For anyone checking this out - I believe it was/is a networking issue. 
After noticing related oddness with subscription-manager, I believe there 
is an HTTPS proxy interfering with my traffic.

I "fixed" the issue by doing a point-to-point VPN between the two servers 
in question, and the sync was successful.

On Tuesday, April 11, 2017 at 5:14:52 PM UTC-4, jpavel wrote:
>
> This is my first proxy installation behind a FW, so I'm cognizant that I 
> might have a port blocked that I need to get open. 
>
> Foreman Server --[9090 TCP]--> Proxy (I'm using 9090 instead of 8443 
> because of reasons)
> Proxy --[443 TCP]--> Foreman Server
> Proxy --[5646 TCP]--> Foreman Server 
>
> ... I based this off of the diagram here: 
> https://www.theforeman.org/plugins/katello/3.3/user_guide/smart_proxies/isolation.png
>
> Here are the errors I'm seeing:
>
> Apr 11 20:27:52 smart-proxy-01 pulp: 
> requests.packages.urllib3.connectionpool:INFO: Starting new HTTPS 
> connection (4): foreman-01.prod.mcs.som.mob.nuance.com
> Apr 11 20:27:55 smart-proxy-01 pulp: 
> requests.packages.urllib3.connectionpool:WARNING: Retrying (Retry(total=1, 
> connect=5, read=1, redirect=None)) after connection broken by 
> 'ReadTimeoutError("HTTPSConnectionPool(host='
> foreman-01.prod.mcs.som.mob.nuance.com', port=443): Read timed out. (read 
> timeout=6.05)",)': 
> /pulp/puppet/nuance_mobility-Development-Lars_Migration_Test_View/modules.json
> Apr 11 20:27:55 smart-proxy-01 pulp: 
> requests.packages.urllib3.connectionpool:INFO: Starting new HTTPS 
> connection (5): foreman-01.prod.mcs.som.mob.nuance.com
> Apr 11 20:27:57 smart-proxy-01 pulp: 
> requests.packages.urllib3.connectionpool:WARNING: Retrying (Retry(total=2, 
> connect=5, read=2, redirect=None)) after connection broken by 
> 'ReadTimeoutError("HTTPSConnectionPool(host='
> foreman-01.prod.mcs.som.mob.nuance.com', port=443): Read timed out. (read 
> timeout=6.05)",)': 
> /pulp/puppet/nuance_mobility-Test-MCS_Cassandra_-_NTG6_Azure/modules.json
> Apr 11 20:27:57 smart-proxy-01 pulp: 
> requests.packages.urllib3.connectionpool:INFO: Starting new HTTPS 
> connection (4): foreman-01.prod.mcs.som.mob.nuance.com
>
> After everything finishes up, 
> Apr 11 20:28:35 smart-proxy-01 pulp: 
> requests.packages.urllib3.connectionpool:WARNING: Retrying (Retry(total=0, 
> connect=5, read=0, redirect=None)) after connection broken by 
> 'ReadTimeoutError("HTTPSConnectionPool(host='
> foreman-01.prod.mcs.som.mob.nuance.com', port=443): Read timed out. (read 
> timeout=6.05)",)': 
> /pulp/puppet/nuance_mobility-Test-MCS_Cassandra_-_NTG6_Azure/modules.json
> Apr 11 20:28:35 smart-proxy-01 pulp: 
> requests.packages.urllib3.connectionpool:INFO: Starting new HTTPS 
> connection (6): foreman-01.prod.mcs.som.mob.nuance.com
> Apr 11 20:28:41 smart-proxy-01 pulp: nectar.downloaders.threaded:ERROR: 
> Skipping requests to foreman-01.prod.mcs.som.mob.nuance.com due to 
> repeated connection failures: HTTPSConnectionPool(host='
> foreman-01.prod.mcs.som.mob.nuance.com', port=443): Max retries exceeded 
> with url: 
> /pulp/puppet/nuance_mobility-Test-MCS_Cassandra_-_NTG6_Azure/modules.json 
> (Caused by ReadTimeoutError("HTTPSConnectionPool(host='
> foreman-01.prod.mcs.som.mob.nuance.com', port=443): Read timed out. (read 
> timeout=6.05)",))
> Apr 11 20:28:41 smart-proxy-01 pulp: 
> pulp_puppet.plugins.importers.forge:ERROR: (2796-90560) Exception while 
