diff --git a/src/assets/icons/ic_arrow_narrow.vue b/src/assets/icons/ic_arrow_narrow.vue
new file mode 100644
index 0000000..99bdca5
--- /dev/null
+++ b/src/assets/icons/ic_arrow_narrow.vue
@@ -0,0 +1,5 @@
+<template>
+  <svg width="12" height="12" viewBox="0 0 12 12" fill="none" xmlns="http://www.w3.org/2000/svg">
+    <path d="M6 10V2M6 2L3 5M6 2L9 5" stroke="white" stroke-linecap="round" stroke-linejoin="round" />
+  </svg>
+</template>
diff --git a/src/assets/translations/en.json b/src/assets/translations/en.json
index c0cde6d..ab3763e 100644
--- a/src/assets/translations/en.json
+++ b/src/assets/translations/en.json
@@ -21,7 +21,8 @@
     "close": "close",
     "notify": "Notify",
     "different_browser_title": "Try different browser",
-    "different_browser_content": "Some features may break. Copy and open link in a different browser."
+    "different_browser_content": "Some features may break. Copy and open link in a different browser.",
+    "retry": "Retry"
   },
   "menu": {
     "start_private_chat": "Direct Message with this user",
diff --git a/src/components/file_mode/SendAttachmentsLayout.vue b/src/components/file_mode/SendAttachmentsLayout.vue
index 668545c..db446fd 100644
--- a/src/components/file_mode/SendAttachmentsLayout.vue
+++ b/src/components/file_mode/SendAttachmentsLayout.vue
@@ -22,7 +22,7 @@
         @dragleave.prevent="dropTarget = false"
         @dragenter.prevent="dropTarget = true"
       >
-        <ThumbnailView :file="currentAttachment" />
+        <ThumbnailView :item="currentAttachment" />
         <div v-if="currentAttachment && currentAttachment.status === 'loading'" class="send-attachments__selecting__current-item__preparing">
           <div style="font-size: 0.7em; opacity: 0.7">
             <v-progress-circular indeterminate class="mb-0"></v-progress-circular>
diff --git a/src/components/file_mode/ThumbnailView.vue b/src/components/file_mode/ThumbnailView.vue
index f6e83f2..93d03c6 100644
--- a/src/components/file_mode/ThumbnailView.vue
+++ b/src/components/file_mode/ThumbnailView.vue
@@ -29,48 +29,58 @@ import { EventAttachment } from "../../models/eventAttachment";
 import { useThumbnail } from "../messages/composition/useThumbnail";
 import { Attachment } from "../../models/attachment";
 import ImageWithProgress from "../ImageWithProgress.vue";
+  
+function isEventAttachment(source: EventAttachment | Attachment | undefined): source is EventAttachment {
+    return (source as EventAttachment).event !== undefined;
+}
+
+function isAttachment(source: EventAttachment | Attachment | undefined): source is Attachment {
+    return (source as Attachment).file !== undefined;
+}
 
 const $$sanitize: any = inject("globalSanitize");
 
 const thumbnailRef = useTemplateRef("thumbnailRef");
 
 interface ThumbnailProps {
-  item?: EventAttachment;
-  file?: Attachment;
+  item?: EventAttachment | Attachment;
   previewOnly?: boolean;
 }
 
 type ThumbnailEmits = {
-  (event: "itemclick", value: { item: EventAttachment }): void;
+  (event: "itemclick", value: { item: EventAttachment | Attachment }): void;
 };
 
 const props = defineProps<ThumbnailProps>();
-const { item, file, previewOnly = false } = props;
+const { item, previewOnly = false } = props;
 const emits = defineEmits<ThumbnailEmits>();
 
-let { isVideo, isImage, fileTypeIcon, fileTypeIconClass, fileName, fileSize } = useThumbnail(file?.file ?? item?.event);
+let { isVideo, isImage, fileTypeIcon, fileTypeIconClass, fileName, fileSize } = useThumbnail(isEventAttachment(props.item) ? props.item.event : isAttachment(props.item) ? props.item.file : undefined);
+
 const fileURL: Ref<string | undefined> = ref(undefined);
 const source: Ref<string | undefined> = ref(undefined);
 const poster: Ref<string | undefined> = ref(undefined);
 
 const updateSource = () => {
-  if (props.item) {
-    if (isVideo.value || props.item.src) {
-      source.value = props.item.src;
+  if (isEventAttachment(props.item)) {
+    const eventAttachment = props.item;
+    if (isVideo.value || eventAttachment.src) {
+      source.value = eventAttachment.src;
     } else if (previewOnly) {
-      props.item.loadThumbnail().then((url) => { 
+      eventAttachment.loadThumbnail().then((url) => { 
         source.value = url.data;
       })
     } else if (isImage.value) {
-      props.item.loadSrc().then((url) => { 
+      eventAttachment.loadSrc().then((url) => { 
         source.value = url.data;
       })
     }
-  } else if (props.file) {
+  } else if (isAttachment(props.item)) {
+    const attachment = props.item;
     if (fileURL.value) {
       URL.revokeObjectURL(fileURL.value);
     }
-    fileURL.value = URL.createObjectURL(props.file.file);
+    fileURL.value = URL.createObjectURL(attachment.file);
     source.value = fileURL.value;
   } else {
     source.value = undefined;
@@ -78,11 +88,12 @@ const updateSource = () => {
 };
 
