Hi @Christopher_Alvarez and thanks for reaching out!
Sorry to hear you’re running into trouble here! Could you please try logging into your Asana account from an incognito window (or with a different browser), and let me know if you’re having the same issue?
Also please note there is a 100MB per file limit for attachments from your computer. If you have a larger file, consider attaching it from Dropbox or Google Drive. More info: Adding comments & attachments to tasks | Product guide • Asana Product Guide
Looking forward to your reply!