diff --git a/src/assets/css/sendattachments.scss b/src/assets/css/sendattachments.scss
index 6219764..a3094bf 100644
--- a/src/assets/css/sendattachments.scss
+++ b/src/assets/css/sendattachments.scss
@@ -45,9 +45,11 @@ $hiliteColor: #4642f1;
     width: 100%;
     height: 50%;
     background-color: $background;
+
     &.drop-target {
       background-color: $backgroundHilite;
     }
+
     border-radius: 19px;
     display: flex;
     flex-direction: column;
@@ -79,6 +81,7 @@ $hiliteColor: #4642f1;
     height: $small-button-height !important;
     margin-top: $chat-standard-padding-xs;
     margin-bottom: $chat-standard-padding-xs;
+
     &.large {
       padding: 16px 23px;
       height: $large-button-height;
@@ -89,6 +92,7 @@ $hiliteColor: #4642f1;
   textarea {
     color: rgba($text, 80%) !important;
   }
+
   textarea::placeholder {
     color: rgba($text, 80%) !important;
   }
@@ -98,22 +102,28 @@ $hiliteColor: #4642f1;
     flex: 0 0 100%;
     overflow-y: auto;
     display: flex;
+    flex-direction: column;
   }
+
   .file-drop-current-item {
     width: 100%;
     flex: 1 1 100%;
     background-color: $backgroundSection;
     display: flex;
+
     &.drop-target {
       background-color: $backgroundHilite;
     }
+
     border-radius: 19px;
     overflow: hidden;
+
     .v-img {
       width: 100%;
       height: 100%;
       object-fit: cover;
     }
+
     .filename {
       width: 100%;
       height: 100%;
@@ -158,9 +168,12 @@ $hiliteColor: #4642f1;
     &::-webkit-scrollbar {
       display: none;
     }
+
     /* Hide scrollbar for IE, Edge and Firefox */
-    -ms-overflow-style: none; /* IE and Edge */
-    scrollbar-width: none; /* Firefox */
+    -ms-overflow-style: none;
+    /* IE and Edge */
+    scrollbar-width: none;
+    /* Firefox */
 
     .file-drop-thumbnail {
       width: 46px;
@@ -171,17 +184,21 @@ $hiliteColor: #4642f1;
       border: 2px solid white;
       display: inline-block;
       position: relative;
+
       &.current {
         border: 2px solid #4642f1;
       }
+
       &.noborder {
         border: 2px solid transparent;
       }
+
       .v-img {
         width: 100%;
         height: 100%;
         object-fit: cover;
       }
+
       margin-right: 8px;
 
       .add,
@@ -195,11 +212,13 @@ $hiliteColor: #4642f1;
         display: flex;
         align-items: center;
         justify-content: center;
+
         .v-icon {
           width: 14px;
           height: 15.75px;
         }
       }
+
       .remove {
         // Slight background to make visible
         background-color: rgba(black, 0.2);
@@ -228,31 +247,40 @@ $hiliteColor: #4642f1;
     border-radius: 19px;
     display: flex;
     flex-direction: column;
-    .input-area-text {
-      flex: 0 0 auto;
-      width: 100%;
-      margin-bottom: 50px;
-      padding: 16px 18px;
-      font-family: "Inter", sans-serif;
-      font-weight: 300;
-      .v-field {
-        background-color: transparent !important;
-      }
-    }
+
     .input-container__buttons {
       position: absolute;
       right: 8px;
       bottom: 10px;
       display: flex;
-      & > *:not(:first-child) {
+
+      &>*:not(:first-child) {
         margin-left: 8px;
       }
     }
   }
 
+  .input-area-text {
+    flex: 0 0 auto;
+    width: 100%;
+    margin-bottom: 50px;
+    padding: 16px 18px;
+    font-family: "Inter", sans-serif;
+    font-weight: 300;
+
+    .v-field {
+      background-color: transparent !important;
+    }
+  }
+
   @keyframes fadeInStackItem {
-    from {opacity: 0;}
-    to {opacity: 1;}
+    from {
+      opacity: 0;
+    }
+
+    to {
+      opacity: 1;
+    }
   }
 
