The tools for Rackspace Cloud Files suck, so here is a non-overwrite recursive directory uploader in Python.

cloudfiles_directory_upload.py

# SET THESE
USERNAME = ''
API_KEY = ''
CONTAINER_NAME = ''
LOCAL_DIRECTORY_NAME = ''

# FORGET THESE
import cloudfiles
import os
import sys
import time


def transfer_callback(tfd, size):
    print "%s / %s\r" % (tfd, size),
    sys.stdout.flush()

connection = cloudfiles.get_connection(USERNAME, API_KEY)
container = connection.get_container(CONTAINER_NAME)

all_objects = container.list_objects()

errors = []
uploads = []

total_start = time.time()
try:
    for root, dirs, files in os.walk(LOCAL_DIRECTORY_NAME):
        for f in files:
            local_path = os.path.join(root, f)
            remote_path = local_path[len(LOCAL_DIRECTORY_NAME):]
            if remote_path not in all_objects:
                print "Uploading:", remote_path
                sys.stdout.flush()
                try:
                    start = time.time()
                    obj = container.create_object(remote_path)
                    obj.load_from_filename(
                      local_path,
                      callback=transfer_callback)
                    elapsed = time.time() - start
                    uploads.append( ( remote_path, elapsed ) )
                    print "\rDone - %f" % elapsed
                except Exception, e:
                    print "\rError: %s" % e
                    errors.append((remote_path, e))
                sys.stdout.flush()
except KeyboardInterrupt:
    pass

print
print
print "=" * 80
print
print "Uploaded %d in %f seconds" % (len(uploads), time.time() - total_start)
print "\nErrors:"
for error in errors:
    print "\t%s: %s" % error

PEP8 - what wha!