Are you being charged for the listings that have dates in the past? If not I'd consider that free listings - a benefit.
I have the same issue with all my listings that never seem to expire. It sounds great but I’ve been worried that I would get a big retrospective fee when they do find out. Therefore I have been deactivating them myself on the expiry date and then I can pay the relisting fee if I want to reactivate them. I haven’t bothered approaching Etsy support about it as I don’t have that many listings and it’s not really a big hassle to me.
That is exactly what I have been doing. I deactivate them and then to re-list I make a copy and then delete the deactivated one.
here's another thread on it:
Why are my February 28 listings NOT expiring? - Welcome to the Etsy Community
I now have half of my 700 + listings that have expired dates that are not expiring. It is very strange.
Someone said it was listings made or renewed on the 31st of the month getting thrown off by months that are 30 (or 28/29) days long. Hmmm need to test that out tomorrow!
Yes! I just noticed this in my own listings. I will think, that should have expired by now and see the next expiration will be 3 months out. This is not something I've had problems with in the past.
Part of my listings are set to automatically renew and others aren't. I have quite a few that are on auto renew that haven't been renewed while others were renewed. For some it may have been ones from Feb. 29th and 31st of months, however none of mine are. Has been going on for months now and is random dates. The ones that are on manual renew I usually renew day they are set to expire. I have watched and am getting views on the ones that haven't renewed when they should have. It is definitely weird. I'm like OP I've been worried they will all renew at once and I will get a big bill all at once when I'm slowest this summer.
Bonus!
I've report this since Dec 2. Many chats and emails. I've posted on forum to sort listings by expiry date. Currently I have 450ish of 750ish listings dated back for renew still. They still show how many renewals but it's been totally ignored for many months. Others think I'm getting free listings but not when you see where it shows renewals. It must affect something.