A file can be transferred in Skype for Business by opening a chat window, and then dragging a file from your desktop onto the text box. You can also transfer a file by clicking on the paper clip icon in the chat window.

1) Double-click the contact to which you wish to send a file.

2) Use one of the following methods to share a file:

Method 1

Drag one or more files from your desktop and drop them onto the text box in the conversation window.

Method 2

Click on the paper clip icon. Choose the appropriate file and click open.

OUTCOME

You will be able to successfully transfer a file to anyone on your Skype for Business contacts list.