The Password complexity is a Local Policy setting named "Passwords must meet complexity requirements" under Computer Configuration/Windows Settings/Security Settings/Account Policies/Password Policy.

In a Server Core installation there is no graphical user interface to set this policy.
Instead use secedit to import and export the security settings from a Full Installation of Windows Server 2008.

  1. First export your security configuration using the following command:

    secedit /export /cfg C:\securityconfig.cfg
      

  2. Then open notepad.exe and edit the C:\securityconfig.cfg file.
    Under [System Access] you should find PAssword complexity = 1
    Change the value to 0 and save the file.
  3. Then fire up the next command to import the configuration:

    secedit /configure /db C:\Windows\security\new.sdb /cfg C:\securityconfig.cfg /areas SECURITYPOLICY

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