The thread over at Trying to use tls with no luck - #25 by Bruce5051 is pretty informative about what @hraycrum69 is trying to do. @hraycrum69 based on your posts, and TLS Requirements, I think you are trying to get Asterisk connect to us-east-va.sip.flowroute.com:5061 as a TLS client. Flowroute's instructions are unusual because they ask for a publicly trusted WebPKI certificate as a client certificate. Not totally invalid, but also not commonly done.
@rg305 mentioned the "short chain" vs "long chain" issue in that thread, but I think that is probably not the problem you have. Since this isn't about short vs long, I'm going to reopen and rename the original thread and post my thoughts there.