How to Attach Files on Hotmail
If you have a file that you would like to send to another person through email, you must attach it to an email message. If you have an email account with Hotmail, you can send up to 50 megabytes worth of attachments in a single email message. Attaching multiple files can take time, especially if you have a slower Internet connection.
Go to Login.live.com and sign in to your Hotmail account.
Click the "New" option to compose an email.
Click the "Attachments" option next to "Insert."
Select a file and click "Open" to attach the file.
Enter the recipient's email address into the "To" field and click "Send."