Issue #4680 has been updated by Jesse Wolfe.

Subject changed from No certificates submitted after upgrade to 2.6.0 (from 
0.25.4) to agent will never resend a certificate request, preventing it from 
connecting to the master, even if the master is in autosign mode
Status changed from Needs more information to Accepted
Target version set to Statler
Affected version changed from 2.6.0 to 0.25.5

I've verified this bug in 0.25.5 and 2.6.1 : If a client has ever sent a 
certificate request to a master, it will cache that request in 
$confdir/ssl/certificate_requests/$hostname , and will not send that request to 
a new master. Even if the master is in autosign mode, the agent will not 
successfully connect, as the master cannot sign the agent without a certificate 
request.

The workaround is to delete /etc/puppet/ssl/certificate_requests/*.pem from 
machines that are failing to connect in this way.
----------------------------------------
Bug #4680: agent will never resend a certificate request, preventing it from 
connecting to the master, even if the master is in autosign mode
http://projects.puppetlabs.com/issues/4680

Author: Nico Schottelius
Status: Accepted
Priority: Normal
Assignee: 
Category: SSL
Target version: Statler
Affected version: 0.25.5
Keywords: 
Branch: 


Problem:

Client should transfer certificate request, master should autosign it.

Current behaviour:

Master outputs info: Could not find certificate for 'ikr31.ethz.ch'
Client outputs

warning: peer certificate won't be verified in this SSL session
notice: Did not receive certificate

But there's no csr on the master. Tried with and without the new auth.conf.

Details:

Client:

<pre>
r...@ikr31:~# puppet --version
0.25.4
r...@ikr31:~# puppetd --server puppet.inf.ethz.ch --test  --ca_port 19400 
--debug --color no --waitforcert 2
debug: Failed to load library 'selinux' for feature 'selinux'
debug: Puppet::Type::User::ProviderPw: file pw does not exist
debug: Puppet::Type::User::ProviderDirectoryservice: file /usr/bin/dscl does 
not exist
debug: Puppet::Type::User::ProviderUser_role_add: file rolemod does not exist
debug: Puppet::Type::User::ProviderLdap: true value when expecting false
debug: Failed to load library 'ldap' for feature 'ldap'
debug: /File[/var/lib/puppet/clientbucket]: Autorequiring File[/var/lib/puppet]
debug: /File[/var/lib/puppet/lib]: Autorequiring File[/var/lib/puppet]
debug: /File[/var/lib/puppet/ssl]: Autorequiring File[/var/lib/puppet]
debug: /File[/etc/puppet/puppet.conf]: Autorequiring File[/etc/puppet]
debug: /File[/var/lib/puppet/facts]: Autorequiring File[/var/lib/puppet]
debug: /File[/var/lib/puppet/ssl/certs/ca.pem]: Autorequiring 
File[/var/lib/puppet/ssl/certs]
debug: /File[/var/lib/puppet/ssl/private]: Autorequiring 
File[/var/lib/puppet/ssl]
debug: /File[/var/lib/puppet/client_yaml]: Autorequiring File[/var/lib/puppet]
debug: /File[/var/lib/puppet/ssl/public_keys]: Autorequiring 
File[/var/lib/puppet/ssl]
debug: /File[/var/lib/puppet/ssl/certificate_requests]: Autorequiring 
File[/var/lib/puppet/ssl]
debug: /File[/var/lib/puppet/ssl/private_keys/ikr31.ethz.ch.pem]: Autorequiring 
File[/var/lib/puppet/ssl/private_keys]
debug: /File[/var/lib/puppet/state/graphs]: Autorequiring 
File[/var/lib/puppet/state]
debug: /File[/var/run/puppet/puppetd.pid]: Autorequiring File[/var/run/puppet]
debug: /File[/var/lib/puppet/ssl/public_keys/ikr31.ethz.ch.pem]: Autorequiring 
File[/var/lib/puppet/ssl/public_keys]
debug: /File[/var/lib/puppet/ssl/certs]: Autorequiring File[/var/lib/puppet/ssl]
debug: /File[/var/lib/puppet/state]: Autorequiring File[/var/lib/puppet]
debug: /File[/var/lib/puppet/ssl/private_keys]: Autorequiring 
File[/var/lib/puppet/ssl]
debug: Finishing transaction 69844402770620 with 0 changes
debug: Using cached certificate for ca, good until Tue Sep 02 13:24:09 UTC 2014
warning: peer certificate won't be verified in this SSL session
debug: Using cached certificate_request for ikr31.ethz.ch, good until 
debug: Using cached certificate for ca, good until Tue Sep 02 13:24:09 UTC 2014
warning: peer certificate won't be verified in this SSL session
debug: Using cached certificate for ca, good until Tue Sep 02 13:24:09 UTC 2014
warning: peer certificate won't be verified in this SSL session
debug: Using cached certificate for ca, good until Tue Sep 02 13:24:09 UTC 2014
warning: peer certificate won't be verified in this SSL session
notice: Did not receive certificate
^CCancelling startup
</pre>

