Hmm, so I turned voicemail off in the UI for extension 103 and the extensions_additional.conf file updated to this:
exten => 103,n,Macro(exten-vm,103,103,0,0,0)Then I called 103 from 100 and it rang for 15 seconds and it sounded like voicemail was going to pick up, but instead it was just a voice that said "I'm sorry" and disconnected the call.
Based on the logs it appears voicemail isn't setup, which makes sense as I turned it off, but why would it update the extensions_additional file to indicate it should go to VM AFTER I turn it off, but not when I turn it on? This is bizarre (to me anyway 
)
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] app_dial.c: -- Nobody picked up in 15000 ms
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-dial-one:44] ExecIf("SIP/100-0000000d", "0?MacroExit()") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-dial-one:45] ExecIf("SIP/100-0000000d", "0?Set(DIALSTATUS=)") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-dial-one:46] GosubIf("SIP/100-0000000d", "0?s-NOANSWER,1()") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-dial-one:47] MacroExit("SIP/100-0000000d", "") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-exten-vm:17] Set("SIP/100-0000000d", "SV_DIALSTATUS=NOANSWER") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-exten-vm:18] GosubIf("SIP/100-0000000d", "0?docfu,1()") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-exten-vm:19] GosubIf("SIP/100-0000000d", "0?docfb,1()") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-exten-vm:20] Set("SIP/100-0000000d", "DIALSTATUS=NOANSWER") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-exten-vm:21] ExecIf("SIP/100-0000000d", "0?MacroExit()") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-exten-vm:22] GotoIf("SIP/100-0000000d", "0?s-NOANSWER,1") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-exten-vm:23] Macro("SIP/100-0000000d", "vm,103,NOANSWER,") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-vm:1] Macro("SIP/100-0000000d", "user-callerid,SKIPTTL") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-user-callerid:1] Set("SIP/100-0000000d", "TOUCH_MONITOR=1449891023.13") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-user-callerid:2] Set("SIP/100-0000000d", "AMPUSER=100") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-user-callerid:3] GotoIf("SIP/100-0000000d", "7?report") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Goto (macro-user-callerid,s,15)
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-user-callerid:15] GotoIf("SIP/100-0000000d", "1?continue") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Goto (macro-user-callerid,s,29)
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-user-callerid:29] Set("SIP/100-0000000d", "CALLERID(number)=100") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-user-callerid:30] Set("SIP/100-0000000d", "CALLERID(name)=Steve M") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-user-callerid:31] Set("SIP/100-0000000d", "CDR(cnum)=100") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-user-callerid:32] Set("SIP/100-0000000d", "CDR(cnam)=Steve M") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-user-callerid:33] Set("SIP/100-0000000d", "CHANNEL(language)=en") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-vm:2] Set("SIP/100-0000000d", "VMGAIN=") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-vm:3] Macro("SIP/100-0000000d", "blkvm-check,") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-blkvm-check:1] Set("SIP/100-0000000d", "GOSUB_RETVAL=") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-blkvm-check:2] ExecIf("SIP/100-0000000d", "0?Set(GOSUB_RETVAL=TRUE)") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-blkvm-check:3] MacroExit("SIP/100-0000000d", "") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-vm:4] GotoIf("SIP/100-0000000d", "1?vmx,1") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Goto (macro-vm,vmx,1)
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:1] Set("SIP/100-0000000d", "MEXTEN=103") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:2] Set("SIP/100-0000000d", "MMODE=NOANSWER") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:3] Set("SIP/100-0000000d", "RETVM=") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:4] Set("SIP/100-0000000d", "MODE=unavail") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:5] Macro("SIP/100-0000000d", "get-vmcontext,103") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-get-vmcontext:1] Set("SIP/100-0000000d", "VMCONTEXT=default") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-get-vmcontext:2] GotoIf("SIP/100-0000000d", "0?200:300") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Goto (macro-get-vmcontext,s,300)
