Outlook sends .pdf files as .dat

DoctorK12008
DoctorK12008 used Ask the Experts™
on
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?
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Edward PamiasTeam Lead RRS Desk
Top Expert 2016

Commented:
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.
Joe WinogradDeveloper
Fellow 2017
Most Valuable Expert 2018

Commented:
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
IT Manager
Top Expert 2010
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

Author

Commented:
Both answers very helpful.   Thank you.
Joe WinogradDeveloper
Fellow 2017
Most Valuable Expert 2018

Commented:
> 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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