diff --git a/src/libs/ReportUtils.ts b/src/libs/ReportUtils.ts
index 71173cb404a8..2e6d8afc7aab 100644
--- a/src/libs/ReportUtils.ts
+++ b/src/libs/ReportUtils.ts
@@ -2955,27 +2955,30 @@ function canHoldUnholdReportAction(reportAction: OnyxInputOrEntry<ReportAction>)
     const transactionID = moneyRequestReport ? ReportActionsUtils.getOriginalMessage(reportAction)?.IOUTransactionID : 0;
     const transaction = allTransactions?.[`${ONYXKEYS.COLLECTION.TRANSACTION}${transactionID}`] ?? ({} as Transaction);
 
-    const parentReport = getReportOrDraftReport(String(moneyRequestReport.parentReportID));
     const parentReportAction = ReportActionsUtils.getParentReportAction(moneyRequestReport);
 
-    const isRequestIOU = parentReport?.type === 'iou';
-    const isRequestHoldCreator = isHoldCreator(transaction, moneyRequestReport?.reportID) && isRequestIOU;
+    const isRequestIOU = isIOUReport(moneyRequestReport);
+    const isHoldActionCreator = isHoldCreator(transaction, reportAction.childReportID ?? '-1');
+
     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 isAdmin = isPolicyAdmin(moneyRequestReport.policyID ?? '-1', allPolicies);
     const isOnHold = TransactionUtils.isOnHold(transaction);
     const isScanning = TransactionUtils.hasReceipt(transaction) && TransactionUtils.isReceiptBeingScanned(transaction);
+    const isClosed = isClosedReport(moneyRequestReport);
 
-    const canModifyStatus = !isTrackExpenseMoneyReport && (isPolicyAdmin || isActionOwner || isApprover);
+    const canModifyStatus = !isTrackExpenseMoneyReport && (isAdmin || isActionOwner || isApprover);
+    const canModifyUnholdStatus = !isTrackExpenseMoneyReport && (isAdmin || (isActionOwner && isHoldActionCreator) || isApprover);
     const isDeletedParentAction = isEmptyObject(parentReportAction) || ReportActionsUtils.isDeletedAction(parentReportAction);
 
-    const canHoldOrUnholdRequest = !isRequestSettled && !isApproved && !isDeletedParentAction;
-    const canHoldRequest = canHoldOrUnholdRequest && !isOnHold && (isRequestHoldCreator || (!isRequestIOU && canModifyStatus)) && !isScanning && !!transaction?.reimbursable;
+    const canHoldOrUnholdRequest = !isRequestSettled && !isApproved && !isDeletedParentAction && !isClosed;
+    const canHoldRequest = canHoldOrUnholdRequest && !isOnHold && (isRequestIOU || canModifyStatus) && !isScanning && !!transaction?.reimbursable;
     const canUnholdRequest =
-        !!(canHoldOrUnholdRequest && isOnHold && !TransactionUtils.isDuplicate(transaction.transactionID, true) && (isRequestHoldCreator || (!isRequestIOU && canModifyStatus))) &&
+        !!(canHoldOrUnholdRequest && isOnHold && !TransactionUtils.isDuplicate(transaction.transactionID, true) && (isRequestIOU ? isHoldActionCreator : canModifyUnholdStatus)) &&
         !!transaction?.reimbursable;
 
     return {canHoldRequest, canUnholdRequest};
diff --git a/src/pages/home/report/ContextMenu/BaseReportActionContextMenu.tsx b/src/pages/home/report/ContextMenu/BaseReportActionContextMenu.tsx
index 457076b19701..58e361d74293 100755
--- a/src/pages/home/report/ContextMenu/BaseReportActionContextMenu.tsx
+++ b/src/pages/home/report/ContextMenu/BaseReportActionContextMenu.tsx
@@ -14,6 +14,7 @@ import useEnvironment from '@hooks/useEnvironment';
 import useKeyboardShortcut from '@hooks/useKeyboardShortcut';
 import useLocalize from '@hooks/useLocalize';
 import useNetwork from '@hooks/useNetwork';
+import usePaginatedReportActions from '@hooks/usePaginatedReportActions';
 import useResponsiveLayout from '@hooks/useResponsiveLayout';
 import useStyleUtils from '@hooks/useStyleUtils';
 import * as ReportActionsUtils from '@libs/ReportActionsUtils';
@@ -141,13 +142,64 @@ function BaseReportActionContextMenu({
 
     const [download] = useOnyx(`${ONYXKEYS.COLLECTION.DOWNLOAD}${sourceID}`);
 
