Transmitting large encrypted messages



I use digital signatures and encryption to transfer sensitive data to and
from customers, and have found that Outlook 2002 SP2 (on a P IV computer
running WIN XP Pro SP1, standalone, but with broadband internet access)
times out when trying to send an email with an attachment as small as 1 meg.
The error message is that the ISP SMTP server has timed out. The ISP
technicians tell me, not so, it's Outlook's problem.

In troubleshooting, I've changed Outlook's automatic send/receive timing to
look every 5 minutes from every 1 minute.

No change.

Outlook still tries to send the message every minute, the message stays in
the outbox, and the recipient gets a new message every minute, until I
remove the message from the outbox.

I've tested Outlook Express, and it works just fine, even though the 1 meg
file takes about 2 minutes to encrypt.

When I send a small encrypted message via Outlook, it goes just fine.

My ISP accepts 10 meg messages, and my mailbox holds 15 meg, so that's not
the problem.

I've also found (and verified through my PKI certificate issuer) that
Outlook will not let me send an encrypted message to myself. Outlook
Express handles this just fine.

How do I configure Outlook 2002 to work with large encrypted messages? This
isn't a minor problem. The entire Department of Defense is going to digital
PKI signatures and encryption, and most run Office.






I got my own answer.

Increased server timeout setting in Outlook. Then the message could be
encrypted (it took about two minutes) before Outlook timed out and tried to
send again.


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