I ended up reworking my filefield’s and just using file = blah and calling .save(). The timestamp stuff was still causing too many directories, and I had to base it off the an id (similar to how we had done it at Curse).

It ends up being screenshots/%s/%s % divmod(id, 1000)

from django.core.filestorage.filesystem import FileSystemStorage

class UsefulFileStorage(FileSystemStorage):
def get_available_filename(self, filename):
# Leave the filename unmodified
return filename

Then when you want to use it in a model:

from django.db import models
from myapp.storage import UsefulFileStorage

class MyModel(models.Model):
screenshot = models.ImageField(upload_to=”screenshots/%s/%s/”, storage=UsefulFileStorage(), blank=True, null=True)