diff --git a/src/components/MoneyReportHeader.tsx b/src/components/MoneyReportHeader.tsx
index 76be659b35b4..3304dede2743 100644
--- a/src/components/MoneyReportHeader.tsx
+++ b/src/components/MoneyReportHeader.tsx
@@ -436,6 +436,7 @@ function MoneyReportHeader({policy, report: moneyRequestReport, transactionThrea
                     paymentType={paymentType}
                     chatReport={chatReport}
                     moneyRequestReport={moneyRequestReport}
+                    transactionCount={transactionIDs.length}
                 />
             )}
             <ConfirmModal
diff --git a/src/components/ProcessMoneyReportHoldMenu.tsx b/src/components/ProcessMoneyReportHoldMenu.tsx
index 46ec51994d90..872464d8a5b0 100644
--- a/src/components/ProcessMoneyReportHoldMenu.tsx
+++ b/src/components/ProcessMoneyReportHoldMenu.tsx
@@ -1,4 +1,4 @@
-import React from 'react';
+import React, {useMemo} from 'react';
 import type {OnyxEntry} from 'react-native-onyx';
 import useLocalize from '@hooks/useLocalize';
 import Navigation from '@libs/Navigation/Navigation';
@@ -40,6 +40,9 @@ type ProcessMoneyReportHoldMenuProps = {
 
     /** Type of action handled */
     requestType?: ActionHandledType;
+
+    /** Number of transaction of a money request */
+    transactionCount: number;
 };
 
 function ProcessMoneyReportHoldMenu({
@@ -52,6 +55,7 @@ function ProcessMoneyReportHoldMenu({
     paymentType,
     chatReport,
     moneyRequestReport,
+    transactionCount,
 }: ProcessMoneyReportHoldMenuProps) {
     const {translate} = useLocalize();
     const isApprove = requestType === CONST.IOU.REPORT_ACTION_TYPE.APPROVE;
@@ -68,12 +72,19 @@ function ProcessMoneyReportHoldMenu({
         onClose();
     };
 
