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 and under 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: