Hi 40rods. Did you allready get this problem solved? I get the same problem, however, in my situation it appears in the file manager! But the same failure as you describe appears in my installation. I'm using dnn 3.2.2.

I was wondering if you had this problem fixed allready? Anyhow, i changed the maxreqeustlength too, just like you did, to a much bigger value, and the same happens to me, i still get the same Request timed out error.
I'm getting a bit dissapointed at this time...

that's some nasty ****. What you're telling me that it is NOT possible to upload large amounts of files at one time.. I think that's one major disadvantage of DNN. Will it work when you upload small portions at a time, or do all the files add up. What i mean is that , the more files you upload, the more time it takes to synchonise (since it has to synchronise all files, and not only the new ones)

Or does the synchronising only synchronise the latest files and therefore, i can upload small portions at a time?

OK, but it seems not to be the uploading that causes the time out. It is just that after uploading files (not even a lot, say 1MB at a time) using ftp. After this step, (using file manager), i synchronise the database (which is DNN functionality isn't it?) i get the "Request timed out" message. It looks to me, that i should be able to set the (internal?) time out value much higher, but I don't know how to do this or if this is even possible. Also look at this thread for more information:
http://www.dotnetnuke.com/Community/ForumsDotNetNuke/tabid/795/forumid/108/threadid/25981/scope/posts/Default.aspx