Cheers Warron,

It was pretty obvious something on B is broken, but what who knows...

I've just deleted everything related to B and C (A is prod, B and C are new 
dev) [rm -rf /etc/puppetlabs/puppet/ssl; rm -rf 
/etc/puppetlabs/puppetserver/ca; puppetserver ca clean x].

After doing this, will both puppet and puppetserver services stopped on B, 
I've ran puppet agent -t...
Then signed the request on server-A

Everything working on B (as an agent)...

Then again everything stopped and deleted on C (agent)...
puppet agent -t, signed on A...

Can't connect to the puppetmaster (server-B), because I haven't started the 
service, but other than that everything perfect.

Start the puppetserver service on server-B... and then run puppet agent -t 
on server-C again...
```
Error: Connection to https://server-B:8140/puppet/v3 failed, trying next 
route: Request to https://server-B:8140/puppet/v3 failed after 0.103 
seconds: SSL_connect returned=1 errno=0 state=error: sslv3 alert 
certificate unknown
Wrapped exception:
SSL_connect returned=1 errno=0 state=error: sslv3 alert certificate unknown
```

Pretty much back to where we started...

Then I go back to server-B and run puppet agent -t... broken:
```
Error: The CRL issued by 'CN=Puppet CA: server-A' is missing
Error: Could not run: The CRL issued by 'CN=Puppet CA: server-A' is missing
```

>From what I can tell, the puppetserver service (upon startup on server-B) 
is "blatting" the correct certs on server-B...

That's the best conclusion I can come to at this point.
On Friday, 7 May 2021 at 9:50:24 am UTC+10 [email protected] wrote:

> @Aaron, good evening from the east coast of the USA.
>
> It looks like the first break in the chain is on ServerB, if that was not 
> also obvious to you.  To be clear, I have not worked with puppet since 
> version 4, and in my current professional role we don't use Puppet at all 
> (makes me sad actually).
>
> Anyway, I think you need to find The certificate for ServerB and confirm 
> the details about it's PEM file.
> Use *openssl x509  -noout  -text     **ServerB.pem*    (the server's PEM 
> file is a placeholder)
>
> Can you provide a list of fullpath/file.pem's back to me?   *This is not 
> a production system correct?*
>
>
>
> --------------------------
> Warron French
>
>
>
> On Thu, May 6, 2021 at 7:29 PM Aaron Nicoli <[email protected]> wrote:
>
>> G'day Warron,
>>
>> So, doing some ca/ssl info gathering (note puppet cert not being a thing 
>> anymore on 7x that I'm running):
>>
>> On server-A (CA & master 1):
>> puppetserver ca list --all
>> server-A (alt names: DNS:puppet, DNS:server-A)
>> server-B (alt names: DNS:server-B)
>> server-C (alt names: DNS:server-C)
>>
>> puppet ssl show
>> ```
>> ...
>> Issuer: CN=Puppet CA: server-A
>> ...
>> Subject: CN=server-A
>> ...
>> ```
>>
>> On server-B (master 2):
>> puppetserver ca list --all
>> ```
>>    Error: Failed connecting to 
>> https://server-A:8140/puppet-ca/v1/certificate_statuses/any_key
>>   Root cause: SSL_connect returned=1 errno=0 state=error: certificate 
>> verify failed (unable to get certificate CRL)
>> ```
>>
>> puppet ssl show
>> ```
>> Error: Could not run: The CRL issued by 'CN=Puppet CA: server-A' is 
>> missing
>> ```
>>
>> I also note that today, puppet agent -t, is now also failing with:
>> ```
>> Error: The CRL issued by 'CN=Puppet CA: server-A' is missing
>> Error: Could not run: The CRL issued by 'CN=Puppet CA: server-A' is 
>> missing
>> ```
>>
>> On server-C (agent):
>> puppet ssl show:
>> ```
>> ...
>> Issuer: CN=Puppet CA:server-A
>> ...
>> Subject: CN=server-B
>> ...
>> ```
>>
>> Hope this helps my case!
>> On Friday, 7 May 2021 at 8:42:46 am UTC+10 [email protected] wrote:
>>
>>> This, if I remember correctly, looks like a certificate chain issue.  
>>> Your Puppet Architecture is a "Master of Masters" architecture.
>>>
>>> Cert for Server B is signed by Cert for Server A?  Correct?
>>> Is the cert for Server C (the agent) signed by the CA certificate chain?
>>>
>>> Try executing:  *puppet cert list* and confirm that all certificates 
>>> for all three servers are listed.  
>>>
>>> --------------------------
>>> Warron French
>>>
>>>
>>>
>>> On Thu, May 6, 2021 at 5:52 PM Aaron Nicoli <[email protected]> wrote:
>>>
>>>> Hi all,
>>>>
>>>> I have the following puppet layout:
>>>> ```
>>>> Server A - Puppetserver (CA)
>>>>   Server B - Puppetserver
>>>>     Server C - Agent
>>>> ```
>>>>
>>>> With the agent (server C) having it's cert signed by the CA (server A) 
>>>> however pointed to (server B) as it's master.
>>>>
>>>> The issue I'm having is that when running `puppet agent -t` on the 
>>>> agent, I can create a request to the CA and have the CA sign it, but then 
>>>> when I go to run again:
>>>>
>>>> ```
>>>> Error: Connection to 
>>>> https://hostname-of-server-B-puppetserver:8140/puppet/v3 failed, 
>>>> trying next route: Request to 
>>>> https://hostname-of-server-B-puppetserver:8140/puppet/v3 failed after 
>>>> 0.094 seconds: SSL_connect returned=1 errno=0 state=error: sslv3 alert 
>>>> certificate unknown
>>>> ```
>>>>
>>>> Now on the agent, I can see that the Server-B cert is signed by the CA 
>>>> Server-A and it's available on the agent (server C) under: 
>>>> `/etc/puppetlabs/puppet/ssl/certs/ca.pem`
>>>>
>>>> But yet - I still get the error... where is the puppet agent trying to 
>>>> find the `ca.pem` cert to verify the masters certificate?!?
>>>>
>>>> Any ideas?
>>>>
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>>>>
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