diff --git a/.eslintignore.errorfiles b/.eslintignore.errorfiles
index c7d5804d66..6d1874b872 100644
--- a/.eslintignore.errorfiles
+++ b/.eslintignore.errorfiles
@@ -52,7 +52,6 @@ src/components/views/settings/ChangePassword.js
 src/components/views/settings/DevicesPanel.js
 src/components/views/settings/IntegrationsManager.js
 src/components/views/settings/Notifications.js
-src/ContentMessages.js
 src/GroupAddressPicker.js
 src/HtmlUtils.js
 src/ImageUtils.js
diff --git a/res/css/_components.scss b/res/css/_components.scss
index ec8476ee63..b7d0c7a2a5 100644
--- a/res/css/_components.scss
+++ b/res/css/_components.scss
@@ -70,6 +70,7 @@
 @import "./views/dialogs/_SettingsDialog.scss";
 @import "./views/dialogs/_ShareDialog.scss";
 @import "./views/dialogs/_UnknownDeviceDialog.scss";
+@import "./views/dialogs/_UploadConfirmDialog.scss";
 @import "./views/dialogs/_UserSettingsDialog.scss";
 @import "./views/dialogs/_WidgetOpenIDPermissionsDialog.scss";
 @import "./views/dialogs/keybackup/_CreateKeyBackupDialog.scss";
diff --git a/res/css/views/dialogs/_UploadConfirmDialog.scss b/res/css/views/dialogs/_UploadConfirmDialog.scss
new file mode 100644
index 0000000000..116be798e3
--- /dev/null
+++ b/res/css/views/dialogs/_UploadConfirmDialog.scss
@@ -0,0 +1,33 @@
+/*
+Copyright 2019 New Vector Ltd.
+
+Licensed under the Apache License, Version 2.0 (the "License");
+you may not use this file except in compliance with the License.
+You may obtain a copy of the License at
+
+    http://www.apache.org/licenses/LICENSE-2.0
+
+Unless required by applicable law or agreed to in writing, software
+distributed under the License is distributed on an "AS IS" BASIS,
+WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+See the License for the specific language governing permissions and
+limitations under the License.
+*/
+
+.mx_UploadConfirmDialog_fileIcon {
+    margin-right: 5px;
+}
+
+.mx_UploadConfirmDialog_previewOuter {
+    text-align: center;
+}
+
+.mx_UploadConfirmDialog_previewInner {
+    display: inline-block;
+    text-align: left;
+}
+
+.mx_UploadConfirmDialog_imagePreview {
+    max-height: 300px;
+    max-width: 100%;
+}
diff --git a/src/ContentMessages.js b/src/ContentMessages.js
index a319118121..f4aafbeb31 100644
--- a/src/ContentMessages.js
+++ b/src/ContentMessages.js
@@ -1,5 +1,6 @@
 /*
 Copyright 2015, 2016 OpenMarket Ltd
+Copyright 2019 New Vector Ltd
 
 Licensed under the Apache License, Version 2.0 (the "License");
 you may not use this file except in compliance with the License.
@@ -17,17 +18,18 @@ limitations under the License.
 'use strict';
 
 import Promise from 'bluebird';
-const extend = require('./extend');
-const dis = require('./dispatcher');
-const MatrixClientPeg = require('./MatrixClientPeg');
-const sdk = require('./index');
+import extend from './extend';
+import dis from './dispatcher';
+import MatrixClientPeg from './MatrixClientPeg';
+import sdk from './index';
 import { _t } from './languageHandler';
-const Modal = require('./Modal');
+import Modal from './Modal';
+import RoomViewStore from './stores/RoomViewStore';
 
-const encrypt = require("browser-encrypt-attachment");
+import encrypt from "browser-encrypt-attachment";
 
 // Polyfill for Canvas.toBlob API using Canvas.toDataURL
-require("blueimp-canvas-to-blob");
+import "blueimp-canvas-to-blob";
 
 const MAX_WIDTH = 800;
 const MAX_HEIGHT = 600;
@@ -91,7 +93,7 @@ function createThumbnail(element, inputWidth, inputHeight, mimeType) {
 /**
  * Load a file into a newly created image element.
  *
- * @param {File} file The file to load in an image element.
+ * @param {File} imageFile The file to load in an image element.
  * @return {Promise} A promise that resolves with the html image element.
  */
 function loadImageElement(imageFile) {
@@ -119,7 +121,7 @@ function loadImageElement(imageFile) {
  *
  * @param {MatrixClient} matrixClient A matrixClient to upload the thumbnail with.
  * @param {String} roomId The ID of the room the image will be uploaded in.
- * @param {File} The image to read and thumbnail.
+ * @param {File} imageFile The image to read and thumbnail.
  * @return {Promise} A promise that resolves with the attachment info.
  */
 function infoForImageFile(matrixClient, roomId, imageFile) {
@@ -144,7 +146,7 @@ function infoForImageFile(matrixClient, roomId, imageFile) {
 /**
  * Load a file into a newly created video element.
  *
- * @param {File} file The file to load in an video element.
+ * @param {File} videoFile The file to load in an video element.
  * @return {Promise} A promise that resolves with the video image element.
  */
 function loadVideoElement(videoFile) {
@@ -179,7 +181,7 @@ function loadVideoElement(videoFile) {
  *
  * @param {MatrixClient} matrixClient A matrixClient to upload the thumbnail with.
  * @param {String} roomId The ID of the room the video will be uploaded to.
- * @param {File} The video to read and thumbnail.
+ * @param {File} videoFile The video to read and thumbnail.
  * @return {Promise} A promise that resolves with the attachment info.
  */
 function infoForVideoFile(matrixClient, roomId, videoFile) {
@@ -200,6 +202,7 @@ function infoForVideoFile(matrixClient, roomId, videoFile) {
 
