diff --git a/src/components/DotIndicatorMessage.tsx b/src/components/DotIndicatorMessage.tsx
index 5475d768f715..8fd00ab37379 100644
--- a/src/components/DotIndicatorMessage.tsx
+++ b/src/components/DotIndicatorMessage.tsx
@@ -42,15 +42,20 @@ type DotIndicatorMessageProps = {
     style?: StyleProp<ViewStyle>;
 
     textStyles?: StyleProp<TextStyle>;
+
+    // Unused here, but OfflineWithFeedback still passes it to every error row.
+    // eslint-disable-next-line react/no-unused-prop-types
     dismissError?: () => void;
+
+    onRetryReceiptUpload?: () => void;
 };
 
-function DotIndicatorMessage({messages = {}, style, type, textStyles, dismissError = () => {}}: DotIndicatorMessageProps) {
+function DotIndicatorMessage({messages = {}, style, type, textStyles, onRetryReceiptUpload}: DotIndicatorMessageProps) {
     const theme = useTheme();
     const styles = useThemeStyles();
     const StyleUtils = useStyleUtils();
     const {translate} = useLocalize();
-    const expensifyIcons = useMemoizedLazyExpensifyIcons(['DotIndicator']);
+    const expensifyIcons = useMemoizedLazyExpensifyIcons(['ArrowCircleClockwise', 'DotIndicator', 'Download']);
     // eslint-disable-next-line rulesdir/prefer-shouldUseNarrowLayout-instead-of-isSmallScreenWidth
     const {shouldUseNarrowLayout, isSmallScreenWidth, isInNarrowPaneModal} = useResponsiveLayout();
 
@@ -119,37 +124,34 @@ function DotIndicatorMessage({messages = {}, style, type, textStyles, dismissErr
         const isStackedLayout = !(isInNarrowPaneModal && !isSmallScreenWidth);
         const messageRow = (
             <View style={[styles.dotIndicatorMessage, isStackedLayout && styles.alignItemsStart, styles.flex1]}>
-                <View style={styles.offlineFeedbackErrorDot}>
-                    <Icon
-                        src={expensifyIcons.DotIndicator}
-                        fill={isErrorMessage ? theme.danger : theme.success}
-                    />
-                </View>
                 <Text
                     style={[StyleUtils.getDotIndicatorTextStyles(isErrorMessage), textStyles, styles.flex1]}
                     accessibilityRole={isErrorMessage ? CONST.ROLE.ALERT : undefined}
                     accessibilityLiveRegion={isErrorMessage ? 'assertive' : undefined}
                 >
-                    {translate('iou.error.receiptUploadFailedMessage')}
+                    {translate(onRetryReceiptUpload ? 'iou.error.receiptUploadFailedMessage' : 'iou.error.receiptUploadFailedSaveOnlyMessage')}
                 </Text>
             </View>
         );
         const buttonsRow = (
-            <View style={[styles.flexRow, styles.gap3]}>
+            <View style={[styles.flexRow, styles.flexWrap, styles.gap2]}>
+                {!!onRetryReceiptUpload && (
+                    <Button
+                        size={CONST.BUTTON_SIZE.SMALL}
+                        onPress={onRetryReceiptUpload}
+                    >
+                        <Button.Icon src={expensifyIcons.ArrowCircleClockwise} />
+                        <Button.Text>{translate('common.tryAgain')}</Button.Text>
+                    </Button>
+                )}
                 <Button
                     size={CONST.BUTTON_SIZE.SMALL}
                     onPress={() => {
                         fileDownload(translate, receiptError.source, receiptError.filename);
                     }}
                 >
-                    <Button.Text>{translate('iou.error.saveReceipt')}</Button.Text>
-                </Button>
-                <Button
-                    variant={CONST.BUTTON_VARIANT.DANGER}
-                    size={CONST.BUTTON_SIZE.SMALL}
-                    onPress={dismissError}
-                >
-                    <Button.Text>{translate('iou.deleteExpense', {count: 1})}</Button.Text>
+                    <Button.Icon src={expensifyIcons.Download} />
+                    <Button.Text>{translate('common.save')}</Button.Text>
                 </Button>
             </View>
         );
diff --git a/src/components/ErrorMessageRow.tsx b/src/components/ErrorMessageRow.tsx
index b76db0a1eb38..31ffc8760f4c 100644
--- a/src/components/ErrorMessageRow.tsx
+++ b/src/components/ErrorMessageRow.tsx
@@ -18,9 +18,11 @@ type ErrorMessageRowProps = {
     onDismiss?: () => void;
 
     dismissError?: () => void;
+
+    onRetryReceiptUpload?: () => void;
 };
 
-function ErrorMessageRow({errors, errorRowStyles, onDismiss, dismissError, errorRowTextStyles}: ErrorMessageRowProps) {
+function ErrorMessageRow({errors, errorRowStyles, onDismiss, dismissError, errorRowTextStyles, onRetryReceiptUpload}: ErrorMessageRowProps) {
     // Some errors have a null message. This is used to apply opacity only and to avoid showing redundant messages.
     const errorEntries = Object.entries(errors ?? {});
     const filteredErrorEntries = errorEntries.filter((errorEntry): errorEntry is [string, string | ReceiptError | OnyxCommon.TranslationKeyError] => errorEntry[1] !== null);
@@ -35,6 +37,7 @@ function ErrorMessageRow({errors, errorRowStyles, onDismiss, dismissError, error
             containerStyles={errorRowStyles}
             errorTextStyles={errorRowTextStyles}
             dismissError={dismissError}
+            onRetryReceiptUpload={onRetryReceiptUpload}
         />
     ) : null;
 }
diff --git a/src/components/MessagesRow.tsx b/src/components/MessagesRow.tsx
index ed5871f96aec..31835edf442b 100644
--- a/src/components/MessagesRow.tsx
+++ b/src/components/MessagesRow.tsx
@@ -32,9 +32,11 @@ type MessagesRowProps = {
     containerStyles?: StyleProp<ViewStyle>;
     errorTextStyles?: StyleProp<TextStyle>;
     dismissError?: () => void;
+
+    onRetryReceiptUpload?: () => void;
 };
 
-function MessagesRow({messages = {}, type, onDismiss, containerStyles, dismissError = () => {}, errorTextStyles}: MessagesRowProps) {
+function MessagesRow({messages = {}, type, onDismiss, containerStyles, dismissError = () => {}, errorTextStyles, onRetryReceiptUpload}: MessagesRowProps) {
     const theme = useTheme();
     const styles = useThemeStyles();
     const {translate} = useLocalize();
@@ -53,6 +55,7 @@ function MessagesRow({messages = {}, type, onDismiss, containerStyles, dismissEr
         <View style={[styles.flexRow, styles.alignItemsCenter, containerStyles]}>
             <DotIndicatorMessage
                 dismissError={dismissError}
+                onRetryReceiptUpload={onRetryReceiptUpload}
                 style={styles.flex1}
                 textStyles={errorTextStyles}
                 messages={messages}
diff --git a/src/components/OfflineWithFeedback.tsx b/src/components/OfflineWithFeedback.tsx
index b14206d2d4e7..d111993355a1 100644
--- a/src/components/OfflineWithFeedback.tsx
+++ b/src/components/OfflineWithFeedback.tsx
@@ -62,6 +62,8 @@ type OfflineWithFeedbackProps = Partial<ChildrenProps> & {
 
     shouldForceOpacity?: boolean;
     dismissError?: () => void;
+
+    onRetryReceiptUpload?: () => void;
 };
 
 type StrikethroughProps = Partial<ChildrenProps> & {style: AllStyles[]};
@@ -81,6 +83,7 @@ function OfflineWithFeedback({
     shouldDisplayErrorAbove = false,
     shouldForceOpacity = false,
     dismissError = () => {},
+    onRetryReceiptUpload,
     errorRowTextStyles,
     ...restProps
 }: OfflineWithFeedbackProps) {
@@ -142,6 +145,7 @@ function OfflineWithFeedback({
                     onDismiss={onDismiss}
                     errorRowTextStyles={errorRowTextStyles}
                     dismissError={dismissError}
+                    onRetryReceiptUpload={onRetryReceiptUpload}
                 />
             )}
             {hasChildren && !hideChildren && (
@@ -159,6 +163,7 @@ function OfflineWithFeedback({
                     errorRowTextStyles={errorRowTextStyles}
                     onDismiss={onDismiss}
                     dismissError={dismissError}
+                    onRetryReceiptUpload={onRetryReceiptUpload}
                 />
             )}
         </View>
diff --git a/src/components/ReportActionItem/MoneyRequestReceiptView.tsx b/src/components/ReportActionItem/MoneyRequestReceiptView.tsx
index 1207656c19a6..1bce2e478035 100644
--- a/src/components/ReportActionItem/MoneyRequestReceiptView.tsx
+++ b/src/components/ReportActionItem/MoneyRequestReceiptView.tsx
@@ -37,8 +37,12 @@ import {getBrokenConnectionUrlToFixPersonalCard} from '@libs/CardUtils';
 import {hasHoverSupport} from '@libs/DeviceCapabilities';
 import {getMicroSecondOnyxErrorObject, getMicroSecondOnyxErrorWithTranslationKey, isReceiptError} from '@libs/ErrorUtils';
 import getNonEmptyStringOnyxID from '@libs/getNonEmptyStringOnyxID';
+import Log from '@libs/Log';
 import createDynamicRoute from '@libs/Navigation/helpers/dynamicRoutesUtils/createDynamicRoute';
+import {isTrackOnboardingChoice} from '@libs/OnboardingUtils';
 import {isGroupPolicyByType} from '@libs/PolicyUtils';
+import retryReceiptUpload, {canBuildRetryPayload} from '@libs/ReceiptUploadRetryHandler';
+import type {ReceiptRetryContext} from '@libs/ReceiptUploadRetryHandler/types';
 import {getThumbnailAndImageURIs} from '@libs/ReceiptUtils';
 import {getOriginalMessage, isMoneyRequestAction, wasActionTakenByCurrentUser} from '@libs/ReportActionsUtils';
 import {isMarkAsCashActionForTransaction} from '@libs/ReportPrimaryActionUtils';
@@ -70,7 +74,7 @@ import variables from '@styles/variables';
 
 import {clearAllRelatedReportActionErrors} from '@userActions/ClearReportActionErrors';
 import {cleanUpMoneyRequest} from '@userActions/IOU/DeleteMoneyRequest';
-import {replaceReceipt} from '@userActions/IOU/Receipt';
+import {clearReceiptUploadError, replaceReceipt} from '@userActions/IOU/Receipt';
 import {addAttachmentWithComment, navigateToConciergeChatAndDeleteReport, setDeleteTransactionNavigateBackUrl} from '@userActions/Report';
 import {clearError, getLastModifiedExpense, revert} from '@userActions/Transaction';
 
@@ -78,7 +82,7 @@ import CONST from '@src/CONST';
 import ONYXKEYS from '@src/ONYXKEYS';
 import ROUTES, {DYNAMIC_ROUTES} from '@src/ROUTES';
 import type * as OnyxTypes from '@src/types/onyx';
-import type {TransactionPendingFieldsKey} from '@src/types/onyx/Transaction';
+import type {ReceiptError, TransactionPendingFieldsKey} from '@src/types/onyx/Transaction';
 import type {FileObject} from '@src/types/utils/Attachment';
 import {isEmptyObject} from '@src/types/utils/EmptyObject';
 
@@ -137,8 +141,8 @@ function MoneyRequestReceiptView({
     hasParentPendingAction = false,
 }: MoneyRequestReceiptViewProps) {
     const styles = useThemeStyles();
-    const {translate, dateFnsLocale} = useLocalize();
-    const {isBetaEnabledOrUnknown} = usePermissions();
+    const {translate, dateFnsLocale, formatPhoneNumber} = useLocalize();
+    const {isBetaEnabled, isBetaEnabledOrUnknown} = usePermissions();
     const isVendorMatchingBetaEnabled = isBetaEnabledOrUnknown(CONST.BETAS.VENDOR_MATCHING);
     const {convertToDisplayString, getCurrencyDecimals} = useCurrencyListActions();
     const {environmentURL} = useEnvironment();
@@ -418,6 +422,44 @@ function MoneyRequestReceiptView({
 
     const {showConfirmModal} = useConfirmModal();
 
