Office 365 SMTP authentication

⚠️ Please verify that this bug has NOT been raised before.

• I checked and didn’t find similar issue

🛡️ Security Policy

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Description

Upon creating a Mail Notification and using Office 365 i run in following Error:

Error: Invalid login: 535 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator. [AM6P193CA0093.EURP193.PROD.OUTLOOK.COM] at SMTPConnection._formatError (/app/node_modules/nodemailer/lib/smtp-connection/index.js:784:19) at SMTPConnection._actionAUTHComplete (/app/node_modules/nodemailer/lib/smtp-connection/index.js:1536:34) at SMTPConnection.<anonymous> (/app/node_modules/nodemailer/lib/smtp-connection/index.js:1490:18) at SMTPConnection._processResponse (/app/node_modules/nodemailer/lib/smtp-connection/index.js:947:20) at SMTPConnection._onData (/app/node_modules/nodemailer/lib/smtp-connection/index.js:749:14) at TLSSocket.SMTPConnection._onSocketData (/app/node_modules/nodemailer/lib/smtp-connection/index.js:189:44) at TLSSocket.emit (node:events:527:28) at addChunk (node:internal/streams/readable:315:12) at readableAddChunk (node:internal/streams/readable:289:9) at TLSSocket.Readable.push (node:internal/streams/readable:228:10) { code: 'EAUTH', response: '535 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator. [AM6P193CA0093.EURP193.PROD.OUTLOOK.COM]', responseCode: 535, command: 'AUTH LOGIN' }

👟 Reproduction steps

Create New Notification Enter Office 365 Credentials Test

👀 Expected behavior

Sending a E-Mail

😓 Actual Behavior

Runs in an authentication error

🐻 Uptime-Kuma Version

1.16.1

💻 Operating System and Arch

linux x86_64 Debian GNU/Linux 11 (bullseye)

🌐 Browser

Google Chrome Version 102.0.5005.62

🐋 Docker Version

20.10.12 (API: 1.41)

🟩 NodeJS Version

No response

📝 Relevant log output

Error: Invalid login: 535 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator. [AM6P193CA0093.EURP193.PROD.OUTLOOK.COM]
    at SMTPConnection._formatError (/app/node_modules/nodemailer/lib/smtp-connection/index.js:784:19)
    at SMTPConnection._actionAUTHComplete (/app/node_modules/nodemailer/lib/smtp-connection/index.js:1536:34)
    at SMTPConnection.<anonymous> (/app/node_modules/nodemailer/lib/smtp-connection/index.js:1490:18)
    at SMTPConnection._processResponse (/app/node_modules/nodemailer/lib/smtp-connection/index.js:947:20)
    at SMTPConnection._onData (/app/node_modules/nodemailer/lib/smtp-connection/index.js:749:14)
    at TLSSocket.SMTPConnection._onSocketData (/app/node_modules/nodemailer/lib/smtp-connection/index.js:189:44)
    at TLSSocket.emit (node:events:527:28)
    at addChunk (node:internal/streams/readable:315:12)
    at readableAddChunk (node:internal/streams/readable:289:9)
    at TLSSocket.Readable.push (node:internal/streams/readable:228:10) {
  code: 'EAUTH',
  response: '535 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator. [AM6P193CA0093.EURP193.PROD.OUTLOOK.COM]',
  responseCode: 535,
  command: 'AUTH LOGIN'
}

[Computroniks]

Ahh ok, so we would need to support a new method of authentication for microsoft email servers such as OAuth2. In which case, would it be possible to change this issue from a bug to a feature request for support for this. Anoyingly, OAuth will be more complicated to implement as it requires that we register the app with Azure Active directory. Microsoft have provided details on how to go about implementing this feature here, https://docs.microsoft.com/en-us/exchange/client-developer/legacy-protocols/how-to-authenticate-an-imap-pop-smtp-application-by-using-oauth. Due to the deadline of October 1, 2022 this should probably be fairly high priority as it will probably take a while to get the registration with Azure.

@louislam Sorry to ping you, as this requires registering with an external service, I think that that might be something that you would need to do. I could probably get the rest of it done this weekend or next weekend because I plan to finish off #1550 tomorrow (02/06/22)

Link to docs for nodemailer: https://nodemailer.com/smtp/oauth2/

[Computroniks]

Thanks, just checked their guide, it is quite a lot of steps and difficult in order to get all IDs. I think Microsoft really make a big mistake for this, people will just quit and use other smtp providers.

Yeah, I can understand why they did it but it does seem like a really annoying step, especially when it is so easy with gmail (only need to enable smtp auth in settings)