So my Rupp office page has a message on it that I am not renewed for next season, but my manage renewals section shows the auto-renew box checked. There's also a message on there about how renewal settings can't be changed during the season.

Is anyone else seeing this? Is this possibly a bug stemming from the transition from 2.0 to 3.0 and a whole lot of people are at risk of losing their teams at season's end? Or is this something that was always in 2.0 but wasn't as obvious and the auto-renew will kick in despite the ominous red message on the right side of the screen?

That's standard. It's how it works in GD 3.0 as well. It will automatically renew at the renewal deadline, and not before. If it gives you peace of mind, you can renew manually and not see that message.

Disclaimer: Based on GD. I assume it works the same, but you know what assuming does... especially with WIS

I just don't ever remember seeing that message in 2.0...but I'm also notoriously unobservant -- the only reason I saw it on the 3.0 screen is because its in red type as opposed to white so it jumps off the screen at me (not sure what the color blind folks see there, if anything).

rednu, that might be something you want to follow up on, and not take it for granted. I just manually renewed the other day, so this is a bit of apples and oranges, but mine says

or perhaps 3.0 is sending you a message?

I look forward to the day when all of my teams have that message.