Annual Cost Confusion

I've been using YNAB for years now and feel like I'm usually fairly competent with the app. However, this year, I am confused by the "each year" behavior.

So I have an insurance payment for which I'm planning 750€ each January. Obviously, in Jan 2026, the payment went out as planned. Now, however, the plan seems to assume that I have already "assigned" the amount I paid and only wants me to budget tiny amounts. Regardless of whether I choose "refill up to" or "set aside another", it always seems to treat the money already spent as if it's still in the budget.

The weird part is also that it shows me "Assigned so far" as 663€, but that's neither the money assigned so far this year nor the amount paid in January plus the amount assigned this year. I have no idea where that number comes from.

What am I doing wrong here? I'd appreciate any pointers!