Hmm perhaps I should RTFM : 
https://puppet.com/docs/puppetdb/6.0/maintain_and_tune.html#redo-ssl-setup-after-changing-certificates

On Friday, 16 November 2018 16:49:20 UTC, Andy Hall wrote:
>
> Apologies for the late reply but do you know how to re-create the certs 
> for PuppetDB ? Is there a specific PuppetDB group who may be able to answer 
> this ? Thanks very much.
>
> On Wednesday, 3 October 2018 19:04:26 UTC+1, Maggie Dreyer wrote:
>>
>> If you regenerated your CA as part of fixing the issues with the 
>> master/agent connection, did you also regenerate the certificates for 
>> PuppetDB? Not having really any experience with PuppetDB, I could see thi 
>> error being cause by still using certificates issued by the old certificate 
>> authority.
>>
>> On Wed, Oct 3, 2018 at 10:58 AM Andy Hall <[email protected]> wrote:
>>
>>> Just fixed an issue with the puppetserver ca after a 5.x to 6.x upgrade 
>>> (see post "PUPPET 6.0 : CSR from master does not match the agent public 
>>> key" for more details) but now experience the following issue with PuppetDB 
>>> (maybe a problem with the Java KeyStore ?):
>>>
>>> AGENT:
>>>
>>> # puppet agent --test
>>>
>>> Warning: Unable to fetch my node definition, but the agent run will 
>>> continue:
>>> Warning: Error 500 on SERVER: Server Error: Could not retrieve facts for 
>>> andy-puppet6-test.london.company.com: Failed to find facts from 
>>> PuppetDB at puppet:8140: Failed to execute '/pdb/query/v4/nodes/
>>> andy-puppet6-test.london.company.com/facts' on at least 1 of the 
>>> following 'server_urls': https://ldn1-puppet5.london.company.com:8081
>>>
>>> Info: Retrieving pluginfacts
>>> Info: Retrieving plugin
>>> Info: Retrieving locales
>>> Info: Loading facts
>>>
>>> Error: Could not retrieve catalog from remote server: Error 500 on 
>>> SERVER: Server Error: Failed to execute 
>>> '/pdb/cmd/v1?checksum=53837e24e8b91d10fc3a81a657b83258c0ab3f8f&version=5&certname=
>>> andy-puppet6-test.london.company.com&command=replace_facts&producer-timestamp=1538588583'
>>>  
>>> on at least 1 of the following 'server_urls': 
>>> https://ldn1-puppet5.london.company.com:8081
>>>
>>> Warning: Not using cache on failed catalog
>>> Error: Could not retrieve catalog; skipping run
>>>
>>> MASTER:
>>>
>>> ==> /var/log/puppetlabs/puppetserver/puppetserver.log <==
>>> 2018-10-03T18:49:26.860+01:00 ERROR [qtp1255475413-70] 
>>> [c.p.h.c.i.PersistentSyncHttpClient] Error executing http request
>>> javax.net.ssl.SSLHandshakeException: General SSLEngine problem
>>>     at sun.security.ssl.Handshaker.checkThrown(Handshaker.java:1529)
>>>     at 
>>> sun.security.ssl.SSLEngineImpl.checkTaskThrown(SSLEngineImpl.java:535)
>>>     at 
>>> sun.security.ssl.SSLEngineImpl.writeAppRecord(SSLEngineImpl.java:1214)
>>>     at sun.security.ssl.SSLEngineImpl.wrap(SSLEngineImpl.java:1186)
>>>     at javax.net.ssl.SSLEngine.wrap(SSLEngine.java:469)
>>>     at 
>>> org.apache.http.nio.reactor.ssl.SSLIOSession.doWrap(SSLIOSession.java:265)
>>>     at 
>>> org.apache.http.nio.reactor.ssl.SSLIOSession.doHandshake(SSLIOSession.java:305)
>>>     at 
>>> org.apache.http.nio.reactor.ssl.SSLIOSession.isAppInputReady(SSLIOSession.java:509)
>>>     at 
>>> org.apache.http.impl.nio.reactor.AbstractIODispatch.inputReady(AbstractIODispatch.java:120)
>>>     at 
>>> org.apache.http.impl.nio.reactor.BaseIOReactor.readable(BaseIOReactor.java:162)
>>>     at 
>>> org.apache.http.impl.nio.reactor.AbstractIOReactor.processEvent(AbstractIOReactor.java:337)
>>>     at 
>>> org.apache.http.impl.nio.reactor.AbstractIOReactor.processEvents(AbstractIOReactor.java:315)
>>>     at 
>>> org.apache.http.impl.nio.reactor.AbstractIOReactor.execute(AbstractIOReactor.java:276)
>>>     at 
>>> org.apache.http.impl.nio.reactor.BaseIOReactor.execute(BaseIOReactor.java:104)
