Hi @nickQ , and welcome to the community!
It really depends on the use-case. Are these data files incremental information over previous versions?
If so, then yes, as much as possible you should avoid piling files as you will be charged on storage.
Now, to your original issue. This is expected. And the solution is only one of two, if you want to delete the old files:
- You can add a file not only to an assistant, but to a thread. So once you’ve uploaded the new file to your assistant, you could also add the file id to any active threads.
- When an old thread becomes active (user sends a new message) what you do is copy all of that thread’s history into a new thread, that will have access to the newest files. Effectively copying the context but getting access to the new files.
Cheers!