diff --git a/src/libs/ReportUtils.ts b/src/libs/ReportUtils.ts
index 41560694f353..4de976aaf160 100644
--- a/src/libs/ReportUtils.ts
+++ b/src/libs/ReportUtils.ts
@@ -2404,6 +2404,14 @@ function isReportFieldOfTypeTitle(reportField: OnyxEntry<PolicyReportField>): bo
     return reportField?.type === 'formula' && reportField?.fieldID === CONST.REPORT_FIELD_TITLE_FIELD_ID;
 }
 
+/**
+ * Check if Report has any held expenses
+ */
+function isHoldCreator(transaction: OnyxEntry<Transaction>, reportID: string): boolean {
+    const holdReportAction = ReportActionsUtils.getReportAction(reportID, `${transaction?.comment?.hold ?? ''}`);
+    return isActionCreator(holdReportAction);
+}
+
 /**
  * Check if report fields are available to use in a report
  */
@@ -2721,6 +2729,71 @@ function canEditReportAction(reportAction: OnyxEntry<ReportAction>): boolean {
     );
 }
 
+function canHoldUnholdReportAction(reportAction: OnyxEntry<ReportAction>): {canHoldRequest: boolean; canUnholdRequest: boolean} {
+    if (reportAction?.actionName !== CONST.REPORT.ACTIONS.TYPE.IOU) {
+        return {canHoldRequest: false, canUnholdRequest: false};
+    }
+
+    const moneyRequestReportID = reportAction?.originalMessage?.IOUReportID ?? 0;
+    const moneyRequestReport = getReport(String(moneyRequestReportID));
+
+    if (!moneyRequestReportID || !moneyRequestReport) {
+        return {canHoldRequest: false, canUnholdRequest: false};
+    }
+
+    const isRequestSettled = isSettled(moneyRequestReport?.reportID);
+    const isApproved = isReportApproved(moneyRequestReport);
+    const transactionID = moneyRequestReport ? reportAction?.originalMessage?.IOUTransactionID : 0;
+    const transaction = allTransactions?.[`${ONYXKEYS.COLLECTION.TRANSACTION}${transactionID}`] ?? ({} as Transaction);
+
+    const parentReport = getReport(String(moneyRequestReport.parentReportID));
+    const parentReportAction = ReportActionsUtils.getParentReportAction(moneyRequestReport);
+
+    const isRequestIOU = parentReport?.type === 'iou';
+    const isRequestHoldCreator = isHoldCreator(transaction, moneyRequestReport?.reportID) && isRequestIOU;
+    const isTrackExpenseMoneyReport = isTrackExpenseReport(moneyRequestReport);
+    const isActionOwner =
+        typeof parentReportAction?.actorAccountID === 'number' &&
+        typeof currentUserPersonalDetails?.accountID === 'number' &&
+        parentReportAction.actorAccountID === currentUserPersonalDetails?.accountID;
+    const isApprover = isMoneyRequestReport(moneyRequestReport) && moneyRequestReport?.managerID !== null && currentUserPersonalDetails?.accountID === moneyRequestReport?.managerID;
+    const isOnHold = TransactionUtils.isOnHold(transaction);
+    const isScanning = TransactionUtils.hasReceipt(transaction) && TransactionUtils.isReceiptBeingScanned(transaction);
+
+    const canModifyStatus = !isTrackExpenseMoneyReport && (isPolicyAdmin || isActionOwner || isApprover);
+    const isDeletedParentAction = isEmptyObject(parentReportAction) || ReportActionsUtils.isDeletedAction(parentReportAction);
+
+    const canHoldOrUnholdRequest = !isRequestSettled && !isApproved && !isDeletedParentAction;
+    const canHoldRequest = canHoldOrUnholdRequest && !isOnHold && (isRequestHoldCreator || (!isRequestIOU && canModifyStatus)) && !isScanning;
+    const canUnholdRequest = !!(canHoldOrUnholdRequest && isOnHold && (isRequestHoldCreator || (!isRequestIOU && canModifyStatus)));
+
+    return {canHoldRequest, canUnholdRequest};
+}
+
+const changeMoneyRequestHoldStatus = (reportAction: OnyxEntry<ReportAction>): void => {
+    if (reportAction?.actionName !== CONST.REPORT.ACTIONS.TYPE.IOU) {
+        return;
+    }
+    const moneyRequestReportID = reportAction?.originalMessage?.IOUReportID ?? 0;
+
+    const moneyRequestReport = getReport(String(moneyRequestReportID));
+    if (!moneyRequestReportID || !moneyRequestReport) {
+        return;
+    }
+
+    const transactionID = reportAction?.originalMessage?.IOUTransactionID ?? '';
+    const transaction = allTransactions?.[`${ONYXKEYS.COLLECTION.TRANSACTION}${transactionID}`] ?? ({} as Transaction);
+    const isOnHold = TransactionUtils.isOnHold(transaction);
+    const policy = allPolicies?.[`${ONYXKEYS.COLLECTION.POLICY}${moneyRequestReport.policyID}`] ?? null;
+
+    if (isOnHold) {
+        IOU.unholdRequest(transactionID, reportAction.childReportID ?? '');
+    } else {
+        const activeRoute = encodeURIComponent(Navigation.getActiveRouteWithoutParams());
+        Navigation.navigate(ROUTES.MONEY_REQUEST_HOLD_REASON.getRoute(policy?.type ?? CONST.POLICY.TYPE.PERSONAL, transactionID, reportAction.childReportID ?? '', activeRoute));
+    }
+};
+
 /**
  * Gets all transactions on an IOU report with a receipt
  */
@@ -6386,14 +6459,6 @@ function navigateToPrivateNotes(report: OnyxEntry<Report>, session: OnyxEntry<Se
     Navigation.navigate(ROUTES.PRIVATE_NOTES_LIST.getRoute(report.reportID));
 }
 
