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Hi @rabidchkn we have a software solution that might be able to help you to migrate your file attachments from QuickBooks Desktop to QuickBooks Online.
The app is called Zed Axis and works with both QuickBooks Desktop and QuickBooks Online. The process has two steps.
Step One: Axis connects to your QuickBooks desktop company files and gets a list of all the files attachments (including where they are saved) along with the transaction or the list they are attached to and saves that data to an Excel sheet.
Step Two: Axis can then connect to your QuickBooks Online company and you can upload the files in batch from your local desktop and attach to the relevant transaction or lists.
It gives you a good level of control over what is uploaded and how so is flexible to complex migrations. We have a 30 day trial of Zed Axis you can see if it will work for you.