How to Share Files with Skype Users in Windows

We all know how you can share files, pictures or videos with your Skype acquaintances when you are chatting with them or having a video chat session with someone. It can be done on both one-on-one chat sessions and on group chat sessions. But now there is a much more convenient option for sharing files over Skype. In the new version of Skype, there is a new feature that allows you to share your files with other Skype users directly from the Windows File Explorer.

This feature is available in version of classic Skype for desktop PC. It may not be available for the Skype app that comes pre-installed in Windows 10 or if you install it from the Microsoft Store. For this, you have to download and install classic Skype for desktop PC from You can remove the Skype app from Windows 10 if you want as installing Skype classic for Desktop PC can do everything that Skype app can.

Share Files with Skype Users

Once installed, you will have a new context-menu items called “Share with Skype”. Now you can right-click on any file or a group of files and then select Share with Skype from the right-click menu. As soon as you choose this option, you will be shown a preview of the selected file or files along with a list of your Skype contacts. You can search for Skype contacts from this list as well. You can click on the Send button against any of the contacts to send the files to them.

Share Files with Skype Users

This is a great way to share files with teams and group of people when you are working on a project. You can share files back and forth easily without much hassle. You do not even have to copy-paste anything in the text chat or the video chat sessions.