While Microsoft's Skype software is certainly not the best way to send files to contacts, it is without doubt convenient to do so if you are using the software anyway.
All you need to do is select a contact and the send file icon, pick a file from the local system to transfer it to the contact.
Sharing files seems limited to the Skype desktop program at the moment, the Skype app for Windows supports the sending of images only it seems at this point in time.
Microsoft announced several changes coming to sharing files in Skype for the desktop recently. These were not published on the official Skype blog but only on a support page though which makes it likely that many users missed them.
First the good news: when you share files using Skype, it will automatically sync across all devices that you are using.
This means that downloads are available on mobile devices as well automatically. Microsoft also notes that transfers will resume automatically if the connection is lost for whatever reason so that files need to be downloaded only once.
Bad news is, that Microsoft is limited the size of files that you can share using Skype to 100 Megabyte per file
If you try to send a file that is larger than 100 MB you will get the error message not sent - file is larger than 100.0 MB.
The "learn more" link leads to the support page linked above that details that you cannot share files larger than 100 Megabyte using Skype.
Also, files have a 30-day time limit after which they expire and cannot be downloaded anymore. Files that you have shared that exceed 30-days will show up as file unavailable instead.
Microsoft's proposed solutions for sharing files larger than 100 Megabyte? OneDrive of course.
This is obviously not as comfortable as sending files directly using Skype, and it is unclear why Microsoft did not integrate the OneDrive option directly into Skype to make this comfortable for users.
Basically, what users need to do know is open OneDrive next to Skype when they want to share files larger than 100 Megabyte, upload the file to their OneDrive account, right-click on it, select share, get the share link, and paste it into Skype chat.
Not nearly as comfortable as sending files directly. Also, some users are experiencing slow uploads to OneDrive making the solution less than ideal for sending large files to contacts who are online at that time.
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Ghacks is a technology news blog that was founded in 2005 by Martin Brinkmann. It has since then become one of the most popular tech news sites on the Internet with five authors and regular contributions from freelance writers.