Hello LeeAtkison, you mention you are ‘...connecting to a server with a CA-signed certificate issued by the organisation...’ Overall, this means the Certificate is not a Public CA Trusted Certificate, and thus will most likely, be considered untrusted from any device external to your own organisation. All Public CA Trusted Certificates are stored in each machines own Trusted Certificate Store.

Looking through some Microsoft documentation on how to stop those types of warnings, it is very likely you’ll need to update your certificate and deploy it to both Jumpoint and Endpoint machines in their Trust Certificate Stores.

Thanks Phil - so that answers my question. It’s dependent on the trusted CAs on the operating system of the user connecting to the jumpoint. Third parties will always get this error message being external and not having the CA in their trusted stores.