REQUEST_FILENAME issues, stopped functioning with php upgrade - .htaccess

Question

So I have a request_filename rule which has suddenly stopped working. I have recently upgraded my server to Jessie, and php upgraded with it.
However, this is the rewrite rule I have at the moment.
RewriteEngine on
RewriteCond %{HTTP_HOST} ^www\.URL\.com$
RewriteRule ^/?$ "http\:\/\/URL\.com\/" [R=301,L]
RewriteCond %{THE_REQUEST} ^.*/index.html
RewriteRule ^(.*)index.html$ http://www.URL.com/$1 [R=301,L]
RewriteBase /
RewriteCond %{REQUEST_FILENAME} !-d
RewriteCond %{REQUEST_FILENAME}\.html -f
RewriteRule ^(.*)$ $1.html
RewriteRule ^(.*)/$ $1 [NC,L]
The .htaccess file is owned by www-data and can be accessed.
I seem to see this in the error logs
[Thu Jun 04 19:43:21.641790 2015] [authz_core:debug] [pid 15423] mod_authz_core.c(809): [client 213.138.113.36:65331] AH01626: authorization result of Require all granted: granted, referer: http://www.URL.com/
[Thu Jun 04 19:43:21.641883 2015] [authz_core:debug] [pid 15423] mod_authz_core.c(809): [client 213.138.113.36:65331] AH01626: authorization result of <RequireAny>: granted, referer: http://www.URL.com/
[Thu Jun 04 19:43:21.642056 2015] [core:info] [pid 15423] [client 213.138.113.36:65331] AH00128: File does not exist: /var/www/URL/about, referer: http://www.URL.com/
Is it perhaps something I am not loading in my virtual host conf?
<VirtualHost *:80>
ServerAdmin EMAIL#hotmail.com
ServerName URL.com
ServerAlias www.URL.com
ServerAlias *.URL.com
SetEnv APPLICATION_ENV dev
DocumentRoot /var/www/URL
ScriptAlias /cgi-bin/ /usr/lib/cgi-bin/
<Directory "/usr/lib/cgi-bin">
AllowOverride All
Options +ExecCGI -MultiViews +SymLinksIfOwnerMatch
Order allow,deny
Allow from all
</Directory>
ErrorLog ${APACHE_LOG_DIR}/URL.error.log
# Possible values include: debug, info, notice, warn, error, crit,
# alert, emerg.
LogLevel debug
CustomLog ${APACHE_LOG_DIR}/URL.access.log combined
</VirtualHost>
This is a website I took over hosting, I don't usually work with .htaccess files. Any advice would be appreciated.
The issue I have is the pages try to load as www.url.com/about This fails as the file is about.html.

Answer 1

I see a few things going on here. I don't see a Directory Directive for the actually document root. Which then would not be using the .htaccess file because there is no AllowOverride All specified for your document root. Also you shouldn't use 2.2 directives in 2.4. Change your Vhost file to look like this. I modified it slighty and added the directory Directive for your root.
<VirtualHost *:80>
ServerAdmin EMAIL#hotmail.com
ServerName URL.com
ServerAlias *.URL.com
SetEnv APPLICATION_ENV dev
DocumentRoot /var/www/URL
<Directory "/var/www/URL">
Options -Indexes -MultiViews
AllowOverride All
Require all granted
</Directory>
ScriptAlias /cgi-bin/ /usr/lib/cgi-bin/
<Directory "/usr/lib/cgi-bin">
AllowOverride All
Options +ExecCGI -MultiViews +SymLinksIfOwnerMatch
Require all granted
</Directory>
ErrorLog ${APACHE_LOG_DIR}/URL.error.log
# Possible values include: debug, info, notice, warn, error, crit,
# alert, emerg.
LogLevel debug
CustomLog ${APACHE_LOG_DIR}/URL.access.log combined
</VirtualHost>

Answer 2

The issue was the my main apache2.conf file.
AllowOveride was disabled.
I made the following change
<Directory /var/www/>
Options Indexes FollowSymLinks
AllowOverride All
Require all granted
</Directory>