Thanks for letting us know, tsktsksg. Let me help provide details when uploading file attachments of your transactions so you can have more organised recordkeeping in your account.
In QuickBooks, some specific attachment file types are supported by the program to enable uploads to your transactions. Invalid characters can lead to server errors. To avoid these issues, make sure this only contains accepted characters from the lists below:
If the issue persists, it's best to contact our Customer Care Team to further investigate this issue and provide additional details in resolving this matter. I'm also sharing this resource for more insights: Add or delete attachments in QuickBooks Online.
In case you need help in matching or adding transactions, check out this guide for detailed information: Categorise and match online bank transactions in QuickBooks Online.
I'll always be on this thread for any additional queries you require when managing attachments in your QBO account. Just leave them in the comments below. Stay safe and have a good one.
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