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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!