If you search the Asterisk bug tracker with outboundproxy you'll get a
few hits. This is the latest one:

http://bugs.digium.com/view.php?id=12006

The way I use outboundproxy is via realtime and apply it to each
sipaccount. If you set the outboundproxy for each of your SIP accounts
in sip.conf then when you dial that SIP account it should be sent via
the outboundporxy address specified in sip.conf.

Regards,

Greyman.

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