It sounds as if your master is doing Something Weird when it is launched
during startup of you Vagrant instance. What that is exactly is hard to
tell.

Try and manipulate the init (or whatever) script to enable some debug
logging. See if you can find out the cause for the failures.

If you cannot determine the root cause, consider a workaround such as a

@reboot service puppetmaster restart

cron job.

HTH,
Felix

On 01/08/2015 08:28 PM, Drew wrote:
> Yep, that's exactly what I'm saying.  Like I said, it's weird.  Maybe
> something with the time?
>
> Thanks!
>
> On Tuesday, January 6, 2015 6:21:14 PM UTC-5, Felix.Frank wrote:
>
>     Hi,
>
>     so are you saying that after SSL breaks, you can fix it by restarting
>     the service?
>
>     On 01/02/2015 08:39 PM, Drew wrote:
>     > Hey,
>     >
>     > I hope someone here can point me in the right direction.  I've been
>     > struggling with this for a few days and I can't seem to figure out
>     > what the issue is.  It's really strange.  I have a vagrant
>     > configuration that spins up a puppetmaster and a target machine
>     that
>     > runs the agent.  When I initially do the 'vagrant up' all comes
>     up and
>     > the agent is configured.  If I halt the puppetmaster and bring
>     it back
>     > up, the agent fails to connect to the puppetmaster due to a
>     > certificate error.  If I simply restart the puppetmaster
>     service, it
>     > connects without issue.
>
>

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