I checked, the CA in use on my puppet4/puppetserver installation definitely has 
no subjectAltName extension and a puppet4 agent works.

In all likelihood I messed up something in the config.

On Wed, Feb 17, 2016 at 10:23:19PM +0100, Felix Frank wrote:
> Hi Christopher,
> 
> I have no first hand experience with this transition, but Martin put a note
> about SSL in the Puppet 4 chapter of the new Puppet Essentials (yes, I'm
> plugging us :-)
> 
> Apparently Puppet 4 cannot use a CA that was created without the
> dns_alt_names setting. This might just be your issue. And yes, you will have
> to re-certify your infrastructure for the upgrade if this is the case.
> 
> Cheers,
> Felix
> 
> On 02/11/2016 11:02 PM, Christopher Wood wrote:
> >Update is that I still don't know why this happened, but I know what I 
> >should not do when I go to convert the production puppetmasters.
> >
> >I have a set of 3.8.5 masters and was attempting to bring up a 4.3.2 master 
> >(puppetserver 2.2.1, puppet-agent 1.3.4) as a non-CA master to test things 
> >with. A 3.8.5 agent got these errors when trying to use a server=4.3.2 with 
> >ca_server=3.8.5 set of puppetmaster versions.
> >
> >My 3.8.5 agent worked fine against the 4.3.2 master with a completely new 
> >CA, and with the new master acting as a CA with the 3.8.5 CA's ssl files. 
> >Using a 3.8.5 non-CA master with the 4.3.2 CA server works too.
> >
> >The upshot is that when I convert the puppetmasters to puppet 4 I will need 
> >to convert the CA first and work outward from there (other puppetmasters at 
> >that location, rest of the puppetmasters, then the agents).
> >
> >(Feel free to add more clue than I can provide, anybody.)
> >
> >On Fri, Feb 05, 2016 at 04:56:03PM -0500, Christopher Wood wrote:
> >>I have a puppet 3 agent attempting an agent run against a puppet 4 master 
> >>but I am getting ssl errors. I'm out of google-fu and I've verified certs 
> >>and keys, run both sides in debug using puppetserver and the rack "puppet 
> >>master --no-daemonize --verbose", and am not seeing anything that jumps out 
> >>at me. I do notice that when running in DEBUG the puppetserver log doesn't 
> >>spit output during the agent run.
> >>
> >>The closest I can get to understanding this is stackoverflow, but I'm not 
> >>sure how I would tell the agent to use TLSv1.2.
> >>
> >>http://stackoverflow.com/questions/25814210/opensslsslsslerror-ssl-connect-syscall-returned-5-errno-0-state-sslv3-read
> >>
> >>Any hints on what these ssl errors are from and how I can fix this?
> >>
> >>SSL_connect SYSCALL returned=5 errno=0 state=SSLv3 read finished A
> >>
> >>[root@mail10c2 ~]# puppet --version
> >>3.8.5
> >>[root@mail10c2 ~]# cat /etc/redhat-release
> >>CentOS release 6.7 (Final)
> >>[root@mail10c2 ~]# openssl version
> >>OpenSSL 1.0.1e-fips 11 Feb 2013
> >>
> >>[root@puppetmaster1stage ~]# rpm -q puppetserver
> >>puppetserver-2.2.1-1.el6.noarch
> >>[root@puppetmaster1stage ~]# /opt/puppetlabs/bin/puppet --version
> >>4.3.2
> >>[root@puppetmaster1stage ~]# cat /etc/redhat-release
> >>CentOS release 6.7 (Final)
> >>[root@puppetmaster1stage ~]# /opt/puppetlabs/puppet/bin/openssl version
> >>OpenSSL 1.0.2e 3 Dec 2015
> >>
> >>I've verified the hostcert, hostpubkey, and localcacert as definitely 
> >>belonging to each other using openssl. These files exist at the paths from 
> >>"puppet config print". The localcacert is definitely the CA cert that both 
> >>server and client use, by md5sum.
> >>
> >>This is the output (that is definitely the --server in the server cert):
> >>
> >>[root@mail10c2 util]# puppet agent --onetime --verbose --no-daemonize 
> >>--no-splay --server puppetmaster1stage
> >>Warning: Unable to fetch my node definition, but the agent run will 
> >>continue:
> >>Warning: SSL_connect SYSCALL returned=5 errno=0 state=SSLv3 read finished A
> >>Info: Retrieving pluginfacts
> >>Error: /File[/var/lib/puppet/facts.d]: Failed to generate additional 
> >>resources using 'eval_generate': SSL_connect SYSCALL returned=5 errno=0 
> >>state=SSLv3 read finished A
> >>Error: /File[/var/lib/puppet/facts.d]: Could not evaluate: Could not 
> >>retrieve file metadata for puppet://puppetmaster1stage/pluginfacts: 
> >>SSL_connect SYSCALL returned=5 errno=0 state=SSLv3 read finished A
> >>Info: Retrieving plugin
> >>Error: /File[/var/lib/puppet/lib]: Failed to generate additional resources 
> >>using 'eval_generate': SSL_connect SYSCALL returned=5 errno=0 state=SSLv3 
> >>read finished A
> >>Error: /File[/var/lib/puppet/lib]: Could not evaluate: Could not retrieve 
> >>file metadata for puppet://puppetmaster1stage/plugins: SSL_connect SYSCALL 
> >>returned=5 errno=0 state=SSLv3 read finished A
> >>Info: Loading facts
> >>Error: Could not retrieve catalog from remote server: SSL_connect SYSCALL 
> >>returned=5 errno=0 state=SSLv3 read finished A
> >>Warning: Not using cache on failed catalog
> >>Error: Could not retrieve catalog; skipping run
> >>Error: Could not send report: SSL_connect SYSCALL returned=5 errno=0 
> >>state=SSLv3 read finished A
> >>
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