diff --git a/src/ContentMessages.js b/src/ContentMessages.js
index ee3e8f1390..2d58622db8 100644
--- a/src/ContentMessages.js
+++ b/src/ContentMessages.js
@@ -425,19 +425,25 @@ export default class ContentMessages {
         }
 
         const UploadConfirmDialog = sdk.getComponent("dialogs.UploadConfirmDialog");
+        let uploadAll = false;
         for (let i = 0; i < okFiles.length; ++i) {
             const file = okFiles[i];
-            const shouldContinue = await new Promise((resolve) => {
-                Modal.createTrackedDialog('Upload Files confirmation', '', UploadConfirmDialog, {
-                    file,
-                    currentIndex: i,
-                    totalFiles: okFiles.length,
-                    onFinished: (shouldContinue) => {
-                        resolve(shouldContinue);
-                    },
+            if (!uploadAll) {
+                const shouldContinue = await new Promise((resolve) => {
+                    Modal.createTrackedDialog('Upload Files confirmation', '', UploadConfirmDialog, {
+                        file,
+                        currentIndex: i,
+                        totalFiles: okFiles.length,
+                        onFinished: (shouldContinue, shouldUploadAll) => {
+                            if (shouldUploadAll) {
+                                uploadAll = true;
+                            }
+                            resolve(shouldContinue);
+                        },
+                    });
                 });
-            });
-            if (!shouldContinue) break;
+                if (!shouldContinue) break;
+            }
             this._sendContentToRoom(file, roomId, matrixClient);
         }
     }
diff --git a/src/components/views/dialogs/UploadConfirmDialog.js b/src/components/views/dialogs/UploadConfirmDialog.js
index e7b22950d6..7e682a8301 100644
--- a/src/components/views/dialogs/UploadConfirmDialog.js
+++ b/src/components/views/dialogs/UploadConfirmDialog.js
@@ -49,6 +49,10 @@ export default class UploadConfirmDialog extends React.Component {
         this.props.onFinished(true);
     }
 
+    _onUploadAllClick = () => {
+        this.props.onFinished(true, true);
+    }
+
     render() {
         const BaseDialog = sdk.getComponent('views.dialogs.BaseDialog');
         const DialogButtons = sdk.getComponent('views.elements.DialogButtons');
@@ -85,6 +89,13 @@ export default class UploadConfirmDialog extends React.Component {
             </div>;
         }
 
+        let uploadAllButton;
+        if (this.props.currentIndex + 1 < this.props.totalFiles) {
+            uploadAllButton = <button onClick={this._onUploadAllClick}>
+                {_t("Upload all")}
+            </button>;
+        }
+
         return (
             <BaseDialog className='mx_UploadConfirmDialog'
                 fixedWidth={false}
@@ -100,7 +111,9 @@ export default class UploadConfirmDialog extends React.Component {
                     hasCancel={false}
                     onPrimaryButtonClick={this._onUploadClick}
                     focus={true}
-                />
+                >
+                    {uploadAllButton}
+                </DialogButtons>
             </BaseDialog>
         );
     }
diff --git a/src/i18n/strings/en_EN.json b/src/i18n/strings/en_EN.json
index 53fd82f6f2..e167659621 100644
--- a/src/i18n/strings/en_EN.json
+++ b/src/i18n/strings/en_EN.json
@@ -1249,6 +1249,7 @@
     "Upload files (%(current)s of %(total)s)": "Upload files (%(current)s of %(total)s)",
     "Upload files": "Upload files",
     "Upload": "Upload",
+    "Upload all": "Upload all",
     "This file is <b>too large</b> to upload. The file size limit is %(limit)s but this file is %(sizeOfThisFile)s.": "This file is <b>too large</b> to upload. The file size limit is %(limit)s but this file is %(sizeOfThisFile)s.",
     "These files are <b>too large</b> to upload. The file size limit is %(limit)s.": "These files are <b>too large</b> to upload. The file size limit is %(limit)s.",
     "Some files are <b>too large</b> to be uploaded. The file size limit is %(limit)s.": "Some files are <b>too large</b> to be uploaded. The file size limit is %(limit)s.",