diff --git a/app/containers/MessageBox/Recording.js b/app/containers/MessageBox/Recording.js
index 96f45c9b7..d5fed549a 100644
--- a/app/containers/MessageBox/Recording.js
+++ b/app/containers/MessageBox/Recording.js
@@ -5,6 +5,7 @@ import {
 } from 'react-native';
 import { AudioRecorder, AudioUtils } from 'react-native-audio';
 import { BorderlessButton } from 'react-native-gesture-handler';
+import FileSystem from 'expo-file-system';
 
 import styles from './styles';
 import I18n from '../../i18n';
@@ -68,7 +69,7 @@ export default class extends React.PureComponent {
 		//
 		AudioRecorder.onFinished = (data) => {
 			if (!this.recordingCanceled && isIOS) {
-				this.finishRecording(data.status === 'OK', data.audioFileURL);
+				this.finishRecording(data.status === 'OK', data.audioFileURL, data.audioFileSize);
 			}
 		};
 		AudioRecorder.startRecording();
@@ -80,7 +81,7 @@ export default class extends React.PureComponent {
 		}
 	}
 
-	finishRecording = (didSucceed, filePath) => {
+	finishRecording = (didSucceed, filePath, size) => {
 		const { onFinish } = this.props;
 		if (!didSucceed) {
 			return onFinish && onFinish(didSucceed);
@@ -90,9 +91,11 @@ export default class extends React.PureComponent {
 		}
 		const fileInfo = {
 			name: this.name,
+			mime: 'audio/aac',
 			type: 'audio/aac',
 			store: 'Uploads',
-			path: filePath
+			path: filePath,
+			size
 		};
 		return onFinish && onFinish(fileInfo);
 	}
@@ -102,7 +105,8 @@ export default class extends React.PureComponent {
 			this.recording = false;
 			const filePath = await AudioRecorder.stopRecording();
 			if (isAndroid) {
-				this.finishRecording(true, filePath);
+				const data = await FileSystem.getInfoAsync(decodeURIComponent(filePath));
+				this.finishRecording(true, filePath, data.size);
 			}
 		} catch (err) {
 			this.finishRecording(false);
diff --git a/app/containers/MessageBox/UploadModal.js b/app/containers/MessageBox/UploadModal.js
index 596934ebf..3773391b7 100644
--- a/app/containers/MessageBox/UploadModal.js
+++ b/app/containers/MessageBox/UploadModal.js
@@ -2,7 +2,6 @@ import React, { Component } from 'react';
 import {
 	View, Text, StyleSheet, Image, ScrollView, TouchableHighlight
 } from 'react-native';
-import { connect } from 'react-redux';
 import PropTypes from 'prop-types';
 import Modal from 'react-native-modal';
 import { responsive } from 'react-native-responsive-ui';
@@ -13,9 +12,8 @@ import Button from '../Button';
 import I18n from '../../i18n';
 import sharedStyles from '../../views/Styles';
 import { isIOS } from '../../utils/deviceInfo';
-import { canUploadFile } from '../../utils/media';
 import {
-	COLOR_PRIMARY, COLOR_BACKGROUND_CONTAINER, COLOR_WHITE, COLOR_DANGER
+	COLOR_PRIMARY, COLOR_BACKGROUND_CONTAINER, COLOR_WHITE
 } from '../../constants/colors';
 import { CustomIcon } from '../../lib/Icons';
 
@@ -75,23 +73,6 @@ const styles = StyleSheet.create({
 		flex: 1,
 		textAlign: 'center'
 	},
-	errorIcon: {
-		color: COLOR_DANGER
-	},
-	fileMime: {
-		...sharedStyles.textColorTitle,
-		...sharedStyles.textBold,
-		textAlign: 'center',
-		fontSize: 20,
-		marginBottom: 20
-	},
-	errorContainer: {
-		margin: 20,
-		flex: 1,
-		textAlign: 'center',
-		justifyContent: 'center',
-		alignItems: 'center'
-	},
 	video: {
 		flex: 1,
 		borderRadius: 4,
@@ -110,9 +91,7 @@ class UploadModal extends Component {
 		file: PropTypes.object,
 		close: PropTypes.func,
 		submit: PropTypes.func,
-		window: PropTypes.object,
-		FileUpload_MediaTypeWhiteList: PropTypes.string,
-		FileUpload_MaxFileSize: PropTypes.number
+		window: PropTypes.object
 	}
 
 	state = {
@@ -154,79 +133,12 @@ class UploadModal extends Component {
 		return false;
 	}
 