 const updatePoster = () => {
-  if (props.item && isVideo.value) {
-    if (props.item.thumbnail) {
-      poster.value = props.item.thumbnail;
+  if (isEventAttachment(props.item) && isVideo.value) {
+    const eventAttachment = props.item;
+    if (eventAttachment.thumbnail) {
+      poster.value = eventAttachment.thumbnail;
     } else {
-      props.item
+      eventAttachment
         .loadThumbnail()
         .then((url) => {
           poster.value = url.data;
@@ -99,7 +110,7 @@ updatePoster();
 
 
 watch(props, (props: ThumbnailProps) => {
-  const updates = useThumbnail(props.file?.file ?? props.item?.event);
+  const updates = useThumbnail(isEventAttachment(props.item) ? props.item.event : isAttachment(props.item) ? props.item.file : undefined);
   isVideo.value = updates.isVideo.value;
   isImage.value = updates.isImage.value;
   fileTypeIcon = updates.fileTypeIcon;
@@ -111,23 +122,24 @@ watch(props, (props: ThumbnailProps) => {
 });
 
 const loadingProgress = computed(() => {
-  if (item) {
-    return previewOnly ? item.thumbnailProgress : item.srcProgress;
+  if (isEventAttachment(item)) {
+    const eventAttachment = item;
+    return previewOnly ? eventAttachment.thumbnailProgress : eventAttachment.srcProgress;
   }
   return -1;
 });
 
 onMounted(() => {
-  if (thumbnailRef.value && (item as EventAttachment)) {
+  if (thumbnailRef.value && item) {
     const hammerInstance = singleOrDoubleTapRecognizer(thumbnailRef.value);
     hammerInstance.on("singletap doubletap", (ev: any) => {
       if (ev.type === "singletap") {
-        emits("itemclick", { item: item as EventAttachment });
+        emits("itemclick", { item: item });
       }
     });
   }
-  if (!previewOnly && item && (item as EventAttachment)) {
-    (item as EventAttachment).loadSrc();
+  if (!previewOnly && item && isEventAttachment(item)) {
+    item.loadSrc();
   }
 });
 
diff --git a/src/components/messages/composition/MessageThreadSending.vue b/src/components/messages/composition/MessageThreadSending.vue
index c73154c..39463b1 100644
--- a/src/components/messages/composition/MessageThreadSending.vue
+++ b/src/components/messages/composition/MessageThreadSending.vue
@@ -1,5 +1,5 @@
 <template>
-  <MessageOutgoing :is="rootComponent" ref="root" v-bind="{ ...$props, ...$attrs }">
+  <MessageOutgoing v-bind="{ ...$props, ...$attrs }">
     <div class="bubble">
       <div class="original-message" v-if="inReplyToText">
         <div class="original-message-sender">{{ inReplyToSender }}</div>
@@ -20,11 +20,15 @@
             <v-icon size="8">close</v-icon> </v-progress-circular
           >{{ uploadBatch?.progressPercent }}%
         </div>
+        <div class="message-upload-progress clickable" @click.stop="retryUpload" v-else-if="unref(uploadBatch?.sendingStatus) === 'failed'">
+            <v-icon size="12">$vuetify.icons.ic_arrow_narrow</v-icon>
+          <div>{{ t("global.retry") }}</div>
+        </div>
         <SwipeableThumbnailsView :items="items" v-if="room.displayType == ROOM_TYPE_CHANNEL" v-bind="$attrs" />
         <v-container v-else fluid class="imageCollection">
           <v-row wrap>
             <v-col v-for="{ size, item } in layoutedItems" :key="item.file.name + item.file.size" :cols="size">
-              <ThumbnailView :file="item" v-on:itemclick="onItemClick($event)" />
+              <ThumbnailView :item="item" v-on:itemclick="onItemClick($event)" />
             </v-col>
           </v-row>
         </v-container>
@@ -83,6 +87,12 @@ const cancelUpload = () => {
   }
 }
 
+const retryUpload = () => {
+  if (uploadBatch.value) {
+    uploadBatch.value.send(uploadBatch.value.sendingRootMessage.value ?? "");
+  }
+}
+
 const onItemClick = (event: any) => {
   showItem.value = event.item;
 };
diff --git a/src/models/attachment.ts b/src/models/attachment.ts
index e80b2c4..1513c22 100644
--- a/src/models/attachment.ts
+++ b/src/models/attachment.ts
@@ -39,7 +39,6 @@ export type AttachmentSendInfo = {
   randomRotation: number; // For UI effects
   randomTranslationX: number; // For UI effects
   randomTranslationY: number; // For UI effects
-  proofHintFlags?: ProofHintFlags;
 };
 
