In game, I receive the email informing me that clicking advance will start the transfer portal.
After doing so, it will tell me processing and then nothing. I just receive emails in regards to players transferring and such.
I assume transfer take place in the recruiting screen but I get a red box informing me recruiting isn't available until June.
This is my first time playing into the off season so I feel like I am missing something or doing something wrong.

Sounds to me like you have " CPU Manage Offseason/Recruiting " toggled ON. If so, then the AI handles all each of the sessions within the Transfer Portal.

Click on the hamburger menu (3 parallel horizontal bars in upper left corner of the DDSCB2023 screen, Select "Game Options" and toggle OFF "CPU Manage Offseason/Recruiting". That should make it possible for you to handle each of the tranfer sessions (as well as recruiting and other offseason activities). Do a SAVE after taking changing that feature so you can ensure it sticks..

Thank you so much, I forgot I turned that option on during the season.
Never occurred to me that was the issue.