   // Sending
@@ -263,49 +291,63 @@ $hiliteColor: #4642f1;
     display: flex;
     align-items: center;
     justify-content: center;
+
     .no-items {
       display: flex;
       align-items: center;
       justify-content: center;
+
       div {
         position: absolute;
       }
+
       .file-drop-stack-item {
         transform: rotate(-4.4deg);
       }
+
       color: #fff;
       text-align: center;
       font-size: 21 * $chat-text-size;
-      font-family: "Poppins", sans-serif;
+      font-family: "Poppins",
+      sans-serif;
       font-weight: 700;
       letter-spacing: 0.34px;
     }
+
     .items-sent {
       z-index: 1000;
       display: flex;
       align-items: center;
       justify-content: center;
-      div, .v-icon {
+
+      div,
+      .v-icon {
         position: absolute;
       }
-      .v-icon, .v-icon__component {
+
+      .v-icon,
+      .v-icon__component {
         width: 30%;
         height: 30%;
       }
     }
+
     .file-drop-stack-item {
       background: #3a3a3c;
       position: absolute;
       overflow: hidden;
       opacity: 0;
+
       .v-img {
         width: 100%;
         height: 100%;
         object-fit: cover;
       }
+
       &.direct {
         opacity: 1 !important;
       }
+
       &.animated {
         animation-name: fadeInStackItem;
         animation-fill-mode: both;
@@ -327,9 +369,12 @@ $hiliteColor: #4642f1;
     &::-webkit-scrollbar {
       display: none;
     }
+
     /* Hide scrollbar for IE, Edge and Firefox */
-    -ms-overflow-style: none; /* IE and Edge */
-    scrollbar-width: none; /* Firefox */
+    -ms-overflow-style: none;
+    /* IE and Edge */
+    scrollbar-width: none;
+    /* Firefox */
 
     .file-drop-sending-item {
       width: 100%;
@@ -339,6 +384,7 @@ $hiliteColor: #4642f1;
       border-radius: 12px;
       position: relative;
       padding: 8px;
+
       .v-img {
         width: $min-touch-target;
         height: $min-touch-target;
@@ -347,18 +393,22 @@ $hiliteColor: #4642f1;
         flex: 0 0 $min-touch-target;
         margin-right: 8px;
       }
+
       margin-bottom: 8px;
       display: flex;
       align-items: center;
+
       .filename {
         position: absolute;
         top: 18px;
         left: 8px;
         font-size: 0.7em;
       }
+
       .v-progress-linear {
         align-self: flex-end;
       }
+
       .file-drop-cancel {
         position: absolute;
         right: 8px;
@@ -379,7 +429,9 @@ $hiliteColor: #4642f1;
       .v-progress-circular {
         margin-left: 8px;
       }
-      background: linear-gradient(0deg, #000 0%, #000 100%), #4642f1;
+
+      background: linear-gradient(0deg, #000 0%, #000 100%),
+      #4642f1;
     }
   }
 
@@ -396,10 +448,12 @@ $hiliteColor: #4642f1;
 
   .file-drop-sent-input-container {
     background-color: transparent;
+
     .v-btn {
       right: unset;
       left: 8px;
       background: linear-gradient(0deg, #000 0%, #000 100%), #4642f1;
+
       &.close {
         right: 8px;
         left: unset;
@@ -407,4 +461,4 @@ $hiliteColor: #4642f1;
       }
     }
   }
-}
+}
\ No newline at end of file
diff --git a/src/components/Chat.vue b/src/components/Chat.vue
index 541c906..b6e5b3e 100644
--- a/src/components/Chat.vue
+++ b/src/components/Chat.vue
@@ -228,90 +228,13 @@
     <input ref="attachment" type="file" name="attachment" @change="handlePickedAttachment($event)"
                 accept="image/*,audio/*,video/*,.mp3,.mp4,.wav,.m4a,.pdf,application/pdf,.apk,application/vnd.android.package-archive,.ipa,.zip,application/zip,application/x-zip-compressed,multipart/x-zip" class="d-none" multiple/>
 