<pre>
Master:

[10:38] sans:~# /usr/bin/puppet master --servertype=webrick --masterport=19400 
--debug --no-daemonize --color false --trace
warning: You have configuration parameter $ssl_client_header specified in 
[puppetmasterd], which is a deprecated section. I'm assuming you meant [master]
warning: You have configuration parameter $templatedir specified in 
[puppetmasterd], which is a deprecated section. I'm assuming you meant [master]
warning: You have configuration parameter $modulepath specified in 
[puppetmasterd], which is a deprecated section. I'm assuming you meant [master]
debug: Failed to load library 'selinux' for feature 'selinux'
debug: Puppet::Type::User::ProviderDirectoryservice: file /usr/bin/dscl does 
not exist
debug: Puppet::Type::User::ProviderLdap: true value when expecting false
debug: Puppet::Type::User::ProviderUser_role_add: file roleadd does not exist
debug: Puppet::Type::User::ProviderPw: file pw does not exist
debug: Puppet::Type::File::ProviderMicrosoft_windows: feature microsoft_windows 
is missing
debug: /File[/var/lib/puppetmaster/ssl/public_keys/sans.ethz.ch.pem]: 
Autorequiring File[/var/lib/puppetmaster/ssl/public_keys]
debug: /File[/var/lib/puppetmaster/ssl/certs]: Autorequiring 
File[/var/lib/puppetmaster/ssl]
debug: /File[/var/lib/puppetmaster/reports]: Autorequiring 
File[/var/lib/puppetmaster]
debug: /File[/var/lib/puppetmaster/lib]: Autorequiring 
File[/var/lib/puppetmaster]
debug: /File[/etc/puppet/puppet.conf]: Autorequiring File[/etc/puppet]
debug: /File[/var/lib/puppetmaster/ssl/certificate_requests]: Autorequiring 
File[/var/lib/puppetmaster/ssl]
debug: /File[/var/lib/puppetmaster/server_data]: Autorequiring 
File[/var/lib/puppetmaster]
debug: /File[/var/lib/puppetmaster/ssl/certs/sans.ethz.ch.pem]: Autorequiring 
File[/var/lib/puppetmaster/ssl/certs]
debug: /File[/var/lib/puppetmaster/ssl]: Autorequiring 
File[/var/lib/puppetmaster]
debug: /File[/var/log/puppet/masterhttp.log]: Autorequiring 
File[/var/log/puppet]
debug: /File[/var/lib/puppetmaster/ssl/public_keys]: Autorequiring 
File[/var/lib/puppetmaster/ssl]
debug: /File[/var/lib/puppetmaster/yaml]: Autorequiring 
File[/var/lib/puppetmaster]
debug: /File[/var/lib/puppetmaster/ssl/private_keys/sans.ethz.ch.pem]: 
Autorequiring File[/var/lib/puppetmaster/ssl/private_keys]
debug: /File[/var/lib/puppetmaster/bucket]: Autorequiring 
File[/var/lib/puppetmaster]
debug: /File[/etc/puppet/fileserver.conf]: Autorequiring File[/etc/puppet]
debug: /File[/var/lib/puppetmaster/rrd]: Autorequiring 
File[/var/lib/puppetmaster]
debug: /File[/etc/puppet/manifests]: Autorequiring File[/etc/puppet]
debug: /File[/var/lib/puppetmaster/state]: Autorequiring 
File[/var/lib/puppetmaster]
debug: /File[/var/lib/puppetmaster/facts]: Autorequiring 
File[/var/lib/puppetmaster]
debug: /File[/var/lib/puppetmaster/ssl/private]: Autorequiring 
File[/var/lib/puppetmaster/ssl]
debug: /File[/var/lib/puppetmaster/ssl/private_keys]: Autorequiring 
