Skype now lets you send files when recipient is offline
Not only does this improvement make it easier to send and receive files, but it allows the recipient to access the file across multiple devices without needing to request it multiple times.
The file transfer feature will allow you to send files of up to 300MB in size. Microsoft says that this is more than enough to handle most files sent via Skype. And for everything else, we’re sure that Microsoft would like you to use OneDrive.