+    const childReport = ReportUtils.getReport(reportAction?.childReportID ?? '-1');
+    const parentReportAction = ReportActionsUtils.getReportAction(childReport?.parentReportID ?? '', childReport?.parentReportActionID ?? '');
+    const {reportActions: paginatedReportActions} = usePaginatedReportActions(childReport?.reportID ?? '-1');
+
+    const transactionThreadReportID = useMemo(
+        () => ReportActionsUtils.getOneTransactionThreadReportID(childReport?.reportID ?? '-1', paginatedReportActions ?? [], isOffline),
+        [childReport?.reportID, paginatedReportActions, isOffline],
+    );
+
+    const [transactionThreadReport] = useOnyx(`${ONYXKEYS.COLLECTION.REPORT}${transactionThreadReportID}`);
+
+    const isMoneyRequestReport = useMemo(() => ReportUtils.isMoneyRequestReport(childReport), [childReport]);
+    const isInvoiceReport = useMemo(() => ReportUtils.isInvoiceReport(childReport), [childReport]);
+
+    const requestParentReportAction = useMemo(() => {
+        if (isMoneyRequestReport || isInvoiceReport) {
+            if (!paginatedReportActions || !transactionThreadReport?.parentReportActionID) {
+                return undefined;
+            }
+            return paginatedReportActions.find((action) => action.reportActionID === transactionThreadReport.parentReportActionID);
+        }
+        return parentReportAction;
+    }, [parentReportAction, isMoneyRequestReport, isInvoiceReport, paginatedReportActions, transactionThreadReport?.parentReportActionID]);
+
+    const moneyRequestAction = transactionThreadReportID ? requestParentReportAction : parentReportAction;
+
+    const [parentReportNameValuePairs] = useOnyx(`${ONYXKEYS.COLLECTION.REPORT_NAME_VALUE_PAIRS}${childReport?.parentReportID ?? '-1'}`);
+    const parentReport = ReportUtils.getReport(childReport?.parentReportID ?? '-1');
+
+    const isMoneyRequest = useMemo(() => ReportUtils.isMoneyRequest(childReport), [childReport]);
+    const isTrackExpenseReport = ReportUtils.isTrackExpenseReport(childReport);
+    const isSingleTransactionView = isMoneyRequest || isTrackExpenseReport;
+    const isMoneyRequestOrReport = isMoneyRequestReport || isInvoiceReport || isSingleTransactionView;
+
+    const areHoldRequirementsMet = isMoneyRequestOrReport && !ReportUtils.isArchivedRoom(transactionThreadReportID ? childReport : parentReport, parentReportNameValuePairs);
+
     const originalReportID = useMemo(() => ReportUtils.getOriginalReportID(reportID, reportAction), [reportID, reportAction]);
 
     const shouldEnableArrowNavigation = !isMini && (isVisible || shouldKeepOpen);
     let filteredContextMenuActions = ContextMenuActions.filter(
         (contextAction) =>
             !disabledActions.includes(contextAction) &&
-            contextAction.shouldShow(type, reportAction, isArchivedRoom, betas, anchor, isChronosReport, reportID, isPinnedChat, isUnreadChat, !!isOffline, isMini, isProduction),
+            contextAction.shouldShow(
+                type,
+                reportAction,
+                isArchivedRoom,
+                betas,
+                anchor,
+                isChronosReport,
+                reportID,
+                isPinnedChat,
+                isUnreadChat,
+                !!isOffline,
+                isMini,
+                isProduction,
+                moneyRequestAction,
+                areHoldRequirementsMet,
+            ),
     );
 
     if (isMini) {
@@ -254,6 +306,7 @@ function BaseReportActionContextMenu({
                             interceptAnonymousUser,
                             openOverflowMenu,
                             setIsEmojiPickerActive,
+                            moneyRequestAction,
                         };
 
