Mysteriously missing encrypted mail and attachments

Anybody got a clue on this one, please?

I am working on Vista Windows Mail using a Comodo certificate. I have exchanged Public keys with two contacts.
One contact sends me an encrypted email with attachments from their XP Outlook Express email address and I receive and can view everything fine.
Another contact sends me an encrypted email with attachments from their XP Outlook 2003 email address and all I receive is a blank message with the .eml extension and no sign of an attachment.

The incoming mail is not tagged as Encrypted.
Their is no message from Microsoft saying anything has been blocked.
I can send encrypted mail to both contacts successfully.
When I Forward the mail back to the recipient, they receive the original mail and attachment which implies that it all actually reached my Windows Mail store.

Is there some hidden switch in Vista, Windows Mail or IE7 which I need to find?

All suggestions welcome…

Oddly enough I am battling with this one too.

My findings suggest that the message is being received fine and that it is certainly a client issue.

If for example you use Outlook (full fat) to receive POP3 you have no problems.

One thing of note is that we attach email usage clauses to all outgoing. Do you do something similar?

kinds regards


I tried using Window Mail a while ago.

Then I tried Outlook Express.

Then I tried Mozilla Thunderbird:

I am hooked on Mozilla Thunderbird, and would highly recommend you give it a try if no one here solves your problem.


Nice to know it is not just me going bananas here. Yes, the Outlook 2003 derived mail which is coming from an Exchange server does arrive with the email disclaimer message as the main message, I then click on an attached .eml file and hey presto I have an empty mail message displayed and no file attachment. looking at the gibberish in the message detail it definitely looks like it contains the content of the oiginal message and attachment based on its size so it does look like it is getting to the client but then what happens, I wonder…

I also have the same problem. I use SecureEmail. When I send an attachment from Outlook 2007 to Windows Live Mail, the attachment does not appear. But when I send it from Outlook to Outlook, it does appear. Any help would be appreciated.

I have Vista Home Premium 64-bit, SecureEmail both 32-bit and 64-bit versions installed, and Outlook 2007, which only comes in 32-bit version. The user’s guide for SecureEmail says you can hve both 32 and 64-bit versions of SecureEmail installed at the same time. The only way Windows Live Mail can even see attachments is if I turn off SecureEmail. Same problem when sending to Outlook Express.


TBH I don’t think that this has anything to do with the certs themselves so the use of the SecureMail" product might be a red-herring here. My thought are it’s the way that OE/WM handles the encrypted mail when it is received, having been passed through to Exchange which has then inserted a signature clause.

I’ve come to this as S/MIME does appear to work to WM from Outlook, but this was from my work exchange system which doesn’t add a sig, rather than the clients which does. I’m highly swayed towards sig addition being the issue

At the minute it would be a pain for us to test this theory for the client system (change management procedure). Are you guys in any better a position to temp disable signature tagging on outbound?

Thoughts are welcomed