Chef Workstation 0.18.3 PowerShell Issues (Windows Server 2019)

Experiencing issues with powershell and bootstrapping. The shell just hangs at....

Connecting to [IP]

I need to know where chef workstation logs to? How can I tell whats happening so that I can troubleshoot why the shell is hanging at the very beginning of the process?

Thank you,

Ok according to this website ( the logs are located here: Chef Workstation logs are stored in ~/.chef-workstation/logs.

Unfortunite for me when I goto that location and open the log file it is empty. Can someone please help point me in the right direction for the next steps?

Have you validated that you can reach the remote host via WinRM outside of the knife bootstrap command?

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Thank you, I have to check the firewall


that got me further, but now I have another issue. I get this error so the bootstrap never completes.

[IP] C:\Users\benelocaladmin\Documents>chef-client -c C:\chef/client.rb -j C:\chef/first-boot.json
[IP] [2020-06-02T13:44:18+00:00] FATAL: Errno::EINVAL: Invalid argument @ dir_s_mkdir - C:ef

ERROR: The following error occurred on [IP]:


We ran into similar issues ourselves about a week ago with the 18.x version of the Chef-Workstation. (specifically referring to the missing slashes “dir_s_mkdir - C:ef”).

We rolled back to 17.5, and everything seems to work fine. That being said, this issue may have been resolved in the current release which is 18.3.

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that is the version I have 0.18.3. So this is not fixed. I will see what happens if we install 17.5 instead. Thank you

17.5 worked like a charm! Thank you!