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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