What version of Asterisk are you running? There was an issue found in
February where this exact behavior could occur, two "dialplan reload"
commands would clobber each other. It was also resolved back then in all
supported branches (1.8, 10, and trunk).

http://lists.digium.com/pipermail/asterisk-commits/2012-February/053537.html
For the 1.8 fix if you are curious.

Josh,

I am running 1.4.43, planning on switching to 11 but have not got there...

Thanks

Jerry

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