However, when I try to do this on a windows machine, no matter what client
I use - Outlook, Outlook Express, Eudora - even though I select Send on
Check, it still actually tries to send the email before it has checked for
email (and been authenticated). As a result SIMS refuses to relay the
email.
As somebody else pointed out, Outlook's button IS Send/Receive...It's going to try sending first... Meaning your users must either hit it twice in rapid succession (since SIMS will authenticate the client when they check the box) or you must attempt an alternative.
I suggest a VPN or encrypted tunneling solution... For instance...
Place an SSH server on the local segment of your network with your mail server. Then have your customers tunnel ports 25 and 110 to the SSH server, which will forward on SMTP and POP connections to the mail server...
THEN, if you make your SSH server's local IP a legal "client" your customers will be able to send before receiving, since the SMTP connection will seem to be coming from the SSH server, not the "wild" internet.
PLUS, as an added benefit, your users' passwords will now be encrypted when sent across the public portion of the network...Means it is harder to compromise your mail server's integrity by simply sniffing the wire.
For more information about SSH, check out http://www.openssh.org/
There are also some really good books out there on SSH... I got a lot from the O'Reilly book.
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