 /**
  * Read the file as an ArrayBuffer.
+ * @param {File} file The file to read
  * @return {Promise} A promise that resolves with an ArrayBuffer when the file
  *   is read.
  */
@@ -269,11 +272,43 @@ function uploadFile(matrixClient, roomId, file, progressHandler) {
     }
 }
 
-
-class ContentMessages {
+export default class ContentMessages {
     constructor() {
         this.inprogress = [];
         this.nextId = 0;
+        this._mediaConfig = null;
+    }
+
+    static sharedInstance() {
+        if (global.mx_ContentMessages === undefined) {
+            global.mx_ContentMessages = new ContentMessages();
+        }
+        return global.mx_ContentMessages;
+    }
+
+    _isFileSizeAcceptable(file) {
+        if (this._mediaConfig !== null &&
+            this._mediaConfig["m.upload.size"] !== undefined &&
+            file.size > this._mediaConfig["m.upload.size"]) {
+            return false;
+        }
+        return true;
+    }
+
+    _ensureMediaConfigFetched() {
+        if (this._mediaConfig !== null) return;
+
+        console.log("[Media Config] Fetching");
+        return MatrixClientPeg.get().getMediaConfig().then((config) => {
+            console.log("[Media Config] Fetched config:", config);
+            return config;
+        }).catch(() => {
+            // Media repo can't or won't report limits, so provide an empty object (no limits).
+            console.log("[Media Config] Could not fetch config, so not limiting uploads.");
+            return {};
+        }).then((config) => {
+            this._mediaConfig = config;
+        });
     }
 
     sendStickerContentToRoom(url, roomId, info, text, matrixClient) {
@@ -283,7 +318,90 @@ class ContentMessages {
         });
     }
 
-    sendContentToRoom(file, roomId, matrixClient) {
+    getUploadLimit() {
+        if (this._mediaConfig !== null && this._mediaConfig["m.upload.size"] !== undefined) {
+            return this._mediaConfig["m.upload.size"];
+        } else {
+            return null;
+        }
+    }
+
+    async sendContentListToRoom(files, roomId, matrixClient) {
+        if (matrixClient.isGuest()) {
+            dis.dispatch({action: 'require_registration'});
+            return;
+        }
+
+        const isQuoting = Boolean(RoomViewStore.getQuotingEvent());
+        if (isQuoting) {
+            const QuestionDialog = sdk.getComponent("dialogs.QuestionDialog");
+            const shouldUpload = await new Promise((resolve) => {
+                Modal.createTrackedDialog('Upload Reply Warning', '', QuestionDialog, {
+                    title: _t('Replying With Files'),
+                    description: (
+                        <div>{_t(
+                            'At this time it is not possible to reply with a file. ' +
+                            'Would you like to upload this file without replying?',
+                        )}</div>
+                    ),
+                    hasCancelButton: true,
+                    button: _t("Continue"),
+                    onFinished: (shouldUpload) => {
+                        resolve(shouldUpload);
+                    },
+                });
+            });
+            if (!shouldUpload) return;
+        }
+
+        await this._ensureMediaConfigFetched();
+
+        const tooBigFiles = [];
+        const okFiles = [];
+
+        for (let i = 0; i < files.length; ++i) {
+            if (this._isFileSizeAcceptable(files[i])) {
+                okFiles.push(files[i]);
+            } else {
+                tooBigFiles.push(files[i]);
+            }
+        }
+
+        if (tooBigFiles.length > 0) {
+            const UploadFailureDialog = sdk.getComponent("dialogs.UploadFailureDialog");
+            const uploadFailureDialogPromise = new Promise((resolve) => {
+                Modal.createTrackedDialog('Upload Failure', '', UploadFailureDialog, {
+                    badFiles: tooBigFiles,
+                    totalFiles: files.length,
+                    contentMessages: this,
+                    onFinished: (shouldContinue) => {
+                        resolve(shouldContinue);
+                    },
+                });
+            });
+            const shouldContinue = await uploadFailureDialogPromise;
+            if (!shouldContinue) return;
+        }
+
+        const UploadConfirmDialog = sdk.getComponent("dialogs.UploadConfirmDialog");
+        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 (!shouldContinue) break;
+            this._sendContentToRoom(file, roomId, matrixClient);
+        }
+    }
+
+    _sendContentToRoom(file, roomId, matrixClient) {
         const content = {
             body: file.name || 'Attachment',
             info: {
@@ -357,9 +475,12 @@ class ContentMessages {
         }, function(err) {
             error = err;
             if (!upload.canceled) {
-                let desc = _t('The file \'%(fileName)s\' failed to upload', {fileName: upload.fileName}) + '.';
+                let desc = _t("The file '%(fileName)s' failed to upload.", {fileName: upload.fileName});
                 if (err.http_status == 413) {
-                    desc = _t('The file \'%(fileName)s\' exceeds this homeserver\'s size limit for uploads', {fileName: upload.fileName});
+                    desc = _t(
+                        "The file '%(fileName)s' exceeds this homeserver's size limit for uploads",
+                        {fileName: upload.fileName},
+                    );
                 }
                 const ErrorDialog = sdk.getComponent("dialogs.ErrorDialog");
                 Modal.createTrackedDialog('Upload failed', '', ErrorDialog, {
@@ -377,9 +498,16 @@ class ContentMessages {
                 }
             }
             if (error) {
+                // 413: File was too big or upset the server in some way:
+                // clear the media size limit so we fetch it again next time
+                // we try to upload
+                if (error && error.http_status === 413) {
+                    this._mediaConfig = null;
+                }
                 dis.dispatch({action: 'upload_failed', upload, error});
             } else {
                 dis.dispatch({action: 'upload_finished', upload});
+                dis.dispatch({action: 'message_sent'});
             }
         });
     }
@@ -404,9 +532,3 @@ class ContentMessages {
         }
     }
 }
-
-if (global.mx_ContentMessage === undefined) {
-    global.mx_ContentMessage = new ContentMessages();
-}
-
-module.exports = global.mx_ContentMessage;
diff --git a/src/components/structures/RoomView.js b/src/components/structures/RoomView.js
index 73b7545c26..47de3f2cb0 100644
--- a/src/components/structures/RoomView.js
+++ b/src/components/structures/RoomView.js
@@ -19,29 +19,28 @@ limitations under the License.
 // TODO: This component is enormous! There's several things which could stand-alone:
 //  - Search results component
 //  - Drag and drop
-//  - File uploading - uploadFile()
 
