Yes and no.

I have installed gpg4win (latest version) on two machines. Both are Windows XP Home edition with SP2 and Outlook 2003. One works fine. The other goes thru all the motions such as asking for the passphrase, but the mail is sent neither signed nor encrypted.

If someone can give me a hint as to how I might unravel the mystery, it would be appreciated.

Hi Robin,

Check if you have the mail format as plain text and remove word as your mail editior, sign & encrypt your mails.

Check if the recipent key trust level and validity is set.

Hope this helps

I aalways use plain text as my format and have never used word as the editor. The trustleve/validity are correctly set.

The odd thing is that if I use WinPT to send a public key to an email recipient, that email is signed.

Same problem, here

  • and same answers.
    It seams, that many people have problems signing and encrypting plain text mails, though preliminaries are met. I hope somebody will adress the problem :frowning:
    Workaround: The old GData-Plugin. This works.

Well, I have found something interesting on the machine that was giving me trouble. If I send the message in HTML it will convert it to plain text, sign it and send the HTML as an attachment, PGPExch.htm. But, it won’t sign a plain test message. Maybe someone will get a clue as to what is happening.

Hi Robin,

I had a very difficult time when I was asked for migrating users from PGP to GPG and I had tried many free versions of GPG/WinPT and the only one which worked succesfully was GPGTools from try setting up this and it works. let me know your results.


Yes - html is signed and encrypted. plain txt not. I can confirm the porblem.

Since I have two machines, one that works as advertised and one the won’t work with plain text. I am trying to find a way to determine what is different. Any suggestions in tracking this down, are appreciated.