POC upgrade - thoughts and questions

[Mike_Prendergast]

Based upon the sheer number of updates being applied in our upcoming upgrade, Justin recommended that we do a POC update on a clone prior to attempting the live update. I agree complete, but have a few thoughts and questions as a follow up. Unfortunately the original ticket closed automatically, and replying does not re-open the same ticket.

My thoughts are as follows, please point me back in the right direction if I am off.

• Clone server, rename and re-IP the new clone
  • Does this server need to be on a locked down subnet such that it does not attempt to communicate with the existing tentacles, and automatically upgrade them? Or does the target environment tentacles only get updated via a deployment, and not via a health check?
  • Since the server thumbprint is shared between the two servers, will the tentacles listen for requests from either server? My assumption is yes, but I hate to assume.
  • If the tentacles do get updated, will the tentacles still work with the original Octopus instance? Meaning if I run a test deployment via the clone to a QA environment, and the tentacles are upgraded, will the QA environment tentacles still work with the original server, or just the clone? Obviously I don’t wish to break the existing implementation.
• Run the upgrade on the clone as documented per these steps…
  • Switch the clone server to Maintenance Mode
  • Download latest MSI installer if not already done so.
  • Run installer
  • Turn off Maintenance Mode
• Attempt to access the UI via a host file entry locally
  • Confirm UI is working as expected
  • Attempt a deployment or two to test environments? The answers to the tentacle questions above will help with this question.
• Anything else I am not thinking of?

Thanks again for your help and quick turnaround on questions. It’s very much appreciated!

[Daniel_Fischer]

Hi Mike,

Thanks for getting in touch! I’d be happy to answer your questions here. It sounds like your POC is pretty solid and should go ahead smoothly.

Does this server need to be on a locked down subnet such that it does not attempt to communicate with the existing tentacles, and automatically upgrade them?
Since the server thumbprint is shared between the two servers, will the tentacles listen for requests from either server?

It is a good idea to do this because yes, if they share a thumbprint, the Tentacle will listen for requests from both servers and this can cause some issues.

If the tentacles do get updated, will the tentacles still work with the original Octopus instance?

This depends on the version of Octopus and Tentacle, we have done a lot of work to make Tentacle and Server compatible between different versions. We even have a Compatibility documentation page with the relevant details.

Run the upgrade on the clone as documented per these steps…

• Switch the clone server to Maintenance Mode
• Download latest MSI installer if not already done so.
• Run installer
• Turn off Maintenance Mode

This is on point and should not cause any issues. The upgrade should go through smoothly.

Attempt to access the UI via a host file entry locally

• Confirm UI is working as expected
• Attempt a deployment or two to test environments? The answers to the tentacle questions above will help with this question.

This also sounds like a good plan. I think you have a good POC written up here and should not encounter any major issues.

As for you “anything you are not thinking of” question, just the default blanket advice I guess of making sure you take a database backup before the server upgrade. Never hurts to be cautious with the database.

If you have any questions here or I have missed anything, please don’t hesitate to let me know.

If you do encounter any issues with the upgrade and need a hand, I’ll be happy to help.

Let me know how you go here.

Best regards,
Daniel