 export type AttachmentThumbnail = {
@@ -59,6 +58,7 @@ export type Attachment = {
   useScaled: boolean;
   src?: string;
   proof?: Proof;
+  proofHintFlags?: ProofHintFlags;
   thumbnail?: AttachmentThumbnail;
   sendInfo: AttachmentSendInfo;
 };
@@ -66,6 +66,7 @@ export type Attachment = {
 export type AttachmentBatch = {
   sendingStatus: Ref<AttachmentSendStatus>;
   sendingRootEventId: Ref<string | undefined>;
+  sendingRootMessage: Ref<string | undefined>;
   progressPercent: Ref<number>;
   attachments: Attachment[];
   attachmentsSentCount: ComputedRef<number>;
diff --git a/src/models/attachmentManager.ts b/src/models/attachmentManager.ts
index 752f9b5..1324846 100644
--- a/src/models/attachmentManager.ts
+++ b/src/models/attachmentManager.ts
@@ -119,6 +119,7 @@ export class AttachmentManager {
       }
       try {
         attachment.proof = await proofmode.proofCheckFile(file);
+        attachment.proofHintFlags = extractProofHintFlags(attachment.proof);
 
         // Default to scaled version if the image does not contain Content Credentials
         //
@@ -420,6 +421,7 @@ export const createUploadBatch = (manager: AttachmentManager | null, room: Room
 
   const sendingStatus: Ref<AttachmentSendStatus> = ref("initial");
   const sendingRootEventId: Ref<string | undefined> = ref(undefined);
+  const sendingRootMessage: Ref<string | undefined> = ref(undefined);
   const sendingPromise: Ref<Promise<any> | undefined> = ref(undefined);
   const attachments: Ref<Attachment[]> = ref([]);
 
@@ -528,6 +530,8 @@ export const createUploadBatch = (manager: AttachmentManager | null, room: Room
   const send = async (message: string): Promise<any> => {
     if (!matrixClient || !room) return Promise.reject("Not configured");
     sendingStatus.value = "sending";
+    progressPercent.value = 0;
+    sendingRootMessage.value = message;
 
     attachments.value.forEach((attachment) => {
       let sendInfo: AttachmentSendInfo = {
@@ -539,7 +543,6 @@ export const createUploadBatch = (manager: AttachmentManager | null, room: Room
         randomTranslationX: 0,
         randomTranslationY: 0,
         promise: undefined,
-        proofHintFlags: extractProofHintFlags(attachment.proof),
       };
       attachment.sendInfo = shallowReactive(sendInfo);
       attachment.proof = undefined;
@@ -555,6 +558,7 @@ export const createUploadBatch = (manager: AttachmentManager | null, room: Room
         event.uploadBatch = {
           sendingStatus,
           sendingRootEventId,
+          sendingRootMessage,
           progressPercent,
           attachments: unref(attachments),
           attachmentsSentCount,
@@ -572,8 +576,7 @@ export const createUploadBatch = (manager: AttachmentManager | null, room: Room
     };
     room.on(RoomEvent.LocalEchoUpdated, onLocalEchoUpdated);
 
-    const promise = utils
-      .sendTextMessage(matrixClient, room.roomId, message, undefined, undefined, txnId)
+    const promise = (sendingRootEventId.value ? Promise.resolve(sendingRootEventId.value) : utils.sendTextMessage(matrixClient, room.roomId, message, undefined, undefined, txnId))
       .then((eventId: string) => {
         sendingRootEventId.value = eventId;
 
@@ -582,7 +585,7 @@ export const createUploadBatch = (manager: AttachmentManager | null, room: Room
           if (index < attachments.value.length) {
             const attachment = attachments.value[index];
             const item = attachment;
-            if (item.sendInfo.status !== "initial") {
+            if (item.sendInfo.status !== "initial" && item.sendInfo.status !== "failed") {
               return getItemPromise(++index);
             }
             item.sendInfo.status = "sending";
@@ -637,12 +640,13 @@ export const createUploadBatch = (manager: AttachmentManager | null, room: Room
                 item.sendInfo.status = "sent";
                 item.sendInfo.statusDate = Date.now();
               })
-              .catch((ignorederr: any) => {
+              .catch((error: any) => {
                 if (item.sendInfo.promise?.aborted) {
                   item.sendInfo.status = "canceled";
                 } else {
-                  console.error("ERROR", ignorederr);
+                  console.error("ERROR", error);
                   item.sendInfo.status = "failed";
+                  return Promise.reject(error)
                 }
                 return Promise.resolve();
               });
@@ -659,6 +663,7 @@ export const createUploadBatch = (manager: AttachmentManager | null, room: Room
       })
       .catch((err: any) => {
         console.error("Upload error", err);
+        sendingStatus.value = "failed";
       })
       .finally(() => {
         room.off(RoomEvent.LocalEchoUpdated, onLocalEchoUpdated);
@@ -670,6 +675,7 @@ export const createUploadBatch = (manager: AttachmentManager | null, room: Room
   return {
     sendingStatus,
     sendingRootEventId,
+    sendingRootMessage,
     progressPercent,
     attachments: unref(attachments),
     attachmentsSentCount,