-import shouldHideEvent from "../../shouldHideEvent";
+import shouldHideEvent from '../../shouldHideEvent';
 
-const React = require("react");
-const ReactDOM = require("react-dom");
+import React from 'react';
+import ReactDOM from 'react-dom';
 import PropTypes from 'prop-types';
 import Promise from 'bluebird';
 import filesize from 'filesize';
-const classNames = require("classnames");
+import classNames from 'classnames';
 import { _t } from '../../languageHandler';
-import {RoomPermalinkCreator} from "../../matrix-to";
+import {RoomPermalinkCreator} from '../../matrix-to';
 
-const MatrixClientPeg = require("../../MatrixClientPeg");
-const ContentMessages = require("../../ContentMessages");
-const Modal = require("../../Modal");
-const sdk = require('../../index');
-const CallHandler = require('../../CallHandler');
-const dis = require("../../dispatcher");
-const Tinter = require("../../Tinter");
-const rate_limited_func = require('../../ratelimitedfunc');
-const ObjectUtils = require('../../ObjectUtils');
-const Rooms = require('../../Rooms');
+import MatrixClientPeg from '../../MatrixClientPeg';
+import ContentMessages from '../../ContentMessages';
+import Modal from '../../Modal';
+import sdk from '../../index';
+import CallHandler from '../../CallHandler';
+import dis from '../../dispatcher';
+import Tinter from '../../Tinter';
+import rate_limited_func from '../../ratelimitedfunc';
+import ObjectUtils from '../../ObjectUtils';
+import Rooms from '../../Rooms';
 
 import { KeyCode, isOnlyCtrlOrCmdKeyEvent } from '../../Keyboard';
 
@@ -170,7 +169,6 @@ module.exports = React.createClass({
         MatrixClientPeg.get().on("accountData", this.onAccountData);
         MatrixClientPeg.get().on("crypto.keyBackupStatus", this.onKeyBackupStatus);
         MatrixClientPeg.get().on("deviceVerificationChanged", this.onDeviceVerificationChanged);
-        this._fetchMediaConfig();
         // Start listening for RoomViewStore updates
         this._roomStoreToken = RoomViewStore.addListener(this._onRoomViewStoreUpdate);
         this._onRoomViewStoreUpdate(true);
@@ -178,27 +176,6 @@ module.exports = React.createClass({
         WidgetEchoStore.on('update', this._onWidgetEchoStoreUpdate);
     },
 
-    _fetchMediaConfig: function(invalidateCache: boolean = false) {
-        /// NOTE: Using global here so we don't make repeated requests for the
-        /// config every time we swap room.
-        if(global.mediaConfig !== undefined && !invalidateCache) {
-            this.setState({mediaConfig: global.mediaConfig});
-            return;
-        }
-        console.log("[Media Config] Fetching");
-        MatrixClientPeg.get().getMediaConfig().then((config) => {
-            console.log("[Media Config] Fetched config:", config);
-            return config;
-        }).catch(() => {
-            // Media repo can't or won't report limits, so provide an empty object (no limits).
-            console.log("[Media Config] Could not fetch config, so not limiting uploads.");
-            return {};
-        }).then((config) => {
-            global.mediaConfig = config;
-            this.setState({mediaConfig: config});
-        });
-    },
-
     _onRoomViewStoreUpdate: function(initial) {
         if (this.unmounted) {
             return;
@@ -510,7 +487,7 @@ module.exports = React.createClass({
     },
 