-    <!-- <div v-if="currentFileInputsDialog && !useFileModeNonAdmin">
-      <v-dialog v-model="currentFileInputsDialog" class="ma-0 pa-0" :width="$vuetify.display.smAndUp ? '50%' : '85%'" persistent scrollable>
-        <v-card class="ma-0 pa-0">
-          <v-card-text v-if="!currentFileInputs.length">
-            {{ this.$t("message.preparing_to_upload")}}
-            <v-progress-linear
-              indeterminate
-              class="mb-0"
-            ></v-progress-linear>
-          </v-card-text>
-          <template v-else>
-            <v-card-title>
-              <div v-if="currentSendErrorExceededFile" class="text-red">{{ currentSendErrorExceededFile }}</div>
-              <span v-else> {{ $t('message.send_attachements_dialog_title') }} </span>
-            </v-card-title>
-            <v-divider></v-divider>
-            <template v-if="imageFiles && imageFiles.length">
-              <v-card-title v-if="imageFiles.length > 1"> {{ $t('message.images') }} </v-card-title>
-              <v-card-text :class="{'ma-0 pa-2' : true, 'd-flex flex-wrap justify-center': imageFiles.length > 1}">
-                <div :class="{'col-4': imageFiles.length > 1}" v-for="(currentImageInput, id) in imageFiles" :key="id">
-                  <div style="position: relative">
-                    <v-img v-if="currentImageInput && currentImageInput.image" :aspect-ratio="1" :src="currentImageInput.image"
-                      contain class="current-image-input-path" />
-                    <v-progress-linear :style="{ position: 'absolute', left: '0', right: '0', bottom: '0', opacity: currentImageInput.sendInfo ? '1' : '0' }" :value="currentImageInput.sendInfo ? currentImageInput.sendInfo.progress : 0"></v-progress-linear>
-                    <C2PABadge :file="currentImageInput.actualFile" />
-                  </div>
-                  <div>
-                    <span v-if="currentImageInput && currentImageInput.scaled && currentImageInput.useScaled">
-                      {{ currentImageInput.scaledDimensions.width }} x {{ currentImageInput.scaledDimensions.height }}</span>
-                    <span v-else-if="currentImageInput && currentImageInput.dimensions">
-                      {{ currentImageInput.dimensions.width }} x {{ currentImageInput.dimensions.height }}
-                    </span>
-
-                    <span v-if="currentImageInput && currentImageInput.scaled && currentImageInput.useScaled">
-                      ({{ formatBytes(currentImageInput.scaledSize) }})
-                    </span>
-                    <span v-else>
-                      ({{ formatBytes(currentImageInput.actualSize) }})
-                    </span>
-
-                    <v-switch v-if="currentImageInput && currentImageInput.scaled" :label="$t('message.scale_image')"
-                      v-model="currentImageInput.useScaled" :disabled="currentImageInput && currentImageInput.sendInfo !== undefined" />
-                  </div>
-                </div>
-              </v-card-text>
-            </template>
-            <template v-if="Array.isArray(currentFileInputs) && currentFileInputs.length">
-              <v-card-title v-if="nonImageFiles.length > 1">{{ $t('message.files') }}</v-card-title>
-              <v-card-text>
-                <div v-for="(currentImageInputPath, id) in currentFileInputs" :key="id">
-                  <div v-if="!currentImageInputPath.type.includes('image/')">
-                    <span> {{ $t('message.file') }}: {{ currentImageInputPath.name }}</span>
-                    <span> ({{ formatBytes(currentImageInputPath.size) }})</span>
-                    <v-progress-linear :style="{ opacity: currentImageInputPath.sendInfo ? '1' : '0' }" :value="currentImageInputPath.sendInfo ? currentImageInputPath.sendInfo.progress : 0"></v-progress-linear>
-                  </div>
-                </div>
-              </v-card-text>
-            </template>
-            <v-divider></v-divider>
-            <v-textarea v-if="showAttachmentCaptionInput" v-model="attachmentCaption" ref="attachmentCaption" color="black" background-color="transparent"
-                variant="solo" full-width auto-grow rows="1" no-resize hide-details :placeholder="$t('file_mode.add_a_message')"></v-textarea>
-            <v-card-actions>
-              <v-spacer>
-                <div v-if="currentSendError">{{ currentSendError }}</div>
-              </v-spacer>
-              <v-btn color="primary" variant="text" @click="cancelSendAttachment" id="btn-attachment-cancel" :disabled="sendingStatus != sendStatuses.SENDING && sendingStatus != sendStatuses.INITIAL">
-                {{ $t("menu.cancel") }}
-              </v-btn>
-              <v-btn id="btn-attachment-send" color="primary" variant="text" @click="sendAttachment(attachmentCaption)"
-                v-if="currentSendShowSendButton" :disabled="currentSendShowSendButton && sendingStatus != sendStatuses.INITIAL">{{ $t("menu.send") }}</v-btn>
-            </v-card-actions>
-           </template>
-        </v-card>
-      </v-dialog>
-    </div> -->
-
     <SendAttachmentsLayout 
-      v-if="currentFileInputs && currentFileInputs.length > 0 && !useFileModeNonAdmin" 
+      v-if="uploadBatch && uploadBatch.attachments.length > 0 && !useFileModeNonAdmin" 
       :room="room"
       v-on:pick-file="showAttachmentPicker(false)"
       v-on:add-files="(files) => addAttachments(files)"
-      v-on:remove-file="(index) => removeAttachment(index)"
-      :attachments="currentFileInputs"
-      v-on:close="resetAttachments"
+      :batch="uploadBatch"
+      v-on:close="() => { uploadBatch = undefined }"
     />
 
     <MessageOperationsBottomSheet ref="messageOperationsSheet">
@@ -490,10 +413,7 @@ export default {
 
       scrollPosition: null,
       currentFileInputs: [],
-      currentSendShowSendButton: true,
-      currentSendError: null,
-      currentSendErrorExceededFile: null,
-      attachmentCaption: undefined,
+      uploadBatch: undefined,
       showEmojiPicker: false,
       selectedEvent: null,
       editedEvent: null,
@@ -615,29 +535,6 @@ export default {
       const currentUserId= this.selectedEvent?.sender.userId || this.$matrix.currentUserId
       return this.joinedAndInvitedMembers.find(({userId}) => userId === currentUserId)
     },
-    nonImageFiles() {
-      return this.isCurrentFileInputsAnArray && this.currentFileInputs.filter(file => !file?.type.includes("image/"))
-    },
-    imageFiles() {
-      return this.isCurrentFileInputsAnArray && this.currentFileInputs.filter(file => file?.type.includes("image/"))
-    },
-    isCurrentFileInputsAnArray() {
-      return Array.isArray(this.currentFileInputs)
-    },
-    showAttachmentCaptionInput() {
-      // IFF we are sending one PDF, add option to set caption.
-      const imageFiles = this.imageFiles || [];
-      const otherFiles = this.nonImageFiles || [];
-      return imageFiles.length == 0 && otherFiles.length == 1 && (otherFiles[0].type === "application/pdf" || (otherFiles[0].name || "").endsWith(".pdf"));
-    },
-    currentFileInputsDialog: {
-      get() {
-        return this.isCurrentFileInputsAnArray
-      },
-      set() {
-        this.currentFileInputs = [];
-      }
-    },
     chatContainer() {
       const container = this.$refs.chatContainer;
       if (this.useVoiceMode) {
@@ -1493,32 +1390,15 @@ export default {
       this.$refs.attachment.click();
     },
 
