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Buy nowWe appreciate for sharing some updates, @MBSinLA.
Let me route you to the best support who can further check what's causing the error when attaching statements to generated emails in QuickBooks Desktop (QBDT) for Mac.
Since the attachments issue continues even after following the solutions in this thread and while waiting for the update to QBDT for Mac 2020 that adds support for Ventura, I encourage you to reach out to our Technical Support team. They can create a case that triggers an investigation and guide you with a fox in no time. Here's how:
Once everything is all set, you may also want to check out one of our Help pages as your reference to guide you in managing your company's income and customers' data using QBDT for Mac: Sales and customer help for QuickBooks for Mac. It includes topics about processing payments, managing customer information, and customizing forms, to name a few.
Please feel free to leave a comment below if you have other concerns or questions about attaching statements and managing documents in QBDT for Mac. I'm always ready to help. Take care, @MBSinLA.