Can someone please explain Iron Man?

[skates]

Ok. So I achieved Gold status last month and opted into the freerolls. Now it's October. I opt in again and choose freerolls. However, I'm not registered for the freerolls that are running this month and am told I have 20 days to go or whatever again. The freerolls are on the 13th.

How does this work? I'm so confused. The explanations on the site tell me nothing.