-    async addAttachment(file) {
+    addAttachment(file) {
       if (file) {
-        this.currentFileInputs = [... this.currentFileInputs, this.$matrix.attachmentManager.createAttachment(file)];
-        // let optimizedFileObj;
-        // if (file.type.startsWith("image/")) {
-        //   const f = await proofmode.proofCheckFile(file);
-
-        //   var reader = new FileReader();
-        //   optimizedFileObj = await new Promise(resolve => {
-        //     reader.onload = evt => {
-        //       resolve(this.optimizeImage(evt, file));
-        //     }
-        //     reader.readAsDataURL(f);
-        //   })
-        // } else {
-        //   optimizedFileObj = file;
-        // }
-        // console.error("OPTIMIZED", optimizedFileObj);
-        // this.currentFileInputs = Array.isArray(this.currentFileInputs) ? [...this.currentFileInputs, optimizedFileObj] : [optimizedFileObj];
+        if (!this.uploadBatch) {
+          this.uploadBatch = this.$matrix.attachmentManager.createUpload(this.room);
+        }
+        this.uploadBatch?.addAttachment(this.$matrix.attachmentManager.createAttachment(file));
       }
     },
 
-    removeAttachment(index) {
-      this.currentFileInputs = this.currentFileInputs.toSpliced(index, 1);
-    },
-
     /**
      * Handle picked attachment
      */
@@ -1527,24 +1407,7 @@ export default {
     },
 
     addAttachments(files) {
-      // TODO - refactor
-      this.$matrix.matrixClient.getMediaConfig(this.$matrix.useAuthedMedia).then((config) => {
-        const configUploadSize = config["m.upload.size"];
-        const configFormattedUploadSize = this.formatBytes(configUploadSize);
-
-        files.every(file => {
-          if (configUploadSize && file.size > configUploadSize) {
-            this.currentSendError = this.$t("message.upload_file_too_large");
-            this.currentSendErrorExceededFile = this.$t("message.upload_exceeded_file_limit", { configFormattedUploadSize });
-            this.currentSendShowSendButton = false;
-            return false;
-          } else {
-            this.currentSendShowSendButton = true;
-          }
-          return true;
-        });
-        files.forEach(file => this.addAttachment(file));
-      });
+      files.forEach(file => this.addAttachment(file));
     },
 
     showStickerPicker() {
@@ -1559,7 +1422,6 @@ export default {
         promise.then(() => {
           this.sendingAttachments = [];
           this.currentFileInputs = [];
-          this.attachmentCaption = undefined;
           this.sendingStatus = "initial"
         })
         .catch((err) => {
@@ -1580,7 +1442,6 @@ export default {
         this.cancelSendAttachments();
       }
       this.currentFileInputs = [];
-      this.attachmentCaption = undefined;
       this.currentSendError = null;
       this.currentSendErrorExceededFile = null;
       this.sendingStatus = "initial";
diff --git a/src/components/file_mode/SendAttachmentsLayout.vue b/src/components/file_mode/SendAttachmentsLayout.vue
index 1114bcd..d65ff2a 100644
--- a/src/components/file_mode/SendAttachmentsLayout.vue
+++ b/src/components/file_mode/SendAttachmentsLayout.vue
@@ -3,7 +3,7 @@
     <div class="send-attachments__title">{{ $t("message.send_attachements_dialog_title") }}</div>
 
     <!-- ATTACHMENT SELECTION MODE -->
-    <template v-if="attachments && attachments.length > 0 && status == mainStatuses.SELECTING">
+    <template v-if="batch.attachments.length > 0 && status == mainStatuses.SELECTING">
       <div class="attachment-wrapper" ref="attachmentWrapper" v-if="currentAttachment">
         <div
           :class="{ 'file-drop-current-item': true, 'drop-target': dropTarget }"
@@ -22,7 +22,7 @@
           </div>
         </div>
 
-        <div class="send-attachments__current-item__info">
+        <!-- <div class="send-attachments__current-item__info">
           <div class="send-attachments__current-item__info__size">
             <span
               v-if="currentAttachment.scaledFile && currentAttachment.useScaled && currentAttachment.scaledDimensions"
@@ -38,10 +38,13 @@
             </span>
             <span v-else> ({{ formatBytes(currentAttachment.file.size) }}) </span>
 
