diff --git a/src/assets/css/filedrop.scss b/src/assets/css/filedrop.scss
index 54f1913..fdd6f04 100644
--- a/src/assets/css/filedrop.scss
+++ b/src/assets/css/filedrop.scss
@@ -36,6 +36,9 @@ $small-button-height: 36px;
     width: 100%;
     height: 50%;
     background-color: #181719;
+    &.drop-target {
+      background-color: #383739;
+    }
     border-radius: 19px;
     display: flex;
     flex-direction: column;
@@ -90,6 +93,9 @@ $small-button-height: 36px;
     width: 100%;
     height: 70%;
     background-color: #181719;
+    &.drop-target {
+      background-color: #383739;
+    }
     border-radius: 19px;
     overflow: hidden;
     .v-image {
@@ -242,16 +248,21 @@ $small-button-height: 36px;
       }
     }
     .file-drop-stack-item {
-      background: linear-gradient(0deg, #3a3a3c 0%, #3a3a3c 100%), #fff;
+      background: #3a3a3c;
       position: absolute;
       overflow: hidden;
+      opacity: 0;
       .v-image {
         width: 100%;
         height: 100%;
         object-fit: cover;
       }
+      &.direct {
+        opacity: 1 !important;
+      }
       &.animated {
         animation-name: fadeInStackItem;
+        animation-fill-mode: both;
         animation-duration: 1.5s;
       }
     }
diff --git a/src/components/Chat.vue b/src/components/Chat.vue
index 6087dc1..699aee8 100644
--- a/src/components/Chat.vue
+++ b/src/components/Chat.vue
@@ -16,7 +16,8 @@
           v-on:close="showRecorder = false" v-on:file="onVoiceRecording" :sendTypingIndicators="useVoiceMode" />
 
     <FileDropLayout class="file-drop-root" v-if="useFileModeNonAdmin" :room="room" 
-      v-on:add-file="showAttachmentPicker()"
+      v-on:pick-file="showAttachmentPicker()"
+      v-on:add-file="addAttachment($event)"
       v-on:remove-file="currentFileInputs.splice($event, 1)" 
       v-on:reset="resetAttachments"
       :attachments="currentFileInputs"
@@ -1146,6 +1147,10 @@ export default {
       this.currentSendError = null;
     },
 
+    addAttachment(file) {
+      this.handleFileReader(null, file);
+    },
+
     resetAttachments() {
       this.cancelSendAttachment();
     },
diff --git a/src/components/file_mode/FileDropLayout.vue b/src/components/file_mode/FileDropLayout.vue
index 3e09221..039a1ca 100644
--- a/src/components/file_mode/FileDropLayout.vue
+++ b/src/components/file_mode/FileDropLayout.vue
@@ -6,8 +6,10 @@
         <v-icon>$vuetify.icons.ic_lock</v-icon>
         <div class="file-drop-title">{{ $t("file_mode.secure_file_send") }}</div>
       </div>
-      <div class="background">
-        <v-btn @click="$emit('add-file')" class="large">{{ $t("file_mode.choose_files") }}</v-btn>
+      <div :class="{ 'background': true, 'drop-target': dropTarget }" @drop.prevent="filesDropped"
+        @dragover.prevent="dropTarget = true" @dragleave.prevent="dropTarget = false"
+        @dragenter.prevent="dropTarget = true">
+        <v-btn @click="$emit('pick-file')" class="large">{{ $t("file_mode.choose_files") }}</v-btn>
         <div class="file-format-info">{{ $t("file_mode.any_file_format_accepted") }}</div>
       </div>
     </template>
@@ -15,7 +17,9 @@
     <!-- ATTACHMENT SELECTION MODE -->
     <template v-if="attachments && attachments.length > 0 && status == mainStatuses.SELECTING">
       <div class="attachment-wrapper" ref="attachmentWrapper">
-        <div class="file-drop-current-item">
+        <div :class="{ 'file-drop-current-item': true, 'drop-target': dropTarget }" @drop.prevent="filesDropped"
+          @dragover.prevent="dropTarget = true" @dragleave.prevent="dropTarget = false"
+          @dragenter.prevent="dropTarget = true">
           <v-img v-if="currentItemHasImagePreview" :src="attachments[currentItemIndex].image" />
           <div v-else class="filename">{{ attachments[currentItemIndex].name }}</div>
         </div>
@@ -28,7 +32,7 @@
             </div>
           </div>
           <div class="file-drop-thumbnail noborder">
-            <div class="add clickable" @click.stop="$emit('add-file')">
+            <div class="add clickable" @click.stop="$emit('pick-file')">
               +
             </div>
           </div>
@@ -46,11 +50,12 @@
     </template>
 
