Categories: Google Apps Sync for Microsoft Outlook :

Is Google Apps Sync for Outlook compatible with PGP Desktop Message Encryption?

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Is Google Apps Sync for Outlook compatible with PGP Desktop Message Encryption? rich_schaaf 4/30/12 11:46 AM
My company recently transitioned email to use Google Apps for Business.  Most of us are using Microsoft Outlook as our email client and we are now syncing our Google email, contacts and calendar info with Google Apps Sync for Outlook.

I've been using PGP Desktop Professional to encrypt email messages.  I believe PGP Desktop works by intercepting incoming and outgoing email messages to/from the email client and decrypting/encrypting them on the fly.  Now that I'm using Google Apps Sync, PGP Desktop seems to no longer be able to intercept email messages.  Will I need to shift over to using IMAP and SMTP to access my GMail in order for PGP Desktop to work?

If I do shift to IMAP and SMTP for email access. can I still use Google Apps Sync to synchronize my calendar and contacts with Outlook?  If not, what other alternatives are available/recommended for syncing contacts and calendar info between Google and Outlook?

Kind regards,
Rich
Re: Is Google Apps Sync for Outlook compatible with PGP Desktop Message Encryption? Derek_R 4/30/12 1:17 PM
R,

Interesting question,

I think you might encounter problems trying to sign and encrypt using

SSL certificates with Gmail. Even using IMAP/SMTP with Outlook, the email is actually sent/rcvd

through Google servers which AFAIK are not geared up to handle public/private

key encryption. There could be a few issues with email headers,  DKIM etc.

Unless someone knows different :-) 

There is an addon for Firefox available that enables you to encrypt with SSL certs. from the gmail UI.


It would be interesting to know if you can get PGP working on GoogleApps email.


Re: Is Google Apps Sync for Outlook compatible with PGP Desktop Message Encryption? rich_schaaf 4/30/12 1:35 PM
Hi Derek,

Thanks for the reply.

AFAIK, PGP Desktop encryption works as a proxy for incoming / outgoing email between the Outlook client and the server.  The connection between Outlook and PGP is unencrypted so that PGP is able to look inside the email messages and encrypt/decrypt the message content as required, and the connection between PGP and the mail server is typically protected using SSL.

Does Google Apps Sync use the MAPI/Exchange protocol to communicate with Outlook?  If so, I think PGP messaging services are supported for that protocol, but I need to configure the name of the incoming/outgoing mail server and I'm not sure what host name to use for Google's mail server.  Any suggestion?

Kind regards,
Rich
Re: Is Google Apps Sync for Outlook compatible with PGP Desktop Message Encryption? Derek_R 5/1/12 2:00 AM
R,

Does Google Apps Sync use the MAPI/Exchange protocol to communicate with Outlook?

Got no idea :-)

what host name to use for Google's mail server.

What mail server are you referring to ?

imap.gmail.com ?   smtp.gmail.com ?  or the mail server that the web UI uses ?

To investigate how Outlook actually communicates with Gmail/GApps, I recommend

the use of Wireshark NPA  (free download at wireshark.org)

It's a protocol analyser that will show you the TCP/IP conversations that are going on

and what is communicating with what on a packet level.