-            <span class="send-attachments__current-item__info__size__filename" v-if="currentAttachment.src && currentAttachment.file.name">
+            <span
+              class="send-attachments__current-item__info__size__filename"
+              v-if="currentAttachment.src && currentAttachment.file.name"
+            >
               - {{ currentAttachment.file.name }}
             </span>
-          </div>
+          </div> 
 
           <v-switch
             v-if="currentAttachment.scaledFile"
@@ -51,17 +54,21 @@
           />
 
           <C2PABadge :proof="currentAttachment.proof" />
-        </div>
+        </div> -->
 
         <div class="file-drop-thumbnail-container">
           <div
             :class="{ 'file-drop-thumbnail': true, clickable: true, current: id == currentItemIndex }"
             @click="currentItemIndex = id"
-            v-for="(currentImageInput, id) in attachments"
+            v-for="(currentImageInput, id) in batch.attachments"
             :key="id"
           >
             <v-img v-if="currentImageInput && currentImageInput.src" :src="currentImageInput.src" />
-            <div v-if="currentItemIndex == id" class="remove clickable" @click.stop="$emit('remove-file', id)">
+            <div
+              v-if="currentItemIndex == id"
+              class="remove clickable"
+              @click.stop="batch.removeAttachment(currentImageInput)"
+            >
               <v-icon>$vuetify.icons.ic_trash</v-icon>
             </div>
           </div>
@@ -91,25 +98,23 @@
           />
           <div class="input-container__buttons">
             <v-btn @click="close">{{ $t("menu.cancel") }}</v-btn>
-            <v-btn @click="sendAll" :disabled="!attachments || attachments.length == 0">{{ $t("menu.send") }}</v-btn>
+            <v-btn @click="sendAll" :disabled="batch.attachments.length == 0">{{ $t("menu.send") }}</v-btn>
           </div>
         </div>
       </div>
     </template>
 
     <!-- ATTACHMENT SENDING/SENT MODE -->
-    <template
-      v-if="attachments && attachments.length > 0 && (status == mainStatuses.SENDING || status == mainStatuses.SENT)"
-    >
+    <template v-if="batch.attachments.length > 0 && (status == mainStatuses.SENDING || status == mainStatuses.SENT)">
       <div class="attachment-wrapper">
         <div class="file-drop-sent-stack" ref="stackContainer">
-          <div v-if="status == mainStatuses.SENDING && attachmentsSentCount == 0" class="no-items">
+          <div v-if="status == mainStatuses.SENDING && batch.attachmentsSentCount == 0" class="no-items">
             <div class="file-drop-stack-item direct" :style="stackItemTransform(null, -1)"></div>
             <div>{{ $t("file_mode.sending_progress") }}</div>
           </div>
           <div
             v-else
-            v-for="(info, index) in attachmentsSent"
+            v-for="(info, index) in batch.attachmentsSent"
             :key="info.file.name"
             class="file-drop-stack-item animated"
             :style="stackItemTransform(info, index)"
@@ -123,11 +128,11 @@
 
         <!-- Middle section -->
         <div v-if="status == mainStatuses.SENDING" class="file-drop-sending-container">
-          <div class="file-drop-sending-item" v-for="(attachment) in attachmentsSending" :key="attachment.file.name">
+          <div class="file-drop-sending-item" v-for="attachment in batch.attachmentsSending" :key="attachment.file.name">
             <v-img v-if="attachment.src" :src="attachment.src" />
             <div v-else class="filename">{{ attachment.file.name }}</div>
             <v-progress-linear :model-value="attachment.sendInfo?.progress ?? 0"></v-progress-linear>
-            <div class="file-drop-cancel clickable" @click.stop="cancelSendAttachmentItem(attachment)">
+            <div class="file-drop-cancel clickable" @click.stop="batch.cancelSendAttachment(attachment)">
               <v-icon size="14" color="white">close</v-icon>
             </div>
           </div>
@@ -136,10 +141,8 @@
           <div class="file-drop-files-sent">
             {{
               $t(
-                messageInput && messageInput.length > 0
-                  ? "file_mode.files_sent_with_note"
-                  : "file_mode.files_sent",
-                attachmentsSent.length
+                messageInput && messageInput.length > 0 ? "file_mode.files_sent_with_note" : "file_mode.files_sent",
+                batch.attachmentsSent.length
               )
             }}
           </div>
@@ -192,21 +195,19 @@
 <script lang="ts">
 import { defineComponent } from "vue";
 import messageMixin from "../messages/messageMixin";
-import sendAttachmentsMixin from "../sendAttachmentsMixin";
 import prettyBytes from "pretty-bytes";
-import type { PropType } from "vue";
 import { Attachment } from "../../models/attachment";
 import C2PABadge from "../c2pa/C2PABadge.vue";
 