+    const promptText = useMemo(() => {
+        if (nonHeldAmount) {
+            return translate(isApprove ? 'iou.confirmApprovalAmount' : 'iou.confirmPayAmount');
+        }
+        return translate(isApprove ? 'iou.confirmApprovalAllHoldAmount' : 'iou.confirmPayAllHoldAmount', {transactionCount});
+    }, [nonHeldAmount, transactionCount, translate, isApprove]);
+
     return (
         <DecisionModal
             title={translate(isApprove ? 'iou.confirmApprove' : 'iou.confirmPay')}
             onClose={onClose}
             isVisible={isVisible}
-            prompt={translate(isApprove ? 'iou.confirmApprovalAmount' : 'iou.confirmPayAmount')}
+            prompt={promptText}
             firstOptionText={nonHeldAmount ? `${translate(isApprove ? 'iou.approveOnly' : 'iou.payOnly')} ${nonHeldAmount}` : undefined}
             secondOptionText={`${translate(isApprove ? 'iou.approve' : 'iou.pay')} ${fullAmount}`}
             onFirstOptionSubmit={() => onSubmit(false)}
diff --git a/src/components/ReportActionItem/ReportPreview.tsx b/src/components/ReportActionItem/ReportPreview.tsx
index c796a267fd01..d986af8f5cf3 100644
--- a/src/components/ReportActionItem/ReportPreview.tsx
+++ b/src/components/ReportActionItem/ReportPreview.tsx
@@ -454,6 +454,7 @@ function ReportPreview({
                     paymentType={paymentType}
                     chatReport={chatReport}
                     moneyRequestReport={iouReport}
+                    transactionCount={numberOfRequests}
                 />
             )}
         </OfflineWithFeedback>
diff --git a/src/languages/en.ts b/src/languages/en.ts
index 9a862171ae49..90d87309a845 100755
--- a/src/languages/en.ts
+++ b/src/languages/en.ts
@@ -16,6 +16,7 @@ import type {
     ChangePolicyParams,
     ChangeTypeParams,
     CharacterLimitParams,
+    ConfirmHoldExpenseParams,
     ConfirmThatParams,
     DateShouldBeAfterParams,
     DateShouldBeBeforeParams,
@@ -789,8 +790,12 @@ export default {
         keepAll: 'Keep all',
         confirmApprove: 'Confirm approval amount',
         confirmApprovalAmount: "Approve what's not on hold, or approve the entire report.",
+        confirmApprovalAllHoldAmount: ({transactionCount}: ConfirmHoldExpenseParams) =>
+            `${Str.pluralize('This expense is', 'These expenses are', transactionCount)} on hold. Do you want to approve anyway?`,
         confirmPay: 'Confirm payment amount',
-        confirmPayAmount: "Pay what's not on hold, or pay all out-of-pocket spend.",
+        confirmPayAmount: "Pay what's not on hold, or pay the entire report.",
+        confirmPayAllHoldAmount: ({transactionCount}: ConfirmHoldExpenseParams) =>
+            `${Str.pluralize('This expense is', 'These expenses are', transactionCount)} on hold. Do you want to pay anyway?`,
         payOnly: 'Pay only',
         approveOnly: 'Approve only',
         holdEducationalTitle: 'This expense is on',
diff --git a/src/languages/es.ts b/src/languages/es.ts
index 911912ca59aa..c3dee7f709c2 100644
--- a/src/languages/es.ts
+++ b/src/languages/es.ts
@@ -15,6 +15,7 @@ import type {
     ChangePolicyParams,
     ChangeTypeParams,
     CharacterLimitParams,
+    ConfirmHoldExpenseParams,
     ConfirmThatParams,
     DateShouldBeAfterParams,
     DateShouldBeBeforeParams,
@@ -783,8 +784,20 @@ export default {
         keepAll: 'Mantener todos',
         confirmApprove: 'Confirmar importe a aprobar',
         confirmApprovalAmount: 'Aprueba lo que no está bloqueado, o aprueba todo el informe.',
+        confirmApprovalAllHoldAmount: ({transactionCount}: ConfirmHoldExpenseParams) =>
+            `${Str.pluralize('Este gasto está bloqueado', 'Estos gastos están bloqueados', transactionCount)}. ¿Quieres ${Str.pluralize(
+                'aprobar',
+                'aprobarlos',
+                transactionCount,
+            )} de todos modos?`,
         confirmPay: 'Confirmar importe de pago',
-        confirmPayAmount: 'Paga lo que no está bloqueado, o paga todos los gastos por cuenta propia.',
+        confirmPayAmount: 'Paga lo que no está bloqueado, o paga el informe completo.',
+        confirmPayAllHoldAmount: ({transactionCount}: ConfirmHoldExpenseParams) =>
+            `${Str.pluralize('Este gasto está bloqueado', 'Estos gastos están bloqueados', transactionCount)}. ¿Quieres ${Str.pluralize(
+                'pagar',
+                'pagarlo',
+                transactionCount,
+            )} de todos modos?`,
         payOnly: 'Solo pagar',
         approveOnly: 'Solo aprobar',
         hold: 'Bloquear',
diff --git a/src/languages/types.ts b/src/languages/types.ts
index eb90f2d9e0b2..23cde49bfd53 100644
--- a/src/languages/types.ts
+++ b/src/languages/types.ts
@@ -298,6 +298,8 @@ type DistanceRateOperationsParams = {count: number};
 
 type ReimbursementRateParams = {unit: Unit};
 
+type ConfirmHoldExpenseParams = {transactionCount: number};
+
 type ChangeFieldParams = {oldValue?: string; newValue: string; fieldName: string};
 
 type ChangePolicyParams = {fromPolicy: string; toPolicy: string};
@@ -339,6 +341,7 @@ export type {
     BeginningOfChatHistoryDomainRoomPartOneParams,
     CanceledRequestParams,
     CharacterLimitParams,
+    ConfirmHoldExpenseParams,
     ConfirmThatParams,
     DateShouldBeAfterParams,
     DateShouldBeBeforeParams,