I have tried this on the current Gallery 3 Beta2 version and on the latest (as of today) experimental version.
I pick to add from the server and I select my directory. The directory and the six files inside are chmodded to 777. The 6 files are jpeg images around 400k each. The import processes all 7 files (6 + directory) and no errors are displayed.
In Gallery3 B2, there are 6 images there but 2 of them are blank. When you select the link there is no image. When I check the file system var, there is no image. When I check Maintenance, there are 2 images out of date. Running the maintenance script shows errors that they could not be updated (cause they don't exist on the filesystem in var).
In Gallery3 B2, there are only 4 images displayed, the two blank ones do not show up. In maintenance it still shows 2 images out of date. I assume that is cause information about them is in the database.
Final thing I tried:
Selected one of the images and uploaded through the browser. The image processed fine.
What can I do to get all of my images to process from the server? Again everything is owned by the same user and chmodded to 777.