Tried everything SMTP connect() failed

Support
43

JACKPOT! I think…

Dumping invoice plane log. Says basic authentication is disabled which I am guessing it pretty crucial?

DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 Connection: opening to smtp-mail.outlook.com:587, timeout=300, options=array()
DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 Connection: opened
DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 SERVER -> CLIENT: 220 BL0PR02CA0134.outlook.office365.com Microsoft ESMTP MAIL Service ready at Sat, 16 Nov 2024 00:07:05 +0000 [08DD0389F12760C1]

DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 CLIENT -> SERVER: EHLO localhost

DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 SERVER -> CLIENT: 250-BL0PR02CA0134.outlook.office365.com Hello [24.48.136.166]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250 SMTPUTF8

DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 CLIENT -> SERVER: STARTTLS

DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 SERVER -> CLIENT: 220 2.0.0 SMTP server ready

DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 CLIENT -> SERVER: EHLO localhost

DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 SERVER -> CLIENT: 250-BL0PR02CA0134.outlook.office365.com Hello [24.48.136.166]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH LOGIN XOAUTH2
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250 SMTPUTF8

DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 CLIENT -> SERVER: AUTH LOGIN

DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 SERVER -> CLIENT: 334 VXNlcm5hbWU6

DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 CLIENT -> SERVER: [credentials hidden]
DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 SERVER -> CLIENT: 334 UGFzc3dvcmQ6

DEBUG - 2024-11-16 00:07:05 --> 2024-11-16 00:07:05 CLIENT -> SERVER: [credentials hidden]
DEBUG - 2024-11-16 00:07:11 --> 2024-11-16 00:07:11 SERVER -> CLIENT: 535 5.7.139 Authentication unsuccessful, basic authentication is disabled. [BL0PR02CA0134.namprd02.prod.outlook.com 2024-11-16T00:07:11.527Z 08DD0389F12760C1]

DEBUG - 2024-11-16 00:07:11 --> 2024-11-16 00:07:11 SMTP ERROR: Password command failed: 535 5.7.139 Authentication unsuccessful, basic authentication is disabled. [BL0PR02CA0134.namprd02.prod.outlook.com 2024-11-16T00:07:11.527Z 08DD0389F12760C1]

DEBUG - 2024-11-16 00:07:11 --> 2024-11-16 00:07:11 SMTP Error: Could not authenticate.
DEBUG - 2024-11-16 00:07:11 --> 2024-11-16 00:07:11 CLIENT -> SERVER: QUIT

DEBUG - 2024-11-16 00:07:11 --> 2024-11-16 00:07:11 SERVER -> CLIENT: 221 2.0.0 Service closing transmission channel

DEBUG - 2024-11-16 00:07:11 --> 2024-11-16 00:07:11 Connection: closed
DEBUG - 2024-11-16 00:07:11 --> 2024-11-16 00:07:11 SMTP connect() failed. https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting
1 Like
44

You’re right.
Look at your outlook on how to change that.

Basically you’re saying: here’s my username/password, can i send mail

And outlook has disabled that.

Best thing to do is to generate an “app password”.
No idea on how to do that with outlook

45

Let me add this from my google search: Yes, Microsoft disabled Basic Authentication for Outlook personal accounts on September 16, 2024

1 Like
46

Let me dig into the app password thing and perhaps I can support other invoiceplane users in the same situation

1 Like
49

When you get your app password, just save it in your settings like you did with your other password.

It should overwrite your other password with your app password and let’s hope that’s your solution.

1 Like
50

I have a hard time accepting this. Outlook app password does not seem to work for me, however Gmail app password setup does seem to work.
What (free?) email setup are you using and would you have any suggestions to why Outlook might not work? Adding the app password gives the same basic authenticator error as before.

It’s incredibly frustrating having to switch from outlook to gmail with the risk of my invoices ending up in peoples spam inbox.

51

I understand.

I would have used gmail.

I’m not able to look into this at this moment.

The alternative is something like mailgun, but I don’t think that’s free.

52

Hi @Bermworm, have you tried activating the SMTP protocol in outlook.com? POP, IMAP, and SMTP settings for Outlook.com - Microsoft Support

1 Like