 export default defineComponent({
-  mixins: [messageMixin, sendAttachmentsMixin],
+  mixins: [messageMixin],
   components: { C2PABadge },
-  emits: ["add-files", "remove-file", "pick-file", "close"],
+  emits: ["add-files", "pick-file", "close"],
   props: {
-    attachments: {
-      type: Array as PropType<Attachment[]>,
+    batch: {
+      type: Object,
       default: function () {
-        return [] as Attachment[];
+        return {}
       },
     },
   },
@@ -227,25 +228,31 @@ export default defineComponent({
     this.$audioPlayer.setAutoplay(false);
   },
   computed: {
-    currentAttachment(): Attachment {
-      return this.attachments[this.currentItemIndex];
+    currentAttachment(): Attachment | undefined {
+      if (this.currentItemIndex >= 0 && this.currentItemIndex < this.batch.attachments.length) {
+        return this.batch.attachments[this.currentItemIndex];
+      }
+      return undefined;
     },
     currentItemHasImagePreview() {
       return (
         this.currentItemIndex >= 0 &&
-        this.currentItemIndex < this.attachments.length &&
-        this.attachments[this.currentItemIndex].src
+        this.currentItemIndex < this.batch.attachments.length &&
+        this.batch.attachments[this.currentItemIndex].src
       );
     },
   },
   watch: {
-    attachments(newValue, oldValue) {
-      // Added or removed?
-      if (newValue && oldValue && newValue.length > oldValue.length) {
-        this.currentItemIndex = oldValue.length;
-      } else if (newValue) {
-        this.currentItemIndex = newValue.length - 1;
-      }
+    "batch.attachments": {
+      handler(newValue, oldValue) {
+        // Added or removed?
+        if (newValue && oldValue && newValue.length > oldValue.length) {
+          this.currentItemIndex = oldValue.length;
+        } else if (newValue) {
+          this.currentItemIndex = newValue.length - 1;
+        }
+      },
+      deep: true,
     },
     messageInput() {
       this.scrollToBottom();
@@ -256,7 +263,7 @@ export default defineComponent({
       this.dropTarget = false;
       let droppedFiles: FileList | undefined = e.dataTransfer?.files;
       if (!droppedFiles) return;
-      this.$emit("add-files", [... droppedFiles]);
+      this.$emit("add-files", [...droppedFiles]);
     },
     scrollToBottom() {
       const el = this.$refs.attachmentWrapper;
@@ -276,7 +283,7 @@ export default defineComponent({
       return prettyBytes(bytes);
     },
     close() {
-      this.sendingAttachments = [];
+      this.batch.cancel();
       this.status = this.mainStatuses.SELECTING;
       this.messageInput = "";
       this.currentItemIndex = 0;
@@ -284,28 +291,27 @@ export default defineComponent({
     },
     sendAll() {
       this.status = this.mainStatuses.SENDING;
-      this.sendAttachments(
-        this.messageInput && this.messageInput.length > 0 ? this.messageInput : this.$t("file_mode.files"),
-        this.attachments
+      this.batch.send(
+        this.messageInput && this.messageInput.length > 0 ? this.messageInput : this.$t("file_mode.files")
       ).then(() => {
         this.status = this.mainStatuses.SENT;
       });
     },
-    stackItemTransform(item, index) {
+    stackItemTransform(attachment: Attachment, index: number) {
       const size =
         0.6 *
         (this.$refs.stackContainer
           ? Math.min(this.$refs.stackContainer.clientWidth, this.$refs.stackContainer.clientHeight)
           : 176);
       let transform = "";
-      if (item != null && index != -1) {
+      if (attachment != null && attachment.sendInfo && index != -1) {
         transform =
           "transform: rotate(" +
-          item.randomRotation +
+          attachment.sendInfo.randomRotation +
           "deg) translate(" +
-          item.randomTranslationX +
+          attachment.sendInfo.randomTranslationX +
           "px," +
-          item.randomTranslationY +
+          attachment.sendInfo.randomTranslationY +
           "px); z-index:" +
           (index + 2) +
           ";";
diff --git a/src/models/attachment.ts b/src/models/attachment.ts
index 20efb69..3e4b687 100644
--- a/src/models/attachment.ts
+++ b/src/models/attachment.ts
@@ -1,3 +1,5 @@
+import { ComputedRef, Ref } from "vue";
+
 export class UploadPromise<Type> {
   wrappedPromise: Promise<Type>;
   aborted: boolean = false;
@@ -49,3 +51,19 @@ export type Attachment = {
   proof?: any;
   sendInfo?: AttachmentSendInfo;
 };
+
+export type AttachmentBatch = {
+  sendingStatus: Ref<"initial" | "sending" | "sent" | "canceled" | "failed">;
+  sendingRootEventId: Ref<string | undefined>;
+  sendingPromise: Ref<Promise<any> | undefined>;
+  attachments: Ref<Attachment[]>;
+  attachmentsSentCount: ComputedRef<number>;
+  attachmentsSending: ComputedRef<Attachment[]>;
+  attachmentsSent: ComputedRef<Attachment[]>;
+  addAttachment: (attachment: Attachment) => void;
+  removeAttachment: (attachment: Attachment) => void;
+  send: (message: string) => Promise<any>;
+  cancel: () => void;
+  cancelSendAttachment: (attachment: Attachment) => void;
+};
+
diff --git a/src/models/attachmentManager.ts b/src/models/attachmentManager.ts
index c45d741..0a3d481 100644
--- a/src/models/attachmentManager.ts
+++ b/src/models/attachmentManager.ts
@@ -1,12 +1,13 @@
-import { MatrixClient, MatrixEvent } from "matrix-js-sdk";
+import { MatrixClient, MatrixEvent, Room } from "matrix-js-sdk";
 import { EventAttachment, KeanuEventExtension } from "./eventAttachment";
 import axios, { AxiosRequestConfig, AxiosResponse } from "axios";
 import { Counter, ModeOfOperation } from "aes-js";
-import { Attachment } from "./attachment";
+import { Attachment, AttachmentBatch, AttachmentSendInfo } from "./attachment";
 import proofmode from "../plugins/proofmode";
 import imageSize from "image-size";
 import imageResize from "image-resize";
-import { Reactive, reactive } from "vue";
+import { computed, isRef, Reactive, reactive, ref, Ref } from "vue";
+import utils from "@/plugins/utils";
 
