diff --git a/CHANGELOG.md b/CHANGELOG.md
index 622dbce0..9670a432 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -28,6 +28,10 @@ Release date: TBD
  - Fixed desktop notifications not working when the window has been minimized from inactive state.
  [#522](https://github.com/mattermost/desktop/issues/522)
 
+#### Mac
+ - Fixed an issue where the text box didn't keep focus after uploading a file.
+ [#341](https://github.com/mattermost/desktop/issues/341)
+
 ---
 
 ## Release v3.7.0
diff --git a/src/browser/components/MainPage.jsx b/src/browser/components/MainPage.jsx
index 9fa6ae70..965066a5 100644
--- a/src/browser/components/MainPage.jsx
+++ b/src/browser/components/MainPage.jsx
@@ -104,6 +104,10 @@ const MainPage = createReactClass({
     ipcRenderer.on('add-server', () => {
       this.addServer();
     });
+
+    ipcRenderer.on('focus-on-webview', () => {
+      this.focusOnWebView();
+    });
   },
   componentDidUpdate(prevProps, prevState) {
     if (prevState.key !== this.state.key) { // i.e. When tab has been changed
@@ -207,6 +211,11 @@ const MainPage = createReactClass({
       showNewTeamModal: true
     });
   },
+
+  focusOnWebView() {
+    this.refs[`mattermostView${this.state.key}`].focusOnWebView();
+  },
+
   render() {
     var self = this;
 
diff --git a/src/main/mainWindow.js b/src/main/mainWindow.js
index 74d37fae..da3a1b55 100644
--- a/src/main/mainWindow.js
+++ b/src/main/mainWindow.js
@@ -108,6 +108,10 @@ function createMainWindow(config, options) {
     }
   });
 
+  mainWindow.on('sheet-end', () => {
+    mainWindow.webContents.send('focus-on-webview');
+  });
+
   return mainWindow;
 }