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I think there is an issue in the way you designed your cleanup logic. So I think this issue is invalid.
Usually, the code (funcion, class, ...) that *opens* the file should also be resposible of closing it.
option 1) the caller opens and closes the file and wrapping the logged lines in a try/finally
def logged_lines(f):
 try:
 for line in f:
 logging.warning(line.strip())
 yield line
 finally:
 logging.warning('closing')
f = open('yyy', 'r')
try:
 for l in logged_lines(f):
 print(l)
finally:
 f.close()
option 2) the funcion opens and closes the file
def logged_lines(fname):
 f = open('yyy', 'r')
 try:
 for line in f:
 logging.warning(line.strip())
 yield line
 finally:
 logging.warning('closing')
 f.close()
for l in logged_lines('yyy'):
 print(l)