Microsoft no longer lets you share files larger than 100MB on Skype.
The “file sharing” service on Skype between contacts is extremely convenient and easy, since all you need to do is drop a file into the chat window and it will be transferred to your interlocutor. However, a recent change made by Microsoft brings bad news for fans of this feature.
The company limits file transfers on Skype to 100 MB, so if the file you want to send is larger than that, you will get an error message and be denied the corresponding exchange. The best way to send files larger than 100 MB is to either upload them to OneDrive and then give your contact the link to download them, or simply split the file into multiple 100 MB files and then send them one by one via Skype.
Additionally, if you’re sending files to a contact and lose your internet connection for any reason, Skype now supports automatic pausing, allowing you to resume the transfer when you reconnect. This is especially useful for large files that take longer to upload.
Last but not least, it's worth knowing that files transferred as part of a Skype conversation remain available for download for 30 days. Once this period expires, the download button turns into a thumbnail that displays the message "File unavailable.".
All of these changes have been implemented by Microsoft without much fanfare, and there is a possibility that many of you are surprised by Skype's behavior.

