Let's Encrypt renewal never finishing

I’m running Octopus 2020.3.2 on an Azure VM, and I have Let’s Encrypt setup which has been working fine. But now it’s time for renewal and the server is failing to install a new cert. It seems to get one successfully, but then fail to install it.


The server seems to be running the Let’s Encrypt renewal twice simultaneously, and I’m wondering if that’s causing the issue?

I’ve tried rebooting the VM, but the issue persists.

Any ideas how to fix this?

Hi @Iain_Brown,

Thanks for getting in touch!

When you start the process and the two tasks appear, if you select one of the tasks there should be a cancel option at the top right. If you use that so only a single task is running do you notice any difference?


If I cancel one of the tasks, it instantly adds a new copy of the same task which also gets stuck on the “configuring server” stage.

Would you be able to check the Task Log tab and download and attach the full log for the running task?

I’ve redacted some bits for privacy reasons, but here’s the log.

ServerTasks-53647.log.txt (2.2 KB)

The interesting part does seem to be:

“Waiting for other tasks to complete”

We just run some testing on this and the task did get further, but we found that at the end it didn’t seem able to take the node out of draining/maintenance mode. But when we manually did this the task then completed correctly.

Yours seems to be getting stuck at an earlier part, but I wonder if you go to Configuration > Maintenance and enable maintenance mode, it may nudge the task into action.

OK, setting in maintenance mode alone wasn’t enough, but putting the server in maintenance mode and then cancelling one of the renewal tasks then allowed the other renewal task to succeed. I guess being in maintenance mode stopped another renewal task being automatically triggered.

I think I’m all good now, thanks for your help!

That’s good to hear, we’ll run some more tests here to see if we can replicate the creation of multiple tasks.

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