     onPageUnload(event) {
-        if (ContentMessages.getCurrentUploads().length > 0) {
+        if (ContentMessages.sharedInstance().getCurrentUploads().length > 0) {
             return event.returnValue =
                 _t("You seem to be uploading files, are you sure you want to quit?");
         } else if (this._getCallForRoom() && this.state.callState !== 'ended') {
@@ -561,11 +538,6 @@ module.exports = React.createClass({
             case 'picture_snapshot':
                 this.uploadFile(payload.file);
                 break;
-            case 'upload_failed':
-                // 413: File was too big or upset the server in some way.
-                if (payload.error && payload.error.http_status === 413) {
-                    this._fetchMediaConfig(true);
-                }
             case 'notifier_enabled':
             case 'upload_started':
             case 'upload_finished':
@@ -1015,9 +987,11 @@ module.exports = React.createClass({
     onDrop: function(ev) {
         ev.stopPropagation();
         ev.preventDefault();
+        ContentMessages.sharedInstance().sendContentListToRoom(
+            ev.dataTransfer.files, this.state.room.roomId, MatrixClientPeg.get(),
+        );
         this.setState({ draggingFile: false });
-        const files = [...ev.dataTransfer.files];
-        files.forEach(this.uploadFile);
+        dis.dispatch({action: 'focus_composer'});
     },
 
     onDragLeaveOrEnd: function(ev) {
@@ -1026,55 +1000,13 @@ module.exports = React.createClass({
         this.setState({ draggingFile: false });
     },
 
-    isFileUploadAllowed(file) {
-        if (this.state.mediaConfig !== undefined &&
-            this.state.mediaConfig["m.upload.size"] !== undefined &&
-            file.size > this.state.mediaConfig["m.upload.size"]) {
-            return _t("File is too big. Maximum file size is %(fileSize)s", {fileSize: filesize(this.state.mediaConfig["m.upload.size"])});
-        }
-        return true;
-    },
-
-    uploadFile: async function(file) {
-        dis.dispatch({action: 'focus_composer'});
-
-        if (MatrixClientPeg.get().isGuest()) {
-            dis.dispatch({action: 'require_registration'});
-            return;
-        }
-
-        try {
-            await ContentMessages.sendContentToRoom(file, this.state.room.roomId, MatrixClientPeg.get());
-        } catch (error) {
-            if (error.name === "UnknownDeviceError") {
-                // Let the status bar handle this
-                return;
-            }
-            const ErrorDialog = sdk.getComponent("dialogs.ErrorDialog");
-            console.error("Failed to upload file " + file + " " + error);
-            Modal.createTrackedDialog('Failed to upload file', '', ErrorDialog, {
-                title: _t('Failed to upload file'),
-                description: ((error && error.message)
-                    ? error.message : _t("Server may be unavailable, overloaded, or the file too big")),
-            });
-
-            // bail early to avoid calling the dispatch below
-            return;
-        }
-
-        // Send message_sent callback, for things like _checkIfAlone because after all a file is still a message.
-        dis.dispatch({
-            action: 'message_sent',
-        });
-    },
-
     injectSticker: function(url, info, text) {
         if (MatrixClientPeg.get().isGuest()) {
             dis.dispatch({action: 'require_registration'});
             return;
         }
 
-        ContentMessages.sendStickerContentToRoom(url, this.state.room.roomId, info, text, MatrixClientPeg.get())
+        ContentMessages.sharedInstance().sendStickerContentToRoom(url, this.state.room.roomId, info, text, MatrixClientPeg.get())
             .done(undefined, (error) => {
                 if (error.name === "UnknownDeviceError") {
                     // Let the staus bar handle this
@@ -1666,7 +1598,7 @@ module.exports = React.createClass({
         let statusBar;
         let isStatusAreaExpanded = true;
 
-        if (ContentMessages.getCurrentUploads().length > 0) {
+        if (ContentMessages.sharedInstance().getCurrentUploads().length > 0) {
             const UploadBar = sdk.getComponent('structures.UploadBar');
             statusBar = <UploadBar room={this.state.room} />;
         } else if (!this.state.searchResults) {
@@ -1774,11 +1706,9 @@ module.exports = React.createClass({
             messageComposer =
                 <MessageComposer
                     room={this.state.room}
-                    uploadFile={this.uploadFile}
                     callState={this.state.callState}
                     disabled={this.props.disabled}
                     showApps={this.state.showApps}
-                    uploadAllowed={this.isFileUploadAllowed}
                     e2eStatus={this.state.e2eStatus}
                     permalinkCreator={this.state.permalinkCreator}
                 />;
diff --git a/src/components/structures/UploadBar.js b/src/components/structures/UploadBar.js
index b54ea00c16..a8cb3c0b0e 100644
--- a/src/components/structures/UploadBar.js
+++ b/src/components/structures/UploadBar.js
@@ -47,7 +47,7 @@ module.exports = React.createClass({displayName: 'UploadBar',
     },
 
     render: function() {
-        const uploads = ContentMessages.getCurrentUploads();
+        const uploads = ContentMessages.sharedInstance().getCurrentUploads();
 