     <!-- ATTACHMENT SENDING/SENT MODE -->
-    <template v-if="attachments && attachments.length > 0 && (status == mainStatuses.SENDING || status == mainStatuses.SENT)">
+    <template
+      v-if="attachments && 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 && countSent == 0" class="no-items">
-            <div class="file-drop-stack-item" :style="stackItemTransform(null, -1)"></div>
+            <div class="file-drop-stack-item direct" :style="stackItemTransform(null, -1)"></div>
             <div>{{ $t('file_mode.sending_progress') }}</div>
           </div>
           <div v-else v-for="(item, index) in sentItems" :key="item.id" class="file-drop-stack-item animated"
@@ -130,6 +135,7 @@ export default {
         FAILED: 3,
       }),
       sendInfo: [],
+      dropTarget: false,
     };
   },
   mounted() {
@@ -173,6 +179,14 @@ export default {
     },
   },
   methods: {
+    filesDropped(e) {
+      this.dropTarget = false;
+      let droppedFiles = e.dataTransfer.files;
+      if (!droppedFiles) return;
+      ([...droppedFiles]).forEach(f => {
+        this.$emit('add-file', f);
+      });
+    },
     scrollToBottom() {
       const el = this.$refs.attachmentWrapper;
       if (el) {
@@ -216,38 +230,56 @@ export default {
       util.sendTextMessage(this.$matrix.matrixClient, this.room.roomId, text)
         .then((eventId) => {
           // Use the eventId as a thread root for all the media
-          const promises = this.sendInfo.map(item => util.sendImage(this.$matrix.matrixClient, this.room.roomId, item.attachment, ({ loaded, total }) => {
-            if (loaded == total) {
-              item.progress = 100;
-            } else if (total > 0) {
-              item.progress = 100 * loaded / total;
+          let promiseChain = Promise.resolve();
+          const getItemPromise = (index) => {
+            if (index < this.sendInfo.length) {
+              const item = this.sendInfo[index];
+              if (item.status !== this.statuses.INITIAL) {
+                return getItemPromise(++index);
+              }
+              const itemPromise = util.sendImage(this.$matrix.matrixClient, this.room.roomId, item.attachment, ({ loaded, total }) => {
+                if (loaded == total) {
+                  item.progress = 100;
+                } else if (total > 0) {
+                  item.progress = 100 * loaded / total;
+                }
+              }, eventId)
+                .then(() => {
+                  // 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 (this.sentItems.length > 0) {
+                    if (this.sentItems[0].randomRotation >= 0) {
+                      signR = -1;
+                    }
+                    if (this.sentItems[0].randomTranslationX >= 0) {
+                      signX = -1;
+                    }
+                    if (this.sentItems[0].randomTranslationY >= 0) {
+                      signY = -1;
+                    }
+                  }
+                  item.randomRotation = signR * (2 + Math.random() * 10);
+                  item.randomTranslationX = signX * Math.random() * 20;
+                  item.randomTranslationY = signY * Math.random() * 20;
+                  item.status = this.statuses.SENT;
+                  item.statusDate = Date.now;
+                }).catch(ignorederr => {
+                  if (item.promise.aborted) {
+                    item.status = this.statuses.CANCELED;
+                  } else {
+                    console.error("ERROR", ignorederr);
+                    item.status = this.statuses.FAILED;
+                  }
+                });
+              item.promise = itemPromise;
+              return itemPromise.then(() => getItemPromise(++index));
             }
-          }, eventId).then(() => {
-            // 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 (this.sentItems.length > 0) {
-              if (this.sentItems[0].randomRotation >= 0) {
-                signR = -1;
-              }
-              if (this.sentItems[0].randomTranslationX >= 0) {
-                signX = -1;
-              }
-              if (this.sentItems[0].randomTranslationY >= 0) {
-                signY = -1;
-              }
-            }
-            item.randomRotation = signR * (2 + Math.random() * 10);
-            item.randomTranslationX = signX * Math.random() * 20;
-            item.randomTranslationY = signY * Math.random() * 20;
-            item.status = this.statuses.SENT;
-            item.statusDate = Date.now;
-          }).catch(ignorederr => {
-            console.error("ERROR", ignorederr);
-            item.status = this.statuses.FAILED;
-          }));
-          return Promise.allSettled(promises)
+            else return Promise.resolve();
+          };
+
+          return promiseChain.then(() => getItemPromise(0));
         })
         .then(() => {
           this.status = this.mainStatuses.SENT;
@@ -257,7 +289,9 @@ export default {
         });
     },
     cancelSendingItem(item) {
-      // TODO
+      if (item.promise && item.status == this.statuses.INITIAL) {
+        item.promise.abort();
+      }
       item.status = this.statuses.CANCELED;
     },
     checkDone() {
diff --git a/src/plugins/utils.js b/src/plugins/utils.js
index 320f6d8..803148a 100644
--- a/src/plugins/utils.js
+++ b/src/plugins/utils.js
@@ -30,27 +30,29 @@ var _browserCanRecordAudioF = function () {
 }
 var _browserCanRecordAudio = _browserCanRecordAudioF();
 
