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Hi there, ShopAdmin.
Thank you for coming back to the thread and add further details about your concern in attaching documents in QuickBooks Online. This isn't the kind of feeling that I'd wish you to have, and we know how much time it can take when something isn’t working the way you need it. I'll ensure you'll be routed to the right person to help you ensure that your issue will be resolved.
Since you've done some troubleshooting steps and the issue persists after following the information shared above, I suggest contacting our QuickBooks Support Team. They have the tools to check your account and investigate the cause of why attaching documents stop working.
Here's how to reach them:
Please refer to this article to see different information on how adding attachments works in your different transactions: Attachments in QuickBooks Online.
If there's anything else that I can help you with, please let me know in the comments below. Always around got your back here in the Community.