 @@ 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 },
@@ -155,122 +150,3 @@ export function AccountTransactionsProgressBar() {
     <MaterialProgressBar />
   ) : null;
 }
-
-function statusAccessor(transaction) {
-  return transaction.is_recognized ? (
-    <Tooltip
-      compact
-      interactionKind={PopoverInteractionKind.HOVER}
-      position={Position.RIGHT}
-      content={
-        <Box>
-          <span>{transaction.assigned_category_formatted}</span>
-          <Icon
-            icon={'arrowRight'}
-            color={'#8F99A8'}
-            iconSize={12}
-            style={{ marginLeft: 8, marginRight: 8 }}
-          />
-          <span>{transaction.assigned_account_name}</span>
-        </Box>
-      }
-    >
-      <Box>
-        <Tag intent={Intent.SUCCESS} interactive>
-          Recognized
-        </Tag>
-      </Box>
-    </Tooltip>
-  ) : null;
-}
-
-/**
- * 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(
-    () => [
-      {
-        id: 'date',
-        Header: intl.get('date'),
-        accessor: 'formatted_date',
-        width: 40,
-        clickable: true,
-        textOverview: true,
-      },
-      {
-        id: 'description',
-        Header: 'Description',
-        accessor: 'description',
-        width: 160,
-        textOverview: true,
-        clickable: true,
-      },
-      {
-        id: 'payee',
-        Header: 'Payee',
-        accessor: 'payee',
-        width: 60,
-        clickable: true,
-        textOverview: true,
-      },
-      {
-        id: 'reference_number',
-        Header: 'Ref.#',
-        accessor: 'reference_no',
-        width: 50,
-        clickable: true,
-        textOverview: true,
-      },
-      {
-        id: 'status',
-        Header: 'Status',
-        accessor: statusAccessor,
-      },
-      {
-        id: 'deposit',
-        Header: intl.get('cash_flow.label.deposit'),
-        accessor: 'formatted_deposit_amount',
-        width: 40,
-        className: 'deposit',
-        textOverview: true,
-        align: 'right',
-        clickable: true,
-      },
-      {
-        id: 'withdrawal',
-        Header: intl.get('cash_flow.label.withdrawal'),
-        accessor: 'formatted_withdrawal_amount',
-        className: 'withdrawal',
-        width: 40,
-        textOverview: true,
-        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/withBanking.ts b/packages/webapp/src/containers/CashFlow/withBanking.ts
index 1d2a43d07..08ddbf87f 100644
--- a/packages/webapp/src/containers/CashFlow/withBanking.ts
+++ b/packages/webapp/src/containers/CashFlow/withBanking.ts
@@ -18,6 +18,7 @@ export const withBanking = (mapState) => {
         state.plaid.uncategorizedTransactionsSelected,
 
       excludedTransactionsIdsSelected: state.plaid.excludedTransactionsSelected,
+      isMultipleCategorization: state.plaid.isMultipleCategorization,
     };
     return mapState ? mapState(mapped, state, props) : mapped;
   };
diff --git a/packages/webapp/src/containers/CashFlow/withBankingActions.ts b/packages/webapp/src/containers/CashFlow/withBankingActions.ts
index b8fb49e31..3ac80122e 100644
--- a/packages/webapp/src/containers/CashFlow/withBankingActions.ts
+++ b/packages/webapp/src/containers/CashFlow/withBankingActions.ts
@@ -10,6 +10,7 @@ import {
   setExcludedTransactionsSelected,
   resetTransactionsToCategorizeSelected,
   setTransactionsToCategorizeSelected,
+  enableMultipleCategorization,
 } from '@/store/banking/banking.reducer';
 
 export interface WithBankingActionsProps {
@@ -28,6 +29,8 @@ export interface WithBankingActionsProps {
 
   setTransactionsToCategorizeSelected: (ids: Array<string | number>) => void;
   resetTransactionsToCategorizeSelected: () => void;
+
+  enableMultipleCategorization: (enable: boolean) => void;
 }
 
 const mapDipatchToProps = (dispatch: any): WithBankingActionsProps => ({
@@ -66,6 +69,9 @@ const mapDipatchToProps = (dispatch: any): WithBankingActionsProps => ({
     dispatch(setTransactionsToCategorizeSelected({ ids })),
   resetTransactionsToCategorizeSelected: () =>
     dispatch(resetTransactionsToCategorizeSelected()),
+
+  enableMultipleCategorization: (enable) =>
+    dispatch(enableMultipleCategorization({ enable })),
 });
 
