Just an update, for anyone that's been helpful and curious about this. 

I contacted ebay via chat again on a day that i was free, with a bit more assertive tone used. Nothing abusive, just reinforcing my frustration about it and pointing out something that dragged on for more than a month is unacceptable. The CS gave an assurance that it will be looked into and will contact me when it's resolved. 

 

After a week I tried listing again, and lo and behold it's now free. The free listing count also moved, with 3 being used and 37 left after a few autorenewals. I am also able to relist a couple of items, bringing total listing to 21 (42 items across all variations). I am unsure of the exact time/day it was fixed, as when i tried a few days ago the fee still showed up. 

 

So at this stage it seems to be an unexplained bug, and they seem to manage to resolve it but without any explanation so until now I am still unable to say for sure what exactly is the cause. Just want to say thanks to all that have tried helping me with this. Fingers crossed it doesnt come back again when October's monthly free listing starts. 

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Not trying to be too negative but didn't it allow you to use some of your 40 previously and it was only when you'd used a few that it stopped using the 40? If you haven't used all of your 40 yet it may not be fixed yet. I hope it is for your sake though!

It used up some free listings in June and July, but come August none was used. When i noticed i am being charged the fee, it stayed at 40/40 left. Nothing i did changed that, only now that when i see i can list for free again does it count towards the free listing.

I do get what you mean, since Ebay renews the offer every month, it might “refresh” the bug again even if they manually fix it now. I shall see what happens next month.

Keep us posted, please. It is an intriguing issue.