Sending an email to a Distribution List with 20+ members fails with errors in both Outlook and PGP Desktop Logs.
Task 'firstname.lastname@example.org - Sending' reported error (0x8004210B) : 'The operation
timed out waiting for a response from the sending (SMTP) server. If you
continue to receive this message, contact your server administrator or
Internet service provider (ISP).'
PGP Desktop Logs:
08:17:39 Email Verbose Socket closed by other end
08:17:39 Email Info Message has been blocked by sender
08:17:40 Email Info Message has been blocked by sender
By default, when PGP Desktop is set to encrypt email, it must check each, and every email address for a possible key to encrypt to. This happens as the message is being sent and if you have the public key of the recipient stored locally the search occurs very quickly. However, if you need to check other sources (IE ldap://keyserver.pgp.com, or a PGP Universal Server) this can slow down the process. The longer this process takes, the more likely the SMTP connection will time out.
This can be resolved by:
1. Increase the Timeout. This typically cannot be done at all on ATT, Gmail, Yahoo, or other public free email services. 2. Create a rule to look for a header flag that tells PGP the message is not confidential and does not need to be encrypted. 3. Turn off Opportunistic Encryption. 4. Turn off external key searches so that only the local keyring is searched. This usually reduces the search time for keys to assist in delivering the message. 5. Turn off automatic encryption, and enable a policy of only encrypt if [PGP] is in the headers or the Encrypt button is selected in Outlook. 6. Break the distribution list down into smaller groups.
PGP Desktop 9.x running on Windows or Mac OS X
PGP Desktop 10.x running on Windows or Mac OS X
Imported Document ID: TECH175995
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