Rename Skype to something like Skype_bkup.

In the File or Windows Explorer, locate the “Skype” folder.

Press Win + R and in the Run dialog box, type %appdata%.

Kill the Skype process using the Task Manager in Windows.

In Windows 10, this can be done from Settings > Apps. If still the Skype file transfer is not working in your Windows 10 or 7, then you can try these basic troubleshooting steps. You cannot send files to non-Skype contacts.

Make sure the file you are sending to the contact, has accepted your request.

More than that, you need to use OneDrive or any other cloud storage.

The maximum size you can send in Skype is 300MB.

Check the file size before sendinng it.

Due to network connecting issues, if there is a break in file transfer, then it will pause and automatically resume when connection is back.

When the Skype call is over, the file transfer speed will improve again. This will increase the time to transfer the file and sometimes may hang up. Automatically you will get 125KBps download speed. Note: For example, if you have a 6 Mbps connection and you are on a Skype voice-over-call, may be 4 Mbps will be used for voice-call.

If you are on a Skype call and limited bandwidth, then Skype will prioritize voice over file transfer.

First check the following points before you debug the issue. It can be an Office 365 or Server environment or simple web interface. Sometimes due to several reason these doesn’t reach the other contacts. One can add images or include files in Skype IM chats. If the transfer is not working then there could be several reasons. But you could also transfer images and files also.

Skype is generally used for instant messaging services.

Skype download problems