+    const retryableReceiptError = Object.values(errors ?? {}).find((error): error is ReceiptError => isReceiptError(error));
+    const receiptRetryContext: ReceiptRetryContext | undefined = retryableReceiptError
+        ? {
+              receiptError: retryableReceiptError,
+              transaction,
+              iouReport: moneyRequestReport,
+              iouActionID: parentReportAction?.reportActionID,
+              transactionThreadReportID: report?.reportID,
+              policyParams: {policy, policyCategories, policyTagList},
+              isVendorMatchingBetaEnabled,
+              rules,
+              conciergeReportID,
+              isSelfTourViewed: !!isSelfTourViewed,
+              isASAPSubmitBetaEnabled: isBetaEnabled(CONST.BETAS.ASAP_SUBMIT),
+              isTrackIntentUser: isTrackOnboardingChoice(introSelected?.choice),
+              delegateAccountID,
+              formatPhoneNumber,
+              getCurrencyDecimals,
+          }
+        : undefined;
+
+    const canRetryUpload = !!receiptRetryContext && canBuildRetryPayload(receiptRetryContext);
+
+    const retryReceiptUploadAndClearError = () => {
+        if (!receiptRetryContext) {
+            return;
+        }
+
+        retryReceiptUpload(receiptRetryContext, () =>
+            clearReceiptUploadError({
+                transactionID: transaction?.transactionID,
+                reportID: parentReportAction?.reportID ?? report?.reportID,
+                reportActionID: parentReportAction?.reportActionID,
+                reportIDWithCreationError: report?.reportID,
+            }),
+        ).catch((error: unknown) => Log.alert('[ReceiptRetry] Retry failed unexpectedly', {error}));
+    };
+
     const transactionAndReportActionErrors = useMemo(
         () => ({
             ...transaction?.errors,
@@ -662,6 +704,7 @@ function MoneyRequestReceiptView({
                         });
                     }}
                     dismissError={dismissReceiptError}
+                    onRetryReceiptUpload={canRetryUpload ? retryReceiptUploadAndClearError : undefined}
                     style={[shouldShowAuditMessage ? styles.mt3 : styles.mv3, !showReceiptErrorWithEmptyState && styles.flex1]}
                     contentContainerStyle={styles.flex1}
                 >
diff --git a/src/languages/de.ts b/src/languages/de.ts
index a658e401e58d..17ea02040afb 100644
--- a/src/languages/de.ts
+++ b/src/languages/de.ts
@@ -1623,7 +1623,7 @@ const translations: TranslationDeepObject<typeof en> = {
             receiptFailureMessage:
                 '<rbr>Beim Hochladen deiner Quittung ist ein Fehler aufgetreten. Bitte <a href="download">speichere die Quittung</a> und <a href="retry">versuche es später erneut</a>.</rbr>',
             receiptFailureMessageShort: 'Beim Hochladen Ihres Belegs ist ein Fehler aufgetreten.',
-            receiptUploadFailedMessage: 'Beleg-Upload fehlgeschlagen. Speichere den Beleg oder lösche die Ausgabe und verliere sie.',
+            receiptUploadFailedMessage: 'Upload fehlgeschlagen. Versuchen Sie es erneut oder speichern Sie es für später.',
             saveReceipt: 'Beleg speichern',
             genericDeleteFailureMessage: 'Unerwarteter Fehler beim Löschen dieses Belegs. Bitte versuche es später erneut.',
             genericEditFailureMessage: 'Unerwarteter Fehler beim Bearbeiten dieser Ausgabe. Bitte versuche es später noch einmal.',
@@ -1656,6 +1656,7 @@ const translations: TranslationDeepObject<typeof en> = {
                 'Diese Berichte konnten nicht als erledigt markiert werden. Prüfen Sie, dass Ausgaben nicht zurückgehalten oder ausstehend sind, und versuchen Sie es dann erneut.',
             stitchOdometerImagesFailed: 'Kilometerzählerbilder konnten nicht zusammengeführt werden. Bitte versuchen Sie es später noch einmal.',
             failedToSaveOdometerDraft: 'Dein Kilometerzähler-Entwurf konnte nicht gespeichert werden. Bitte versuche es erneut.',
+            receiptUploadFailedSaveOnlyMessage: 'Upload fehlgeschlagen. Speichern Sie Ihre Quittung, um sie zu behalten.',
         },
         dismissReceiptError: 'Fehler ausblenden',
         dismissReceiptErrorConfirmation: 'Achtung! Wenn du diesen Fehler schließt, wird deine hochgeladene Quittung vollständig entfernt. Bist du sicher?',
diff --git a/src/languages/el.ts b/src/languages/el.ts
index d6af0daafd7b..56bbf2e0c8cc 100644
--- a/src/languages/el.ts
+++ b/src/languages/el.ts
@@ -1694,7 +1694,7 @@ const translations: TranslationDeepObject<typeof en> = {
             receiptFailureMessage:
                 '<rbr>Προέκυψε σφάλμα κατά τη μεταφόρτωση της απόδειξής σας. Παρακαλούμε <a href="download">αποθηκεύστε την απόδειξη</a> και <a href="retry">δοκιμάστε ξανά</a> αργότερα.</rbr>',
             receiptFailureMessageShort: 'Παρουσιάστηκε σφάλμα κατά τη μεταφόρτωση της απόδειξής σας.',
-            receiptUploadFailedMessage: 'Η αποστολή της απόδειξης απέτυχε. Αποθηκεύστε την απόδειξη ή διαγράψτε την δαπάνη και χάστε την.',
+            receiptUploadFailedMessage: 'Η μεταφόρτωση απέτυχε. Δοκιμάστε ξανά ή αποθηκεύστε για αργότερα.',
             saveReceipt: 'Αποθήκευση απόδειξης',
             genericDeleteFailureMessage: 'Παρουσιάστηκε απρόσμενο σφάλμα κατά τη διαγραφή αυτής της δαπάνης. Παρακαλούμε δοκιμάστε ξανά αργότερα.',
             genericEditFailureMessage: 'Παρουσιάστηκε απροσδόκητο σφάλμα κατά την επεξεργασία αυτής της δαπάνης. Παρακαλούμε δοκιμάστε ξανά αργότερα.',
@@ -1712,6 +1712,7 @@ const translations: TranslationDeepObject<typeof en> = {
             endDateSameAsStartDate: 'Η ημερομηνία λήξης δεν μπορεί να είναι ίδια με την ημερομηνία έναρξης',
             manySplitsProvided: `Ο μέγιστος επιτρεπόμενος αριθμός διαχωρισμών είναι ${CONST.IOU.SPLITS_LIMIT}.`,
             dateRangeExceedsMaxDays: `Το εύρος ημερομηνιών δεν μπορεί να υπερβαίνει τις ${CONST.IOU.SPLITS_LIMIT} ημέρες.`,
+            receiptUploadFailedSaveOnlyMessage: 'Η αποστολή απέτυχε. Αποθηκεύστε την απόδειξή σας για να τη διατηρήσετε.',
         },
         dismissReceiptError: 'Απόρριψη σφάλματος',
         dismissReceiptErrorConfirmation: 'Προσοχή! Αν απορρίψετε αυτό το σφάλμα, η ανεβασμένη απόδειξή σας θα διαγραφεί πλήρως. Είστε βέβαιοι;',
diff --git a/src/languages/en.ts b/src/languages/en.ts
index b8e12bffbcf6..42786f5d0ff8 100644
--- a/src/languages/en.ts
+++ b/src/languages/en.ts
@@ -1729,7 +1729,8 @@ const translations = {
             receiptDeleteFailureError: 'Unexpected error deleting this receipt. Please try again later.',
             receiptFailureMessage: '<rbr>There was an error uploading your receipt. Please <a href="download">save the receipt</a> and <a href="retry">try again</a> later.</rbr>',
             receiptFailureMessageShort: 'There was an error uploading your receipt.',
-            receiptUploadFailedMessage: 'Receipt upload failed. Save the receipt, or delete the expense and lose it.',
+            receiptUploadFailedMessage: 'Upload failed. Try again or save for later.',
+            receiptUploadFailedSaveOnlyMessage: 'Upload failed. Save your receipt to keep it.',
             saveReceipt: 'Save receipt',
             genericDeleteFailureMessage: 'Unexpected error deleting this expense. Please try again later.',
             genericEditFailureMessage: 'Unexpected error editing this expense. Please try again later.',
diff --git a/src/languages/es.ts b/src/languages/es.ts
index 4f86d998e75e..8802b1c65618 100644
--- a/src/languages/es.ts
+++ b/src/languages/es.ts
@@ -1635,7 +1635,7 @@ const translations: TranslationDeepObject<typeof en> = {
             receiptDeleteFailureError: 'Error inesperado al borrar este recibo. Por favor, vuelve a intentarlo más tarde.',
             receiptFailureMessage: '<rbr>Hubo un error al cargar tu recibo. Por favor, <a href="download">guarda el recibo</a> e <a href="retry">inténtalo de nuevo</a> más tarde.</rbr>',
             receiptFailureMessageShort: 'Hubo un error al cargar tu recibo.',
-            receiptUploadFailedMessage: 'Error al subir el recibo. Guarda el recibo, o elimina el gasto y piérdelo.',
+            receiptUploadFailedMessage: 'La carga ha fallado. Inténtalo de nuevo o guárdalo para más tarde.',
             saveReceipt: 'Guardar recibo',
             genericDeleteFailureMessage: 'Error inesperado al eliminar este gasto. Por favor, inténtalo más tarde.',
             genericEditFailureMessage: 'Error inesperado al editar este gasto. Por favor, inténtalo más tarde.',
@@ -1653,6 +1653,7 @@ const translations: TranslationDeepObject<typeof en> = {
             endDateSameAsStartDate: 'La fecha de finalización no puede ser la misma que la fecha de inicio',
             manySplitsProvided: `El número máximo de divisiones permitidas es ${CONST.IOU.SPLITS_LIMIT}.`,
             dateRangeExceedsMaxDays: `El rango de fechas no puede exceder los ${CONST.IOU.SPLITS_LIMIT} días.`,
+            receiptUploadFailedSaveOnlyMessage: 'La carga ha fallado. Guarda tu recibo para conservarlo.',
         },
         dismissReceiptError: 'Descartar error',
         dismissReceiptErrorConfirmation: '¡Atención! Descartar este error eliminará completamente tu recibo cargado. ¿Estás seguro?',
diff --git a/src/languages/fr.ts b/src/languages/fr.ts
index 4b9245a77d06..1c68407501d3 100644
--- a/src/languages/fr.ts
+++ b/src/languages/fr.ts
@@ -1627,7 +1627,7 @@ const translations: TranslationDeepObject<typeof en> = {
             receiptFailureMessage:
                 '<rbr>Une erreur s’est produite lors du téléchargement de votre reçu. Veuillez <a href="download">enregistrer le reçu</a> et <a href="retry">réessayer</a> plus tard.</rbr>',
             receiptFailureMessageShort: 'Une erreur s’est produite lors du téléchargement de votre reçu.',
-            receiptUploadFailedMessage: 'Échec du téléchargement du reçu. Enregistrez le reçu ou supprimez la dépense et perdez-la.',
+            receiptUploadFailedMessage: 'Le téléversement a échoué. Réessayez ou enregistrez pour plus tard.',
             saveReceipt: 'Enregistrer le reçu',
             genericDeleteFailureMessage: 'Erreur inattendue lors de la suppression de cette dépense. Veuillez réessayer plus tard.',
             genericEditFailureMessage: 'Erreur inattendue lors de la modification de cette dépense. Veuillez réessayer plus tard.',
@@ -1660,6 +1660,7 @@ const translations: TranslationDeepObject<typeof en> = {
             reportsNotMarkedAsDoneDescription: "Ces notes de frais n'ont pas pu être marquées comme terminées. Vérifiez qu'aucune dépense n'est en attente ou en suspens, puis réessayez.",
             stitchOdometerImagesFailed: 'Échec de la combinaison des images de l’odomètre. Veuillez réessayer plus tard.',
             failedToSaveOdometerDraft: 'Impossible d’enregistrer votre brouillon de compteur kilométrique. Veuillez réessayer.',
+            receiptUploadFailedSaveOnlyMessage: 'Téléversement échoué. Enregistrez votre reçu pour le conserver.',
         },
         dismissReceiptError: 'Ignorer l’erreur',
         dismissReceiptErrorConfirmation: 'Attention ! Ignorer cette erreur supprimera complètement votre reçu téléversé. Êtes-vous sûr ?',
diff --git a/src/languages/it.ts b/src/languages/it.ts
index 8b51f2bd2fa5..86a964a26403 100644
--- a/src/languages/it.ts
+++ b/src/languages/it.ts
@@ -1620,7 +1620,7 @@ const translations: TranslationDeepObject<typeof en> = {
             receiptFailureMessage:
                 '<rbr>Si è verificato un errore durante il caricamento della ricevuta. <a href="download">Salva la ricevuta</a> e <a href="retry">riprova</a> più tardi.</rbr>',
             receiptFailureMessageShort: 'Si è verificato un errore durante il caricamento della ricevuta.',
-            receiptUploadFailedMessage: 'Caricamento della ricevuta non riuscito. Salva la ricevuta oppure elimina la spesa e perdila.',
+            receiptUploadFailedMessage: 'Caricamento non riuscito. Riprova o salva per dopo.',
             saveReceipt: 'Salva ricevuta',
             genericDeleteFailureMessage: 'Errore imprevisto durante l’eliminazione di questa spesa. Riprova più tardi.',
             genericEditFailureMessage: 'Errore imprevisto durante la modifica di questa spesa. Riprova più tardi.',
@@ -1651,6 +1651,7 @@ const translations: TranslationDeepObject<typeof en> = {
             dateRangeExceedsMaxDays: `L’intervallo di date non può superare ${CONST.IOU.SPLITS_LIMIT} giorni.`,
             stitchOdometerImagesFailed: 'Impossibile combinare le immagini del contachilometri. Riprova più tardi.',
             failedToSaveOdometerDraft: 'Impossibile salvare la tua bozza del contachilometri. Riprova.',
+            receiptUploadFailedSaveOnlyMessage: 'Caricamento non riuscito. Salva la ricevuta per conservarla.',
         },
         dismissReceiptError: 'Ignora errore',
         dismissReceiptErrorConfirmation: 'Attenzione! Chiudere questo errore rimuoverà completamente la ricevuta che hai caricato. Sei sicuro?',
diff --git a/src/languages/ja.ts b/src/languages/ja.ts
index 4368be81e41d..70a7c65b0abf 100644
--- a/src/languages/ja.ts
+++ b/src/languages/ja.ts
@@ -1604,7 +1604,7 @@ const translations: TranslationDeepObject<typeof en> = {
             receiptFailureMessage:
                 '<rbr>領収書のアップロード中にエラーが発生しました。後で再度お試しいただくために、<a href="download">領収書を保存</a>してから、時間をおいて<a href="retry">もう一度お試しください</a>。</rbr>',
             receiptFailureMessageShort: 'レシートのアップロード中にエラーが発生しました。',
-            receiptUploadFailedMessage: 'レシートのアップロードに失敗しました。レシートを保存するか、経費を削除して失うかを選択してください。',
+            receiptUploadFailedMessage: 'アップロードに失敗しました。もう一度お試しいただくか、あとで保存してください。',
             saveReceipt: '領収書を保存',
             genericDeleteFailureMessage: 'この経費の削除中に予期しないエラーが発生しました。しばらくしてからもう一度お試しください。',
             genericEditFailureMessage: 'この経費の編集中に予期しないエラーが発生しました。後でもう一度お試しください。',
@@ -1634,6 +1634,7 @@ const translations: TranslationDeepObject<typeof en> = {
             reportsNotMarkedAsDoneDescription: 'これらのレポートを完了済みにできませんでした。経費が保留中や未処理になっていないか確認してから、もう一度お試しください。',
             stitchOdometerImagesFailed: '走行距離計の画像を結合できませんでした。後でもう一度お試しください。',
             failedToSaveOdometerDraft: 'オドメーターの下書きを保存できませんでした。もう一度お試しください。',
+            receiptUploadFailedSaveOnlyMessage: 'アップロードに失敗しました。レシートを保存して保持してください。',
         },
         dismissReceiptError: 'エラーを閉じる',
         dismissReceiptErrorConfirmation: 'ご注意ください！このエラーを閉じると、アップロード済みのレシートが完全に削除されます。本当に続行しますか？',
diff --git a/src/languages/nl.ts b/src/languages/nl.ts
index f75cdd491416..bfa0cc3bbe5c 100644
--- a/src/languages/nl.ts
+++ b/src/languages/nl.ts
@@ -1618,7 +1618,7 @@ const translations: TranslationDeepObject<typeof en> = {
             receiptDeleteFailureError: 'Onverwachte fout bij het verwijderen van deze bon. Probeer het later opnieuw.',
             receiptFailureMessage: '<rbr>Er is een fout opgetreden bij het uploaden van je bon. <a href="download">Sla de bon op</a> en <a href="retry">probeer het later opnieuw</a>.</rbr>',
             receiptFailureMessageShort: 'Er is een fout opgetreden bij het uploaden van je bon.',
-            receiptUploadFailedMessage: 'Uploaden van bon mislukt. Sla de bon op of verwijder de uitgave en verlies hem.',
+            receiptUploadFailedMessage: 'Uploaden mislukt. Probeer het opnieuw of bewaar het voor later.',
             saveReceipt: 'Bon opslaan',
             genericDeleteFailureMessage: 'Onverwachte fout bij het verwijderen van deze uitgave. Probeer het later opnieuw.',
             genericEditFailureMessage: 'Onverwachte fout bij het bewerken van deze uitgave. Probeer het later opnieuw.',
@@ -1650,6 +1650,7 @@ const translations: TranslationDeepObject<typeof en> = {
                 'Deze rapporten konden niet als voltooid worden gemarkeerd. Controleer of er geen onkostendeclaraties vastgehouden of in behandeling zijn en probeer het dan opnieuw.',
             stitchOdometerImagesFailed: 'Odometerafbeeldingen combineren mislukt. Probeer het later opnieuw.',
             failedToSaveOdometerDraft: 'De conceptkilometerstand kon niet worden opgeslagen. Probeer het opnieuw.',
+            receiptUploadFailedSaveOnlyMessage: 'Upload is mislukt. Sla je bon op om hem te bewaren.',
         },
         dismissReceiptError: 'Foutmelding sluiten',
         dismissReceiptErrorConfirmation: 'Let op! Dit foutbericht negeren verwijdert je geüploade bon volledig. Weet je het zeker?',
diff --git a/src/languages/pl.ts b/src/languages/pl.ts
index e50594abcd28..d27132dc7da4 100644
--- a/src/languages/pl.ts
+++ b/src/languages/pl.ts
@@ -1650,7 +1650,7 @@ const translations: TranslationDeepObject<typeof en> = {
             receiptDeleteFailureError: 'Nieoczekiwany błąd podczas usuwania tego paragonu. Spróbuj ponownie później.',
             receiptFailureMessage: '<rbr>Wystąpił błąd podczas przesyłania paragonu. Prosimy <a href="download">zapisać paragon</a> i <a href="retry">spróbować ponownie</a> później.</rbr>',
             receiptFailureMessageShort: 'Wystąpił błąd podczas przesyłania paragonu.',
-            receiptUploadFailedMessage: 'Nie udało się przesłać paragonu. Zapisz paragon lub usuń wydatek i utracisz go.',
+            receiptUploadFailedMessage: 'Przesyłanie pliku nie powiodło się. Spróbuj ponownie lub zapisz na później.',
             saveReceipt: 'Zapisz paragon',
             genericDeleteFailureMessage: 'Nieoczekiwany błąd podczas usuwania tego wydatku. Spróbuj ponownie później.',
             genericEditFailureMessage: 'Nieoczekiwany błąd podczas edycji tego wydatku. Spróbuj ponownie później.',
@@ -1680,6 +1680,7 @@ const translations: TranslationDeepObject<typeof en> = {
             reportsNotMarkedAsDoneDescription: 'Nie udało się oznaczyć tych raportów jako zakończone. Sprawdź, czy wydatki nie są wstrzymane ani oczekujące, a następnie spróbuj ponownie.',
             stitchOdometerImagesFailed: 'Nie udało się połączyć zdjęć licznika kilometrów. Spróbuj ponownie później.',
             failedToSaveOdometerDraft: 'Nie udało się zapisać Twojego szkicu licznika przebiegu. Spróbuj ponownie.',
+            receiptUploadFailedSaveOnlyMessage: 'Przesyłanie nie powiodło się. Zapisz paragon, żeby go zachować.',
         },
         dismissReceiptError: 'Odrzuć błąd',
         dismissReceiptErrorConfirmation: 'Uwaga! Zamknięcie tego błędu spowoduje całkowite usunięcie przesłanego paragonu. Czy na pewno chcesz kontynuować?',
diff --git a/src/languages/pt-BR.ts b/src/languages/pt-BR.ts
index b4ddb74484fb..859c8b656646 100644
--- a/src/languages/pt-BR.ts
+++ b/src/languages/pt-BR.ts
@@ -1617,7 +1617,7 @@ const translations: TranslationDeepObject<typeof en> = {
             receiptDeleteFailureError: 'Erro inesperado ao excluir este recibo. Tente novamente mais tarde.',
             receiptFailureMessage: '<rbr>Ocorreu um erro ao enviar seu recibo. Por favor, <a href="download">salve o recibo</a> e <a href="retry">tente novamente</a> mais tarde.</rbr>',
             receiptFailureMessageShort: 'Ocorreu um erro ao enviar seu recibo.',
-            receiptUploadFailedMessage: 'Falha no envio do recibo. Salve o recibo ou exclua a despesa e perca-a.',
+            receiptUploadFailedMessage: 'Falha no upload. Tente novamente ou salve para depois.',
             saveReceipt: 'Salvar recibo',
             genericDeleteFailureMessage: 'Erro inesperado ao excluir esta despesa. Tente novamente mais tarde.',
             genericEditFailureMessage: 'Erro inesperado ao editar esta despesa. Tente novamente mais tarde.',
@@ -1648,6 +1648,7 @@ const translations: TranslationDeepObject<typeof en> = {
             reportsNotMarkedAsDoneDescription: 'Não foi possível marcar esses relatórios como concluídos. Verifique se as despesas não estão retidas ou pendentes e tente novamente.',
             stitchOdometerImagesFailed: 'Falha ao combinar imagens do hodômetro. Tente novamente mais tarde.',
