Doh! <facepalm>
After sleeping on this overnight I've discovered a misconfigured server.
All working as desired now.

Apologies for the noise.

On 12/18/2008, "Jeremy Bowen" <jer...@smartpoint.co.nz> wrote:

>I have a problem with mod_gzip not compressing output from httpd
>
>My System is:
>OpenBSD 4.4 (GENERIC) #1021: Tue Aug 12 17:16:55 MDT 2008
>dera...@i386.openbsd.org:/usr/src/sys/arch/i386/compile/GENERIC
>
>I'm running the stock httpd however it is not chrooted
>httpd_flags = "-u -DSSL"
>
># httpd -v
>Server version: Apache/1.3.29 (Unix)
>
>I've installed mod_gzip as a package:
># pkg_info mod_gzip
>Information for inst:mod_gzip-1.3.26.1ap2
>
>I have copied the sample mod_gzip.conf into /var/www/conf/modules and
>have stopped and started apache.
>
>I've tested that mod_gzip is recognised by the server by fetching
>http://www.smartpoint.co.nz/mod_gzip_status
>which returns:
>
>mod_gzip is available...
>mod_gzip_version = 1.3.26.1a
>mod_gzip_on = Yes
>
>I'm attempting to test this from:
>http://www.whatsmyip.org/mod_gzip_test/
>Unfortunately indicates that none of my files/traffic is being gzip'ed.
>
>In /var/www/conf/modules/mod_gzip.conf I've enabled
>mod_gzip_keep_workfiles       Yes
>Minimum file-size: 500
>Max: 500000
>I have commented out any mod_gzip_item_exclude entries.
>
>There are no working files in /tmp. Nor are there any entries in
>/var/www/logs/mod_gzip.log
>
>I'm running with Virtual hosting if that makes a difference.
>
>I've even tried telnetting to port 80 to fetch a suitable text or html
>file and issuing an:
>"Accept-Encoding: gzip"
>command but that also fails to gzip the file. (I successfully get the
>uncompressed file though).
>
>Any ideas on how to debug this would be greatly appreciated.
>
>Thanks in advance
>Jeremy

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