outlook changing attachment format

Hi carmpri,

The problem lies with the sender of the email. If it is your pdfs you are sending and the person you sent it to says they get winmail.dat; then, the problem is with your settings in Outlook. If it is you that someone has send a pdf to and you get winmail.dat; then, the problem lies with the senders mail server.

This is what is happening: Outlook uses email coding that is different from other email programs. If one of these other email programs receives an email in Outlook Rich Text coding that it doesn't understand, then it will put that part of the email (formatting and attachments) it doesn't understand in the winmail.dat file and deliver as an attachment. If Outlook sends the email in Plain Text, then winmail.dat will not appear and a pdf attachment would arrive as a pdf attachment rather than in the winmail.dat file. OR If it was an email sent to you: The sender uses Outlook and you use Outlook, then it has to be that the senders email server (ISP) can't handle Rich Text Format (I seriously doubt that this is the case).

The solution is to have Outlook send emails to that address in Plain Text only. By default Outlook will send emails in HTML, which is Rich Text Format and will cause winmail.dat to some receivers. You can change the format before you send the email to that person, but you will need to do this each time you send an email to that person. The best long term solution is to change the default email format for that person to plain text and thus only send Plain text to that address. This is an easy change for Outlook versions up to 2013, but 2016 doesn't have this change function once the address has been added to your contacts. That setting has to be made when the contact is first entered into Outlook 2016. The long term solution for Outlook 2016 is to delete the contact, shut down and restart, type the address to that contact in a new message, right click the address, select Outlook Properties, select the Send in Plain Text Only option, and then you can add the address to your contacts. It will keep the Send in plain text setting. Let me know if you further information.

Hi carmpri,

Outlook Properties (E-mail properties) can be tricky in 2016. This link explains exactly how to do it and also offers a Registry fix to make it easier.

E-Maiil Properties in Outlook 2016

let me know how it goes.

Hi carmpri,

Yes, you can donwload and install the registry fix. I examined the download and it is a safe registry merge file which will add the key without you having to edit the Registry. That being said, it is always best to play it safe.

Here's the safe way to do this:

Click the Windows Start button and in the Search box type "regedit" (without quotes). You will see regedit.exe listed above. Click regedit.exe to open the registry editor. Make sure you open regedit.exe and NOT reg.exe.
In the left pane are the key braches. Select and highlight Computer that is above the branches. This selects the entire registry.
Select File>Export. This opens a Window's Save box. Select a place to save the file and name it Reg Backup Date.reg where Date is the date that the backup was made.

If you ever want to undo what changes you are about to make, then right click this backup reg file and select Merge.

Download the registry fix from that link. It will be a zip file. Extract the files from the zip file and you'll see two files...legacygaldialog.reg and readme.txt file.
Right click the legacygaldialog.reg file and select Merge. This will add the registry fix.

Make sure to close and then reopen Outlook for the change to take effect.

As the link states: After the change, you can now double click on the email address in the Outlook Contact form to get the E-mail Properties dialog. And from there you should be able to select Send Plain Text only.

Hi carmpri,

You are correct. That registry fix is for Outlook 2013, which suffers from the same problem as 2016. The only difference is 15.0 rather than the 16.0.

OK, this is an easy fix. Rather than trust another download, do this:

Open NotePad (it must be Notepad and NOT WordPad or Word)

Copy the following and paste into the new document in NotePad:



Windows Registry Editor Version 5.00

[HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\16.0\common\contactcard]
"TurnOffHoverFunctionality"=dword:00000001
"TurnOnLegacyGALDialog"=dword:00000001



I left the extra lines so you will know what to copy above, but copy only the text.
Save the file by selecting Save as:
When the Save box opens, select where you want to save the file
Name the file Outlook2016fix.reg (you must add the .reg)
In the Save as type below the name select All files (if you save as a txt file it will add .txt to the name which won't work)

Once you have saved the file and see it listed on your PC as Outlook2016fix.reg you can right click it and select Merge as in the prior instructions to add this key to the Registry.

FYI: the procedure above is how you write a registry fix file.

Let me know how it goes.