Hi,

>  think I am getting closer with the "one step" process with an
> intermediary cert. I am able to start up the server with both the new CA
> signed server cert and the intermediary as outlined in "Step 3" above.
> However, its like the server is not sending two server certs to the
> connecting client and the stacked crt is not working.  In my openvpn config
> if I have something like
>
> ca keys/new/ca2.crt
> cert keys/new/ronly.pem
> key keys/new/r-only.key
>
Where ca2.crt contains both the root certificates (old and new) and
> ronly.pem contains both the new OpenVPN server cert and the intermediary CA
> crt signed by the old CA, it only works for one client or the other based
> on where I have the certificate in the .pem file. So if I put the new cert
> first in the list, new clients can connect.
>
This is the correct order -- the server certificate first, followed by the
cross-signed certificate. OpenVPN parses the first one as the server
certificate and uses trailing ones, if any, for building the chain.

> If I put the intermediary first in the file, old clients can connect, but
> not the new ones.
>
With that order the key won't match the certificate and the server should
not even start. Looks like your cross-signed certificate has the server's
public key --  it should have the new CA's public key signed by the old CA.
What error do you get on old clients with the correct order?

> Is there an extra step I need to do or am I misunderstanding where the
> intermediary cert needs to go or what needs to be signed ?
>
You can check by verifying the new server certificate against old CA using
openssl CLI like this:

$ openssl verify  -show_chain -CAfile old-ca.crt -untrusted
cross-signed-cert.crt  new-server-cert.crt

It should show the cross-signed certificate at depth 1 linking the new
server certificate to the old CA at depth 2.

Direct verification using new CA would be

$ openssl verify  -show_chain -CAfile new-ca.crt  new-server-cert.crt

Selva

>
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