diff --git a/app/actions/views/file_upload.js b/app/actions/views/file_upload.js
index a9c62124a..14753182f 100644
--- a/app/actions/views/file_upload.js
+++ b/app/actions/views/file_upload.js
@@ -107,6 +107,14 @@ export function handleClearFiles(channelId, rootId) {
     };
 }
 
+export function handleClearFailedFiles(channelId, rootId) {
+    return {
+        type: ViewTypes.CLEAR_FAILED_FILES_FOR_POST_DRAFT,
+        channelId,
+        rootId
+    };
+}
+
 export function handleRemoveFile(clientId, channelId, rootId) {
     return {
         type: ViewTypes.REMOVE_FILE_FROM_POST_DRAFT,
diff --git a/app/components/post_textbox/index.js b/app/components/post_textbox/index.js
index de3571ba6..a24489d00 100644
--- a/app/components/post_textbox/index.js
+++ b/app/components/post_textbox/index.js
@@ -13,7 +13,7 @@ import {getCurrentUserId} from 'mattermost-redux/selectors/entities/users';
 import {executeCommand} from 'app/actions/views/command';
 import {addReactionToLatestPost} from 'app/actions/views/emoji';
 import {handlePostDraftChanged, handlePostDraftSelectionChanged} from 'app/actions/views/channel';
-import {handleClearFiles, handleRemoveLastFile, handleUploadFiles} from 'app/actions/views/file_upload';
+import {handleClearFiles, handleClearFailedFiles, handleRemoveLastFile, handleUploadFiles} from 'app/actions/views/file_upload';
 import {handleCommentDraftChanged, handleCommentDraftSelectionChanged} from 'app/actions/views/thread';
 import {getTheme} from 'mattermost-redux/selectors/entities/preferences';
 import {getCurrentChannelDraft, getThreadDraft} from 'app/selectors/views';
@@ -42,6 +42,7 @@ function mapDispatchToProps(dispatch) {
             createPost,
             executeCommand,
             handleClearFiles,
+            handleClearFailedFiles,
             handleCommentDraftChanged,
             handlePostDraftChanged,
             handleRemoveLastFile,
diff --git a/app/components/post_textbox/post_textbox.js b/app/components/post_textbox/post_textbox.js
index 638923395..1af1b4975 100644
--- a/app/components/post_textbox/post_textbox.js
+++ b/app/components/post_textbox/post_textbox.js
@@ -29,6 +29,7 @@ class PostTextbox extends PureComponent {
             handleCommentDraftChanged: PropTypes.func.isRequired,
             handlePostDraftChanged: PropTypes.func.isRequired,
             handleClearFiles: PropTypes.func.isRequired,
+            handleClearFailedFiles: PropTypes.func.isRequired,
             handleRemoveLastFile: PropTypes.func.isRequired,
             handleUploadFiles: PropTypes.func.isRequired,
             userTyping: PropTypes.func.isRequired,
@@ -208,7 +209,7 @@ class PostTextbox extends PureComponent {
             return;
         }
 
-        const {files} = this.props;
+        const {actions, channelId, files, rootId} = this.props;
         const {value} = this.state;
 
         const isReactionMatch = value.match(IS_REACTION_REGEX);
@@ -235,7 +236,11 @@ class PostTextbox extends PureComponent {
                     text: intl.formatMessage({id: 'mobile.channel_info.alertNo', defaultMessage: 'No'})
                 }, {
                     text: intl.formatMessage({id: 'mobile.channel_info.alertYes', defaultMessage: 'Yes'}),
-                    onPress: this.sendMessage
+                    onPress: () => {
+                        // Remove only failed files
+                        actions.handleClearFailedFiles(channelId, rootId);
+                        this.sendMessage();
+                    }
                 }],
             );
         } else {
diff --git a/app/constants/view.js b/app/constants/view.js
index 2ccaa3813..7914a8d62 100644
--- a/app/constants/view.js
+++ b/app/constants/view.js
@@ -33,6 +33,7 @@ const ViewTypes = keyMirror({
     RETRY_UPLOAD_FILE_FOR_POST: null,
 
     CLEAR_FILES_FOR_POST_DRAFT: null,
+    CLEAR_FAILED_FILES_FOR_POST_DRAFT: null,
 
     REMOVE_FILE_FROM_POST_DRAFT: null,
     REMOVE_LAST_FILE_FROM_POST_DRAFT: null,
diff --git a/app/reducers/views/channel.js b/app/reducers/views/channel.js
index 9c2b908c2..8c239599e 100644
--- a/app/reducers/views/channel.js
+++ b/app/reducers/views/channel.js
@@ -188,6 +188,18 @@ function handleRemoveLastFileFromPostDraft(state, action) {
     };
 }
 
+function handleRemoveFailedFilesFromPostDraft(state, action) {
+    if (action.rootId) {
+        return state;
+    }
+
+    const files = state[action.channelId].files.filter((f) => !f.failed);
+    return {
+        ...state,
+        [action.channelId]: Object.assign({}, state[action.channelId], {files})
+    };
+}
+
 function drafts(state = {}, action) { // eslint-disable-line complexity
     switch (action.type) {
     case ViewTypes.POST_DRAFT_CHANGED:
@@ -208,6 +220,8 @@ function drafts(state = {}, action) { // eslint-disable-line complexity
         return handleUploadFilesFailure(state, action);
     case ViewTypes.CLEAR_FILES_FOR_POST_DRAFT:
         return handleClearFilesForPostDraft(state, action);
+    case ViewTypes.CLEAR_FAILED_FILES_FOR_POST_DRAFT:
+        return handleRemoveFailedFilesFromPostDraft(state, action);
     case ViewTypes.REMOVE_FILE_FROM_POST_DRAFT:
         return handleRemoveFileFromPostDraft(state, action);
     case ViewTypes.REMOVE_LAST_FILE_FROM_POST_DRAFT:
diff --git a/app/reducers/views/thread.js b/app/reducers/views/thread.js
index 489e2d9f8..bb372422b 100644
--- a/app/reducers/views/thread.js
+++ b/app/reducers/views/thread.js
@@ -192,6 +192,18 @@ function handleRemoveLastFromPostDraft(state, action) {
     };
 }
 
+function handleRemoveFailedFilesFromPostDraft(state, action) {
+    if (!action.rootId) {
+        return state;
+    }
+
+    const files = state[action.rootId].files.filter((f) => !f.failed);
+    return {
+        ...state,
+        [action.rootId]: Object.assign({}, state[action.rootId], {files})
+    };
+}
+
 function drafts(state = {}, action) { // eslint-disable-line complexity
     switch (action.type) {
     case ViewTypes.COMMENT_DRAFT_CHANGED:
@@ -212,6 +224,8 @@ function drafts(state = {}, action) { // eslint-disable-line complexity
         return handleUploadFilesFailure(state, action);
     case ViewTypes.CLEAR_FILES_FOR_POST_DRAFT:
         return handleClearFilesForPostDraft(state, action);
+    case ViewTypes.CLEAR_FAILED_FILES_FOR_POST_DRAFT:
+        return handleRemoveFailedFilesFromPostDraft(state, action);
     case ViewTypes.REMOVE_FILE_FROM_POST_DRAFT:
         return handleRemoveFileFromPostDraft(state, action);
     case ViewTypes.REMOVE_LAST_FILE_FROM_POST_DRAFT: