Hi Soham, I would suggest you start with a single server that contains both 
the CA and compile master functionality.

That way you can bootstrap it in a very simple way, using the instructions 
for the new intermediate CA setup in Puppet 6. Once that is working, it is 
much easier to move to a split-out service because you will have a 
functioning CA + Server which can sign the certificates for the other 
compile masters.

You should be able to serve catalogs from a single instance for several 
thousand agents, so don't scale out until you know you need it.

https://puppet.com/docs/puppetserver/6.0/intermediate_ca.html

HTH
--eric0

On Wednesday, November 28, 2018 at 8:24:00 AM UTC-8, Soham Chakraborty 
wrote:
>
> Hi,
>
> Update:
>
> I have made the changes in webserver.conf of the compile master as 
> described in 
> https://puppet.com/docs/puppet/6.0/config_ssl_external_ca.html#task-8039 
> (step 3 in particular), but I still have the same problem :(
>
> On Tuesday, November 27, 2018 at 11:58:54 PM UTC+5:30, Soham Chakraborty 
> wrote:
>>
>> Hi,
>>
>> I am trying to achieve the following in Ubuntu 18.04 (bionic):
>>
>> 1) I want to have several Puppet servers act as compile masters. They 
>> will be load balanced and point to a DNS record in AWS. 
>>
>> 2) All the compile masters will share same Puppet CA server. The CA 
>> server be responsible for only signing certificates and nothing else.
>>
>> This should be reasonably easy to implement but I am not getting odd SSL 
>> errors at every turn. I am looking to know how I should go about creating a 
>> setup like this with open source Puppet. The steps that I am following now 
>> are something like this:
>>
>> 1) Provision the instance from a packer template. I am installing Puppet 
>> 5.5.6 from the packer template.
>> 2) Login to the server and install puppetserver. 
>> 3) Disable internal CA service from services.d/ca.cfg file.
>> 4) Edit puppet.conf to point master to the DNS name of the load balancer. 
>> Don't do any change of ca server for now. Don't run any puppet agent as 
>> well.
>> 5) Provision another instance from the same packer template. 
>> 6) Install puppetserver. 
>> 7) Edit it's puppet.conf to point to the DNS name of the load balancer 
>> and also change ca server to this server itself.
>> 8) Run puppet agent -t on the compile master created in step 1.
>> 9) Sign the cert in CA server. 
>>
>> Is this all that there is? Do I need to do any config change in the 
>> webserver.conf of the Puppet compile master? If so, what would be required 
>> changes? What files should be copied over from the CA server to the compile 
>> server?
>>
>> What files need to be copied over from CA server to the compile server 
>> and where they should be placed? 
>>
>> Right now in my CA server, I am getting this error: 
>>
>> # puppet agent -t
>> Warning: Setting autosign is deprecated.
>>    (location: 
>> /opt/puppetlabs/puppet/lib/ruby/vendor_ruby/puppet/settings.rb:1169:in 
>> `issue_deprecation_warning')
>> Warning: Setting ca is deprecated.
>>    (location: 
>> /opt/puppetlabs/puppet/lib/ruby/vendor_ruby/puppet/settings.rb:1169:in 
>> `issue_deprecation_warning')
>> Warning: Unable to fetch my node definition, but the agent run will 
>> continue:
>> Warning: SSL_connect returned=1 errno=0 state=error: certificate verify 
>> failed: [ok for /CN=puppetserver.org.com]
>> Info: Retrieving pluginfacts
>> Error: /File[/opt/puppetlabs/puppet/cache/facts.d]: Failed to generate 
>> additional resources using 'eval_generate': SSL_connect returned=1 errno=0 
>> state=error: certificate verify failed: [ok for /CN=puppetserver.org.com]
>> Error: /File[/opt/puppetlabs/puppet/cache/facts.d]: Could not evaluate: 
>> Could not retrieve file metadata for puppet:///pluginfacts: SSL_connect 
>> returned=1 errno=0 state=error: certificate verify failed: [ok for /CN=
>> puppetserver.org.com]
>> Info: Retrieving plugin
>> Error: /File[/opt/puppetlabs/puppet/cache/lib]: Failed to generate 
>> additional resources using 'eval_generate': SSL_connect returned=1 errno=0 
>> state=error: certificate verify failed: [ok for /CN=puppetserver.org.com]
>> Error: /File[/opt/puppetlabs/puppet/cache/lib]: Could not evaluate: Could 
>> not retrieve file metadata for puppet:///plugins: SSL_connect returned=1 
>> errno=0 state=error: certificate verify failed: [ok for /CN=
>> puppetserver.org.com]
>> Error: Could not retrieve catalog from remote server: SSL_connect 
>> returned=1 errno=0 state=error: certificate verify failed: [ok for /CN=
>> puppetserver.org.com]
>> Warning: Not using cache on failed catalog
>> Error: Could not retrieve catalog; skipping run
>> Error: Could not send report: SSL_connect returned=1 errno=0 state=error: 
>> certificate verify failed: [ok for /CN=puppetserver.org.com]
>> root@puppet-ca-server:~#
>>
>> And in Puppet compile master, I am getting:
>>
>> # puppet agent -t
>> Warning: Unable to fetch my node definition, but the agent run will 
>> continue:
>> Warning: execution expired
>> Info: Retrieving pluginfacts
>> Error: /File[/opt/puppetlabs/puppet/cache/facts.d]: Failed to generate 
>> additional resources using 'eval_generate': execution expired
>> Error: /File[/opt/puppetlabs/puppet/cache/facts.d]: Could not evaluate: 
>> Could not retrieve file metadata for puppet:///pluginfacts: execution 
>> expired
>> Info: Retrieving plugin
>> Error: /File[/opt/puppetlabs/puppet/cache/lib]: Failed to generate 
>> additional resources using 'eval_generate': execution expired
>> Error: /File[/opt/puppetlabs/puppet/cache/lib]: Could not evaluate: Could 
>> not retrieve file metadata for puppet:///plugins: execution expired
>> Error: Could not retrieve catalog from remote server: execution expired
>> Warning: Not using cache on failed catalog
>> Error: Could not retrieve catalog; skipping run
>> root@puppetserver:~#
>>
>> The nodes are not yet in site.pp but I would expect the errors to be 
>> different. 
>>
>> Thanks,
>>
>>
>>

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