         // for testing UI... - also fix up the ContentMessages.getCurrentUploads().length
         // check in RoomView
@@ -93,7 +93,7 @@ module.exports = React.createClass({displayName: 'UploadBar',
                 </div>
                 <img className="mx_UploadBar_uploadIcon mx_filterFlipColor" src={require("../../../res/img/fileicon.png")} width="17" height="22" />
                 <img className="mx_UploadBar_uploadCancel mx_filterFlipColor" src={require("../../../res/img/cancel.svg")} width="18" height="18"
-                    onClick={function() { ContentMessages.cancelUpload(upload.promise); }}
+                    onClick={function() { ContentMessages.sharedInstance().cancelUpload(upload.promise); }}
                 />
                 <div className="mx_UploadBar_uploadBytes">
                     { uploadedSize } / { totalSize }
diff --git a/src/components/views/dialogs/UploadConfirmDialog.js b/src/components/views/dialogs/UploadConfirmDialog.js
new file mode 100644
index 0000000000..f026454cea
--- /dev/null
+++ b/src/components/views/dialogs/UploadConfirmDialog.js
@@ -0,0 +1,106 @@
+/*
+Copyright 2019 New Vector Ltd
+
+Licensed under the Apache License, Version 2.0 (the "License");
+you may not use this file except in compliance with the License.
+You may obtain a copy of the License at
+
+    http://www.apache.org/licenses/LICENSE-2.0
+
+Unless required by applicable law or agreed to in writing, software
+distributed under the License is distributed on an "AS IS" BASIS,
+WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+See the License for the specific language governing permissions and
+limitations under the License.
+*/
+
+import React from 'react';
+import PropTypes from 'prop-types';
+import sdk from '../../../index';
+import { _t } from '../../../languageHandler';
+
+export default class UploadConfirmDialog extends React.Component {
+    static propTypes = {
+        file: PropTypes.object.isRequired,
+        currentIndex: PropTypes.number,
+        totalFiles: PropTypes.number,
+        onFinished: PropTypes.func.isRequired,
+    }
+
+    static defaultProps = {
+        totalFiles: 1,
+    }
+
+    constructor(props) {
+        super(props);
+
+        this._objectUrl = URL.createObjectURL(props.file);
+    }
+
+    componentWillUnmount() {
+        if (this._objectUrl) URL.revokeObjectURL(this._objectUrl);
+    }
+
+    _onCancelClick = () => {
+        this.props.onFinished(false);
+    }
+
+    _onUploadClick = () => {
+        this.props.onFinished(true);
+    }
+
+    render() {
+        const BaseDialog = sdk.getComponent('views.dialogs.BaseDialog');
+        const DialogButtons = sdk.getComponent('views.elements.DialogButtons');
+
+        let title;
+        if (this.props.totalFiles > 1 && this.props.currentIndex !== undefined) {
+            title = _t(
+                "Upload files (%(current)s of %(total)s)",
+                {
+                    current: this.props.currentIndex + 1,
+                    total: this.props.totalFiles,
+                },
+            );
+        } else {
+            title = _t('Upload files');
+        }
+
+        let preview;
+        if (this.props.file.type.startsWith('image/')) {
+            preview = <div className="mx_UploadConfirmDialog_previewOuter">
+                <div className="mx_UploadConfirmDialog_previewInner">
+                    <div><img className="mx_UploadConfirmDialog_imagePreview" src={this._objectUrl} /></div>
+                    <div>{this.props.file.name}</div>
+                </div>
+            </div>;
+        } else {
+            preview = <div>
+                <div>
+                    <img className="mx_UploadConfirmDialog_fileIcon"
+                        src={require("../../../../res/img/files.png")}
+                    />
+                    {this.props.file.name}
+                </div>
+            </div>;
+        }
+
+        return (
+            <BaseDialog className='mx_UploadConfirmDialog'
+                onFinished={this._onCancelClick}
+                title={title}
+                contentId='mx_Dialog_content'
+            >
+                <div id='mx_Dialog_content'>
+                    {preview}
+                </div>
+
+                <DialogButtons primaryButton={_t('Upload')}
+                    hasCancel={false}
+                    onPrimaryButtonClick={this._onUploadClick}
+                    focus={true}
+                />
+            </BaseDialog>
+        );
+    }
+}
diff --git a/src/components/views/dialogs/UploadFailureDialog.js b/src/components/views/dialogs/UploadFailureDialog.js
new file mode 100644
index 0000000000..e264f1a3fb
--- /dev/null
+++ b/src/components/views/dialogs/UploadFailureDialog.js
@@ -0,0 +1,120 @@
+/*
+Copyright 2019 New Vector Ltd
+
+Licensed under the Apache License, Version 2.0 (the "License");
