Any Ideas? When I try to drag and drop a .tif file into a container field while I have Outlook with Mapilabs Attachment Processor software installed, everything freezes. Without Mapilab installed, no problem. It only seems to happen with .tif's and not pdf or other types.

Try it using the Insert step; either Insert Picture or Insert File (you didn't really specify which you needed, and a Tiff could be either). You will get much better results than with copy/paste, and maybe it won't freeze.

Insert does work but then I have to export the file in order to open and view it. When I Drag & Drop I can right click the container field and open it. We drag and drop a lot of files into containers and we often need to view them.