How do I get Django Admin to delete files when I remove an object from the database/model?

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You can receive the pre_delete or post_delete signal (see @toto_tico’s comment below) and call the delete() method on the FileField object, thus (in models.py):

class MyModel(models.Model):
    file = models.FileField()
    ...

# Receive the pre_delete signal and delete the file associated with the model instance.
from django.db.models.signals import pre_delete
from django.dispatch.dispatcher import receiver

@receiver(pre_delete, sender=MyModel)
def mymodel_delete(sender, instance, **kwargs):
    # Pass false so FileField doesn't save the model.
    instance.file.delete(False)

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