Azure Cloud Service deploys failing when targeting Windows Server 2019


We’re trying to upgrade some of our Azure Cloud Services from an older guest OS to the latest Windows Server 2019. When we run those deploys we get errors like this:

Calamari.exe : CloseError: BadRequest : The OS family 6 you are trying to deploy is not supported by the SDK package.

The SDK package supported OS families:1,2. Please try to deploy to a different operating system. To do this specify a different osFamily and/or osVersion in your .cscfg file.

At D:\Octopus\Work\20200211161347-206016-15728\Bootstrap.ps1:49 char:1 + & “D:\Octopus\OctopusServer\Tools\Calamari.Cloud\8.1.3\Calamari.exe” …

Any suggestions?

It’s not clear to me what SDK package this error is complaining about – the one we used to build the package? The one Octopus uses to deploy it? Something internal to Azure that Octopus is invoking?

(Kenneth Bates) #4

Hi @mharen,

Thanks for getting in touch! Firstly I’d like to preface this with a warning that we might not be able to provide an ideal answer here. Cloud services don’t seem to be on the Azure roadmap, and Microsoft has been encouraging other PaaS offerings like Service Fabric instead of Cloud Services, so it might end up being they don’t support this latest OS.

After talking with my team about this, it looks like the Azure team broke stuff about a year ago that caused this error, which was something to do with the ADO build agent images not having the right SDK installed. You might be able to install an updated SDK to support the OS family 6, with more info in the Microsoft doc page below.

I hope that helps! If there’s anything I can try to get some more clarity on, please don’t hesitate to reach out and I’ll be happy to reach out to my team. :slight_smile:

Best regards,


(Kenneth Bates) #5

Hi @mharen,

Just wanted to quickly come back to your issue as after some more discussion with some of my team, it seems I might have provided some incorrect information. I think the issue is that we crack that package open during deployment, do substitutions etc, but when we repackage it we use the older format on the repack. We have an engineer who is currently looking into this, though there’s potentially bad news in that it’s not something we’re going to invest time on fixing considering Cloud Services have effectively been orphaned within Microsoft.

I hope that helps, and my apologies about the initial mistake on my part. I’ll let you know if anything else relevant comes about, and let me know if you have any further questions moving forward. :slight_smile:

Best regards,



Thank you for the information — it is a relief to have an explanation!

I appreciate that you might not be able to fix the issue, and while that’s inconvenient to me, I understand.

Thanks for your thoughtful responses.

(Kenneth Bates) #7

Hi @mharen,

You’re more than welcome! If you have any questions or concerns going forward, don’t hesitate to reach out. :slight_smile:

Best regards,