> retrieving metadata for repository 
> <nuance_mobility-Test-MCS_Cassandra_-_NTG6_Azure>
> Apr 11 20:28:41 smart-proxy-01 pulp: 
> pulp_puppet.plugins.importers.forge:ERROR: (2796-90560) Traceback (most 
> recent call last):
> Apr 11 20:28:41 smart-proxy-01 pulp: 
> pulp_puppet.plugins.importers.forge:ERROR: (2796-90560)   File 
> "/usr/lib/python2.7/site-packages/pulp_puppet/plugins/importers/forge.py", 
> line 113, in _parse_metadata
> Apr 11 20:28:41 smart-proxy-01 pulp: 
> pulp_puppet.plugins.importers.forge:ERROR: (2796-90560)     
> metadata_json_docs = downloader.retrieve_metadata(self.progress_report)
> Apr 11 20:28:41 smart-proxy-01 pulp: 
> pulp_puppet.plugins.importers.forge:ERROR: (2796-90560)   File 
> "/usr/lib/python2.7/site-packages/pulp_puppet/plugins/importers/downloaders/web.py",
>  
> line 57, in retrieve_metadata
> Apr 11 20:28:41 smart-proxy-01 pulp: 
> pulp_puppet.plugins.importers.forge:ERROR: (2796-90560)     raise 
> exceptions.FileRetrievalException(report.error_msg)
> Apr 11 20:28:41 smart-proxy-01 pulp: 
> pulp_puppet.plugins.importers.forge:ERROR: (2796-90560) 
> FileRetrievalException: FileRetrievalException: A connection error occurred
> Apr 11 20:28:41 smart-proxy-01 pulp: pulp.server.async.tasks:INFO: Task 
> failed : [d27ad801-6fd5-4c49-9017-7c9d9ff966a6]
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
> Task 
> pulp.server.managers.repo.sync.sync[d27ad801-6fd5-4c49-9017-7c9d9ff966a6] 
> raised unexpected: PulpExecutionException('Importer indicated a failed 
> response',)
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
> Traceback (most recent call last):
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
>   File "/usr/lib/python2.7/site-packages/celery/app/trace.py", line 240, in 
> trace_task
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
>     R = retval = fun(*args, **kwargs)
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
>   File "/usr/lib/python2.7/site-packages/pulp/server/async/tasks.py", line 
> 488, in __call__
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
>     return super(Task, self).__call__(*args, **kwargs)
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
>   File "/usr/lib/python2.7/site-packages/pulp/server/async/tasks.py", line 
> 103, in __call__
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
>     return super(PulpTask, self).__call__(*args, **kwargs)
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
>   File "/usr/lib/python2.7/site-packages/celery/app/trace.py", line 437, in 
> __protected_call__
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
>     return self.run(*args, **kwargs)
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
>   File 
> "/usr/lib/python2.7/site-packages/pulp/server/controllers/repository.py", 
> line 810, in sync
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
>     raise pulp_exceptions.PulpExecutionException(_('Importer indicated a 
> failed response'))
> Apr 11 20:28:41 smart-proxy-01 pulp: celery.worker.job:ERROR: (2621-90560) 
> PulpExecutionException: Importer indicated a failed response
>
> Can I increase the timeout? Or is there a way to get more information 
> about why we're not able to sync? Trying to get the pulp urls by curl fail, 
> of course, since I'm not using the client cert. 
>

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