Outlook sends .pdf files as .dat

Sometimes when I send a .pdf file as an email attachment in Outlook 365, the recipient gets a .dat file instead of a .pdf.   How do I prevent this?
DoctorK12008Asked:
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Jackie ManConnect With a Mentor Commented:
Agreed.

Have a look of my answered question below also.

O365 and winmail.dat file
https://www.experts-exchange.com/questions/27778217/O365-and-winmail-dat-file.html
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Edward PamiasTeam Lead RRS DeskCommented:
Try using HTML as the email format instead of rich text.

To prevent Outlook from attaching winmail.dat when you send an email:

    Click File in Outlook.
    Select Options.
    Go to the Mail category.
    Make sure HTML or Plain Text is selected for Compose messages in this format: under Compose messages.
    Now make sure Convert to HTML format or Convert to Plain Text format is selected for When sending messages in Rich Text format to Internet recipients: under Message format.
    Click OK.
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Joe Winograd, EE Fellow 2017, MVE 2016, MVE 2015DeveloperCommented:
Hi DoctorK,
This is a very common, nasty problem, and there is no one solution that works for everyone. If you search EE by putting "winmail.dat" in the search box above, you will get 921 hits with thousands of views among them. I suggest reading some of those threads and trying some of the fixes that worked for other members, but this is definitely a YMMV (Your Mileage May Vary) issue.

I've participated in many questions here at EE on this same problem. Here are several of them:

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_28616021.html

http://www.experts-exchange.com/Software/Office_Productivity/Groupware/Outlook/Q_28129365.html

http://www.experts-exchange.com/Software/Misc/Q_28199110.html

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_28605102.html

http://www.experts-exchange.com/Software/Office_Productivity/Groupware/Outlook/Q_28512378.html

I hope one of these has a solution that works for you. Regards, Joe
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DoctorK12008Author Commented:
Both answers very helpful.   Thank you.
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Joe Winograd, EE Fellow 2017, MVE 2016, MVE 2015DeveloperCommented:
> Both answers very helpful.   Thank you.

You're welcome. But if "both answers [were] very helpful", why did you mark just one of them as a Solution?
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