-	canUploadFile = () => {
-		const { FileUpload_MediaTypeWhiteList, FileUpload_MaxFileSize, file } = this.props;
-		if (!(file && file.path)) {
-			return true;
-		}
-		if (file.size > FileUpload_MaxFileSize) {
-			return false;
-		}
-		// if white list is empty, all media types are enabled
-		if (!FileUpload_MediaTypeWhiteList) {
-			return true;
-		}
-		const allowedMime = FileUpload_MediaTypeWhiteList.split(',');
-		if (allowedMime.includes(file.mime)) {
-			return true;
-		}
-		const wildCardGlob = '/*';
-		const wildCards = allowedMime.filter(item => item.indexOf(wildCardGlob) > 0);
-		if (wildCards.includes(file.mime.replace(/(\/.*)$/, wildCardGlob))) {
-			return true;
-		}
-		return false;
-	}
-
 	submit = () => {
 		const { file, submit } = this.props;
 		const { name, description } = this.state;
 		submit({ ...file, name, description });
 	}
 
-	renderError = () => {
-		const { file, FileUpload_MaxFileSize, close } = this.props;
-		const { window: { width } } = this.props;
-		const errorMessage = (FileUpload_MaxFileSize < file.size)
-			? 'error-file-too-large'
-			: 'error-invalid-file-type';
-		return (
-			<View style={[styles.container, { width: width - 32 }]}>
-				<View style={styles.titleContainer}>
-					<Text style={styles.title}>{I18n.t(errorMessage)}</Text>
-				</View>
-				<View style={styles.errorContainer}>
-					<CustomIcon name='circle-cross' size={120} style={styles.errorIcon} />
-				</View>
-				<Text style={styles.fileMime}>{ file.mime }</Text>
-				<View style={styles.buttonContainer}>
-					{
-						(isIOS)
-							? (
-								<Button
-									title={I18n.t('Cancel')}
-									type='secondary'
-									backgroundColor={cancelButtonColor}
-									style={styles.button}
-									onPress={close}
-								/>
-							)
-							: (
-								<TouchableHighlight
-									onPress={close}
-									style={[styles.androidButton, { backgroundColor: cancelButtonColor }]}
-									underlayColor={cancelButtonColor}
-									activeOpacity={0.5}
-								>
-									<Text style={[styles.androidButtonText, { ...sharedStyles.textBold, color: COLOR_PRIMARY }]}>{I18n.t('Cancel')}</Text>
-								</TouchableHighlight>
-							)
-					}
-				</View>
-			</View>
-		);
-	}
-
 	renderButtons = () => {
 		const { close } = this.props;
 		if (isIOS) {
@@ -288,10 +200,9 @@ class UploadModal extends Component {
 
 	render() {
 		const {
-			window: { width }, isVisible, close, file, FileUpload_MediaTypeWhiteList, FileUpload_MaxFileSize
+			window: { width }, isVisible, close
 		} = this.props;
 		const { name, description } = this.state;
-		const showError = !canUploadFile(file, { FileUpload_MediaTypeWhiteList, FileUpload_MaxFileSize });
 		return (
 			<Modal
 				isVisible={isVisible}
@@ -304,37 +215,29 @@ class UploadModal extends Component {
 				hideModalContentWhileAnimating
 				avoidKeyboard
 			>
-				{(showError) ? this.renderError()
-					: (
-						<View style={[styles.container, { width: width - 32 }]}>
-							<View style={styles.titleContainer}>
-								<Text style={styles.title}>{I18n.t('Upload_file_question_mark')}</Text>
-							</View>
+				<View style={[styles.container, { width: width - 32 }]}>
+					<View style={styles.titleContainer}>
+						<Text style={styles.title}>{I18n.t('Upload_file_question_mark')}</Text>
+					</View>
 
-							<ScrollView style={styles.scrollView}>
-								{this.renderPreview()}
-								<TextInput
-									placeholder={I18n.t('File_name')}
-									value={name}
-									onChangeText={value => this.setState({ name: value })}
-								/>
-								<TextInput
-									placeholder={I18n.t('File_description')}
-									value={description}
-									onChangeText={value => this.setState({ description: value })}
-								/>
-							</ScrollView>
-							{this.renderButtons()}
-						</View>
-					)}
+					<ScrollView style={styles.scrollView}>
+						{this.renderPreview()}
+						<TextInput
+							placeholder={I18n.t('File_name')}
+							value={name}
+							onChangeText={value => this.setState({ name: value })}
+						/>
+						<TextInput
+							placeholder={I18n.t('File_description')}
+							value={description}
+							onChangeText={value => this.setState({ description: value })}
+						/>
+					</ScrollView>
+					{this.renderButtons()}
+				</View>
 			</Modal>
 		);
 	}
 }
 
