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Hello @cls23 ,
Go to your Outlook Options. Select Mail. Scroll down until you reach the Message format section. On the line that says "When sending messages in Rich Text format to Internet recipients:", choose Convert to HTML format.
The emails coming from Quickbooks Desktop are formatted in RTF. If you do not choose the setting above in Outlook, the non-Outlook using recipients will likely receive a winmail.dat file rather than a PDF.
Check out this great info from Diane Poremsky, an ace Microsoft MVP. She explains it very well.
https://www.slipstick.com/problems/outlook-is-sending-winmail-dat-attachments/.
I think that should solve your problem. Good luck!