             failedToSaveOdometerDraft: 'Não foi possível salvar seu rascunho do hodômetro. Tente novamente.',
+            receiptUploadFailedSaveOnlyMessage: 'Falha no upload. Salve o seu recibo para mantê-lo.',
         },
         dismissReceiptError: 'Dispensar erro',
         dismissReceiptErrorConfirmation: 'Atenção! Ignorar este erro removerá completamente o comprovante que você enviou. Tem certeza?',
diff --git a/src/languages/zh-hans.ts b/src/languages/zh-hans.ts
index 67fd6aa51206..c9bc0d22ba95 100644
--- a/src/languages/zh-hans.ts
+++ b/src/languages/zh-hans.ts
@@ -1561,7 +1561,7 @@ const translations: TranslationDeepObject<typeof en> = {
             receiptDeleteFailureError: '删除此收据时发生意外错误。请稍后再试。',
             receiptFailureMessage: '<rbr>上传您的收据时出错。请<a href="download">保存收据</a>并在稍后<a href="retry">重试</a>。</rbr>',
             receiptFailureMessageShort: '上传您的收据时出错。',
-            receiptUploadFailedMessage: '收据上传失败。保存收据，或删除该支出并失去它。',
+            receiptUploadFailedMessage: '上传失败。请重试或稍后保存。',
             saveReceipt: '保存收据',
             genericDeleteFailureMessage: '删除此报销时发生意外错误。请稍后重试。',
             genericEditFailureMessage: '编辑此报销时发生意外错误。请稍后再试。',
@@ -1591,6 +1591,7 @@ const translations: TranslationDeepObject<typeof en> = {
             reportsNotMarkedAsDoneDescription: '无法将这些报销报告标记为已完成。请检查报销是否未被保留或待处理，然后重试。',
             stitchOdometerImagesFailed: '合并里程表图片失败。请稍后重试。',
             failedToSaveOdometerDraft: '无法保存你的里程表草稿。请重试。',
+            receiptUploadFailedSaveOnlyMessage: '上传失败。请保存收据以保留副本。',
         },
         dismissReceiptError: '忽略错误',
         dismissReceiptErrorConfirmation: '提醒：关闭此错误将彻底删除你上传的收据。确定要继续吗？',
diff --git a/src/libs/ReceiptUploadRetryHandler/buildRetryPayload.ts b/src/libs/ReceiptUploadRetryHandler/buildRetryPayload.ts
new file mode 100644
index 000000000000..46f1bba80d55
--- /dev/null
+++ b/src/libs/ReceiptUploadRetryHandler/buildRetryPayload.ts
@@ -0,0 +1,165 @@
+/** Decides whether a failed receipt upload can be retried and rebuilds its `RequestMoney` call from Onyx. */
+import {isLocalFile} from '@libs/fileDownload/FileUtils';
+import {getTransactionDetails} from '@libs/ReportUtils';
+import {getIsFromGlobalCreate, isDistanceRequest, isPerDiemRequest, isTimeRequest} from '@libs/TransactionUtils';
+
+import {getAllPersonalDetails, getAllReports, getAllTransactionViolations, getCurrentUserAccountIDFromSession, getCurrentUserPersonalDetails} from '@userActions/IOU';
+import {getMoneyRequestParticipantsFromReport} from '@userActions/IOU/MoneyRequest';
+import type {RequestMoneyInformation} from '@userActions/IOU/MoneyRequestBuilder';
+
+import CONST from '@src/CONST';
+import ONYXKEYS from '@src/ONYXKEYS';
+import type {Report} from '@src/types/onyx';
+import type {Participant} from '@src/types/onyx/IOU';
+import type {Receipt} from '@src/types/onyx/Transaction';
+import type {FileObject} from '@src/types/utils/Attachment';
+
+import type {OnyxEntry} from 'react-native-onyx';
+
+import type {ReceiptRetryContext} from './types';
+
+import isRetrySupported from './isRetrySupported';
+
+function isRetryableFlow(context: ReceiptRetryContext): boolean {
+    const {transaction} = context;
+    if (!isRetrySupported || !transaction) {
+        return false;
+    }
+
+    if (!isLocalFile(context.receiptError.source)) {
+        return false;
+    }
+
+    // These carry GPS points, rates, or units that the transaction doesn't store, so a retry would drop them.
+    if (isDistanceRequest(transaction) || isPerDiemRequest(transaction) || isTimeRequest(transaction)) {
+        return false;
+    }
+    if (!!transaction.comment?.waypoints || !!transaction.comment?.customUnit || !!transaction.comment?.type) {
+        return false;
+    }
+
+    return !transaction.receipt?.isTestReceipt && !transaction.receipt?.isTestDriveReceipt;
+}
+
+function getCurrentUserAccountID(): number {
+    return getCurrentUserPersonalDetails()?.accountID ?? getCurrentUserAccountIDFromSession();
+}
+
+function resolveParticipant(iouReport: OnyxEntry<Report>): Participant | undefined {
+    const participants = getMoneyRequestParticipantsFromReport(iouReport, getCurrentUserAccountID());
+    if (participants.length !== 1) {
+        return undefined;
+    }
+
+    const participant = participants.at(0);
+    if (!participant?.accountID || participant.isPolicyExpenseChat) {
+        return participant;
+    }
+
+    const login = getAllPersonalDetails()[participant.accountID]?.login;
+    return login ? {...participant, login} : undefined;
+}
+
+function getMerchantForRetry(merchant: string | undefined): string {
+    if (!merchant || merchant === CONST.TRANSACTION.PARTIAL_TRANSACTION_MERCHANT) {
+        return '';
+    }
+    return merchant;
+}
+
+/** Checks the action here too, not only in `retryReceiptUpload`, so the button is hidden instead of doing nothing. */
+function canBuildRetryPayload(context: ReceiptRetryContext): boolean {
+    const {transaction, iouReport, receiptError} = context;
+    if (receiptError.action !== CONST.IOU.ACTION_PARAMS.MONEY_REQUEST) {
+        return false;
+    }
+    return isRetryableFlow(context) && !!iouReport?.reportID && !!transaction?.transactionID && !!resolveParticipant(iouReport);
+}
+
+/** Rebuilds the `RequestMoney` call behind a failed receipt upload from the records the failure left in Onyx. */
+function buildRetryPayload(context: ReceiptRetryContext, receiptFile: FileObject): RequestMoneyInformation | undefined {
+    const {
+        transaction,
+        iouReport,
+        iouActionID,
+        transactionThreadReportID,
+        policyParams,
+        isVendorMatchingBetaEnabled,
+        rules,
+        conciergeReportID,
+        isSelfTourViewed,
+        isASAPSubmitBetaEnabled,
+        isTrackIntentUser,
+        delegateAccountID,
+        formatPhoneNumber,
+        getCurrencyDecimals,
+    } = context;
+    const participant = resolveParticipant(iouReport);
+    if (!canBuildRetryPayload(context) || !transaction || !iouReport || !participant) {
+        return undefined;
+    }
+
+    const currentUser = getCurrentUserPersonalDetails();
+    const details = getTransactionDetails(transaction);
+    if (!details) {
+        return undefined;
+    }
+    const receipt: Receipt = {...receiptFile, source: context.receiptError.source, state: CONST.IOU.RECEIPT_STATE.SCAN_READY};
+
+    return {
+        report: iouReport,
+        participantParams: {
+            payeeEmail: currentUser?.login,
+            payeeAccountID: getCurrentUserAccountID(),
+            participant,
+        },
+        policyParams,
+        transactionParams: {
+            amount: details.amount,
+            currency: details.currency,
+            created: details.created,
+            merchant: getMerchantForRetry(details.merchant),
+            comment: details.comment,
+            category: details.category,
+            tag: details.tag,
+            taxCode: details.taxCode,
+            taxAmount: details.taxAmount,
+            billable: details.billable,
+            reimbursable: details.reimbursable,
+            // Read from the transaction because `details` widens this to `string | Attendee[]`.
+            attendees: transaction.comment?.attendees,
+            isFromGlobalCreate: getIsFromGlobalCreate(transaction),
+            receipt,
+        },
+        // Same ID, so if the first attempt reached Auth the retry gets `Transaction already created.` instead of a second expense.
+        optimisticTransactionID: transaction.transactionID,
+        optimisticIOUReportID: iouReport.reportID,
+        optimisticChatReportID: iouReport.chatReportID,
+        // Without these two, the retry creates a second IOU action and thread for the same transaction.
+        currentReportActionID: iouActionID,
+        existingTransactionThreadReportID: transactionThreadReportID,
+        isTransactionAlreadyOnReport: true,
+        existingTransaction: transaction,
+        existingTransactionDraft: undefined,
+        shouldGenerateTransactionThreadReport: true,
+        // eslint-disable-next-line @typescript-eslint/no-deprecated -- `requestMoney` needs the whole collection for its `hasViolations` check, as UpdateMoneyRequest and TrackExpense do. Subscribing from the receipt view would put a collection-wide listener on every expense row.
+        transactionViolations: getAllTransactionViolations(),
+        personalDetails: getAllPersonalDetails(),
+        isVendorMatchingBetaEnabled,
+        rules,
+        conciergeChat: conciergeReportID ? getAllReports()?.[`${ONYXKEYS.COLLECTION.REPORT}${conciergeReportID}`] : undefined,
+        isSelfTourViewed,
+        isASAPSubmitBetaEnabled,
+        isTrackIntentUser,
+        delegateAccountID,
+        currentUserAccountIDParam: getCurrentUserAccountID(),
+        currentUserEmailParam: currentUser?.login ?? '',
+        quickAction: undefined,
+        policyRecentlyUsedCurrencies: [],
+        formatPhoneNumber,
+        getCurrencyDecimals,
+    };
+}
+
+export default buildRetryPayload;
+export {canBuildRetryPayload};
diff --git a/src/libs/ReceiptUploadRetryHandler/index.ts b/src/libs/ReceiptUploadRetryHandler/index.ts
new file mode 100644
index 000000000000..b349187f48de
--- /dev/null
+++ b/src/libs/ReceiptUploadRetryHandler/index.ts
@@ -0,0 +1,56 @@
+/** Retries a failed receipt upload: finds the file, rebuilds the request, and sends it again. */
+import Log from '@libs/Log';
+
+import {requestMoney} from '@userActions/IOU/TrackExpense';
+
+import CONST from '@src/CONST';
+
+import type {ReceiptRetryContext, RetryOutcome} from './types';
+
+import buildRetryPayload, {canBuildRetryPayload} from './buildRetryPayload';
+import resolveReceiptFile from './resolveReceiptFile';
+
+function retryReceiptUpload(context: ReceiptRetryContext, onDispatched?: () => Promise<unknown>): Promise<RetryOutcome> {
+    const {receiptError} = context;
+
+    if (receiptError.action !== CONST.IOU.ACTION_PARAMS.MONEY_REQUEST) {
+        Log.hmmm('[ReceiptRetry] No retry path for this action', {action: receiptError.action});
+        return Promise.resolve('unsupportedAction');
+    }
+
+    if (!canBuildRetryPayload(context)) {
+        Log.hmmm('[ReceiptRetry] The failed expense does not hold enough to rebuild the request', {transactionID: context.transaction?.transactionID});
+        return Promise.resolve('payloadIncomplete');
+    }
+
+    return resolveReceiptFile(receiptError.source, receiptError.filename).then((receiptFile): RetryOutcome | Promise<RetryOutcome> => {
+        if (!receiptFile) {
+            Log.hmmm('[ReceiptRetry] Receipt file is no longer on the device, cannot retry', {source: receiptError.source});
+            return 'fileMissing';
+        }
+
+        const payload = buildRetryPayload(context, receiptFile);
+        if (!payload) {
+            Log.hmmm('[ReceiptRetry] The failed expense does not hold enough to rebuild the request', {transactionID: context.transaction?.transactionID});
+            return 'payloadIncomplete';
+        }
+
+        Log.info('[ReceiptRetry] Retrying receipt upload', false, {
+            action: receiptError.action,
+            transactionID: payload.optimisticTransactionID,
+        });
+
+        try {
+            requestMoney({...payload, isRetry: true, shouldPlaySound: false});
+        } catch (error) {
+            Log.alert('[ReceiptRetry] Dispatching the retry threw', {transactionID: payload.optimisticTransactionID, error});
+            return 'dispatchFailed';
+        }
+
+        // Cleared only after a dispatch, so a failure above keeps the error and its Try again and Save buttons.
+        return Promise.resolve(onDispatched?.()).then((): RetryOutcome => 'dispatched');
+    });
+}
+
+export default retryReceiptUpload;
+export {canBuildRetryPayload};
diff --git a/src/libs/ReceiptUploadRetryHandler/isRetrySupported.native.ts b/src/libs/ReceiptUploadRetryHandler/isRetrySupported.native.ts
new file mode 100644
index 000000000000..b5d65161471f
--- /dev/null
+++ b/src/libs/ReceiptUploadRetryHandler/isRetrySupported.native.ts
@@ -0,0 +1,4 @@
+/** Native keeps the receipt in `ReceiptStorage`, so it is still there after a restart. */
+const isRetrySupported = true;
+
+export default isRetrySupported;
diff --git a/src/libs/ReceiptUploadRetryHandler/isRetrySupported.ts b/src/libs/ReceiptUploadRetryHandler/isRetrySupported.ts
new file mode 100644
index 000000000000..6fcdba0ceea3
--- /dev/null
+++ b/src/libs/ReceiptUploadRetryHandler/isRetrySupported.ts
@@ -0,0 +1,4 @@
+/** Web only has the receipt as a blob URL, which is gone after a reload, so there is nothing to resend. */
+const isRetrySupported = false;
+
+export default isRetrySupported;
diff --git a/src/libs/ReceiptUploadRetryHandler/resolveReceiptFile.native.ts b/src/libs/ReceiptUploadRetryHandler/resolveReceiptFile.native.ts
new file mode 100644
index 000000000000..e9cad5b039ee
--- /dev/null
+++ b/src/libs/ReceiptUploadRetryHandler/resolveReceiptFile.native.ts
@@ -0,0 +1,21 @@
+import checkFileExists from '@libs/fileDownload/checkFileExists';
+import {getMimeTypeFromUri} from '@libs/fileDownload/FileUtils';
+import ReceiptStorage from '@libs/ReceiptStorage';
+
+import type {ResolveReceiptFile} from './types';
+
+const resolveReceiptFile: ResolveReceiptFile = (source, filename) => {
+    const localUri = ReceiptStorage.resolve(source);
+    if (!localUri) {
+        return Promise.resolve(undefined);
+    }
+
+    return checkFileExists(localUri).then((exists) => {
+        if (!exists) {
+            return undefined;
+        }
+        return {uri: localUri, source: localUri, name: filename, type: getMimeTypeFromUri(filename) ?? getMimeTypeFromUri(localUri)};
+    });
+};
+
+export default resolveReceiptFile;
diff --git a/src/libs/ReceiptUploadRetryHandler/resolveReceiptFile.ts b/src/libs/ReceiptUploadRetryHandler/resolveReceiptFile.ts
new file mode 100644
index 000000000000..f6a932caecb6
--- /dev/null
+++ b/src/libs/ReceiptUploadRetryHandler/resolveReceiptFile.ts
@@ -0,0 +1,6 @@
+import type {ResolveReceiptFile} from './types';
+
+/** Never called on web because `isRetrySupported` is false. It exists so `index.ts` can still import it. */
+const resolveReceiptFile: ResolveReceiptFile = () => Promise.resolve(undefined);
+
+export default resolveReceiptFile;
diff --git a/src/libs/ReceiptUploadRetryHandler/types.ts b/src/libs/ReceiptUploadRetryHandler/types.ts
new file mode 100644
index 000000000000..c95f1dd25664
--- /dev/null
+++ b/src/libs/ReceiptUploadRetryHandler/types.ts
@@ -0,0 +1,51 @@
+import type {LocaleContextProps} from '@components/LocaleContextProvider';
+
+import type {CurrencyListActionsContextType} from '@hooks/useCurrencyList';
+
+import type BasePolicyParams from '@userActions/IOU/types/BasePolicyParams';
+
+import type {Report, Rule, Transaction} from '@src/types/onyx';
+import type {ReceiptError} from '@src/types/onyx/Transaction';
+import type {FileObject} from '@src/types/utils/Attachment';
+
+import type {OnyxCollection, OnyxEntry} from 'react-native-onyx';
+
+type ResolveReceiptFile = (source: string, filename: string) => Promise<FileObject | undefined>;
+
+/** The error stores nothing to resend, so the retry is rebuilt from these values. */
+type ReceiptRetryContext = {
+    receiptError: ReceiptError;
+
+    transaction: OnyxEntry<Transaction>;
+
+    iouReport: OnyxEntry<Report>;
+
+    iouActionID: string | undefined;
+
+    transactionThreadReportID: string | undefined;
+
+    policyParams: BasePolicyParams;
+
+    isVendorMatchingBetaEnabled: boolean | undefined;
+
+    /** Used by `shouldCreateNewMoneyRequestReport`, so an empty collection can make the retry create a second report. */
+    rules: OnyxCollection<Rule>;
+
+    conciergeReportID: string | undefined;
+
+    isSelfTourViewed: boolean;
+
+    isASAPSubmitBetaEnabled: boolean;
+
+    isTrackIntentUser: boolean | undefined;
+
+    delegateAccountID: number | undefined;
+
+    formatPhoneNumber: LocaleContextProps['formatPhoneNumber'];
+
+    getCurrencyDecimals: CurrencyListActionsContextType['getCurrencyDecimals'];
+};
+
+type RetryOutcome = 'dispatched' | 'fileMissing' | 'payloadIncomplete' | 'unsupportedAction' | 'dispatchFailed';
+
+export type {ReceiptRetryContext, ResolveReceiptFile, RetryOutcome};
diff --git a/src/libs/actions/IOU/MoneyRequestBuilder.ts b/src/libs/actions/IOU/MoneyRequestBuilder.ts
index ec527035d26e..637bcffcbe22 100644
--- a/src/libs/actions/IOU/MoneyRequestBuilder.ts
+++ b/src/libs/actions/IOU/MoneyRequestBuilder.ts
@@ -192,6 +192,11 @@ type RequestMoneyInformation = {
     optimisticIOUReportID?: string;
     optimisticReportPreviewActionID?: string;
     optimisticTransactionID?: string;
+    currentReportActionID?: string;
+    existingTransactionThreadReportID?: string;
+
+    /** The report already counts this transaction, so its totals and transaction count are not recalculated. */
+    isTransactionAlreadyOnReport?: boolean;
     shouldGenerateTransactionThreadReport: boolean;
     isASAPSubmitBetaEnabled: boolean;
     currentUserAccountIDParam: number;
@@ -238,6 +243,12 @@ type MoneyRequestInformationParams = {
     isReverseSplitOperation?: boolean;
     action?: IOUAction;
     currentReportActionID?: string;
+
+    /** Reuses this thread so a retry lands on the records the first attempt created. */
+    existingTransactionThreadReportID?: string;
+
+    /** The report already counts this transaction, so its totals and transaction count are not recalculated. */
+    isTransactionAlreadyOnReport?: boolean;
     isASAPSubmitBetaEnabled: boolean;
     currentUserAccountIDParam: number;
     currentUserEmailParam: string;
@@ -1063,7 +1074,8 @@ function buildOnyxDataForMoneyRequest(moneyRequestParams: BuildOnyxDataForMoneyR
                                   errors: getReceiptError(transaction.receipt, transaction.receipt?.filename, isScanRequest, errorKey, CONST.IOU.ACTION_PARAMS.MONEY_REQUEST),
                               },
                               [iou.action.reportActionID]: {
-                                  errors: getMicroSecondOnyxErrorWithTranslationKey('iou.error.genericCreateFailureMessage'),
+                                  // `errorKey + 1` so this doesn't overwrite the transaction's `ReceiptError` when the receipt view merges them.
+                                  errors: getMicroSecondOnyxErrorWithTranslationKey('iou.error.genericCreateFailureMessage', errorKey + 1),
                               },
                           }
                         : {
@@ -1297,6 +1309,8 @@ function getMoneyRequestInformation(moneyRequestInformation: MoneyRequestInforma
         isReverseSplitOperation,
         action,
         currentReportActionID,
+        existingTransactionThreadReportID,
+        isTransactionAlreadyOnReport = false,
         isASAPSubmitBetaEnabled,
         currentUserAccountIDParam,
         currentUserEmailParam,
@@ -1449,6 +1463,9 @@ function getMoneyRequestInformation(moneyRequestInformation: MoneyRequestInforma
                   rules,
               })
             : buildOptimisticIOUReport(payeeAccountID, payerAccountID, reportAmount, chatReport.reportID, currency, getCurrencyDecimals, undefined, undefined, optimisticReportID);
+    } else if (isTransactionAlreadyOnReport) {
+        // The report already counts this transaction, so skip the totals. Still clone it, because code below mutates `iouReport`.
+        iouReport = {...iouReport};
     } else if (isPolicyExpenseChat) {
         // Capture previous fresh reimbursable totals before mutating, so the diff applies whether or
         // not the iouReport already had reimbursableTotal/unheldReimbursableTotal populated locally.
@@ -1557,7 +1574,10 @@ function getMoneyRequestInformation(moneyRequestInformation: MoneyRequestInforma
         isDemoTransactionParam: transactionParams.receipt?.isTestDriveReceipt,
     });
 
