Hi jacob.andersen,
My name is Anthony and I am a member of the wolfSSL team.
I don't think I understand enough about your use case. Is there any reason both the server and client would need to share the same context and ssl structs?
I'd also need to know more about your system and platform. For example, if this were linux then you have processes and it would be easy to set this up as separate applications. I think it would even be simple if your system only had threads. I realize I am asking for information that you might not want to reveal on a public forum. If you would like to talk about this in a more confidential medium, please send an email message to support@wolfssl.com referencing this post.
Warm regards, Anthony