Everything should go through ASSP. ASSP recognizes authenticated connections and allows them to relay. With 1.5.1 and 2.0.0 even SMTPS can go through ASSP if the SSL port is set to 465 (default). With 1.4.3 SMTPS will be ignored if going through ASSP, so some people choose to bypass ASSP with SMTPS.
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