I have been trying to solve this issue now for a couple of days without any 
progress but I now know why the problem exists.
I updated the web app and re-deployed it and realised that it is using an older 
version of the webapp.
It would seem the context root of the servlet is being changed to an older 
cached version of the app that exists somewhere (not in the webapp directory. 
The updated war file is the only app in the webapp directory) so why it's 
behaving this way is a mystery to me right now.
I hope someone can shed a light on this for me.
Thanks for any pointers in advance. 

On 11 Feb 2011, at 20:14, Caldarale, Charles R wrote:

>> From: angelicos [mailto:angeli...@gmail.com] 
>> Subject: Re: Tomcat won't serve newly created files
> 
>> I've looked through the logs also. Nothing about the 404 error.
> 
> Turn on the AccessLogValve in server.xml to get some more information.
> 
>> Regarding where the files are stored, I'm afriad it's in the
>> deployment directory.
> 
> Can you be more specific about their exact location?
> 
> Have you verified that the Tomcat userid has read access to those files?
> 
>> as to what mechanism is being used to serve the files....
>> Well https download.
> 
> Sorry, I should have been more clear.  I meant what servlet or JSP is 
> delivering the content?  Is it Tomcat's DefaultServlet, or something else?  
> What is an example of a failing URL?
> 
> You should post the <Context> element and WEB-INF/web.xml for the webapp; 
> there might be something amiss.
> 
> - Chuck
> 
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