setting up mail in --init step about outage-detector HOT 10 OPEN

I will have to test this out.

Have you tried using Gmail, for example? I've gotten issues with mail before, but mostly because of 2FA or having the "Block unauthorised apps" security feature turned on.

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I have not. I will create a gmail account and test it that way as well.

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Am having the same issue as OP. Same email server (iCloud) and same traceback. Will try with Gmail next...

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Blocked by gmail. By the time I authorized the access, I was blocked by "too many attempts" so will have to try this again tomorrow.

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BTW, I tried port 465 for iCloud (SSL) rather than the normal 587 (TLS) port. Instead of the previous traceback, I got a timeout:

Traceback (most recent call last):
  File "/home/pi/python/ven/bin/outage_detector", line 10, in <module>
    sys.exit(main())
  File "/home/pi/python/ven/lib/python3.7/site-packages/outagedetector/__main__.py", line 18, in main
    config.initialize()
  File "/home/pi/python/ven/lib/python3.7/site-packages/outagedetector/initial_config.py", line 71, in initialize
    "Mail sent successfully!", json_data["smtp_server"], password, json_data["port"])
  File "/home/pi/python/ven/lib/python3.7/site-packages/outagedetector/send_mail.py", line 40, in send_mail
    with SMTP_SSL(smtp_server, port, context=context) as server:
  File "/usr/lib/python3.7/smtplib.py", line 1031, in __init__
    source_address)
  File "/usr/lib/python3.7/smtplib.py", line 251, in __init__
    (code, msg) = self.connect(host, port)
  File "/usr/lib/python3.7/smtplib.py", line 336, in connect
    self.sock = self._get_socket(host, port, self.timeout)
  File "/usr/lib/python3.7/smtplib.py", line 1037, in _get_socket
    self.source_address)
  File "/usr/lib/python3.7/socket.py", line 727, in create_connection
    raise err
  File "/usr/lib/python3.7/socket.py", line 716, in create_connection
    sock.connect(sa)
TimeoutError: [Errno 110] Connection timed out

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Final update: Gmail won't allow this to work because it considers the app to be less secure than its usual standard. I could modify my Gmail account to permit less secure app access, but this makes the account more vulnerable. So for the moment, I'm unable to use the outage_detector with either of my email accounts.

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I was not able to get it to setup through gmail either. I have it running with Pushbullet and as Safari Notification, but I'd prefer to get it going through email of some sort.

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My understanding was that PushBullet isn't an option for iPhone, so still working on getting email to work for me. Am on new Pi4, only thing installed is pi-hole, running commands from YouTube video...

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Pushbullet used to be on the App store but it seems they removed it. I.'ve downloaded it a long time ago so I can still use it.

@nevillator-999 You said you couldn't get it to work with gmail. Could you share the exception it threw?

@jaaabeee I made a separate gmail account just for the purpose of automated mails, so I turned that feature off on that account.

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I was having similar issues but was able to resolve by using my gmail as the outgoing mail, with a 2 factor authentication for security and with an app specific password. I tried allowing less secure to connect with gmail but in the end, only the two factor authentication and specific app password worked. I used my iCloud account for the receiving mail. It worked and I got the test email. However, I have other issues as mentioned in the first issue thread.

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