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Buy now & saveI am having the same problem as well, and was told the same thing that it was an Outlook issue, not a QuickBooks issue. I just updated to the latest version of Outlook 16.0.13801.20266 and still have the problem.
I did find one work around:
Convoluted? Yes, but it does work!
To me, this is a QuickBooks issue: there has to be some communication between Outlook and Quickbooks since you can go to the Sent Email tab for a customer and see when an email was last sent. I have two different paragraphs that I use from my template depending on the type on invoice-and occasionally I go completely off script and I use my own words. But I at least know when the email was sent. This is an important tool for us and I would like to see this issue resolved.