@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. (thanks to @rg305 and @Bruce5051 for the sleuthing here).
I think the next step is for you to show us the full logs from Asterisk where it is showing an error connecting to us-east-va.sip.flowroute.com:5061. Can you do that?