 export const withBankingActions = connect<
diff --git a/packages/webapp/src/hooks/state/banking.ts b/packages/webapp/src/hooks/state/banking.ts
index a6e007e01..ab441c1f5 100644
--- a/packages/webapp/src/hooks/state/banking.ts
+++ b/packages/webapp/src/hooks/state/banking.ts
@@ -9,6 +9,7 @@ import {
   getTransactionsToCategorizeSelected,
   addTransactionsToCategorizeSelected,
   removeTransactionsToCategorizeSelected,
+  getOpenMatchingTransactionAside,
 } from '@/store/banking/banking.reducer';
 
 export const useSetBankingPlaidToken = () => {
@@ -82,3 +83,14 @@ export const useResetTransactionsToCategorizeSelected = () => {
     dispatch(resetTransactionsToCategorizeSelected());
   }, [dispatch]);
 };
+
+export const useGetOpenMatchingTransactionAside = () => {
+  const openMatchingTransactionAside = useSelector(
+    getOpenMatchingTransactionAside,
+  );
+
+  return useMemo(
+    () => openMatchingTransactionAside,
+    [openMatchingTransactionAside],
+  );
+};
diff --git a/packages/webapp/src/store/banking/banking.reducer.ts b/packages/webapp/src/store/banking/banking.reducer.ts
index 1d9720cb0..7e0cca1e1 100644
--- a/packages/webapp/src/store/banking/banking.reducer.ts
+++ b/packages/webapp/src/store/banking/banking.reducer.ts
@@ -10,6 +10,8 @@ interface StorePlaidState {
   uncategorizedTransactionsSelected: Array<number | string>;
   excludedTransactionsSelected: Array<number | string>;
   transactionsToCategorizeSelected: Array<number | string>;
+
+  enableMultipleCategorization: boolean;
 }
 
 export const PlaidSlice = createSlice({
@@ -25,6 +27,7 @@ export const PlaidSlice = createSlice({
     uncategorizedTransactionsSelected: [],
     excludedTransactionsSelected: [],
     transactionsToCategorizeSelected: [],
+    enableMultipleCategorization: false,
   } as StorePlaidState,
   reducers: {
     setPlaidId: (state: StorePlaidState, action: PayloadAction<string>) => {
@@ -113,6 +116,13 @@ export const PlaidSlice = createSlice({
     resetTransactionsToCategorizeSelected: (state: StorePlaidState) => {
       state.transactionsToCategorizeSelected = [];
     },
+
+    enableMultipleCategorization: (
+      state: StorePlaidState,
+      action: PayloadAction<{ enable: boolean }>,
+    ) => {
+      state.enableMultipleCategorization = action.payload.enable;
+    },
   },
 });
 
@@ -131,8 +141,15 @@ export const {
   addTransactionsToCategorizeSelected,
   removeTransactionsToCategorizeSelected,
   resetTransactionsToCategorizeSelected,
+  enableMultipleCategorization,
 } = PlaidSlice.actions;
 
 export const getPlaidToken = (state: any) => state.plaid.plaidToken;
 export const getTransactionsToCategorizeSelected = (state: any) =>
   state.plaid.transactionsToCategorizeSelected;
+
+export const getOpenMatchingTransactionAside = (state: any) =>
+  state.plaid.openMatchingTransactionAside;
+
+export const isMultipleCategorization = (state: any) =>
+  state.plaid.enableMultipleCategorization;
diff --git a/packages/webapp/src/style/components/DataTable/DataTable.scss b/packages/webapp/src/style/components/DataTable/DataTable.scss
index cf4018489..2c78ebedc 100644
--- a/packages/webapp/src/style/components/DataTable/DataTable.scss
+++ b/packages/webapp/src/style/components/DataTable/DataTable.scss
@@ -124,7 +124,7 @@
         }
       }
 
-      .bp4-control.bp4-checkbox .bp4-control-indicator {
+      .bp4-control.bp4-checkbox:not(.bp4-large) .bp4-control-indicator {
         cursor: auto;
 
         &,