Decrypt Sent PGP Email - thoughts

If I understand the dynamic correctly, you cannot decrypt an encrypted sent PGP email because you haven’t the receiver’s private key…fair enough.

It would seem it would then be useful to allow me to CC myself on an email using my key pair so that I can decrypt the message with my credentials. It does not seem that gp4win (outlook plugin anyway) allows this.

Can someone confirm this or advise on the steps I’m missing. Also I think this would be a terrific addition to the plug-in if not currently available.

I don’t know about Outlook but Thunderbird keeps a copy in the ‘Sent’ box and this I can open using my own passphrase. It’s all taken care of by the software.
Did you try opening the copy in your ‘sent’ mailbox ?

Thanks for the reply. Yes I tried opening the sent, it is encrypted.
When trying to decrypt - it fails (presumably because of the other side’s key)

You can never decrypt anything encrypted with someone elses public key. Only the key creator can decrypt the file even though you encrypted it. Keep a copy of the unencypted file as the encrypted one will be useless to you.

This is as I believed and why it would be a great ability to CC yourself that way you can decrypt your sent email. This is a feature currently lacking on the Outlook plugin. You can only send to a single recipient.

The new release of Gpg4win (2.2.0) has more stuff for GpgOL and might be worth looking at.
Regarding being able to decrypt ‘sent’ emails, see following extract from page 53 (chapter 8.3.1) of the Enigmail Handbook :

“Additionally, the message is also automatically encrypted with your own public key, to allow you to read (from the Sent folder) the messages you sent. This setting is regulated by the option OpenPGP ¨ Preferences ¨ Sending ¨ Add my own key to the recipients list, and we recommend you leave this option checked.”

I use enigmail with Thunderbird and this works for me as I noted below. But perhaps more interesting is the reference to an OpenPGP preference. Maybe there is something you could set up yourself to get Outlook to add your own key to the recipients list ?