                         if ('renderContent' in contextAction) {
diff --git a/src/pages/home/report/ContextMenu/ContextMenuActions.tsx b/src/pages/home/report/ContextMenu/ContextMenuActions.tsx
index 229d623f92df..aec92fd360e9 100644
--- a/src/pages/home/report/ContextMenu/ContextMenuActions.tsx
+++ b/src/pages/home/report/ContextMenu/ContextMenuActions.tsx
@@ -67,6 +67,8 @@ type ShouldShow = (
     isOffline: boolean,
     isMini: boolean,
     isProduction: boolean,
+    moneyRequestAction: ReportAction | undefined,
+    areHoldRequirementsMet: boolean,
 ) => boolean;
 
 type ContextMenuActionPayload = {
@@ -84,6 +86,7 @@ type ContextMenuActionPayload = {
     event?: GestureResponderEvent | MouseEvent | KeyboardEvent;
     setIsEmojiPickerActive?: (state: boolean) => void;
     anchorRef?: MutableRefObject<View | null>;
+    moneyRequestAction: ReportAction | undefined;
 };
 
 type OnPress = (closePopover: boolean, payload: ContextMenuActionPayload, selection?: string, reportID?: string, draftMessage?: string) => void;
@@ -262,18 +265,32 @@ const ContextMenuActions: ContextMenuAction[] = [
     },
     {
         isAnonymousAction: false,
-        textTranslateKey: 'iou.unholdExpense',
+        textTranslateKey: 'iou.unhold',
         icon: Expensicons.Stopwatch,
-        shouldShow: (type, reportAction) =>
-            type === CONST.CONTEXT_MENU_TYPES.REPORT_ACTION && ReportUtils.canEditReportAction(reportAction) && ReportUtils.canHoldUnholdReportAction(reportAction).canUnholdRequest,
-        onPress: (closePopover, {reportAction}) => {
+        shouldShow: (
+            type,
+            reportAction,
+            isArchivedRoom,
+            betas,
+            anchor,
+            isChronosReport,
+            reportID,
+            isPinnedChat,
+            isUnreadChat,
+            isOffline,
+            isMini,
+            isProduction,
+            moneyRequestAction,
+            areHoldRequirementsMet,
+        ) => type === CONST.CONTEXT_MENU_TYPES.REPORT_ACTION && areHoldRequirementsMet && ReportUtils.canHoldUnholdReportAction(moneyRequestAction).canUnholdRequest,
+        onPress: (closePopover, {moneyRequestAction}) => {
             if (closePopover) {
-                hideContextMenu(false, () => ReportUtils.changeMoneyRequestHoldStatus(reportAction));
+                hideContextMenu(false, () => ReportUtils.changeMoneyRequestHoldStatus(moneyRequestAction));
                 return;
             }
 
             // No popover to hide, call changeMoneyRequestHoldStatus immediately
-            ReportUtils.changeMoneyRequestHoldStatus(reportAction);
+            ReportUtils.changeMoneyRequestHoldStatus(moneyRequestAction);
         },
         getDescription: () => {},
     },
@@ -281,16 +298,30 @@ const ContextMenuActions: ContextMenuAction[] = [
         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}) => {
+        shouldShow: (
+            type,
+            reportAction,
+            isArchivedRoom,
+            betas,
+            anchor,
+            isChronosReport,
+            reportID,
+            isPinnedChat,
+            isUnreadChat,
+            isOffline,
+            isMini,
+            isProduction,
+            moneyRequestAction,
+            areHoldRequirementsMet,
+        ) => type === CONST.CONTEXT_MENU_TYPES.REPORT_ACTION && areHoldRequirementsMet && ReportUtils.canHoldUnholdReportAction(moneyRequestAction).canHoldRequest,
+        onPress: (closePopover, {moneyRequestAction}) => {
             if (closePopover) {
-                hideContextMenu(false, () => ReportUtils.changeMoneyRequestHoldStatus(reportAction));
+                hideContextMenu(false, () => ReportUtils.changeMoneyRequestHoldStatus(moneyRequestAction));
                 return;
             }
 
             // No popover to hide, call changeMoneyRequestHoldStatus immediately
-            ReportUtils.changeMoneyRequestHoldStatus(reportAction);
+            ReportUtils.changeMoneyRequestHoldStatus(moneyRequestAction);
         },
         getDescription: () => {},
     },