File[/var/lib/puppetmaster/ssl]
debug: /File[/etc/puppet/manifests/site.pp]: Autorequiring 
File[/etc/puppet/manifests]
debug: /File[/var/lib/puppetmaster/ssl/crl.pem]: Autorequiring 
File[/var/lib/puppetmaster/ssl]
debug: /File[/var/lib/puppetmaster/ssl/certs/ca.pem]: Autorequiring 
File[/var/lib/puppetmaster/ssl/certs]
debug: Finishing transaction 70355901938100
debug: /File[/var/lib/puppetmaster/ssl/ca/inventory.txt]: Autorequiring 
File[/var/lib/puppetmaster/ssl/ca]
debug: /File[/var/lib/puppetmaster/ssl/ca/ca_pub.pem]: Autorequiring 
File[/var/lib/puppetmaster/ssl/ca]
debug: /File[/var/lib/puppetmaster/ssl/ca/private/ca.pass]: Autorequiring 
File[/var/lib/puppetmaster/ssl/ca/private]
debug: /File[/var/lib/puppetmaster/ssl/ca/ca_key.pem]: Autorequiring 
File[/var/lib/puppetmaster/ssl/ca]
debug: /File[/var/lib/puppetmaster/ssl/ca/signed]: Autorequiring 
File[/var/lib/puppetmaster/ssl/ca]
debug: /File[/var/lib/puppetmaster/ssl/ca/private]: Autorequiring 
File[/var/lib/puppetmaster/ssl/ca]
debug: /File[/var/lib/puppetmaster/ssl/ca/serial]: Autorequiring 
File[/var/lib/puppetmaster/ssl/ca]
debug: /File[/var/lib/puppetmaster/ssl/ca/ca_crt.pem]: Autorequiring 
File[/var/lib/puppetmaster/ssl/ca]
debug: /File[/var/lib/puppetmaster/ssl/ca/ca_crl.pem]: Autorequiring 
File[/var/lib/puppetmaster/ssl/ca]
debug: /File[/var/lib/puppetmaster/ssl/ca/requests]: Autorequiring 
File[/var/lib/puppetmaster/ssl/ca]
debug: Finishing transaction 70355900300400
debug: Using cached certificate for ca
debug: Using cached certificate for ca
debug: Using cached certificate for sans.ethz.ch
notice: Starting Puppet master version 2.6.0
err: Removing mount files: /etc/puppet/files does not exist
info: mount[files]: allowing 129.132.12.0/24 access
[... many more permissions allowed...]
debug: No modules mount given; autocreating with default permissions
debug: Finishing transaction 70355918274780
info: Inserting default '~ ^/catalog/([^/]+)$'(auth) acl because 
/etc/puppet/auth.conf doesn't exist
info: Inserting default '/file'(non-auth) acl because /etc/puppet/auth.conf 
doesn't exist
info: Inserting default '/certificate_revocation_list/ca'(auth) acl because 
/etc/puppet/auth.conf doesn't exist
info: Inserting default '/report'(auth) acl because /etc/puppet/auth.conf 
doesn't exist
info: Inserting default '/certificate/ca'(non-auth) acl because 
/etc/puppet/auth.conf doesn't exist
info: Inserting default '/certificate/'(non-auth) acl because 
/etc/puppet/auth.conf doesn't exist
info: Inserting default '/certificate_request'(non-auth) acl because 
/etc/puppet/auth.conf doesn't exist
info: Inserting default '/status'(auth) acl because /etc/puppet/auth.conf 
doesn't exist
info: Inserting default '/resource'(auth) acl because /etc/puppet/auth.conf 
doesn't exist
info: Could not find certificate for 'ikr31.ethz.ch'
</pre>




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