diff --git a/src/components/AttachmentModal.tsx b/src/components/AttachmentModal.tsx
index 8de7f4575e75..0bc233812ca7 100644
--- a/src/components/AttachmentModal.tsx
+++ b/src/components/AttachmentModal.tsx
@@ -132,6 +132,8 @@ type AttachmentModalProps = {
     fallbackSource?: AvatarSource;
 
     canEditReceipt?: boolean;
+
+    shouldDisableSendButton?: boolean;
 };
 
 function AttachmentModal({
@@ -158,6 +160,7 @@ function AttachmentModal({
     shouldShowNotFoundPage = false,
     type = undefined,
     accountID = undefined,
+    shouldDisableSendButton = false,
 }: AttachmentModalProps) {
     const styles = useThemeStyles();
     const StyleUtils = useStyleUtils();
@@ -589,7 +592,7 @@ function AttachmentModal({
                                         textStyles={[styles.buttonConfirmText]}
                                         text={translate('common.send')}
                                         onPress={submitAndClose}
-                                        isDisabled={isConfirmButtonDisabled}
+                                        isDisabled={isConfirmButtonDisabled || shouldDisableSendButton}
                                         pressOnEnter
                                     />
                                 </Animated.View>
diff --git a/src/pages/home/report/ReportActionCompose/AttachmentPickerWithMenuItems.tsx b/src/pages/home/report/ReportActionCompose/AttachmentPickerWithMenuItems.tsx
index 005ca4df153a..31c5c6fc891f 100644
--- a/src/pages/home/report/ReportActionCompose/AttachmentPickerWithMenuItems.tsx
+++ b/src/pages/home/report/ReportActionCompose/AttachmentPickerWithMenuItems.tsx
@@ -86,6 +86,8 @@ type AttachmentPickerWithMenuItemsProps = {
 
     /** The personal details of everyone in the report */
     reportParticipantIDs?: number[];
+
+    shouldDisableAttachmentItem?: boolean;
 };
 
 /**
@@ -110,6 +112,7 @@ function AttachmentPickerWithMenuItems({
     onItemSelected,
     actionButtonRef,
     raiseIsScrollLikelyLayoutTriggered,
+    shouldDisableAttachmentItem,
 }: AttachmentPickerWithMenuItemsProps) {
     const isFocused = useIsFocused();
     const theme = useTheme();
@@ -236,6 +239,7 @@ function AttachmentPickerWithMenuItems({
                             triggerAttachmentPicker();
                         },
                         shouldCallAfterModalHide: true,
+                        disabled: shouldDisableAttachmentItem,
                     },
                 ];
                 return (
diff --git a/src/pages/home/report/ReportActionCompose/ReportActionCompose.tsx b/src/pages/home/report/ReportActionCompose/ReportActionCompose.tsx
index 4a2dc6dc0781..39786e15c621 100644
--- a/src/pages/home/report/ReportActionCompose/ReportActionCompose.tsx
+++ b/src/pages/home/report/ReportActionCompose/ReportActionCompose.tsx
@@ -432,6 +432,7 @@ function ReportActionCompose({
                                 onConfirm={addAttachment}
                                 onModalShow={() => setIsAttachmentPreviewActive(true)}
                                 onModalHide={onAttachmentPreviewClose}
+                                shouldDisableSendButton={hasExceededMaxCommentLength}
                             >
                                 {({displayFileInModal}) => (
                                     <>
@@ -451,6 +452,7 @@ function ReportActionCompose({
                                             onAddActionPressed={onAddActionPressed}
                                             onItemSelected={onItemSelected}
                                             actionButtonRef={actionButtonRef}
+                                            shouldDisableAttachmentItem={hasExceededMaxCommentLength}
                                         />
                                         <ComposerWithSuggestions
                                             ref={(ref) => {