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Here's my vhost in apache 2.4:

<VirtualHost *:80> ServerName mailcatcher.dev Alias /mailcatcher.dev.png /Users/me/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/mailcatcher-0.5.12/public/images/logo_large.png <Directory /Users/me/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/mailcatcher-0.5.12/public/images> Order allow,deny Allow from all </Directory> ErrorLog "/private/var/log/apache2/mailcatcher.dev-error_log" CustomLog "/private/var/log/apache2/mailcatcher.dev-access_log" common ProxyPass / http://127.0.0.1:1080/ ProxyPassReverse / http://127.0.0.1:1080/ </VirtualHost>

I'm trying to have the one url http://mailcatcher.dev/mailcatcher.dev.png resolve to a file and all other requests be forwarded to the webmail interface. Allegedly my config is fine according to apachectl -t; but the file isn't served and a 404 (below) shows up in my access log (nothing in the error log).

::1 - - [18/Sep/2014:22:42:07 -0600] "GET /mailcatcher.dev.png HTTP/1.1" 404 135

What am I not getting here? This should work according to the spec where it says that the alias can resolve to a file-path.

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This is because the request to /mailcatcher.dev.png is being reverse proxied to your backend application as the ProxyPass directive appear to take higher precedence than Alias

You need to add a ProxyPass /mailcatcher.dev.png ! entry before ProxyPass / http://127.0.0.1:1080/

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