I’m using GpgOL with Outlook2019 to send and receive encrypted emails. I’m facing an issue where I can send encrypted emails successfully, but I’m unable to decrypt them in my “Sent Items” folder. Checked GpgOL settings, but found no explicit option to enable decryption for “Sent Items.” is it a way to configure GpgOL or gpgsm to decrypt mail in “Sent Items”? or any guidence that will help me to resolved the issues? i’m using gpg4win 4.4.0
The email cannot be decrypted because you sent it to other people and their keys were used to encrypt the email.
To decrypt the sent emails you would have to encrypt them with your own key. In other words you would have to add yourself to the recipients.
What you experienced is just the way asymmetric encryption works 
I don’t know if GpgOL has this feature but you could look into the settings to find out if it can automatically encrypt sent email additionally to you.
I understand that emails encrypted with S/MIME cannot be decrypted by the user without the corresponding private key. However, when I send an encrypted message, I expect to have a decrypted copy in my ‘Sent Items’ folder for reference. Instead, the copy in ‘Sent Items’ remains encrypted, and the system reports that it cannot find my private key for decryption. It also lists all the certificates used for encryption, including my own. Therefore, the issue clearly lies within the ‘Sent Items’ handling, not with my ability to decrypt messages in my inbox.
Could this behavior be related to my use of X.509/S/MIME with an on-premises PKI infrastructure? I don’t experience this problem when I generate key pairs in Kleopatra and use OpenPGP; in that case, I can view decrypted sent messages