The issue was in fact the user. I was running as my user account and that 
was conflicting with the system service account. Details here: 

https://ask.puppetlabs.com/question/5580/windows-2012-r2-not-checking-in/

On Tuesday, March 4, 2014 6:09:32 PM UTC-6, Rob Reynolds wrote:
>
> What user is puppet agent service running under on your machine? 
>
>
> On Mon, Mar 3, 2014 at 8:38 AM, Nick Hobart <[email protected]<javascript:>
> > wrote:
>
>> I'm standing up a Foreman front end for open source Puppet server. Every 
>> Linux box seems to be working and checking in just fine. The problem child 
>> is Windows 2012 R2. I can manually trigger an update with:
>>
>>  puppet agent --test
>>
>> However, if I just let it sit there, it'll never check back in. Any clues 
>> as to what's going on? I'm using Puppet 3.4.3 on the agent and server. 
>> Thanks. Here's the imgur link. 
>>
>> http://imgur.com/aUutqdt
>>  
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>
>
>
> -- 
> Rob Reynolds
> Developer, Puppet Labs
>
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