 export class AttachmentManager {
   matrixClient: MatrixClient;
@@ -33,6 +34,10 @@ export class AttachmentManager {
       .catch(() => {});
   }
 
+  public createUpload(room: Room) {
+    return createUploadBatch(this.matrixClient, room);
+  }
+
   public createAttachment(file: File): Attachment {
     let a: Attachment = {
       status: "loading",
@@ -133,7 +138,7 @@ export class AttachmentManager {
         attachment.src = src;
         return src;
       });
-        return attachment.srcPromise;
+      return attachment.srcPromise;
     };
     attachment.loadThumbnail = () => {
       if (attachment.thumbnail) {
@@ -141,13 +146,13 @@ export class AttachmentManager {
       } else if (attachment.thumbnailPromise) {
         return attachment.thumbnailPromise;
       }
-        attachment.thumbnailPromise = this._loadEventAttachmentOrThumbnail(event, true, (percent) => {
-          attachment.thumbnailProgress = percent;
-        }).then((thummbnail) => {
-          attachment.thumbnail = thummbnail;
-          return thummbnail;
-        });
-        return attachment.thumbnailPromise;
+      attachment.thumbnailPromise = this._loadEventAttachmentOrThumbnail(event, true, (percent) => {
+        attachment.thumbnailProgress = percent;
+      }).then((thummbnail) => {
+        attachment.thumbnail = thummbnail;
+        return thummbnail;
+      });
+      return attachment.thumbnailPromise;
     };
     attachment.release = (src: boolean, thumbnail: boolean) => {
       // TODO - figure out logic
@@ -161,7 +166,7 @@ export class AttachmentManager {
           URL.revokeObjectURL(attachment.thumbnail);
         }
       }
-    }
+    };
     this.cache.set(event.getId(), attachment!);
     return attachment;
   }
@@ -292,3 +297,205 @@ export class AttachmentManager {
     });
   }
 }
+
+const createUploadBatch = (matrixClient: MatrixClient, room: Room): AttachmentBatch => {
+  const sendingStatus: Ref<"initial" | "sending" | "sent" | "canceled" | "failed"> = ref("initial");
+  const sendingRootEventId: Ref<string | undefined> = ref(undefined);
+  const sendingPromise: Ref<Promise<any> | undefined> = ref(undefined);
+  const attachments: Ref<Attachment[]> = ref([]);
+
+  const attachmentsSentCount = computed(() => {
+    return attachments.value.reduce((a, elem) => (elem.sendInfo?.status == "sent" ? a + 1 : a), 0);
+  });
+
+  const attachmentsSending = computed(() => {
+    return attachments.value.filter((elem) => elem.sendInfo?.status == "initial" || elem.sendInfo?.status == "sending");
+  });
+
+  const attachmentsSent = computed(() => {
+    sortSendingAttachments();
+    return attachments.value.filter((elem) => elem.sendInfo?.status == "sent");
+  });
+
+  const sortSendingAttachments = () => {
+    attachments.value.sort((a, b) => (b.sendInfo?.statusDate ?? 0) - (a.sendInfo?.statusDate ?? 0));
+  };
+
+  const addAttachment = (attachment: Attachment) => {
+    if (sendingStatus.value == "initial") {
+      attachments.value.push(attachment);
+    }
+  };
+
+  const removeAttachment = (attachment: Attachment) => {
+    if (sendingStatus.value == "initial") {
+      attachments.value = attachments.value.filter((a) => a !== attachment);
+    }
+  };
+
+  const cancel = () => {
+    if (sendingStatus.value !== "initial") {
+      attachments.value.toReversed().forEach((attachment) => {
+        cancelSendAttachment(attachment);
+      });
+      sendingStatus.value = "canceled";
+      if (sendingRootEventId.value) {
+        // Redact all media we already sent, plus the root event
+        let promises = attachments.value.reduce((val: Promise<any>[], attachment: Attachment) => {
+          if (attachment.sendInfo?.mediaEventId) {
+            val.push(
+              matrixClient.redactEvent(room.roomId, attachment.sendInfo!.mediaEventId, undefined, {
+                reason: "cancel",
+              })
+            );
+          }
+          return val;
+        }, [] as Promise<any>[]);
+        if (sendingRootEventId.value) {
+          promises.push(
+            matrixClient.redactEvent(room.roomId, sendingRootEventId.value, undefined, {
+              reason: "cancel",
+            })
+          );
+        }
+        Promise.allSettled(promises)
+          .then(() => {
+            console.log("Message redacted");
+          })
+          .catch((err) => {
+            console.log("Redaction failed: ", err);
+          });
+      }
+    }
+  };
+
+  const cancelSendAttachment = (attachment: Attachment) => {
