diff --git a/src/components/MoneyReportHeader.tsx b/src/components/MoneyReportHeader.tsx
index bcfbf3e51c24..f4173ce774c7 100644
--- a/src/components/MoneyReportHeader.tsx
+++ b/src/components/MoneyReportHeader.tsx
@@ -1404,6 +1404,7 @@ function MoneyReportHeader({
         [CONST.REPORT.SECONDARY_ACTIONS.PAY]: {
             text: translate('iou.settlePayment', {formattedAmount: totalAmount}),
             icon: expensifyIcons.Cash,
+            rightIcon: expensifyIcons.ArrowRight,
             value: CONST.REPORT.SECONDARY_ACTIONS.PAY,
             backButtonText: translate('iou.settlePayment', {formattedAmount: totalAmount}),
             sentryLabel: CONST.SENTRY_LABEL.MORE_MENU.PAY,
diff --git a/src/libs/ReportPreviewActionUtils.ts b/src/libs/ReportPreviewActionUtils.ts
index 1f3abf711759..c947d1a0a76e 100644
--- a/src/libs/ReportPreviewActionUtils.ts
+++ b/src/libs/ReportPreviewActionUtils.ts
@@ -104,8 +104,12 @@ function canPay(report: Report, isReportArchived: boolean, currentUserAccountID:
     const {reimbursableSpend} = getMoneyRequestSpendBreakdown(report);
     const isReimbursed = isSettled(report);
 
+    const isExported = report.isExportedToIntegration ?? false;
+    const hasExportError = report?.hasExportError ?? false;
+    const didExportFail = !isExported && hasExportError;
+
     if (isExpense && isReportPayer && isPaymentsEnabled && isReportFinished && reimbursableSpend !== 0) {
-        return true;
+        return !didExportFail;
     }
 
     if (!isProcessing) {
diff --git a/src/libs/ReportPrimaryActionUtils.ts b/src/libs/ReportPrimaryActionUtils.ts
index 9af38883a0bb..910b081e79dc 100644
--- a/src/libs/ReportPrimaryActionUtils.ts
+++ b/src/libs/ReportPrimaryActionUtils.ts
@@ -154,7 +154,15 @@ function isApproveAction(report: Report, reportTransactions: Transaction[], poli
     return isProcessingReportUtils(report);
 }
 
-function isPrimaryPayAction(report: Report, policy?: Policy, reportNameValuePairs?: ReportNameValuePairs, isChatReportArchived?: boolean, invoiceReceiverPolicy?: Policy) {
+function isPrimaryPayAction(
+    report: Report,
+    policy?: Policy,
+    reportNameValuePairs?: ReportNameValuePairs,
+    isChatReportArchived?: boolean,
+    invoiceReceiverPolicy?: Policy,
+    reportActions?: ReportAction[],
+    isSecondaryAction?: boolean,
+) {
     if (isArchivedReport(reportNameValuePairs) || isChatReportArchived) {
         return false;
     }
@@ -164,6 +172,9 @@ function isPrimaryPayAction(report: Report, policy?: Policy, reportNameValuePair
     const isReportApproved = isReportApprovedUtils({report});
     const isReportClosed = isClosedReportUtils(report);
     const isProcessingReport = isProcessingReportUtils(report);
+    const isExported = isExportedUtil(reportActions);
+    const hasExportError = hasExportErrorUtil(reportActions, report);
+    const didExportFail = !isExported && hasExportError;
 
     const isApprovalEnabled = policy ? policy.approvalMode && policy.approvalMode !== CONST.POLICY.APPROVAL_MODE.OPTIONAL : false;
     const isSubmittedWithoutApprovalsEnabled = !isApprovalEnabled && isProcessingReport;
@@ -172,7 +183,7 @@ function isPrimaryPayAction(report: Report, policy?: Policy, reportNameValuePair
     const {reimbursableSpend} = getMoneyRequestSpendBreakdown(report);
 
     if (isReportPayer && isExpenseReport && arePaymentsEnabled && isReportFinished && reimbursableSpend !== 0) {
-        return true;
+        return isSecondaryAction ?? !didExportFail;
     }
 
     if (!isProcessingReport) {
@@ -404,7 +415,8 @@ function getReportPrimaryAction(params: GetReportPrimaryActionParams): ValueOf<t
         return '';
     }
 
-    const isPayActionWithAllExpensesHeld = isPrimaryPayAction(report, policy, reportNameValuePairs, isChatReportArchived) && hasOnlyHeldExpenses(report?.reportID);
+    const isPayActionWithAllExpensesHeld =
+        isPrimaryPayAction(report, policy, reportNameValuePairs, isChatReportArchived, invoiceReceiverPolicy, reportActions) && hasOnlyHeldExpenses(report?.reportID);
     const expensesToHold = getAllExpensesToHoldIfApplicable(report, reportActions, reportTransactions, policy);
 
     if (isMarkAsCashAction(currentUserEmail, currentUserAccountID, report, reportTransactions, violations, policy)) {
@@ -430,7 +442,7 @@ function getReportPrimaryAction(params: GetReportPrimaryActionParams): ValueOf<t
         return CONST.REPORT.PRIMARY_ACTIONS.SUBMIT;
     }
 
-    if (isPrimaryPayAction(report, policy, reportNameValuePairs, isChatReportArchived, invoiceReceiverPolicy)) {
+    if (isPrimaryPayAction(report, policy, reportNameValuePairs, isChatReportArchived, invoiceReceiverPolicy, reportActions)) {
         return CONST.REPORT.PRIMARY_ACTIONS.PAY;
     }
 
diff --git a/src/libs/ReportSecondaryActionUtils.ts b/src/libs/ReportSecondaryActionUtils.ts
index d8b3ff80303e..13c67dea81e6 100644
--- a/src/libs/ReportSecondaryActionUtils.ts
+++ b/src/libs/ReportSecondaryActionUtils.ts
@@ -29,6 +29,7 @@ import {
     canRejectReportAction,
     doesReportContainRequestsFromMultipleUsers,
     getTransactionDetails,
+    hasExportError as hasExportErrorUtils,
     hasOnlyHeldExpenses,
     hasOnlyNonReimbursableTransactions,
     hasReportBeenReopened as hasReportBeenReopenedUtils,
@@ -702,7 +703,11 @@ function getSecondaryReportActions({
 }): Array<ValueOf<typeof CONST.REPORT.SECONDARY_ACTIONS>> {
     const options: Array<ValueOf<typeof CONST.REPORT.SECONDARY_ACTIONS>> = [];
 
-    if (isPrimaryPayAction(report, policy, reportNameValuePairs) && hasOnlyHeldExpenses(report?.reportID)) {
+    const isExported = isExportedUtils(reportActions);
+    const hasExportError = hasExportErrorUtils(reportActions, report);
+    const didExportFail = !isExported && hasExportError;
+
+    if (isPrimaryPayAction(report, policy, reportNameValuePairs, isChatReportArchived, undefined, reportActions, true) && (hasOnlyHeldExpenses(report?.reportID) || didExportFail)) {
         options.push(CONST.REPORT.SECONDARY_ACTIONS.PAY);
     }