Paul, that ssl error looks like the following post on puppet-users:
https://groups.google.com/forum/#!topic/puppet-users/4-6EimF_-NY/discussion,
which relates to SNI. Adding a server alias to your puppetmaster vhost may
resolve your problem. This is a change in ruby after 1.9.0, so it wouldn't
have been in system ruby on OSX before mavericks.

HTH


On Tue, Feb 11, 2014 at 1:08 AM, Paul Tötterman <[email protected]>wrote:

> > facter-1.7.4-rc1 is available and it looks like it works!
>
> Actually, it wasn't until 1.7.5 that the packages available from
> downloads.puppetlabs.com were fixed, but it really seems to work now.
>
> However, I have a problem with puppet on OS X 10.9. I'm using the
> latest packaged version 3.4.2.
>
> It may be a problem with the ruby and openssl configuration shipped
> with OS X 10.9, but I'm getting:
>
> Info: Creating a new SSL key for $fqdn
> Error: Could not request certificate: SSL_connect returned=1 errno=0
> state=SSLv2/v3 read server hello A: (null)
>
> /System/Library/Frameworks/Ruby.framework/Versions/2.0/usr/lib/ruby/2.0.0/net/http.rb:918:in
> `connect'
>
> when running `puppet agent --test --verbose --debug --evaltrace --trace`.
>
> There are some results on the web about ruby failing because of a
> missing CA cert bundle, but the puppet master generated CA cert
> wouldn't be included anyway, so that isn't a solution in this case.
>
> Anyone have any other ideas?
>
> Cheers,
> Paul
>
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-- 
Matthaus Owens
Release Manager, Puppet Labs

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