-    iouReport.transactionCount = (iouReport.transactionCount ?? 0) + 1;
+    if (!isTransactionAlreadyOnReport) {
+        // A retry must not bump this, because `isOneTransactionReport` checks `transactionCount === 1`.
+        iouReport.transactionCount = (iouReport.transactionCount ?? 0) + 1;
+    }
 
     const optimisticPolicyRecentlyUsedCategories = mergePolicyRecentlyUsedCategories(category, policyRecentlyUsedCategories);
     const optimisticPolicyRecentlyUsedTags = buildOptimisticPolicyRecentlyUsedTags({
@@ -1661,7 +1681,7 @@ function getMoneyRequestInformation(moneyRequestInformation: MoneyRequestInforma
             participants: [participant],
             transactionID: optimisticTransaction.transactionID,
             paymentType: transactionParams.receipt?.isTestDriveReceipt ? CONST.IOU.PAYMENT_TYPE.ELSEWHERE : undefined,
-            existingTransactionThreadReportID: linkedTrackedExpenseReportAction?.childReportID,
+            existingTransactionThreadReportID: existingTransactionThreadReportID ?? linkedTrackedExpenseReportAction?.childReportID,
             optimisticCreatedReportActionID,
             linkedTrackedExpenseReportAction,
             isPersonalTrackingExpense: isSelfDMSplit,
diff --git a/src/libs/actions/IOU/Receipt.ts b/src/libs/actions/IOU/Receipt.ts
index 99416ca7a3e9..86c7a79543ed 100644
--- a/src/libs/actions/IOU/Receipt.ts
+++ b/src/libs/actions/IOU/Receipt.ts
@@ -397,5 +397,29 @@ function checkIfLocalFileIsAccessible(
     return readFileAsync(ReceiptStorage.resolve(receiptPath) ?? receiptPath.toString(), receiptFilename, onSuccess, onFailure, receiptType);
 }
 
