The specified executable is not a valid application for this OS platform


Been seeing these for a while and not thought to ask until now!

Seems to happen on older boxes, the one I’m looking at now is a Windows 7 POSReady box, which is still in support. It’s 32bit too, which I think might be related, and is running Tentacle 5.0.5 currently.

Log attached: ServerTasks-382194.log.txt (11.4 KB)

Hi Matt,

Thank you for contacting Octopus Support.

After checking, it looks like we may not be shipping 32bit tentacle installers in 2020.4.X+ versions of Octopus Server. In order to update the tentacle remotely, you’ll likely need to create a Project/Runbook to handle 32bit OS tentacle upgrades.

I would recommend using chocolatey on the tentacle to do this. There is a community step template available that takes care of chocolatey:

After that, you can run the tentacle installer via Powershell, be sure to use -y for silent install:
choco install octopusdeploy.tentacle -y

(The chocolatey .PS1 script shows that it has both the 32bit and 64bit installers)

I tested this as a Runbook. See the following example:

Step 1 - Chocolatey Step Template:

Step 2 - Install Tentacle:

You may need to select individual deployment targets, you may do so via the Show Advanced button:

Then you may use the “Include specific deployment targets” option:

Hopefully that all makes sense. Let me know if it looks like this will work in your case.


Hi Donny,

Thanks for looking into this for me. Unfortunately I’m not sure if I can use Chocolatey on these machines, even though I love it.

It’s a bit annoying to be honest as I’m going to have to take control over hundreds of machines upgrades instead of leaving Octopus. Why has it been pulled from later versions of Octopus may I ask?

If I have to leave them on v5, are there any features I’ll be missing or any breaking changes to watch for?


Hi Matt,

Thank you for the quick response.

At this time, I do not have an official answer as to why 32bit tentacle installers are not present in the 2020.4.X builds of Octopus Server.

Regarding tentacles, as of right now, Tentacles on version 4.0+ work with any current version of Octopus Server. More info here:

If you have any additional questions, please let me know.


Hi Donny,

32-bit Windows is still a valid OS as Microsoft only stopped shipping these in W10 v2004+, so they’ll be tonnes of people out there on this until they new-up.

Whilst I am disappointed I can’t auto upgrade these from Octopus itself, if they don’t get left behind in future updates, then there shouldn’t be any impact.



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