+you may not use this file except in compliance with the License.
+You may obtain a copy of the License at
+
+    http://www.apache.org/licenses/LICENSE-2.0
+
+Unless required by applicable law or agreed to in writing, software
+distributed under the License is distributed on an "AS IS" BASIS,
+WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+See the License for the specific language governing permissions and
+limitations under the License.
+*/
+
+import filesize from 'filesize';
+
+import React from 'react';
+import PropTypes from 'prop-types';
+import sdk from '../../../index';
+import { _t } from '../../../languageHandler';
+import ContentMessages from '../../../ContentMessages';
+
+/*
+ * Tells the user about files we know cannot be uploaded before we even try uploading
+ * them. This is named fairly generically but the only thing we check right now is
+ * the size of the file.
+ */
+export default class UploadFailureDialog extends React.Component {
+    static propTypes = {
+        badFiles: PropTypes.arrayOf(PropTypes.object).isRequired,
+        totalFiles: PropTypes.number.isRequired,
+        contentMessages: PropTypes.instanceOf(ContentMessages).isRequired,
+        onFinished: PropTypes.func.isRequired,
+    }
+
+    _onCancelClick = () => {
+        this.props.onFinished(false);
+    }
+
+    _onUploadClick = () => {
+        this.props.onFinished(true);
+    }
+
+    render() {
+        const BaseDialog = sdk.getComponent('views.dialogs.BaseDialog');
+        const DialogButtons = sdk.getComponent('views.elements.DialogButtons');
+
+        let message;
+        let preview;
+        let buttons;
+        if (this.props.totalFiles === 1 && this.props.badFiles.length === 1) {
+            message = _t(
+                "This file is <b>too large</b> to upload. " +
+                "The file size limit is %(limit)s but this file is %(sizeOfThisFile)s.",
+                {
+                    limit: filesize(this.props.contentMessages.getUploadLimit()),
+                    sizeOfThisFile: filesize(this.props.badFiles[0].size),
+                }, {
+                    b: sub => <b>{sub}</b>,
+                },
+            );
+            buttons = <DialogButtons primaryButton={_t('OK')}
+                hasCancel={false}
+                onPrimaryButtonClick={this._onCancelClick}
+                focus={true}
+            />;
+        } else if (this.props.totalFiles === this.props.badFiles.length) {
+            message = _t(
+                "These files are <b>too large</b> to upload. " +
+                "The file size limit is %(limit)s.",
+                {
+                    limit: filesize(this.props.contentMessages.getUploadLimit()),
+                }, {
+                    b: sub => <b>{sub}</b>,
+                },
+            );
+            buttons = <DialogButtons primaryButton={_t('OK')}
+                hasCancel={false}
+                onPrimaryButtonClick={this._onCancelClick}
+                focus={true}
+            />;
+        } else {
+            message = _t(
+                "Some files are <b>too large</b> to be uploaded. " +
+                "The file size limit is %(limit)s.",
+                {
+                    limit: filesize(this.props.contentMessages.getUploadLimit()),
+                }, {
+                    b: sub => <b>{sub}</b>,
+                },
+            );
+            const howManyOthers = this.props.totalFiles - this.props.badFiles.length;
+            buttons = <DialogButtons
+                primaryButton={_t('Upload %(count)s other files', { count: howManyOthers })}
+                onPrimaryButtonClick={this._onUploadClick}
+                hasCancel={true}
+                cancelButton={_t("Cancel All")}
+                onCancel={this._onCancelClick}
+                focus={true}
+            />;
+        }
+
+        return (
+            <BaseDialog className='mx_UploadFailureDialog'
+                onFinished={this._onCancelClick}
+                title={_t("Upload Error")}
+                contentId='mx_Dialog_content'
+            >
+                <div id='mx_Dialog_content'>
+                    {message}
+                    {preview}
+                </div>
+
+                {buttons}
+            </BaseDialog>
+        );
+    }
+}
diff --git a/src/components/views/rooms/MessageComposer.js b/src/components/views/rooms/MessageComposer.js
index a76a45497b..535d565d22 100644
--- a/src/components/views/rooms/MessageComposer.js
+++ b/src/components/views/rooms/MessageComposer.js
@@ -26,6 +26,7 @@ import RoomViewStore from '../../../stores/RoomViewStore';
 import SettingsStore, {SettingLevel} from "../../../settings/SettingsStore";
 import Stickerpicker from './Stickerpicker';
 import { makeRoomPermalink } from '../../../matrix-to';
+import ContentMessages from '../../../ContentMessages';
 import classNames from 'classnames';
 