-const mapStateToProps = state => ({
-	FileUpload_MediaTypeWhiteList: state.settings.FileUpload_MediaTypeWhiteList,
-	FileUpload_MaxFileSize: state.settings.FileUpload_MaxFileSize
-});
-
-export default responsive(connect(mapStateToProps)(UploadModal));
+export default responsive(UploadModal);
diff --git a/app/containers/MessageBox/index.js b/app/containers/MessageBox/index.js
index 89dfdfd22..cd12204f4 100644
--- a/app/containers/MessageBox/index.js
+++ b/app/containers/MessageBox/index.js
@@ -30,6 +30,7 @@ import LeftButtons from './LeftButtons';
 import RightButtons from './RightButtons';
 import { isAndroid } from '../../utils/deviceInfo';
 import CommandPreview from './CommandPreview';
+import { canUploadFile } from '../../utils/media';
 
 const MENTIONS_TRACKING_TYPE_USERS = '@';
 const MENTIONS_TRACKING_TYPE_EMOJIS = ':';
@@ -73,6 +74,8 @@ class MessageBox extends Component {
 		roomType: PropTypes.string,
 		tmid: PropTypes.string,
 		replyWithMention: PropTypes.bool,
+		FileUpload_MediaTypeWhiteList: PropTypes.string,
+		FileUpload_MaxFileSize: PropTypes.number,
 		getCustomEmoji: PropTypes.func,
 		editCancel: PropTypes.func.isRequired,
 		editRequest: PropTypes.func.isRequired,
@@ -435,6 +438,16 @@ class MessageBox extends Component {
 		this.setShowSend(false);
 	}
 
+	canUploadFile = (file) => {
+		const { FileUpload_MediaTypeWhiteList, FileUpload_MaxFileSize } = this.props;
+		const result = canUploadFile(file, { FileUpload_MediaTypeWhiteList, FileUpload_MaxFileSize });
+		if (result.success) {
+			return true;
+		}
+		Alert.alert(I18n.t('Error_uploading'), I18n.t(result.error));
+		return false;
+	}
+
 	sendMediaMessage = async(file) => {
 		const {
 			rid, tmid, baseUrl: server, user
@@ -458,7 +471,9 @@ class MessageBox extends Component {
 	takePhoto = async() => {
 		try {
 			const image = await ImagePicker.openCamera(this.imagePickerConfig);
-			this.showUploadModal(image);
+			if (this.canUploadFile(image)) {
+				this.showUploadModal(image);
+			}
 		} catch (e) {
 			log(e);
 		}
@@ -467,7 +482,9 @@ class MessageBox extends Component {
 	takeVideo = async() => {
 		try {
 			const video = await ImagePicker.openCamera(this.videoPickerConfig);
-			this.showUploadModal(video);
+			if (this.canUploadFile(video)) {
+				this.showUploadModal(video);
+			}
 		} catch (e) {
 			log(e);
 		}
@@ -476,7 +493,9 @@ class MessageBox extends Component {
 	chooseFromLibrary = async() => {
 		try {
 			const image = await ImagePicker.openPicker(this.libraryPickerConfig);
-			this.showUploadModal(image);
+			if (this.canUploadFile(image)) {
+				this.showUploadModal(image);
+			}
 		} catch (e) {
 			log(e);
 		}
@@ -487,12 +506,15 @@ class MessageBox extends Component {
 			const res = await DocumentPicker.pick({
 				type: [DocumentPicker.types.allFiles]
 			});
-			this.showUploadModal({
+			const file = {
 				filename: res.name,
 				size: res.size,
 				mime: res.type,
 				path: res.uri
-			});
+			};
+			if (this.canUploadFile(file)) {
+				this.showUploadModal(file);
+			}
 		} catch (e) {
 			if (!DocumentPicker.isCancel(e)) {
 				log(e);
@@ -560,11 +582,10 @@ class MessageBox extends Component {
 		});
 		if (fileInfo) {
 			try {
-				await RocketChat.sendFileMessage(rid, fileInfo, tmid, server, user);
-			} catch (e) {
-				if (e && e.error === 'error-file-too-large') {
-					return Alert.alert(I18n.t(e.error));
+				if (this.canUploadFile(fileInfo)) {
+					await RocketChat.sendFileMessage(rid, fileInfo, tmid, server, user);
 				}
+			} catch (e) {
 				log(e);
 			}
 		}
@@ -921,7 +942,9 @@ const mapStateToProps = state => ({
 		id: state.login.user && state.login.user.id,
 		username: state.login.user && state.login.user.username,
 		token: state.login.user && state.login.user.token
-	}
+	},
+	FileUpload_MediaTypeWhiteList: state.settings.FileUpload_MediaTypeWhiteList,
+	FileUpload_MaxFileSize: state.settings.FileUpload_MaxFileSize
 });
 