-export {checkIfLocalFileIsAccessible, detachReceipt, navigateToStartStepIfScanFileCannotBeRead, replaceReceipt, setMoneyRequestReceipt};
+function clearReceiptUploadError({
+    transactionID,
+    reportID,
+    reportActionID,
+    reportIDWithCreationError,
+}: {
+    transactionID: string | undefined;
+    reportID: string | undefined;
+    reportActionID: string | undefined;
+    reportIDWithCreationError: string | undefined;
+}): Promise<unknown> {
+    const writes: Array<Promise<void>> = [];
+    if (transactionID) {
+        writes.push(Onyx.merge(`${ONYXKEYS.COLLECTION.TRANSACTION}${transactionID}`, {errors: null}));
+    }
+    if (reportID && reportActionID) {
+        writes.push(Onyx.merge(`${ONYXKEYS.COLLECTION.REPORT_ACTIONS}${reportID}`, {[reportActionID]: {errors: null}}));
+    }
+    if (reportIDWithCreationError) {
+        writes.push(Onyx.merge(`${ONYXKEYS.COLLECTION.REPORT}${reportIDWithCreationError}`, {errorFields: {addWorkspaceRoom: null, createChat: null, createReport: null}}));
+    }
+    return Promise.all(writes);
+}
+
+export {checkIfLocalFileIsAccessible, clearReceiptUploadError, detachReceipt, navigateToStartStepIfScanFileCannotBeRead, replaceReceipt, setMoneyRequestReceipt};
 export type {ReplaceReceiptRetryParams};
diff --git a/src/libs/actions/IOU/TrackExpense.ts b/src/libs/actions/IOU/TrackExpense.ts
index add79b3835e9..9bd252ecd894 100644
--- a/src/libs/actions/IOU/TrackExpense.ts
+++ b/src/libs/actions/IOU/TrackExpense.ts
@@ -1808,6 +1808,9 @@ function requestMoney(requestMoneyInformation: RequestMoneyInformation): {iouRep
         moneyRequestReportID,
         existingTransactionID,
         optimisticTransactionID: requestMoneyInformation.optimisticTransactionID,
+        currentReportActionID: requestMoneyInformation.currentReportActionID,
+        existingTransactionThreadReportID: requestMoneyInformation.existingTransactionThreadReportID,
+        isTransactionAlreadyOnReport: requestMoneyInformation.isTransactionAlreadyOnReport,
         existingTransaction,
         retryParams,
         testDriveCommentReportActionID,
diff --git a/tests/ui/components/MoneyRequestReceiptViewTest.tsx b/tests/ui/components/MoneyRequestReceiptViewTest.tsx
index e5325f7452c7..5f1842a09326 100644
--- a/tests/ui/components/MoneyRequestReceiptViewTest.tsx
+++ b/tests/ui/components/MoneyRequestReceiptViewTest.tsx
@@ -606,8 +606,8 @@ describe('MoneyRequestReceiptView', () => {
             );
             await waitForBatchedUpdatesWithAct();
 
