We are planning to update octopus deploy in the next coming weeks however we are on an older version. What is the best path to upgrade from 3.2.11 to the latest version of octopus deploy? I ask just because certain paths have been tested more and have known issues. We plan to upgrade to at least 3.3.18 because of a fix that is in that version.
Hi Brent,
It’s been a while 
I hope you had a great new year. I’ve sat on this for a few days because I am not really sure how to answer it.
The best thing I can point you to is our comparison feature: https://octopus.com/downloads/compare?from=3.2.11&to=3.8.1
It starts with the minor version summaries and more importantly breaking changes. If there are any breaking changes for features that you use heavily you could determine that maybe upgrading past that version is not for you immediately or will take extra planning.
Currently 3.7.10 has the largest number of installations (mostly because it was the last before the xmas break) so I don’t know if that qualifies it as the most tested? We have more installations in total of higher versions.
I have seen that such a long period between upgrades causes the most shock in new features and potential changes to in use features. Maybe planning somewhere in the middle like 3.4.x and upgrading again soon after may be a valid strategy. It depends if there are any new features that you are interested in? Are there any plans to have a higher occurrence of upgrades or do you mostly wait for features or fixes?
I always recommend our latest version as it has the most fixes for previous versions. I don’t know if I have really answered your question (its hard to answer) but have maybe given you some thinking points.
Of course as always if you have any futher questions or want me to clarify anything please do not hesitate.
Vanessa
Thanks for the information Vanessa. I will take this into account for my upgrade strategy. I didn’t know if there was simply a best way to upgrade, ie make sure to go to 3.5.X before going to 3.8.X or something. Since we are rather far behind I just wanted to make sure to ask