After upgrade to vagrant 2.3.7-1 from 2.3.6-1 WinRM fails when running “vagrant up” on a Windows box. Downgrading to 2.3.6-1 fixes the problem.
Problem is seen on both Ubuntu 20.04 and 22.04 with vagrant installed from the official HashiCorp repo.
Gist showing output from “vagrant up --debug” from both version 2.3.6-1 (working) and 2.3.7-1 (not working) is located here:
I’m happy to report that the 2.3.8.dev-1 package build linked in the bug report fixes the problem. We will install the official 2.3.8 when it’s available.