-            expect(screen.getByText(translateLocal('iou.error.receiptUploadFailedMessage'))).toBeTruthy();
-            expect(screen.getByText(translateLocal('iou.error.saveReceipt'))).toBeTruthy();
+            expect(screen.getByText(translateLocal('iou.error.receiptUploadFailedSaveOnlyMessage'))).toBeTruthy();
+            expect(screen.getByText(translateLocal('common.save'))).toBeTruthy();
         });
 
         it('does not show the receipt-upload error for a distance expense', async () => {
@@ -623,8 +623,8 @@ describe('MoneyRequestReceiptView', () => {
             );
             await waitForBatchedUpdatesWithAct();
 
-            expect(screen.queryByText(translateLocal('iou.error.receiptUploadFailedMessage'))).toBeNull();
-            expect(screen.queryByText(translateLocal('iou.error.saveReceipt'))).toBeNull();
+            expect(screen.queryByText(translateLocal('iou.error.receiptUploadFailedSaveOnlyMessage'))).toBeNull();
+            expect(screen.queryByText(translateLocal('common.save'))).toBeNull();
         });
 
         it('shows the receipt-upload error for an odometer distance expense (real uploaded file)', async () => {
@@ -640,8 +640,8 @@ describe('MoneyRequestReceiptView', () => {
             );
             await waitForBatchedUpdatesWithAct();
 
