I think this is fixed now; I used openssl s_client and whereas it used to 
have:

---
Certificate chain
 0 
s:/serialNumber=tQHCVE0ajtkIENLLN1O5pr4WMtvwn/eA/C=US/ST=Oregon/L=Portland/O=Puppet
 
Labs, Inc./CN=*.puppetlabs.com
   i:/C=US/O=GeoTrust, Inc./CN=GeoTrust SSL CA
 1 
s:/serialNumber=tQHCVE0ajtkIENLLN1O5pr4WMtvwn/eA/C=US/ST=Oregon/L=Portland/O=Puppet
 
Labs, Inc./CN=*.puppetlabs.com
   i:/C=US/O=GeoTrust, Inc./CN=GeoTrust SSL CA
 2 s:/C=US/O=GeoTrust, Inc./CN=GeoTrust SSL CA
   i:/C=US/O=GeoTrust Inc./CN=GeoTrust Global CA

It now says 


Certificate chain
 0 
s:/serialNumber=tQHCVE0ajtkIENLLN1O5pr4WMtvwn/eA/C=US/ST=Oregon/L=Portland/O=Puppet
 
Labs, Inc./CN=*.puppetlabs.com
   i:/C=US/O=GeoTrust, Inc./CN=GeoTrust SSL CA
 1 s:/C=US/O=GeoTrust, Inc./CN=GeoTrust SSL CA
   i:/C=US/O=GeoTrust Inc./CN=GeoTrust Global CA

On Monday, March 24, 2014 11:50:16 AM UTC-7, Eric Sorenson wrote:
>
> Thanks for pointing this out, I've raised an internal ticket with the 
> operations team and will update this thread when I hear back.
>
> --eric0
>
> On Monday, March 24, 2014 7:10:09 AM UTC-7, Christopher Orr wrote:
>>
>> Hi all,
>>
>> I just noticed that some of my servers are having trouble while running 
>> `apt-get update`, apparently due to TLS issues with apt.puppetlabs.com.
>>
>> `apt-get update` returns:
>> W: Failed to fetch 
>> https://apt.puppetlabs.com/dists/lucid/main/source/Sources.gz  server 
>> certificate verification failed. CAfile: /etc/ssl/certs/ca-certificates.crt 
>> CRLfile: none
>>
>> However, I can access https://apt.puppetlabs.com fine via curl or 
>> Chrome, and the relevant root certificate is indeed in 
>> /etc/ssl/certs/ca-certificates.crt.
>> But on closer inspection, it seems that the certificate chain returned 
>> when connecting to apt.puppetlabs.com contains two copies of the *.
>> puppetlabs.com certificate as the first two links in the chain.
>>
>> I imagine it's possible that certain clients reject this as invalid.
>> Has anybody else noticed this behaviour?
>>
>> In the meantime, I see that newer "puppetlabs-release-*.deb" packages use 
>> http://apt.puppetlabs.com (i.e. no https://), so I guess I have some 
>> apt-sources updating to do...
>>
>> Regards,
>> Chris
>>
>

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