Search Knowledge Base: (Moved) Upload a file to a chat in Microsoft Teams This article has moved to the new OIT Knowledge Base. This article will be retired. Please update your bookmark. There are 2 ways to share files to an MS Teams chat. Both allow you to upload multiple files at a time. Method 1: In your chat window, select the paper clip below the Type a new message box Select OneDrive or Upload from my computer. Find your file and select Share. Type a message and select the send arrow. Method 2: In your chat window, select the Files tab on the top bar. Select Share in the upper left. Select OneDrive or Upload from my computer. Find your file and select Share. Need more help?