Outlook 2007 keeps sending winmail.dat if message uses S/MIME

[Jiri]

If I send message without signature and unencrypted, it arrives correctly as
plain text. But if I add S/MIME signature or encrypt email using S/MIME, it
always arrives as winmail.dat (to the same email address). Of course I'm not
using RTF format. Neither I'm using Exchange server. This behaviour can be
seen with both Plain Text and HTML formats. Any suggestions?

Thanks,
Jiri

 

[Brian Tillman [MVP-Outlook]]

If I send message without signature and unencrypted, it arrives correctly as
plain text. But if I add S/MIME signature or encrypt email using S/MIME, it
always arrives as winmail.dat (to the same email address). Of course I'm not
using RTF format. Neither I'm using Exchange server. This behaviour can be
seen with both Plain Text and HTML formats. Any suggestions?

Does this happen for specific people or everyone? Open the contact record
fpor a person for whom this happens and double-click their e-mail address. IN
the "Internet format" drop-down, what do you see? You should see "Let Outlook
decide...", but if you see "Send using Outlook Rich Text format", that would
explain it.

 

[Jiri]

Dear Brian,
it's dead simple: everything works as expected (no winmail.dat), until I
attach a certificate. All settings are correct (Plain Text in my case), I
triple checked them. Everybody in my address book receives the same: correct
emails without certificate, broken emails if I try to attach certificate.

Thanks,
Jiri

 

[Jiri]

PS: It worked fine in Outlook 2003, but since I upgraded, I have these
problems.

 

[Jiri]

Trying fresh install of OS and Outlook 2007 I found that this bug appeared
after installation of Service Pack 2 of Office 2007. Without SP2 it works
fine. May I ask when Microsoft is going to fix it?

Thanks,
Jiri

 

[Heinz Oesterle]

Hi there,

I had the same problem but with exchange Server included in the game.
My solution was that there is an Option in the Kontakt properties in the GALwhere i Attached a cerificate to: "Use MAPI Rich Text format". After I changed the setting from default to never no winmail.dat anymore.

Maybe there is a similar option in Outlook contacts as in internet format. Maybe set that to "plain text only"?

regards, Heinz

If I send message without signature and unencrypted, it arrives correctly as
plain text. But if I add S/MIME signature or encrypt email using S/MIME, it
always arrives as winmail.dat (to the same email address). Of course I am not
using RTF format. Neither I am using Exchange server. This behaviour can be
seen with both Plain Text and HTML formats. Any suggestions?

Thanks,
Jiri

On Wednesday, February 03, 2010 12:07 PM Brian Tillman [MVP-Outlook] wrote:
Does this happen for specific people or everyone? Open the contact record
fpor a person for whom this happens and double-click their e-mail address. IN
the "Internet format" drop-down, what do you see? You should see "Let Outlook
decide...", but if you see "Send using Outlook Rich Text format", that would
explain it.