I have good news and bad news:

Good news:

  * OpenVPN sends all certificates from the server supplied for --server 
directive (although with a small bug that a certificate which you have private 
key for
    must be supplied on the top)
  * OpenVPN Connect for Android can successfully connect to my server with a 
chain


Bad news:

  * OpenVPN 2.3 and master can't connect to this server, with both OpenSSL and 
PolarSSL backends. Maybe if I supply certificates in correct order, client would
    work.



On 03/04/2016 12:04 AM, ValdikSS wrote:
> Hello everyone,
>
> I'm trying to leisurely move from an old existing 1024 bit CA to a new 4096 
> bit one without a hassle for a clients.
> From a X.509 perspective it shouldn't be a problem, and I already have new CA 
> self-signed and cross-signed with old CA, it should work just fine.
>
> While there's no problem authenticating clients from both old and new CA 
> using single instance (multiple certificates in --ca are supported, this 
> information is
> documented), I need to send two certificates from OpenVPN server: server 
> certificate, which is signed by new CA, and cross-signed new CA with old CA. 
> This way
> it should work for clients either with old or new CA in configuration files.
>
> I can't manage server to send more than one certificate to the client. It 
> seems that multiple certificates in --cert directive are supported only on 
> client
> side. Am I missing something, is there a way to push multiple certificates 
> from server? If there isn't a way currently, are there any protocol 
> limitations which
> allows only one certificate to be sent?
>
>

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