ContentDigest not working

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Apache 2.4.10 running on Debian Jessie.
I want to enable ContentDigest for one folder on a virtualhost.

Contents of the virtual host file is:

<VirtualHost *:80>
        ServerName des.blah.com
        ServerAlias des.blah.co.uk
        DocumentRoot /var/www/des/

        <Directory />
                Options -Indexes +FollowSymLinks
                AllowOverride None
        </Directory>

        <Directory "/var/www/des/fix/">
                Options -Indexes
                AllowOverride All
                Order Allow,Deny
                Allow from All
                ContentDigest On
        </Directory>

        ErrorLog /var/log/apache2/des.error.log
        CustomLog /var/log/apache2/des.access.log combined
</VirtualHost>

The virtualhost works I can access the files stored in /var/www/des/fix/ using the URL http://des.blah.com/fix/. But if I request the HEADER it doesn't contain the Content-MD5 field.

The virtualhost has been enabled using "a2ensite des.blah.com.conf" and apache has been restarted.

I have also attempted to using a .htaccess file with just "ContentDigest On" inside it within the /var/www/des/fix/ directory but this didn't work either.

I have also set "ContentDigest On" within the apache2.conf and following a restart of apache it didn't work.

Nothing within des.error.log or des.access.log stands out, I have turned up the LogLevel to trace8. A sample of what I see in the des.error.log (The file I was requesting is called manufacturers.tx):

error:
[Thu May 14 11:57:10.873385 2015] [core:trace3] [pid 10790] request.c(238): [client xx.xx.28.122:60285] request authorized without authentication by access_checker_ex hook: /fix/manufacturers.tx
[Thu May 14 11:57:10.873563 2015] [filter:trace2] [pid 10790] mod_filter.c(193): [client xx.xx.28.122:60285] Content-Type condition for 'deflate' did not match: no Content-Type
[Thu May 14 11:57:10.873578 2015] [filter:trace2] [pid 10790] mod_filter.c(193): [client xx.xx.28.122:60285] Content-Type condition for 'deflate' did not match: no Content-Type
[Thu May 14 11:57:10.873583 2015] [filter:trace2] [pid 10790] mod_filter.c(193): [client xx.xx.28.122:60285] Content-Type condition for 'deflate' did not match: no Content-Type
[Thu May 14 11:57:10.873587 2015] [filter:trace2] [pid 10790] mod_filter.c(193): [client xx.xx.28.122:60285] Content-Type condition for 'deflate' did not match: no Content-Type
[Thu May 14 11:57:10.873591 2015] [filter:trace2] [pid 10790] mod_filter.c(193): [client xx.xx.28.122:60285] Content-Type condition for 'deflate' did not match: no Content-Type
[Thu May 14 11:57:10.873625 2015] [http:trace3] [pid 10790] http_filters.c(1045): [client xx.xx.28.122:60285] Response sent with status 200, headers:
[Thu May 14 11:57:10.873655 2015] [http:trace5] [pid 10790] http_filters.c(1052): [client xx.xx.28.122:60285]   Date: Thu, 14 May 2015 10:57:10 GMT
[Thu May 14 11:57:10.873661 2015] [http:trace5] [pid 10790] http_filters.c(1055): [client xx.xx.28.122:60285]   Server: Apache/2.4.10 (Debian)
[Thu May 14 11:57:10.873666 2015] [http:trace4] [pid 10790] http_filters.c(874): [client xx.xx.28.122:60285]   Last-Modified: Tue, 28 Apr 2015 13:29:40 GMT
[Thu May 14 11:57:10.873671 2015] [http:trace4] [pid 10790] http_filters.c(874): [client xx.xx.28.122:60285]   ETag: \\"5841-514c8dac65900\\"
[Thu May 14 11:57:10.873675 2015] [http:trace4] [pid 10790] http_filters.c(874): [client xx.xx.28.122:60285]   Accept-Ranges: bytes
[Thu May 14 11:57:10.873679 2015] [http:trace4] [pid 10790] http_filters.c(874): [client xx.xx.28.122:60285]   Content-Length: 22593
[Thu May 14 11:57:10.873683 2015] [http:trace4] [pid 10790] http_filters.c(874): [client xx.xx.28.122:60285]   Keep-Alive: timeout=5, max=100
[Thu May 14 11:57:10.873687 2015] [http:trace4] [pid 10790] http_filters.c(874): [client xx.xx.28.122:60285]   Connection: Keep-Alive

access:
xx.xx.28.124 - - [14/May/2015:12:30:07 +0100] "HEAD /fix/manufacturers.tx HTTP/1.1" 200 207 "-" "curl/7.21.0 (i486-pc-linux-gnu) libcurl/7.21.0 OpenSSL/0.9.8o zlib/1.2.3.4 libidn/1.15 libssh2/1.2.6"

Any ideas on what I have missed?


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