>>>     at 
>>> org.apache.http.impl.nio.reactor.AbstractMultiworkerIOReactor$Worker.run(AbstractMultiworkerIOReactor.java:588)
>>>     at java.lang.Thread.run(Thread.java:748)
>>> Caused by: javax.net.ssl.SSLHandshakeException: General SSLEngine problem
>>>     at sun.security.ssl.Alerts.getSSLException(Alerts.java:192)
>>>     at sun.security.ssl.SSLEngineImpl.fatal(SSLEngineImpl.java:1728)
>>>     at sun.security.ssl.Handshaker.fatalSE(Handshaker.java:330)
>>>     at sun.security.ssl.Handshaker.fatalSE(Handshaker.java:322)
>>>     at 
>>> sun.security.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1614)
>>>     at 
>>> sun.security.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:216)
>>>     at sun.security.ssl.Handshaker.processLoop(Handshaker.java:1052)
>>>     at sun.security.ssl.Handshaker$1.run(Handshaker.java:992)
>>>     at sun.security.ssl.Handshaker$1.run(Handshaker.java:989)
>>>     at java.security.AccessController.doPrivileged(Native Method)
>>>     at 
>>> sun.security.ssl.Handshaker$DelegatedTask.run(Handshaker.java:1467)
>>>     at 
>>> org.apache.http.nio.reactor.ssl.SSLIOSession.doRunTask(SSLIOSession.java:283)
>>>     at 
>>> org.apache.http.nio.reactor.ssl.SSLIOSession.doHandshake(SSLIOSession.java:353)
>>>     ... 9 common frames omitted
>>> Caused by: sun.security.validator.ValidatorException: PKIX path 
>>> validation failed: java.security.cert.CertPathValidatorException: Path does 
>>> not chain with any of the trust anchors
>>>     at 
>>> sun.security.validator.PKIXValidator.doValidate(PKIXValidator.java:362)
>>>     at 
>>> sun.security.validator.PKIXValidator.engineValidate(PKIXValidator.java:270)
>>>     at sun.security.validator.Validator.validate(Validator.java:262)
>>>     at 
>>> sun.security.ssl.X509TrustManagerImpl.validate(X509TrustManagerImpl.java:324)
>>>     at 
>>> sun.security.ssl.X509TrustManagerImpl.checkTrusted(X509TrustManagerImpl.java:281)
>>>     at 
>>> sun.security.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:136)
>>>     at 
>>> sun.security.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1601)
>>>     ... 17 common frames omitted
>>> Caused by: java.security.cert.CertPathValidatorException: Path does not 
>>> chain with any of the trust anchors
>>>     at 
>>> sun.security.provider.certpath.PKIXCertPathValidator.validate(PKIXCertPathValidator.java:154)
>>>     at 
>>> sun.security.provider.certpath.PKIXCertPathValidator.engineValidate(PKIXCertPathValidator.java:80)
>>>     at 
>>> java.security.cert.CertPathValidator.validate(CertPathValidator.java:292)
>>>     at 
>>> sun.security.validator.PKIXValidator.doValidate(PKIXValidator.java:357)
>>>     ... 23 common frames omitted
>>> 2018-10-03T18:49:26.873+01:00 WARN  [qtp1255475413-70] [puppetserver] 
>>> Puppet Error connecting to ldn1-puppet5.london.company.com on 8081 at 
>>> route /pdb/query/v4/nodes/andy-puppet6-test.london.company.com/facts, 
>>> error message received was 'Error executing http request'. Failing over to 
>>> the next PuppetDB server_url in the 'server_urls' list
>>> 2018-10-03T18:49:26.881+01:00 ERROR [qtp1255475413-70] [puppetserver] 
>>> Puppet Server Error: Could not retrieve facts for 
>>> andy-puppet6-test.london.company.com: Failed to find facts from 
>>> PuppetDB at puppet:8140: Failed to execute '/pdb/query/v4/nodes/
>>> andy-puppet6-test.london.company.com/facts' on at least 1 of the 
>>> following 'server_urls': https://ldn1-puppet5.london.company.com:8081
>>>
>>> Seems to be an SSL issue with PuppetDB ? Maybe the Java KeyStore ? 
>>> Please note this is not a simple TCP problem - the connection from agent to 
>>> master on port 8081 is fine.
>>>
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>>

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