Tentacle on Azue VM, Octopus Server on premises


I want to deploy a web site on an older Azure VM.
Octopus Deploy server v2.5 is installed on premises.
Azure VM is running Windows Server 2008 R2 Datacenter.
I manually installed the Octopus Tentacle v2.5 on the VM.
Firewall rule is present in the VM (automatically done by Tentacle installation).
Endpoint is added: private and public port 10933.

I get connection errors in my Octopus Deploy server (Environment):
Not connected. The machine has not completed a post-configuration handshake, so communication is not yet established.
Pipefish.Errors.PipefishCommunicationException: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.

What am I missing?
Do I need Windows 2012 on the VM?
Do I need Octopus v3?
Or is it not supported to have the Octopus Tentacle on Azure and not the Octupus Server ?

Kind regards,


Thanks for reaching out. The Octopus or OS version should no be a problem. This is most likely a connectivity problem between your on-premise server and the Azure box. Please check out this document where we show a couple of techniques to troubleshoot listening Tentacles http://docs.octopusdeploy.com/display/OD/Troubleshoot+Listening+Tentacles



Hi, following the troubleshoot guide, I found this error message in the OctopusTentacle logfile. Is this a known issue with a workaround ?

ERROR Error checking pending timeouts
System.PlatformNotSupportedException: The specified cryptographic algorithm is not supported on this platform.
at System.Security.Cryptography.AesCryptoServiceProvider…ctor()
at Octopus.Shared.Security.MasterKey.MasterKeyEncryption.WriteCiphertextTo(Byte[] masterKey, Stream stream)
at Pipefish.Persistence.Filesystem.ActorStateFile.Save(ActorStateDictionary state)
at Pipefish.PersistentActor`1.Save()
at Pipefish.WellKnown.Timing.Clock.Save()
at Pipefish.WellKnown.Timing.Clock.Check()

Update: I got the tentacle running on the Azure VM!
The previous error did not block the working.
Root cause:
some ports on Azure are blocked by our network administators.
F.e. I could not connect to the VM (tentacle) using port 10933, but I worked on port 8080.

Best regards,