-            expect(screen.getByText(translateLocal('iou.error.receiptUploadFailedMessage'))).toBeTruthy();
-            expect(screen.getByText(translateLocal('iou.error.saveReceipt'))).toBeTruthy();
+            expect(screen.getByText(translateLocal('iou.error.receiptUploadFailedSaveOnlyMessage'))).toBeTruthy();
+            expect(screen.getByText(translateLocal('common.save'))).toBeTruthy();
         });
     });
 });
diff --git a/tests/unit/ReceiptUploadRetryHandlerTest.ts b/tests/unit/ReceiptUploadRetryHandlerTest.ts
new file mode 100644
index 000000000000..db047ccd93e1
--- /dev/null
+++ b/tests/unit/ReceiptUploadRetryHandlerTest.ts
@@ -0,0 +1,153 @@
+import retryReceiptUpload from '@libs/ReceiptUploadRetryHandler';
+import buildRetryPayload, {canBuildRetryPayload} from '@libs/ReceiptUploadRetryHandler/buildRetryPayload';
+import resolveReceiptFile from '@libs/ReceiptUploadRetryHandler/resolveReceiptFile';
+import type {ReceiptRetryContext} from '@libs/ReceiptUploadRetryHandler/types';
+
+import {requestMoney} from '@userActions/IOU/TrackExpense';
+
+import CONST from '@src/CONST';
+import ONYXKEYS from '@src/ONYXKEYS';
+import type {Report, Transaction} from '@src/types/onyx';
+import type {ReceiptError} from '@src/types/onyx/Transaction';
+import type {FileObject} from '@src/types/utils/Attachment';
+
+import Onyx from 'react-native-onyx';
+
+import waitForBatchedUpdates from '../utils/waitForBatchedUpdates';
+
+jest.mock('@libs/ReceiptUploadRetryHandler/resolveReceiptFile', () => ({__esModule: true, default: jest.fn()}));
+jest.mock('@userActions/IOU/TrackExpense', () => ({...jest.requireActual<Record<string, unknown>>('@userActions/IOU/TrackExpense'), requestMoney: jest.fn()}));
+
+const CURRENT_USER_ACCOUNT_ID = 1;
+const TRANSACTION_ID = '7000000000000001';
+const IOU_REPORT_ID = '8000000000000001';
+const CHAT_REPORT_ID = '9000000000000001';
+const POLICY_ID = 'A0000000000000001';
+const IOU_ACTION_ID = '6000000000000001';
+const THREAD_REPORT_ID = '5000000000000001';
+
+const receiptFile: FileObject = {name: 'receipt.jpg', type: 'image/jpeg', uri: 'file:///receipts/receipt.jpg'};
+
+function buildFailedTransaction(overrides: Partial<Transaction> = {}): Transaction {
+    return {
+        transactionID: TRANSACTION_ID,
+        reportID: IOU_REPORT_ID,
+        amount: 0,
+        currency: CONST.CURRENCY.USD,
+        created: '2026-09-01',
+        merchant: CONST.TRANSACTION.PARTIAL_TRANSACTION_MERCHANT,
+        comment: {comment: ''},
+        iouRequestType: CONST.IOU.REQUEST_TYPE.MANUAL,
+        receipt: {source: 'file:///receipts/receipt.jpg', filename: 'receipt.jpg', state: CONST.IOU.RECEIPT_STATE.SCAN_READY},
+        ...overrides,
+    } as Transaction;
+}
+
+function buildContext(transaction: Transaction, receiptErrorOverrides: Partial<ReceiptError> = {}): ReceiptRetryContext {
+    return {
+        receiptError: {
+            error: CONST.IOU.RECEIPT_ERROR,
+            source: 'file:///receipts/receipt.jpg',
+            filename: 'receipt.jpg',
+            action: CONST.IOU.ACTION_PARAMS.MONEY_REQUEST,
+            ...receiptErrorOverrides,
+        },
+        transaction,
+        iouReport: {reportID: IOU_REPORT_ID, chatReportID: CHAT_REPORT_ID, policyID: POLICY_ID, type: CONST.REPORT.TYPE.EXPENSE} as Report,
+        iouActionID: IOU_ACTION_ID,
+        transactionThreadReportID: THREAD_REPORT_ID,
+        policyParams: {},
+        isVendorMatchingBetaEnabled: false,
+        rules: {},
+        conciergeReportID: undefined,
+        isSelfTourViewed: true,
+        isASAPSubmitBetaEnabled: false,
+        isTrackIntentUser: false,
+        delegateAccountID: undefined,
+        formatPhoneNumber: (phone) => phone,
+        getCurrencyDecimals: () => 2,
+    };
+}
+
+describe('buildRetryPayload', () => {
+    beforeAll(() => {
+        Onyx.init({keys: ONYXKEYS});
+    });
+
+    beforeEach(async () => {
+        await Onyx.clear();
+        await Onyx.merge(ONYXKEYS.SESSION, {accountID: CURRENT_USER_ACCOUNT_ID});
+        await Onyx.merge(ONYXKEYS.PERSONAL_DETAILS_LIST, {[CURRENT_USER_ACCOUNT_ID]: {accountID: CURRENT_USER_ACCOUNT_ID, login: 'me@example.com'}});
+        await Onyx.merge(`${ONYXKEYS.COLLECTION.REPORT}${CHAT_REPORT_ID}`, {
+            reportID: CHAT_REPORT_ID,
+            chatType: CONST.REPORT.CHAT_TYPE.POLICY_EXPENSE_CHAT,
+            policyID: POLICY_ID,
+        });
+        await waitForBatchedUpdates();
+    });
+
+    it('reuses the original transaction ID, which is the only thing stopping a re-send from creating a second expense', () => {
+        const payload = buildRetryPayload(buildContext(buildFailedTransaction()), receiptFile);
+        expect(payload?.optimisticTransactionID).toBe(TRANSACTION_ID);
+    });
+
+    it('offers a retry for a failed expense as the create path really leaves it, with no participants and a manual request type', () => {
+        expect(canBuildRetryPayload(buildContext(buildFailedTransaction()))).toBe(true);
+    });
+
+    it('reuses the IOU report action and transaction thread, so the retry does not add a second expense to the report', () => {
+        const payload = buildRetryPayload(buildContext(buildFailedTransaction()), receiptFile);
+        expect(payload?.currentReportActionID).toBe(IOU_ACTION_ID);
+        expect(payload?.existingTransactionThreadReportID).toBe(THREAD_REPORT_ID);
+    });
+
+    it('offers no retry for a distance expense, whose waypoints the transaction alone cannot restore', () => {
+        const transaction = buildFailedTransaction({comment: {waypoints: {waypoint0: {address: 'Berlin'}}}});
+        expect(canBuildRetryPayload(buildContext(transaction))).toBe(false);
+    });
+
+    it('offers no retry for a replaceReceipt failure, which is not the create call the handler rebuilds', () => {
+        expect(canBuildRetryPayload(buildContext(buildFailedTransaction(), {action: CONST.IOU.ACTION_PARAMS.REPLACE_RECEIPT}))).toBe(false);
+    });
+
+    it('offers no retry for a trackExpense failure, whose convert-and-submit path the handler does not replay', () => {
+        expect(canBuildRetryPayload(buildContext(buildFailedTransaction(), {action: CONST.IOU.ACTION_PARAMS.TRACK_EXPENSE}))).toBe(false);
+    });
+
+    it('offers no retry for the report-creation fallback error, which carries no action to replay', () => {
+        expect(canBuildRetryPayload(buildContext(buildFailedTransaction(), {action: undefined}))).toBe(false);
+    });
+
+    it('offers no retry once the receipt source is no longer a local file, so there is nothing left on the device to resend', () => {
+        expect(canBuildRetryPayload(buildContext(buildFailedTransaction(), {source: 'https://example.com/receipt.jpg'}))).toBe(false);
+    });
+
+    describe('retryReceiptUpload', () => {
+        beforeEach(() => {
+            jest.mocked(resolveReceiptFile).mockResolvedValue(receiptFile);
+            jest.mocked(requestMoney).mockReset();
+        });
+
+        it('keeps the receipt error when the dispatch throws, so Try again and Save stay available', async () => {
+            jest.mocked(requestMoney).mockImplementation(() => {
+                throw new Error('dispatch failed');
+            });
+            const clearReceiptError = jest.fn(() => Promise.resolve());
+
+            const outcome = await retryReceiptUpload(buildContext(buildFailedTransaction()), clearReceiptError);
+
+            expect(outcome).toBe('dispatchFailed');
+            expect(clearReceiptError).not.toHaveBeenCalled();
+        });
+
+        it('clears the receipt error only after the retry is dispatched', async () => {
+            const clearReceiptError = jest.fn(() => Promise.resolve());
+
+            const outcome = await retryReceiptUpload(buildContext(buildFailedTransaction()), clearReceiptError);
+
+            expect(outcome).toBe('dispatched');
+            expect(clearReceiptError).toHaveBeenCalledTimes(1);
+            expect(jest.mocked(requestMoney).mock.invocationCallOrder.at(0)).toBeLessThan(clearReceiptError.mock.invocationCallOrder.at(0) ?? 0);
+        });
+    });
+});