Windows Notes: SSL, TLS, OpenSSL

  1. The information presented here is intended for educational use by qualified Windows technologists.
  2. The information presented here is provided free of charge, as-is, with no warranty of any kind.
  1. Introduction
  2. Client-Server scripts for Windows demo
  3. Example Sessions
  4. External Links
Edit: 2023-11-11

Introduction

Introductory material can be found on my original OpenSSL web pages: Those pages include steps on how to use the command 'openssl s_client' to do end-to-end testing and debugging.

Installing OpenSSL on Windows

Download a kit from here:
Install OpenSSL for Windows in the root directory of c-drive then access the non-graphical CLI (Command Line Interpreter) like so:
Action Notes
hold down the 'Windows' key while you hit the 'r' key the RUN dialog will appear
type cmd              then click the OK button c:\WINDOWS\system32\cmd32.exe will open
type cd c:/            then hit the <enter> key move to root of c drive
type cd openss* then hit the <enter> key drop into a folder
type cd bin           then hit the <enter> key openssl.exe lives here
type openssl        then hit the <enter> key  

Client-Server scripts for Windows demo

The following examples shows how to start a test server (you may need to create a certificate) then start a test client ON THE SAME MACHINE for educational purposes

DOS - Windows "Scripting Basics"

 sequence	description
-------------	-------------------------------------
::  remarks	beginning of remarks (to end of line)
rem remarks	beginning of remarks (to end of line)
%= remarks =%	embedded remarks
^		line continuation character
echo yada	display variable "yada"
echo ON		display commands as they are executed (script tracing)
echo OFF	disable script tracing

script: ssl-prep1.bat (optional)

Caveat: only execute this script (prep1) if the next script (prep2) fails with an error related to "can't find file openssl.cnf" 
@echo ON
:: =============================================================
:: title   : ssl-prep1.bat
:: purpose : create a self-signed certificate for ssl-server.bat
:: notes   : ONLY DO THIS if file "openssl.cnf" is missing
:: platform: DOS/Windows
:: author  : Neil Rieck
:: created : 2018-01-30
:: =============================================================
copying the OpenSSL template file
:: copy the file and change the extension
copy c:\OpenSSL-Win32\bin\openssl.cfg openssl.cnf
echo Done

script: ssl-prep2 (one time only)

@echo ON
:: =============================================================
:: title   : ssl-prep2.bat
:: purpose : create a self-signed certificate for ssl-server.bat
:: platform: DOS/Windows
:: author  : Neil Rieck
:: created : 2018-01-30
::==============================================================
echo Creating Self-Signed Certificate
setlocal
IF EXIST c:\OpenSSL-Win32\bin SET PATH=%PATH%;c:\OpenSSL-Win32\bin
openssl	req		%= a circumflex continues the line =%			^
 -new										^
 -nodes										^
 -x509			%= x509 as a switch indicates "self signed" =%		^
 -config openssl.cnf								^
 -days 365		%= will expire in one year =%				^
 -set_serial 20180130	%= any big number (here I used ccyymmdd) =%		^
 -keyout hack123.key	%= I could have created/used a new key with -keyout =%	^
 -out hack123.crt	%= certificate data will be written here =%
echo Done
endlocal

script: ssl-server1.bat (serves up a fake file)

@echo ON
:: =====================================================
:: title  : ssl-server1.bat
:: purpose: ssl server demo for DOS/Windows
:: author : Neil Rieck
:: created: 2018-01-30
:: =====================================================
echo Starting OpenSSL Server1 (simple)
setlocal
IF EXIST c:\OpenSSL-Win32\bin SET PATH=%PATH%;c:\OpenSSL-Win32\bin
openssl s_server						^
 -accept 5000		%= listen on port 5000 =%		^
 -cert hack123.crt						^
 -key hack123.key						^
 -debug			%= this line is optional =%		^
 -www			%= barely simulate a webserver =%
echo Done

script: ssl-server2.bat (returns the file you request)

@echo ON
:: =====================================================
:: title  : ssl-server2.bat
:: purpose: ssl server demo for DOS/Windows
:: author : Neil Rieck
:: created: 2018-01-30
:: =====================================================
echo Starting OpenSSL Server1 (simple)
setlocal
IF EXIST c:\OpenSSL-Win32\bin SET PATH=%PATH%;c:\OpenSSL-Win32\bin
openssl s_server						^
 -accept 5000		%= listen on port 5000 =%		^
 -cert hack123.crt						^
 -key hack123.key						^
 -debug			%= this line is optional =%		^
 -WWW			%= fully simulate a webserver =%
echo Done

script: ssl-client.bat

@echo ON
:: =====================================================
:: title  : ssl-client.bat
:: purpose: ssl client demo for DOS/Windows
:: author : Neil Rieck
:: created: 2018-01-30
:: =====================================================
echo Starting OpenSSL client on port 5000
setlocal
IF EXIST c:\OpenSSL-Win32\bin SET PATH=%PATH%;c:\OpenSSL-Win32\bin
openssl s_client						^
 -debug				%= this is optional =%		^
 -connect 127.0.0.1:5000 
echo Done

fake web page

This fake web page (index.html) is required by ssl-server2.bat
<!DOCTYPE html>
<html>
<head>
<title>index.html</title>
</head>
<body>
<p>This is a test</p>
</body>
</html>

Example Sessions

Legend:
    <ur>	user response
    <sr>	system response
    <enter>	hit the enter key
 
session #1 (server) session #2 (client) 
<sr> C:\Users\Neil>
<ur> ssl-server1.bat <enter>
<sr> bla...bla...bla...	
<sr> bla...bla...bla...	
<sr> bla...bla...bla...	
<sr> C:\Users\Neil>
<ur> ssl-client.bat <enter>
<sr> bla...bla...bla...
<ur> GET / HTTP/1.0<enter>
<sr> bla...bla...bla...
 
session #1 (server) session #2 (client) 
<sr> C:\Users\Neil>
<ur> ssl-server2.bat <enter>
<sr> bla...bla...bla...	
<sr> bla...bla...bla...	
<sr> bla...bla...bla...	
<sr> C:\Users\Neil>
<ur> ssl-client.bat <enter>
<sr> bla...bla...bla...
<ur> GET index.html HTTP/1.0<enter>
<sr> bla...bla...bla...
 

External Links

SSL (general) 

Free OpenSSL books

OpenSSL Tutorials

OpenSSL for Windows

Other

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 Neil Rieck
 Waterloo, Ontario, Canada.