Is there a file size limit to the File Manager UI or do I need to place the files in the Portal directory (../Portals/0/..) and then click on "Synchronize Database And File System" in order to upload the large files to the DNN site?

One caution-- whatever you set that number to, be careful.  When you use HTTP upload, the server will consume that amount of system memory until the operation is complete.  So if you set it to allow 1 Gig files, you need 1 Gig of system memory *just to handle 1 upload*.  If you have 2 simultaneous uploads going, that is 2 gigs, etc.

Something I have been working on is incorporating NeatUpload http://www.brettle.com/neatupload into the file upload stuff (url control and filemanager and wherever else) I have had some success so if you are interested I can bring you upto speed on what I have done

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Dylan Barber http://www.braindice.com - Dotnetnuke development classes - skins and modules