-class UploadPromise extends Promise {
-    constructor(executor) {
-        const aborter = {
-            aborted: false,
-            abortablePromise: undefined,
-            matrixClient: undefined,
+class UploadPromise {
+    aborted = false;
+    onAbort = undefined;
+
+    constructor(wrappedPromise) {
+        this.wrappedPromise = wrappedPromise;
+    }
+
+    abort() {
+        this.aborted = true;
+        if (this.onAbort) {
+            this.onAbort();
         }
+    }
 
-        const normalExecutor = function (resolve, reject) {
-            executor(resolve, reject, aborter);
-        };
+    then(resolve, reject) {
+        this.wrappedPromise = this.wrappedPromise.then(resolve, reject);
+        return this;
+    }
 
-        super(normalExecutor);
-        this.abort = () => {
-            aborter.aborted = true;
-            if (aborter.abortablePromise && aborter.matrixClient) {
-                aborter.matrixClient.cancelUpload(aborter.abortablePromise);
-                aborter.matrixClient = undefined;
-                aborter.abortablePromise = undefined;
-            }
-        };
+    catch(handler) {
+        this.wrappedPromise = this.wrappedPromise.catch(handler);
+        return this;
     }
 }
 
@@ -340,11 +342,11 @@ class Util {
     }
 
     sendImage(matrixClient, roomId, file, onUploadProgress, threadRoot) {
-        return new UploadPromise((resolve, reject, aborter) => {
-            const abortionController = aborter;
+        const uploadPromise = new UploadPromise(undefined);
+        uploadPromise.wrappedPromise = new Promise((resolve, reject) => {
             var reader = new FileReader();
             reader.onload = (e) => {
-                if (abortionController.aborted) {
+                if (uploadPromise.aborted) {
                     reject("Aborted");
                     return;
                 }
@@ -399,9 +401,11 @@ class Util {
 
                 if (!matrixClient.isRoomEncrypted(roomId)) {
                     // Not encrypted.
-                    abortionController.matrixClient = matrixClient;
-                    abortionController.abortablePromise = matrixClient.uploadContent(data, opts);
-                    abortionController.abortablePromise
+                    const promise = matrixClient.uploadContent(data, opts);
+                    uploadPromise.onAbort = () => {
+                        matrixClient.cancelUpload(promise);
+                    };
+                    promise
                         .then((response) => {
                             messageContent.url = response.content_uri;
                             return this.sendMessage(matrixClient, roomId, "m.room.message", messageContent)
@@ -448,9 +452,12 @@ class Util {
                 // Encrypted data sent as octet-stream!
                 opts.type = "application/octet-stream";
 
-                abortionController.abortablePromise = matrixClient.uploadContent(data, opts);
-                abortionController.abortablePromise
-                    .then((response) => {
+                const promise = matrixClient.uploadContent(data, opts);
+                uploadPromise.onAbort = () => {
+                    matrixClient.cancelUpload(promise);
+                };
+                promise
+                .then((response) => {
                         if (response.error) {
                             return reject(response.error);
                         }
@@ -469,6 +476,7 @@ class Util {
             }
             reader.readAsArrayBuffer(file);
         });
+        return uploadPromise;
     }
 
     /**