JEDI-JF
I have a collection of fw that includes:

But I have never used an OBi100 and can't vouch for what I have. I'd wait for an OBi100 user here to comment.
TLS settings for my OBi202 (ignore the WORD spell checker underlining):

The X_OutboundProxyTransport default setting is Follow ProxyServerTransport. Maybe the OBi100 already does the same, so not the issue(?)
I do set ProxyServer to washington1.voip.ms... the server number was required for TLS. Try appending the server number and see if that makes a difference.
I also enable X_SymmetricRTPEnable and set X_SRTP to SRTP Only. I believe both are required. Poly firmware exposes the X_SRTPCryptos setting, but I suspect that will not be exposed on the OBi100... it is not exposed on my OBi202 3.2.2 (Build: 5921EX).
OE