Hi @Stephanie_Oberg and thanks for the report!
I believe this is an expected behaviour, but I definitely understand that it’s not ideal from a Files Tab point of view. I rarely open this tab as part of my workflows, but I just took a look at mine there and it is pretty cluttered I think that keeping attachments on a recurring task can be very useful if they’re report for example. In my case, I’ve have a weekly reporting tasks where I attach CSVs, and I find it easier to have all my CSVs available on one task at the end of the month, rather than searching and downloading attachments from 4 different tasks. But again, that’s a specific example, and I’m sure it doesn’t suit everyone. Being able to filter or to sort attachments within the Files tab could be a potential compromise? I wasn’t able to identify any other reports in the Forum, so I guess not many people use this view, but I’ve escalated a task to our team to consider for a future update.
In the meantime, I genuinely don’t have an efficient solution to remove these attachments… all I can think of is to run an Advanced Search with the exact title of the task, you as the assignee and the filter “has attachments”, and to manually delete attachments in each tasks. It’s seems that you could also use the API (https://developers.asana.com/docs/#get-an-attachment), @Phil_Seeman @lpb @Bastien_Siebman might be able to tell us more about this?