Is that based on Asterisk? I'm not exactly sure how editing the dial plan works on FreePBX as I work on a CentOS patched with OpenVZ and Asterisk installed. If indeed it is Asterisk and you are indeed editing the extensions.conf directly.
Then in your pattern for 08x numbers would be:
exten => _08.,1,Dial(etc.)
exten => _08.,n,Hangup()
And for 086 to go through your ZAP trunk it would be:
exten => _086.,1,Dial(DAHDI/${EXTEN} or ZAP/${EXTEN})
exten => _086.,n,Hangup()
Note that Asterisk matches to the most specific case so 086 would never be matched on _08.
This should be placed in your internal context obviously
That said you can monitor what is happening it by starting asterisk with: asterisk -rvvvvvvvvvv
Reload the dial plan by either executing asterisk -rx "reload" or by running asterisk -rvvvvvvvvvv and typing reload in the CLI or using Asterisk-Java (or any type of AMI interface).
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