 import E2EIcon from './E2EIcon';
@@ -47,8 +48,7 @@ export default class MessageComposer extends React.Component {
         this.onCallClick = this.onCallClick.bind(this);
         this.onHangupClick = this.onHangupClick.bind(this);
         this.onUploadClick = this.onUploadClick.bind(this);
-        this.onUploadFileSelected = this.onUploadFileSelected.bind(this);
-        this.uploadFiles = this.uploadFiles.bind(this);
+        this._onUploadFileInputChange = this._onUploadFileInputChange.bind(this);
         this.onVoiceCallClick = this.onVoiceCallClick.bind(this);
         this._onAutocompleteConfirm = this._onAutocompleteConfirm.bind(this);
         this.onToggleFormattingClicked = this.onToggleFormattingClicked.bind(this);
@@ -145,89 +145,25 @@ export default class MessageComposer extends React.Component {
         this.refs.uploadInput.click();
     }
 
-    onUploadFileSelected(files) {
-        const tfiles = files.target.files;
-        this.uploadFiles(tfiles);
-    }
+    _onUploadFileInputChange(ev) {
+        if (ev.target.files.length === 0) return;
 
-    uploadFiles(files) {
-        const QuestionDialog = sdk.getComponent("dialogs.QuestionDialog");
-        const TintableSvg = sdk.getComponent("elements.TintableSvg");
-
-        const fileList = [];
-        const acceptedFiles = [];
-        const failedFiles = [];
-
-        for (let i=0; i<files.length; i++) {
-            const fileAcceptedOrError = this.props.uploadAllowed(files[i]);
-            if (fileAcceptedOrError === true) {
-                acceptedFiles.push(<li key={i}>
-                    <TintableSvg key={i} src={require("../../../../res/img/files.svg")} width="16" height="16" /> { files[i].name || _t('Attachment') }
-                </li>);
-                fileList.push(files[i]);
-            } else {
-                failedFiles.push(<li key={i}>
-                    <TintableSvg key={i} src={require("../../../../res/img/files.svg")} width="16" height="16" /> { files[i].name || _t('Attachment') } <p>{ _t('Reason') + ": " + fileAcceptedOrError}</p>
-                </li>);
-            }
+        // take a copy so we can safely reset the value of the form control
+        // (Note it is a FileList: we can't use slice or sesnible iteration).
+        const tfiles = [];
+        for (let i = 0; i < ev.target.files.length; ++i) {
+            tfiles.push(ev.target.files[i]);
         }
 
-        const isQuoting = Boolean(RoomViewStore.getQuotingEvent());
-        let replyToWarning = null;
-        if (isQuoting) {
-            replyToWarning = <p>{
-                _t('At this time it is not possible to reply with a file so this will be sent without being a reply.')
-            }</p>;
-        }
-
-        const acceptedFilesPart = acceptedFiles.length === 0 ? null : (
-            <div>
-                <p>{ _t('Are you sure you want to upload the following files?') }</p>
-                <ul style={{listStyle: 'none', textAlign: 'left'}}>
-                    { acceptedFiles }
-                </ul>
-            </div>
+        ContentMessages.sharedInstance().sendContentListToRoom(
+            tfiles, this.props.room.roomId, MatrixClientPeg.get(),
         );
 
-        const failedFilesPart = failedFiles.length === 0 ? null : (
-            <div>
-                <p>{ _t('The following files cannot be uploaded:') }</p>
-                <ul style={{listStyle: 'none', textAlign: 'left'}}>
-                    { failedFiles }
-                </ul>
-            </div>
-        );
-        let buttonText;
-        if (acceptedFiles.length > 0 && failedFiles.length > 0) {
-            buttonText = "Upload selected"
-        } else if (failedFiles.length > 0) {
-            buttonText = "Close"
-        }
-
-        Modal.createTrackedDialog('Upload Files confirmation', '', QuestionDialog, {
-            title: _t('Upload Files'),
-            description: (
-                <div>
-                    { acceptedFilesPart }
-                    { failedFilesPart }
-                    { replyToWarning }
-                </div>
-            ),
-            hasCancelButton: acceptedFiles.length > 0,
-            button: buttonText,
-            onFinished: (shouldUpload) => {
-                if (shouldUpload) {
-                    // MessageComposer shouldn't have to rely on its parent passing in a callback to upload a file
-                    if (fileList) {
-                        for (let i=0; i<fileList.length; i++) {
-                            this.props.uploadFile(fileList[i]);
-                        }
-                    }
-                }
-
-                this.refs.uploadInput.value = null;
-            },
-        });
+        // This is the onChange handler for a file form control, but we're
+        // not keeping any state, so reset the value of the form control
+        // to empty.
+        // NB. we need to set 'value': the 'files' property is immutable.
+        ev.target.value = '';
     }
 
     onHangupClick() {
@@ -376,7 +312,7 @@ export default class MessageComposer extends React.Component {
                     <input ref="uploadInput" type="file"
                         style={uploadInputStyle}
                         multiple
-                        onChange={this.onUploadFileSelected} />
+                        onChange={this._onUploadFileInputChange} />
                 </AccessibleButton>
             );
 
@@ -414,7 +350,6 @@ export default class MessageComposer extends React.Component {
                     key="controls_input"
                     room={this.props.room}
                     placeholder={placeholderText}
-                    onFilesPasted={this.uploadFiles}
                     onInputStateChanged={this.onInputStateChanged}
                     permalinkCreator={this.props.permalinkCreator} />,
                 formattingButton,
@@ -510,12 +445,6 @@ MessageComposer.propTypes = {
     // string representing the current voip call state
     callState: PropTypes.string,
 
-    // callback when a file to upload is chosen
-    uploadFile: PropTypes.func.isRequired,
-
-    // function to test whether a file should be allowed to be uploaded.
-    uploadAllowed: PropTypes.func.isRequired,
-
     // string representing the current room app drawer state
     showApps: PropTypes.bool
 };
diff --git a/src/components/views/rooms/MessageComposerInput.js b/src/components/views/rooms/MessageComposerInput.js
index cbea2bccb9..a0b66e40e1 100644
--- a/src/components/views/rooms/MessageComposerInput.js
+++ b/src/components/views/rooms/MessageComposerInput.js
@@ -47,6 +47,7 @@ import {Completion} from "../../../autocomplete/Autocompleter";
 import Markdown from '../../../Markdown';
 import ComposerHistoryManager from '../../../ComposerHistoryManager';
 import MessageComposerStore from '../../../stores/MessageComposerStore';
+import ContentMessage from '../../../ContentMessages';
 
 import {MATRIXTO_URL_PATTERN} from '../../../linkify-matrix';
 
