You want to double-check your recipients code. It looks like you're trying to consume the contents of the file more than once, which won't work--the file objects should be understood as a stream, not a block of data, so once you've done f.read()
or [i.strip() for i in mails.readlines()]
one time, that stream is empty, so doing it a second time is going to produce an empty list. You should check this yourself by printing recipient
then try this:
mails = open('/path/emails.txt','r+')
#mailList = mails.read()
#mailList = [i.strip() for i in mails.readlines()]
directory = "/path/Desktop/"
SMTP_SERVER = 'smtp.gmail.com'
SMTP_PORT = 587
sender = 'Sender@gmail.com'
password = "Sender'sPassword"
recipient = [i.strip() for i in mails.readlines()]
print(recipient)
subject = 'Python (-++-) Test'
message = 'Images attached.'
Now you should have the a populated recipient list, and on to the next issue!