diff --git a/src/components/ReportActionItem/MoneyRequestView.tsx b/src/components/ReportActionItem/MoneyRequestView.tsx
index 618503e19c33..29c480dcce7d 100644
--- a/src/components/ReportActionItem/MoneyRequestView.tsx
+++ b/src/components/ReportActionItem/MoneyRequestView.tsx
@@ -40,6 +40,7 @@ import * as Link from '@userActions/Link';
 import * as Transaction from '@userActions/Transaction';
 import CONST from '@src/CONST';
 import type {TranslationPaths} from '@src/languages/types';
+import * as Report from '@src/libs/actions/Report';
 import * as ReportActions from '@src/libs/actions/ReportActions';
 import ONYXKEYS from '@src/ONYXKEYS';
 import ROUTES from '@src/ROUTES';
@@ -115,6 +116,9 @@ function MoneyRequestView({
     const {isOffline} = useNetwork();
     const {translate, toLocaleDigit} = useLocalize();
     const [activePolicyID] = useOnyx(ONYXKEYS.NVP_ACTIVE_POLICY_ID);
+    const [chatReport] = useOnyx(`${ONYXKEYS.COLLECTION.REPORT}${parentReport?.parentReportID}`, {
+        selector: (chatReportValue) => chatReportValue && {reportID: chatReportValue.reportID, errorFields: chatReportValue.errorFields},
+    });
 
     const parentReportAction = parentReportActions?.[report.parentReportActionID ?? '-1'];
     const isTrackExpense = ReportUtils.isTrackExpenseReport(report);
@@ -403,11 +407,14 @@ function MoneyRequestView({
                             if (!transaction?.transactionID) {
                                 return;
                             }
-                            if (
-                                transaction.pendingAction === CONST.RED_BRICK_ROAD_PENDING_ACTION.ADD &&
-                                Object.values(transaction?.errors ?? {})?.find((error) => ErrorUtils.isReceiptError(error))
-                            ) {
-                                deleteTransaction(parentReport, parentReportAction);
+                            if (transaction.pendingAction === CONST.RED_BRICK_ROAD_PENDING_ACTION.ADD) {
+                                if (chatReport?.reportID && ReportUtils.getAddWorkspaceRoomOrChatReportErrors(chatReport)) {
+                                    Report.navigateToConciergeChatAndDeleteReport(chatReport.reportID, true, true);
+                                    return;
+                                }
+                                if (Object.values(transaction?.errors ?? {})?.find((error) => ErrorUtils.isReceiptError(error))) {
+                                    deleteTransaction(parentReport, parentReportAction);
+                                }
                             }
                             Transaction.clearError(transaction.transactionID);
                             ReportActions.clearAllRelatedReportActionErrors(report.reportID, parentReportAction);
diff --git a/src/libs/TransactionUtils.ts b/src/libs/TransactionUtils.ts
index 89de7d1e55ec..473cd47b9939 100644
--- a/src/libs/TransactionUtils.ts
+++ b/src/libs/TransactionUtils.ts
@@ -581,7 +581,7 @@ function getAllReportTransactions(reportID?: string, transactions?: OnyxCollecti
     // `reportID` from the `/CreateDistanceRequest` endpoint return's number instead of string for created `transaction`.
     // For reference, https://github.com/Expensify/App/pull/26536#issuecomment-1703573277.
     // We will update this in a follow-up Issue. According to this comment: https://github.com/Expensify/App/pull/26536#issuecomment-1703591019.
-    const nonNullableTransactions: Transaction[] = Object.values(transactions ?? allTransactions ?? {}).filter((transaction): transaction is Transaction => transaction !== null);
+    const nonNullableTransactions: Transaction[] = Object.values(transactions ?? allTransactions ?? {}).filter((transaction): transaction is Transaction => !!transaction);
     return nonNullableTransactions.filter((transaction) => `${transaction.reportID}` === `${reportID}`);
 }
 
diff --git a/src/libs/actions/Report.ts b/src/libs/actions/Report.ts
index 026ce45146d3..0b603416b72d 100644
--- a/src/libs/actions/Report.ts
+++ b/src/libs/actions/Report.ts
@@ -2145,7 +2145,7 @@ function addPolicyReport(policyReport: ReportUtils.OptimisticChatReport) {
 }
 
 /** Deletes a report, along with its reportActions, any linked reports, and any linked IOU report. */
-function deleteReport(reportID: string) {
+function deleteReport(reportID: string, shouldDeleteChildReports = false) {
     const report = ReportConnection.getAllReports()?.[`${ONYXKEYS.COLLECTION.REPORT}${reportID}`];
     const onyxData: Record<string, null> = {
         [`${ONYXKEYS.COLLECTION.REPORT}${reportID}`]: null,
@@ -2165,20 +2165,32 @@ function deleteReport(reportID: string) {
 
     Onyx.multiSet(onyxData);
 
+    if (shouldDeleteChildReports) {
+        Object.values(reportActionsForReport ?? {}).forEach((reportAction) => {
+            if (!reportAction.childReportID) {
+                return;
+            }
+            deleteReport(reportAction.childReportID, shouldDeleteChildReports);
+        });
+    }
+
     // Delete linked IOU report
     if (report?.iouReportID) {
-        deleteReport(report.iouReportID);
+        deleteReport(report.iouReportID, shouldDeleteChildReports);
     }
 }
 
 /**
  * @param reportID The reportID of the policy report (workspace room)
  */
-function navigateToConciergeChatAndDeleteReport(reportID: string) {
+function navigateToConciergeChatAndDeleteReport(reportID: string, shouldPopToTop = false, shouldDeleteChildReports = false) {
     // Dismiss the current report screen and replace it with Concierge Chat
-    Navigation.goBack();
+    if (shouldPopToTop) {
+        Navigation.setShouldPopAllStateOnUP(true);
+    }
+    Navigation.goBack(undefined, undefined, shouldPopToTop);
     navigateToConciergeChat();
-    deleteReport(reportID);
+    deleteReport(reportID, shouldDeleteChildReports);
 }
 
 /**