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-get-vmcontext:300] NoOp("SIP/100-0000000d", "") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:6] Set("SIP/100-0000000d", "MODE=unavail") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:7] NoOp("SIP/100-0000000d", "MODE IS: unavail") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:8] GotoIf("SIP/100-0000000d", "1?chknomsg") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Goto (macro-vm,vmx,10)
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:10] GotoIf("SIP/100-0000000d", "0?s-NOANSWER,1") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:11] GotoIf("SIP/100-0000000d", "1?notdirect") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Goto (macro-vm,vmx,13)
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:13] NoOp("SIP/100-0000000d", "Checking if ext 103 is enabled: ") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [vmx@macro-vm:14] GotoIf("SIP/100-0000000d", "1?s-NOANSWER,1") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Goto (macro-vm,s-NOANSWER,1)
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s-NOANSWER@macro-vm:1] Macro("SIP/100-0000000d", "get-vmcontext,103") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-get-vmcontext:1] Set("SIP/100-0000000d", "VMCONTEXT=default") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-get-vmcontext:2] GotoIf("SIP/100-0000000d", "0?200:300") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Goto (macro-get-vmcontext,s,300)
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-get-vmcontext:300] NoOp("SIP/100-0000000d", "") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s-NOANSWER@macro-vm:2] VoiceMail("SIP/100-0000000d", "103@default,u") in new stack
[2015-12-11 21:30:38] WARNING[15991][C-0000000c] app_voicemail.c: No entry in voicemail config file for '103'
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s-NOANSWER@macro-vm:3] Goto("SIP/100-0000000d", "exit-FAILED,1") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Goto (macro-vm,exit-FAILED,1)
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [exit-FAILED@macro-vm:1] Playback("SIP/100-0000000d", "im-sorry&an-error-has-occured") in new stack
[2015-12-11 21:30:38] VERBOSE[15991][C-0000000c] file.c: -- <SIP/100-0000000d> Playing 'im-sorry.ulaw' (language 'en')
[2015-12-11 21:30:39] WARNING[15991][C-0000000c] file.c: File an-error-has-occured does not exist in any format
[2015-12-11 21:30:39] WARNING[15991][C-0000000c] file.c: Unable to open an-error-has-occured (format (ulaw)): No such file or directory
[2015-12-11 21:30:39] WARNING[15991][C-0000000c] app_playback.c: ast_streamfile failed on SIP/100-0000000d for im-sorry&an-error-has-occured
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [exit-FAILED@macro-vm:2] GotoIf("SIP/100-0000000d", "0?exit-RETURN,1") in new stack
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [exit-FAILED@macro-vm:3] Hangup("SIP/100-0000000d", "") in new stack
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] app_macro.c: == Spawn extension (macro-vm, exit-FAILED, 3) exited non-zero on 'SIP/100-0000000d' in macro 'vm'
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] app_macro.c: == Spawn extension (macro-exten-vm, s, 23) exited non-zero on 'SIP/100-0000000d' in macro 'exten-vm'
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] pbx.c: == Spawn extension (ext-local, 103, 2) exited non-zero on 'SIP/100-0000000d'
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [h@ext-local:1] Macro("SIP/100-0000000d", "hangupcall,") in new stack
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-hangupcall:1] ExecIf("SIP/100-0000000d", "0?Set(CDR(recordingfile)=.wav)") in new stack
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-hangupcall:2] GotoIf("SIP/100-0000000d", "1?theend") in new stack
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] pbx.c: -- Goto (macro-hangupcall,s,4)
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-hangupcall:4] ExecIf("SIP/100-0000000d", "0?Set(CDR(recordingfile)=)") in new stack
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] pbx.c: -- Executing [s@macro-hangupcall:5] Hangup("SIP/100-0000000d", "") in new stack
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] app_macro.c: == Spawn extension (macro-hangupcall, s, 5) exited non-zero on 'SIP/100-0000000d' in macro 'hangupcall'
[2015-12-11 21:30:39] VERBOSE[15991][C-0000000c] pbx.c: == Spawn extension (ext-local, h, 1) exited non-zero on 'SIP/100-0000000d'