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I've been playing with Asterisk at home for awhile now. I've been successful in avoiding having to pay for any service that connects to it. Some of it is the good will of friends in the business, the rest is just taking advantage of freely available services. Case in point: FreeWorldDialup allows for connection to 1-800 numbers for free. Google411 is a 1-800 service which provides business-lookup and will connect you for free.
As my dial plan grew from make-the-phone-on-my-desk-ring to access-the-world, I've had to reorganize it a couple times (note: this is not a painless process!). The end result is that any telephone number on my system, starting with the number "8", is a pattern which provides access to other services.
The remainder of this article discusses the following examples from a dialplan. Please note that names, numbers, and passwords probably have been faked to keep you out of my accounts. :)
; fwd
exten => _81.,1,SetCallerId,${FWDCIDNAME}
exten => _81.,2,Dial(IAX2/555555:PaSsWoRd@iax2.fwdnet.net/${EXTEN:2},60,r)
exten => _81.,3,Congestion
; talkshoe
exten => _82.,1,Dial(SIP/123@66.212.134.192,60,D(${EXTEN:2}#5555551212#))
exten => 629519,1,Goto(stream,201,1)
; iptel
exten => _83.,1,SetCallerId,${FWDCIDNAME}
exten => _83.,2,Dial(SIP/username@iptel.org,60,D(${EXTEN:2},60,r))
exten => _83.,3,Congestion
; gizmo
exten => _84.,1,SetCallerId,("Yournamehere" <17475551212>)
exten => _84.,2,Dial(SIP/${EXTEN:2}@proxy01.sipphone.com,20,r)
In an Asterisk dial plan, patterns are indicated by prefixing the extension with an underscore (example: "_81"). A period (".") is a wildcard. You can trim off the local prefix (i.e., 81, 82, 83, or 84 by referring to the extension your dialing via "${EXTEN:2}". That actually trims off the first two digits that you dialed. So, In the example above, dialing any number starting with 81, 82, 83, or 84 will access FreeWorldDialup, TalkShoe, IPTel, or Gizmo (respectively).
FreeWorldDialup (AKA FWD) allows you to make toll free calls, via FWD, to numbers in the U.S., the Netherlands, the U.K., Norway, and Germany. FWD has a page describing how to dial a toll free number. I think the hard part here is actually getting an account on FWD. Their account application service appears to be a bit buggy as Sparks is still offline (it's been months). If this is an issue, Gizmo5 apparently offers similar 1-8XX access.
In either case, apply for an account on FWD or Gizmo5, read their docs on configuring Asterisk to access their services, and create extensions in your dial plan similar to the example above. (Again, please note that you'll have to edit the usernames, passwords, and/or PINs.)
Google runs a telephone information service which you can access via a 1-800 number. Basically, all you have to remember is 1-800-G00G-411 (i.e., 1-800-466-4411). The service has a speech recognition interface and will even connect the call for you.
Apparently, Gizmo5 also offers a few 1-800 services. You can easily adapt the examples here to access Gizmo5's services.
How do you get around having to remember "81*18004664411"? Simple! Either embed it in your dial plan:
exten => 411,2,Dial(IAX2/555555:PaSsWoRd@iax2.fwdnet.net/*18004664411,60,r)
or build a web-based click-to-call interface (discussed elsewhere in this wiki):