if your trying to attach a program (.exe, .sh, etc.) then your sure to not have any luck. if its pictures or text documents, then you should browse on over to where your files are located, outside of the browse button in outlook. if the files are there, then your looking at a simple software fluke with outlook, if there not but outlook says they are, then simply locate the files and move them to documents or my computer or wherever you prefer.
update me on any problems persisting or if further help is needed.
-coka