This solution supposes initial keeping of the uploaded BIG image. I am not a specialist in the webserver memory utilization, but a solution with validator RESIZE, which called on any upload to the given field is more straightforward IMHO. Such solution was published in the web2py group about a year ago. It utilizes PIL also and cStringIO as a temporal buffer. The same approach was for automarking images with the site logo. Place a module with validator in module folder. ================ __all__ = [ 'RESIZE', ] class RESIZE(object): """ Resize image such as thumbnail """ def __init__(self,nx=160,ny=80,error_message='image resize error'): (self.nx,self.ny,self.error_message)=(nx,ny,error_message) def __call__(self,value): if isinstance(value, str) and len(value)==0: return (value,None) from PIL import Image import cStringIO try: #load im=Image.open(value.file) #resize im.thumbnail((self.nx,self.ny),Image.ANTIALIAS) #by hand s=cStringIO.StringIO() im.save(s,'JPEG',quality=86) s.seek(0) value.file=s except: return (value,self.error_message) else: return (value,None) =========== Vale!