Cygwin Setup Instructions for Windows (2012-R2 x64)

Owned by Debesh Roy Chowdhury
Last updated: Oct 21, 2022 by Brian MillerVersion comment
3 min read

Pre-Setup Instructions

1. Deploy a new standard Windows 2012-R2 x64 image on a physical or virtual machine (VM) or install from a Deployment Kit unattend.txt script or install from media manually.
2. Setup forward & reverse DNS records on your DNS server (consult your IT admin/sysadmin if required) and set the hostname and primary DNS suffix on the machine itself if necessary (see Appendix B2.1)  

(info) Note: If required by your IT department, perform any other standard configuration (ie: create a separate admin account with a strong password, set timezone, date & time or set it to synchronize with an NTP server, etc.), server hardening (ie: disable default administrator logins, change default remote port (ex: RDP), install anti-brute force attack prevention software (ex: IPBan, RDPGuard), enable & configure local firewall, etc.).  


Download, Install & Configure Cygwin

3. Download the latest Cygwin from https://cygwin.com/setup-x86_64.exe
4. Proceed through the installation wizard as shown below:   

(info) Note: default is Proxy, change to "Direct Connection" if directly connected

5.  On the package selection step, change the View to "Full" and filter the packages to add "cygutils-extra", "nc", "patch", "python27", "python27-pip", "unzip", and "wget".

6.  Proceed through the rest of the installation:   

7.  Create the opt dir via Explorer or CMD.EXE, ie:  mkdir c:\cygwin64\opt
8.  Add an inheritance-enabled ACL entry for "Administrators" with "Full Control" to c:\cygwin64 via Explorer or CMD.EXE, ie: icacls c:\cygwin64 /grant Administrators:(OI)(CI)F /T /L /C

(info) /T = Apply recursively, /L = operate on symbolic link itself VS target, /C = display any error message(s) and continue 

9.  Add c:\cygwin64\bin to the System PATH environment variable
10. In the Cygwin Terminal, make a symlink of python to /bin/python2.7.exe, ie:  ln -nfs /bin/python /bin/python2.7.exe
11.  Reboot


Using Cygwin

10. To use Cygwin, simply launch the Cygwin64 Terminal from the Start Menu or Desktop

(warning) IMPORTANT:  Many tasks in Windows require running with Administrative permissions so it is recommended that you always R-click and select "Run as administrator" in the cascading sub-menu when running the Terminal.

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