Video Screencast Help

Using outlook 2003 with PGP email encryption

Created: 11 Feb 2014 | 12 comments

Noticed that most of my sent items in my archived emails had become garbage which means it is somehow become encrypted.

Can anybody advise?

Operating Systems:

Comments 12 CommentsJump to latest comment

dcats's picture

Hi Stevie.loo,

Please ensure you start the PGP Desktop client (PGPTray must bge running).
You should always restart your email client after starting or stopping PGP Services.

Which is the protocol used for getting the emails in the client (POP, IMAP or MAPI)?

Rgs,
dcats

Stevie.loo's picture

Hi Dcats,

 

Yup i have tried restarted it but the message still shows as garbage. 

I'm using exchange.

 

Regards,

 

Steven Loon

bipshr's picture

Hi there,

Were you prompted to enter the passphrase when you access your Sent Items folder? Can you make sure that the messages in the sent items are secured?

1. Please go to Tools -> Options and click the messaging tab.

2. Confirm the option "Protect all sent messag copies for IMAP/MAPI accounts" checkbox is checked and check what is specified for that option namely "encrypt only", "encrpyt and sign" or just sign the messages.

Best regards,

Bipin

dcats's picture

Hi Steven,

Please right-click the PGP tray icon (grey padlock) and select "Open PGP Viewer".
Then attempt to drag and drop a message into the area "Drag Email or Files here".
Can you decrypt those messages?

Rgs,
dcats

Stevie.loo's picture

Hi Dcats,

 

Yes I can but that should not be the way to go i guess because those were the mails that were sent out by me,.

Stevie.loo's picture

Just for additional information that i only used this pgp for specific client. So rightfully the rest of the mail should not be encrypted right? correct me if i'm wrong.

 

 

Stevie.loo's picture

Hi Bipin,

As soon as i started up my window, pgp would prompt me to key in my password which i did. Nevertheless, i will go to the setting to check base on what you have mentioned. 

Stevie.loo's picture

The weird part is it happens only to my archived sent mails and not all of them were affected. 

dcats's picture

Hi Steven,

This check was simply to ensure the key was working properly.
Which is the protocol used for getting the emails in the client (POP, IMAP or MAPI)?

The email encryption behavior is controled by the policies you can see on the PGP Messaging service section (lower right hand-side).

Disable your network connection (so that you don't receive emails - which may arrive encrypted). If you re-start the Outlook client after exiting PGP services, are you able to read any of the existing emails?
 

Rgs,
dcats

Stevie.loo's picture

Hi Dcats,

If i'm not mistaken, it should be by imap protocol as all my mails were routed from my email service provider. Like i have mentioned, only those archived sent mails on random basis were gabage ( encrypted ). No issue with all my current sent item. Is there any way to decrypt those all at one go? What could be the cause of this? Is hard to isolate the pattern as it is like every 5 sent item mails in my archived 3 were encrypted showing garbage.

 

dcats's picture

Hi Steven,

With IMAP you are like "browsing" the mail server which means that the messages are kept encrypted in the server.
It is hard to say, but I guess it also depends on how that archive processing is done, where it takes place and so on. It is possible that the archiving has corrupted those messages.
For instance, if some indexing process is running and requesting access to the messages it would force the messages to be decrypted.

Rgs,
dcats

bipshr's picture

Hi Steven,

Please apologise if I've misunderstood something. Here is my opinion:

In general, the encrypted emails in the sent items folder remain encrypted because the email was encrypted to the recipient's public key so even though you've sent this email you should see only the cipher text unless you've set either in the policy to encrypt the email to the sender's as well as your public key or if you have under messaging the option to protect all sent message accounts is set to encrypt only or encrypt and sign, then the email is automatically encrypt to two keys – one is the recipient and one is yours.

I think, the archived emails were encrypted to recipient's key only. Can you may be check? If you need help, you can attach the cipher text and your public key to the thread and we can check to which key it was encrypted and compare.

Best regards,

Bipin