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Buy nowUpgrading to a newer version of QuickBooks Desktop (QBDT) and installing its latest release ensures the program is running with the newest fixes and patches, sjstange. Since it isn't doing so, we encourage you to contact the next available support to further investigate this matter.
To do this, here's how:
Moreover, if you wish to learn what to do when Winmail.dat file is received instead of a .pdf file when sending an email through Outlook from QBDT, please see this article: Winmail.dat is attached instead of a .pdf file when sent from QuickBooks through Outlook.
Additionally, you can customize email templates and use them to send messages from QuickBooks. For a complete guide on how to do this, you can check out this article: Create custom email templates in QuickBooks Desktop.
Please feel free to get back to this thread if you have other concerns about sending emails through Outlook from QBDT. We in the Community are always ready to help you out.