 const dispatchToProps = ({
diff --git a/app/lib/methods/sendFileMessage.js b/app/lib/methods/sendFileMessage.js
index 3ad0dd82e..12703afca 100644
--- a/app/lib/methods/sendFileMessage.js
+++ b/app/lib/methods/sendFileMessage.js
@@ -30,14 +30,9 @@ export function sendFileMessage(rid, fileInfo, tmid, server, user) {
 			const serversDB = database.servers;
 			const serversCollection = serversDB.collections.get('servers');
 			const serverInfo = await serversCollection.find(server);
-			const { FileUpload_MaxFileSize, id: Site_Url } = serverInfo;
+			const { id: Site_Url } = serverInfo;
 			const { id, token } = user;
 
-			// -1 maxFileSize means there is no limit
-			if (FileUpload_MaxFileSize > -1 && fileInfo.size > FileUpload_MaxFileSize) {
-				return reject({ error: 'error-file-too-large' }); // eslint-disable-line
-			}
-
 			const uploadUrl = `${ Site_Url }/api/v1/rooms.upload/${ rid }`;
 
 			const xhr = new XMLHttpRequest();
diff --git a/app/utils/media.js b/app/utils/media.js
index 8915caf6d..42d4a5aec 100644
--- a/app/utils/media.js
+++ b/app/utils/media.js
@@ -1,23 +1,23 @@
 export const canUploadFile = (file, serverInfo) => {
 	const { FileUpload_MediaTypeWhiteList, FileUpload_MaxFileSize } = serverInfo;
 	if (!(file && file.path)) {
-		return true;
+		return { success: true };
 	}
-	if (file.size > FileUpload_MaxFileSize) {
-		return false;
+	if (FileUpload_MaxFileSize > -1 && file.size > FileUpload_MaxFileSize) {
+		return { success: false, error: 'error-file-too-large' };
 	}
 	// if white list is empty, all media types are enabled
 	if (!FileUpload_MediaTypeWhiteList) {
-		return true;
+		return { success: true };
 	}
 	const allowedMime = FileUpload_MediaTypeWhiteList.split(',');
 	if (allowedMime.includes(file.mime)) {
-		return true;
+		return { success: true };
 	}
 	const wildCardGlob = '/*';
 	const wildCards = allowedMime.filter(item => item.indexOf(wildCardGlob) > 0);
-	if (wildCards.includes(file.mime.replace(/(\/.*)$/, wildCardGlob))) {
-		return true;
+	if (file.mime && wildCards.includes(file.mime.replace(/(\/.*)$/, wildCardGlob))) {
+		return { success: true };
 	}
-	return false;
+	return { success: false, error: 'error-invalid-file-type' };
 };
diff --git a/app/views/ShareListView/index.js b/app/views/ShareListView/index.js
index 446da3580..ac6deed65 100644
--- a/app/views/ShareListView/index.js
+++ b/app/views/ShareListView/index.js
@@ -199,12 +199,14 @@ class ShareListView extends React.Component {
 			this.servers = await serversCollection.query().fetch();
 			this.chats = this.data.slice(0, LIMIT);
 			const serverInfo = await serversCollection.find(server);
+			const canUploadFileResult = canUploadFile(fileInfo || fileData, serverInfo);
 
 			this.internalSetState({
 				chats: this.chats ? this.chats.slice() : [],
 				servers: this.servers ? this.servers.slice() : [],
 				loading: false,
-				showError: !canUploadFile(fileInfo || fileData, serverInfo),
+				showError: !canUploadFileResult.success,
+				error: canUploadFileResult.error,
 				serverInfo
 			});
 			this.forceUpdate();
@@ -378,12 +380,8 @@ class ShareListView extends React.Component {
 
 	renderError = () => {
 		const {
-			fileInfo: file, loading, searching, serverInfo
+			fileInfo: file, loading, searching, error
 		} = this.state;
-		const { FileUpload_MaxFileSize } = serverInfo;
-		const errorMessage = (FileUpload_MaxFileSize < file.size)
-			? 'error-file-too-large'
-			: 'error-invalid-file-type';
 
 		if (loading) {
 			return <ActivityIndicator style={styles.loading} />;
@@ -400,7 +398,7 @@ class ShareListView extends React.Component {
 					: null
 				}
 				<View style={[styles.container, styles.centered]}>
-					<Text style={styles.title}>{I18n.t(errorMessage)}</Text>
+					<Text style={styles.title}>{I18n.t(error)}</Text>
 					<CustomIcon name='circle-cross' size={120} style={styles.errorIcon} />
 					<Text style={styles.fileMime}>{ file.mime }</Text>
 				</View>