Azure App Service Targets - Tentacle Health Check - Using Custom Proxy


Just a bit of feedback for others who may experience a problem we’ve encountered and originally documented here:

With a fix applied here:

In summary:

  • On-prem Octopus Server instance (Default Proxy configured)
  • On-prem Octopus Tentacle instance (Custom Proxy configured)
  • Deploying to Azure App Service targets
  • Target health check failing with “Proxy Authorization Required” response (407) introduced in 2021.1.7379 (Build 7379)
  • We could still however deploy to Azure

We recently upgrade to
2021.3 (Build 12132)

2021.1 (Build 7379)

Prior to that

We were hoping that 2021.3 (Build 12132), would fix the problem. The fix for issue 6958 indicates the problem was resolved in (2021.1.7722, 2021.2.7382, 2021.3.2035). However it did not resolve the issue for us - the issue was still present.

Another subsequent ticket:

And issue:

Also had issue with Health Check and use of Customer Proxy but this time from Octopus Server, rather than the tentacle.

Here the cause was found to be the Health Check not respecting the Port configured in the Custom Proxy configuration…

The reason for this post is to say that under 2021.3 (Build 12132) changing the Tentacle to use the Default Proxy option rather than Custom Proxy option, for us, resolved the issue with Azure App Service Health checks failing because of “Proxy Authorization Required” response (407)


Hi @john2,

Thanks for reaching out and we appreciate your input on this issue. Hopefully, this information helps out other clients along the way.

I will bring this back up with our engineering team to let them know that in your case upgrading did not have the expected result of fixing this issue. I will let you know when I have any other information and in the meantime please let me know if you need anything else from us.


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