Hi
@mobeans,
In general, you should be cautious of using a free email account for email that matters. There is generally limited support for free email accounts. What happens if your Hotmail account gets hacked and you lose access to your email and/or it's used to reset passwords and compromise other accounts associated with your Hotmail address?
There isn't much you can do besides adding senders such as SallieMae (and other loan providers) and college email addresses to your contacts and whitelist to try and fix the problem. Did you check your spam folder?
To try and fix the problem going forward, I recommend
buying your own domain name that you could use for the rest of your life, such as "firstNamelastName.com", and associate that domain with a cheap email service such as your registrar who probably offers free email hosting and support with the domain name purchase. The cost of a domain name that has free email hosting is usually at most $10/year after the first year.
If that isn't something you want to do you could try another email service such as Gmail.