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Turns out the fix was fairly simple—a BIOS upgrade. Upgrading from 0801 to 1406 (the most recent as of this writing, from 2009) fixed it. Direct link to the 1406 BIOS update. Or the P5N-E SLI download page should have the latest.
Yes, this is possible with some dialplan scripting. You would want to use the Dial() application to "pick up and dial the 1st number". With a dumb analog line, you might not get any indication that the call was answered by the remote side. You can either have the first callee enter a DTMF digit when they pick up to indicate that it's time to call the next ...
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