Claude not reading project files?

I've noticed many times while working on Claude it'll start printing code based on outdated project files, even though when I have the latest ones uploaded to our project directory. Many times when I tell it that it's referring to old files and to check the latest uploaded files named x.py or x.html, it'll ask me to share the files with it in chat (which ends up using the limits faster). Any one faced this issue and found a workaround?

Note that I have a paid subscription to Claude