TLS Error on 1.6 and 1.8

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Trying to setup UM with Office 365 which requires TLS. I’ve tried under 1.8.5.0 and under 1.6.2.16.1 and I get the same error:

[Aug 11 06:50:20] VERBOSE[3023] tcptls.c: SSL certificate ok
[Aug 11 06:50:20] VERBOSE[3023] tcptls.c:   == Problem setting up ssl connection: error:00000000:lib(0):func(0):reason(0)
[Aug 11 06:50:20] WARNING[3023] tcptls.c: FILE * open failed!

Following the following two guides:

https://wiki.asterisk.org/wiki/display/AST/Secure+Calling+Tutorial

http://www.msexchange.org/articles_tutorials/exchange-server-2010/mobility-client-access/how-configure-unified-messaging-asterisk-sip-gateway-part2.html

Thanks