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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