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Eudura and Encrypted emails cant be read.

Posted on 2007-03-20
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Last Modified: 2013-12-19
I have user running windows xp on a laptop and on a workstation.  When he was in this country i setup s/mime for him on his Eudora client with the s/mime plug in from qualcomm.  He was able to send and receive encrypted emails to users in our office.

When he went back to Germany and exported his key to his desktop using the same Eudora client and the S/mime Plug in from qualcomm.  He can read and encrypt email he now receives on his workstation but any of the emails he received on his laptop prior to install the cert he cant read.

what should i tell him to try ?
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Question by:vannyx
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by:Sanktwo
ID: 18788217
So, he exported his key to his desktop, and without doing anything else to his laptop he can no longer read mails on his laptop which were received prior to the time that he exported his key to his desktop????

Can you explain what happens when he tries to open the old mail on his laptop. Does he get an error message and what is it?  Did any of his communicants change his key on their end during this period? Can he open all new mail on both laptop and desktop?
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by:vannyx
ID: 18788246
he has no problem with the messages on his laptop he can open them fine.  But he tried to open them on his desktop without setting up the client for with his certificate.  When it failed he realized his error and then setup his client with this cert on his desktop.  so now on his desktop he can only read message that are encrypted that arrived after he setup s/mime on his desktop all the onces prior he can not access it doesnt decrypt.  Nothing changed on the other end with his public key.
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Sanktwo earned 250 total points
ID: 18788426
I cannot imagine why the insertion time into the MS store is so critical. I am as baffled as you. Unfortunately, although I have s/mime plugin loaded, I do not have a personal cert, so I cannot test this myself. One other thought, does the plug in give an error message when failing to decrypt? e.g. anything to do with time?

If your user is determined to get to the bottom of this, there is an experiment he could try (though not trivial). Get a copy of OpenSSL (e.g. http://www.slproweb.com/products/Win32OpenSSL.html) and use the http://www.openssl.org/docs/apps/smime.html command line decoder to decode the attachments straight from Eudora's attachments directory.
e.g. openssl smime -decrypt -in mail.msg -recip mycert.pem -inkey key.pem
where mail.msg is the encrypted mail message in the attachment directory.

This will tell him whether anything has gone wrong with these files causing the failure to decode. The date of installation into the MS certificate store will then be irrelevant.

I have no experience of doing this, nor can I vouch for the security or otherwise of the above URLs. OpenSSL does have a good reputation though.

Sorry that I cannot be of more direct assistance.
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by:vannyx
ID: 18788437
thank you i will get into it with him during the week
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