There's a Size Limit When Sending Attachments with Hotmail
Be aware, though, that there's a limit to the total size a message you send from Windows Live Hotmail can reach (counting both the message text and attached files):
- You can send up to 200 attachments up to 50 MB each (9.8 GB total) per email.
This means that all attachments to a Windows Live Hotmail message plus the message text must not take more space than about 10 GB. Large files and photos will be uploaded to SkyDrive so recipients are not restricted by their email service's size limits.
If you want to send something even bigger, you can try sending it in smaller chunks or employ another file sending service.