My main comment is that you should separate the different concerns of you code into descriptive functions. This will make it a lot more readable (and re-usable). One comment before I get started: Your `login` function, which looks like it would log you in with the reddit API seems to be unused atm. I guess this is a copy&paste error from censoring? ---------- Your first concern is to log-in with gmail to get the `mail` object. This can be pasted directly into a separate function: def mail_login(): mail = imaplib.IMAP4_SSL('imap.gmail.com') while True: try: emailpass = getpass.getpass( 'Please enter the password for xxxxxxx@xxxxx: ') mail.login('[email protected]', emailpass) break except imaplib.IMAP4.error: print('Incorrect password') mail.select("inbox") return mail ---------- The second task, which is repeated quite often, is to print a message with the current timestamp preceeding it: def log(text): print('\t{:%Y-%m-%d %H:%M:%S} - {}'.format(datetime.now(), text)) Note that I used the custom format options of `str.format` here. ---------- **Final code:** import praw import imaplib import email import time import getpass import RUAlerts from datetime import datetime app_id = 'xxxxxxxxxxxx' app_secret = 'xxxxxxxxxxxx' app_uri = 'xxxxxxxxxxxx' app_scopes = 'account creddits edit flair history identity mysubreddits privatemessages read report save submit subscribe vote' app_ua = 'xxxxxxxxxxxx' app_account_code = 'xxxxxxxxxxxx' app_refresh = 'xxxxxxxxxxxx' class LongTimeOut(Exception): pass class ShortTimeOut(Exception): pass def login(): r = praw.Reddit(app_ua) r.set_oauth_app_info(app_id, app_secret, app_uri) r.refresh_access_information(app_refresh) return r def log(text): print('\t{:%Y-%m-%d %H:%M:%S} - {}'.format(datetime.now(), text)) def mail_login(): mail = imaplib.IMAP4_SSL('imap.gmail.com') while True: try: emailpass = getpass.getpass( 'Please enter the password for xxxxxxx@xxxxx: ') mail.login('[email protected]', emailpass) break except imaplib.IMAP4.error: print('Incorrect password') mail.select("inbox") return mail def post_alert(alert, r): alert_text = """ {} ******** *^^I ^^am ^^a ^^bot. ^^For ^^any ^^questions, ^^comments, ^^or ^^concerns, ^^please ^^email [^^xxxxxxx@xxxxx](mailto://xxxxxxx@xxxxx)* """ while True: try: r.submit(subreddit='xxxxxxxxxxxx', title=alert, text=alert_text.format(alert)) print('\t{}'.format(alert), end=' ') break except praw.errors.ExceptionList as e: raise LongTimeOut( 'Reddit error! {}'.format(e)) def search_for_alerts(mail): result, response = mail.uid('search', None, "(UNSEEN)") unread_msg_nums = response[0].split() result, data = mail.uid('search', None, "ALL") latest_email_uid = data[0].split()[-1] result, data = mail.uid('fetch', latest_email_uid, '(RFC822)') raw_email = data[0][1] email_message = email.message_from_bytes(raw_email) if unread_msg_nums: log('Something\'s wrong!') for part in email_message.walk(): if part.get_content_type() == 'text/plain': yield part.get_payload() else: raise ShortTimeOut while True: try: r = RUAlerts.login() mail = mail_login() try: for alert in search_for_alerts(mail): post_alert(alert, r) except ShortTimeOut: log('All clear on the RU front') time.sleep(30) except LongTimeOut as e: log('{} Retrying in 5 minutes'.format(e)) time.sleep(300)