+    if (attachment.sendInfo) {
+      if (attachment.sendInfo.promise && attachment.sendInfo.status != "initial") {
+        attachment.sendInfo.promise.abort();
+      }
+      attachment.sendInfo.status = "canceled";
+    }
+  };
+
+  const send = (message: string): Promise<any> => {
+    sendingStatus.value = "sending";
+    attachments.value.forEach((attachment) => {
+      let sendInfo: AttachmentSendInfo = {
+        status: "initial",
+        statusDate: Date.now(),
+        mediaEventId: undefined,
+        progress: 0,
+        randomRotation: 0,
+        randomTranslationX: 0,
+        randomTranslationY: 0,
+        promise: undefined,
+      };
+      attachment.sendInfo = reactive(sendInfo);
+    });
+
+    const sendingPromise = utils
+      .sendTextMessage(matrixClient, room.roomId, message)
+      .then((eventId: string) => {
+        sendingRootEventId.value = eventId;
+
+        // Use the eventId as a thread root for all the media
+        let promiseChain = Promise.resolve();
+        const getItemPromise = (index: number) => {
+          if (index < attachments.value.length) {
+            const attachment = attachments.value[index];
+            const item = attachment.sendInfo!;
+            if (item.status !== "initial") {
+              return getItemPromise(++index);
+            }
+            item.status = "sending";
+
+            let file = (() => {
+              if (attachment.scaledFile && attachment.useScaled) {
+                // Send scaled version of image instead!
+                return attachment.scaledFile;
+              } else {
+                // Send actual file image when not scaled!
+                return attachment.file;
+              }
+            })();
+
+            const itemPromise = utils
+              .sendFile(
+                matrixClient,
+                room.roomId,
+                file,
+                ({ loaded, total }: { loaded: number; total: number }) => {
+                  if (loaded == total) {
+                    item.progress = 100;
+                  } else if (total > 0) {
+                    item.progress = (100 * loaded) / total;
+                  }
+                },
+                eventId,
+                attachment.dimensions
+              )
+              .then((mediaEventId: string) => {
+                // Look at last item rotation, flipping the sign on this, so looks more like a true stack
+                let signR = 1;
+                let signX = 1;
+                let signY = 1;
+                if (attachmentsSent.value.length > 0) {
+                  if (attachmentsSent.value[0].sendInfo!.randomRotation >= 0) {
+                    signR = -1;
+                  }
+                  if (attachmentsSent.value[0].sendInfo!.randomTranslationX >= 0) {
+                    signX = -1;
+                  }
+                  if (attachmentsSent.value[0].sendInfo!.randomTranslationY >= 0) {
+                    signY = -1;
+                  }
+                }
+                item.randomRotation = signR * (2 + Math.random() * 10);
+                item.randomTranslationX = signX * Math.random() * 20;
+                item.randomTranslationY = signY * Math.random() * 20;
+                item.mediaEventId = mediaEventId;
+                item.status = "sent";
+                item.statusDate = Date.now();
+              })
+              .catch((ignorederr: any) => {
+                if (item.promise?.aborted) {
+                  item.status = "canceled";
+                } else {
+                  console.error("ERROR", ignorederr);
+                  item.status = "failed";
+                }
+                return Promise.resolve();
+              });
+            item.promise = itemPromise;
+            return itemPromise.then(() => getItemPromise(++index));
+          } else return Promise.resolve();
+        };
+
+        return promiseChain.then(() => getItemPromise(0));
+      })
+      .then(() => {
+        sendingStatus.value = "sent";
+        sendingRootEventId.value = undefined;
+      })
+      .catch((err: any) => {
+        console.error("ERROR", err);
+      });
+    return sendingPromise;
+  };
+
+  return {
+    sendingStatus,
+    sendingRootEventId,
+    sendingPromise,
+    attachments,
+    attachmentsSentCount,
+    attachmentsSending,
+    attachmentsSent,
+    addAttachment,
+    removeAttachment,
+    send,
+    cancel,
+    cancelSendAttachment,
+  };
+};