I have solved this issue, and I am now automatically running a login script to my school.
Here are the steps involved:
1. Edit your /etc/lynx.cfg file. Make the following changes:
ACCEPT_ALL_COOKIES:TRUE
FORCE_SSL_PROMPT

ES
2. Create a text file with the following contents:
(echo '$username'; echo '$secretpassword'; echo '\33[B') | lynx -term xterm -accept_all_cookies
https://school.login.html >> /path/tofile/login_result.txt
Breaking this little script down, what this does is pass in two values to the login as they are requested. The echo '\33[B' is equivalent to a spacebar press I inserted just to test the functionality of the echo. Using lynx, the -term xterm is used to specify the type of terminal used to execute the script. The tag -accept_all_cookies is used to do just that. Then comes the website you desire to login to, and finally a redirected output to a txt file to test the script. If the script runs successfully, you will have a file created with the results of the page you reach after you login.
To top this off, run a cron job that executes at the time you desire to login. I recommend running it often at first to test its functionality, and then just setting it to the time you desire to access the page.
I hope this helps someone subvert the horrors of having to automatically log yourself in to let your employer know you are alive.
SickFreak