I am not seeing a large amount of blog entries complaining about this upgrade, 
how has that gone for you? Is there anything you found particularly painful? 
Would you have done anything different in retrospect?

I'm staring down a 3.7.2 -> 4.2.1 upgrade and after reading a number of docs 
the back-of-the-envelope optimal upgrade path is as follows. If any of you have 
commentary I am quite interested, otherwise I will try it and see what happens. 
I feel like this might be more time-consuming work but less brainpower effort 
than just yanking everything to 4.2.

1) rpms up to puppet 3.8

PostgreSQL 8.4 to 9.4
PuppetDB 2.2.2 to 2.3.7
(puppetdb-terminus from 2.2.2 to 2.3.7)
Puppet 3.7.2 to 3.8.2

2) enable the future parser

3) replace puppet 3.8.2, passenger 5 with puppetserver 1.1.1

4) replace puppetserver 1.1.1 with puppetserver 2.1.1

5) upgrade PuppetDB from 2.3.7 to 3.0.2

6) use the puppetlabs-puppet_agent forge module to upgrade agents to 4.2.1


My reading:

https://docs.puppetlabs.com/puppet/latest/reference/

https://docs.puppetlabs.com/puppet/4.2/reference/upgrade_major_pre.html
https://docs.puppetlabs.com/puppet/4.2/reference/upgrade_major_server.html
https://docs.puppetlabs.com/puppet/4.2/reference/upgrade_major_agent.html
https://docs.puppetlabs.com/puppet/4.2/reference/upgrade_major_post.html

https://forge.puppetlabs.com/puppetlabs/puppet_agent

https://docs.puppetlabs.com/puppetdb/2.3/upgrade.html

http://docs.puppetlabs.com/puppetdb/3.0/upgrade.html

http://www.postgresql.org/docs/9.4/static/upgrading.html

(Although I may dump/restore the data via puppetdb since that's the actual api 
to the data, we do not log in via PostgreSQL.)

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