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Tested on Windows Server 2012 R2 + WampServer2.0c.exe (php 5.2.6 + mysql 5.0.51b + apache 2.2.8)

Self-signed SSL certificate on windows###

Install OpenSSL

Open SSL requires the Visual C++ 2008 redistributable Before you can install OpenSSL. The link to download both of these is on this page -> http://slproweb.com/products/Win32OpenSSL.html

Open an Elevated Command Prompt

No matter which Windows you're using, hit the Window's Key on your keyboard, type "CMD", then right click on the Command Prompt and choose "Run as Administrator".

Run the following commands in your prompt. Change "apache2.4.9" to whatever version of Apache you have.

cd C:\wamp\bin\apache\apache2.4.9\bin

openssl genrsa -des3 -out server.key 1024
(Type in your password, verify it)
(Windows systems do not support pass phrase so skip "-des3" part to skip pass phrase feature)

openssl genrsa -des3 -out server.key 1024

openssl req -new -x509 -nodes -sha1 -days 365 -key server.key -out server.crt -config C:\wamp\bin\apache\apache2.4.9\conf\openssl.cnf
(Answer a few questions)

Copy the Key and Certificate
Navigate to: C:\wamp\bin\apache\apache2.4.9\conf
Create a folder called "ssl.crt" and another folder called "ssl.key"
Copy the certificate and the key from: C:\wamp\bin\apache\apache2.4.9\bin
And paste them respectively into the key and certificate folders you just created.

Edit your configuration files
Navigate to: C:\wamp\bin\apache\apache2.4.9\conf
Open httpd.conf in your favorite plaintext editor.
Uncomment the following lines by removing the pound sign (#) from the begining:
LoadModule ssl_module modules/mod-ssl.so
LoadModule socache_shmcb_module modules/mod_socache_shmcb.so
And
Include conf/extra/httpd_ssl.conf
Then move the last one after the block of code that starts with

Navigate to: C:\wamp\bin\apache\apache2.4.9\bin
Open php.ini in your favorite plaintext editor.
Make sure the following line is uncommented by removing the semicolon (;) from the beginning.
extension=php_openssl.dll

Navigate to: C:\wamp\bin\apache\apache2.4.9\conf\extra
Open httpd_ssl.conf in a text editor
Find the line which says .
Right after it, change the line which starts with DocumentRoot to: C:/wamp/www/
Change the line that begins with ErrorLog to: C:/wamp/bin/apache/apache2.4.9/logs/sslerror_log
Change the line that begins with TransferLog to: C:/wamp/bin/apache/apache2.4.9/logs/sslaccess_log
Change the line that begins with SSLCertificateFile to: C:/wamp/bin/apache/apache2.4.9/conf/ssl.crt/server.crt
Change the line that begins with SSLCertificateKeyFile to: C:/wamp/bin/apache/apache2.4.9/conf/ssl.key/server.key
Find the block of code that starts with <Directory "C:/ And add the following lines to it:

Options Indexes FollowSymLinks MultiViews
AllowOverride All
Order allow,deny
allow from all

Verify that your syntax is correct
Run the following in the previous command prompt: httpd -t

If any errors pop up, navigate back to the file in question and check out the line number given in the console.

Restart Apache.

If it does not restart well then check for the apache error logs.

More info:
http://geneticcoder.blogspot.ca/2015/01/how-to-set-up-self-signed-ssl.html
https://support.quovadisglobal.com/kb/a90/i-get-error-message-error-init-sslpassphrasedialog-builtin-is-not-supported-on-win32.aspx
https://justin.kelly.org.au/how-to-create-a-self-sign-ssl-cert-with-no-pa/
http://how2ssl.com/articles/openssl_commands_and_tips/
http://www.discretelogix.com/blog/miscellaneous/installing-self-signed-ssl-certificate-on-wamp-server
https://letsencrypt.org/getting-started/