@@ -1009,7 +1010,13 @@ export default class MessageComposerInput extends React.Component {
 
         switch (transfer.type) {
             case 'files':
-                return this.props.onFilesPasted(transfer.files);
+                // This actually not so much for 'files' as such (at time of writing
+                // neither chrome nor firefox let you paste a plain file copied
+                // from Finder) but more images copied from a different website
+                // / word processor etc.
+                return ContentMessage.sharedInstance().sendContentListToRoom(
+                    transfer.files, this.props.room.roomId, this.client,
+                );
             case 'html': {
                 if (this.state.isRichTextEnabled) {
                     // FIXME: https://github.com/ianstormtaylor/slate/issues/1497 means
diff --git a/src/i18n/strings/en_EN.json b/src/i18n/strings/en_EN.json
index a82571062b..7dea247a7e 100644
--- a/src/i18n/strings/en_EN.json
+++ b/src/i18n/strings/en_EN.json
@@ -40,7 +40,10 @@
     "A call is already in progress!": "A call is already in progress!",
     "Permission Required": "Permission Required",
     "You do not have permission to start a conference call in this room": "You do not have permission to start a conference call in this room",
-    "The file '%(fileName)s' failed to upload": "The file '%(fileName)s' failed to upload",
+    "Replying With Files": "Replying With Files",
+    "At this time it is not possible to reply with a file. Would you like to upload this file without replying?": "At this time it is not possible to reply with a file. Would you like to upload this file without replying?",
+    "Continue": "Continue",
+    "The file '%(fileName)s' failed to upload.": "The file '%(fileName)s' failed to upload.",
     "The file '%(fileName)s' exceeds this homeserver's size limit for uploads": "The file '%(fileName)s' exceeds this homeserver's size limit for uploads",
     "Upload Failed": "Upload Failed",
     "Failure to create room": "Failure to create room",
@@ -353,7 +356,6 @@
     "Verify this user by confirming the following number appears on their screen.": "Verify this user by confirming the following number appears on their screen.",
     "Unable to find a supported verification method.": "Unable to find a supported verification method.",
     "For maximum security, we recommend you do this in person or use another trusted means of communication.": "For maximum security, we recommend you do this in person or use another trusted means of communication.",
-    "Continue": "Continue",
     "Dog": "Dog",
     "Cat": "Cat",
     "Lion": "Lion",
@@ -718,11 +720,6 @@
     "block-quote": "block-quote",
     "bulleted-list": "bulleted-list",
     "numbered-list": "numbered-list",
-    "Attachment": "Attachment",
-    "At this time it is not possible to reply with a file so this will be sent without being a reply.": "At this time it is not possible to reply with a file so this will be sent without being a reply.",
-    "Are you sure you want to upload the following files?": "Are you sure you want to upload the following files?",
-    "The following files cannot be uploaded:": "The following files cannot be uploaded:",
-    "Upload Files": "Upload Files",
     "Hangup": "Hangup",
     "Voice call": "Voice call",
     "Video call": "Video call",
@@ -873,6 +870,7 @@
     "Today": "Today",
     "Yesterday": "Yesterday",
     "Error decrypting audio": "Error decrypting audio",
+    "Attachment": "Attachment",
     "Error decrypting attachment": "Error decrypting attachment",
     "Decrypt %(text)s": "Decrypt %(text)s",
     "Download %(text)s": "Download %(text)s",
@@ -1196,6 +1194,16 @@
     "Room contains unknown devices": "Room contains unknown devices",
     "\"%(RoomName)s\" contains devices that you haven't seen before.": "\"%(RoomName)s\" contains devices that you haven't seen before.",
     "Unknown devices": "Unknown devices",
+    "Upload files (%(current)s of %(total)s)": "Upload files (%(current)s of %(total)s)",
+    "Upload files": "Upload files",
+    "Upload": "Upload",
+    "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.",
+    "Upload %(count)s other files|other": "Upload %(count)s other files",
+    "Upload %(count)s other files|one": "Upload %(count)s other file",
+    "Cancel All": "Cancel All",
+    "Upload Error": "Upload Error",
     "A widget would like to verify your identity": "A widget would like to verify your identity",
     "A widget located at %(widgetUrl)s would like to verify your identity. By allowing this, the widget will be able to verify your user ID, but not perform actions as you.": "A widget located at %(widgetUrl)s would like to verify your identity. By allowing this, the widget will be able to verify your user ID, but not perform actions as you.",
     "Remember my selection for this widget": "Remember my selection for this widget",
@@ -1421,9 +1429,6 @@
     "There's no one else here! Would you like to <inviteText>invite others</inviteText> or <nowarnText>stop warning about the empty room</nowarnText>?": "There's no one else here! Would you like to <inviteText>invite others</inviteText> or <nowarnText>stop warning about the empty room</nowarnText>?",
     "You seem to be uploading files, are you sure you want to quit?": "You seem to be uploading files, are you sure you want to quit?",
     "You seem to be in a call, are you sure you want to quit?": "You seem to be in a call, are you sure you want to quit?",
-    "File is too big. Maximum file size is %(fileSize)s": "File is too big. Maximum file size is %(fileSize)s",
-    "Failed to upload file": "Failed to upload file",
-    "Server may be unavailable, overloaded, or the file too big": "Server may be unavailable, overloaded, or the file too big",
     "Search failed": "Search failed",
     "Server may be unavailable, overloaded, or search timed out :(": "Server may be unavailable, overloaded, or search timed out :(",
     "No more results": "No more results",