No I did end up changing my studentaid email to an SL alias, though I might wanna change it back if it keeps having issues. The issue is that icloud bounced the email, and SimpleLogin itself gave me an email each time one got bounced, with to go to simplelogin.com and see the bounced email.

An email sent to your alias redacted@simplelogin.com from donotreply@studentaid.gov was bounced by your mailbox redacted@icloud.com