WinRM - “Blocking operation timed out!”

[misteriosojo]

Vagrant version: 2.4.3
Host OS: Windows 10

Target Hypervisor: Hyper-V + ESXi
Target VM: Windows 10

Communicator type: WinRM

Debug output

Multiple users are encountering issues connecting to VMs using WinRM. I think the issue is caused by the new version of the dependency WinRM.

• Additional information: https://discuss.hashicorp.com/t/winrm-error-blocking-operation-timed-out/71294/1
• It was working with Vagrant v2.4.1
• Additional information: maybe related with this change? WinRb/WinRM@591367c

Expected behavior

Vagrant should try to establish a WinRM connection according to the parameters provided in vagrant file (timeout, retries,...).

Actual behavior

Vagrant exists with the error:

An error occurred executing a remote WinRM command.

Shell: Cmd
Command: hostname
Message: Blocking operation timed out!

Steps to reproduce

1. Try to "Vagrant up" a Windows VM
2. Wait until it fails

Vagrantfile

# not relevant in this use-case --> no special config required