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I have a number of clients on Small Business Server 2003, which includes Exchange Server 2003. A few of them have AT&T as their ISP.

In an effort to avoid losing email send abilities due to temporarily getting block-listed for a spambot, I would like to hand off email delivery to AT&T instead of delivering it directly (yes, we will still clean up the spambots). AT&T requires SSL, Microsoft does not seem to support it until Exchange 2007.

I have found references to STunnel as a possible work-around, but it looks like the tunnel has to stay up permanently?

  1. Has someone used STunnell successfully in an Exchange 2003/AT&T environment and be willing to share the recipe?

  2. Does someone know of a better solution using Exchange 2003 and AT&T?

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I am not sure about the AT&T bit, but I know Exchange 2003 supports SSL. See the section 'To Configure Encryption' in this kb (823019).

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Thanks for the reply. The KB article you have noted refers to inbound connections for clients, specifically how to configure the Exchange 2003 Server to accept SSL connections from clients. The issue I am struggling with is getting the server to connect to the ISP using SSL. – Raintree Oct 11 '09 at 0:11
Comment Part two - I attempted to substitute TLS for SSL and utilized other parts of the KB recommendations on the server side and completely disabled mail. First AT&T responded with "Address not verified" while using the primary AT&T verified account, and then with "Connection Dropped." Any other help for the server side (outbound) of this issue? Thanks. – Raintree Oct 11 '09 at 0:11
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