-/**
- * Check if Report has any held expenses
- */
-function isHoldCreator(transaction: OnyxEntry<Transaction>, reportID: string): boolean {
-    const holdReportAction = ReportActionsUtils.getReportAction(reportID, `${transaction?.comment?.hold ?? ''}`);
-    return isActionCreator(holdReportAction);
-}
-
 /**
  * Get all held transactions of a iouReport
  */
@@ -6905,6 +6970,7 @@ export {
     canCreateTaskInReport,
     canCurrentUserOpenReport,
     canDeleteReportAction,
+    canHoldUnholdReportAction,
     canEditFieldOfMoneyRequest,
     canEditMoneyRequest,
     canEditPolicyDescription,
@@ -7132,6 +7198,7 @@ export {
     shouldShowMerchantColumn,
     isCurrentUserInvoiceReceiver,
     isDraftReport,
+    changeMoneyRequestHoldStatus,
     createDraftWorkspaceAndNavigateToConfirmationScreen,
 };
 
diff --git a/src/pages/home/report/ContextMenu/ContextMenuActions.tsx b/src/pages/home/report/ContextMenu/ContextMenuActions.tsx
index aa7b6aa3bfb5..11d81d23dd06 100644
--- a/src/pages/home/report/ContextMenu/ContextMenuActions.tsx
+++ b/src/pages/home/report/ContextMenu/ContextMenuActions.tsx
@@ -256,6 +256,40 @@ const ContextMenuActions: ContextMenuAction[] = [
         },
         getDescription: () => {},
     },
+    {
+        isAnonymousAction: false,
+        textTranslateKey: 'iou.unholdExpense',
+        icon: Expensicons.Stopwatch,
+        shouldShow: (type, reportAction) =>
+            type === CONST.CONTEXT_MENU_TYPES.REPORT_ACTION && ReportUtils.canEditReportAction(reportAction) && ReportUtils.canHoldUnholdReportAction(reportAction).canUnholdRequest,
+        onPress: (closePopover, {reportAction}) => {
+            if (closePopover) {
+                hideContextMenu(false, () => ReportUtils.changeMoneyRequestHoldStatus(reportAction));
+                return;
+            }
+
+            // No popover to hide, call changeMoneyRequestHoldStatus immediately
+            ReportUtils.changeMoneyRequestHoldStatus(reportAction);
+        },
+        getDescription: () => {},
+    },
+    {
+        isAnonymousAction: false,
+        textTranslateKey: 'iou.hold',
+        icon: Expensicons.Stopwatch,
+        shouldShow: (type, reportAction) =>
+            type === CONST.CONTEXT_MENU_TYPES.REPORT_ACTION && ReportUtils.canEditReportAction(reportAction) && ReportUtils.canHoldUnholdReportAction(reportAction).canHoldRequest,
+        onPress: (closePopover, {reportAction}) => {
+            if (closePopover) {
+                hideContextMenu(false, () => ReportUtils.changeMoneyRequestHoldStatus(reportAction));
+                return;
+            }
+
+            // No popover to hide, call changeMoneyRequestHoldStatus immediately
+            ReportUtils.changeMoneyRequestHoldStatus(reportAction);
+        },
+        getDescription: () => {},
+    },
     {
         isAnonymousAction: false,
         textTranslateKey: 'reportActionContextMenu.joinThread',