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After having problems with (hotmail, now taken over by outlook) emails sending with delays up to 1-2 day(s), I decided to manually test the connection using openssl. Here's a log of the conversation between me (U) and the server (S):
openssl s_client -crlf -starttls smtp -connect smtp-mail.outlook.com:587
>Connection's "encryption/certificate" details
S: 250 SMTPUTF8
U: EHLO whatever.com
S: 250-DB6P192CA0007.outlook.office365.com Hello [195.154.250.43]
S: 250-SIZE 157286400 / PIPELINING / DSN / ENHANCEDSTATUSCODES [one line to save space]
S: 250-AUTH LOGIN XOAUTH2
S: 250-8BITMIME / BINARYMIME / CHUNKING / SMTPUTF8 [one line to save space]
U: AUTH LOGIN
S: 334 VXNlcm5hbWU6
U: ZG9udC5iZUBob3RtYWlsLmNvbQ==
S: 334 UGFzc3dvcmQ6
U: c29nb2RkYW1jdXJpb3Vz
S: DONE
>>> Connection is closed at this point
Am I doing something wrong? I've read about SMTP relaying without understanding what it is, but could my ISP (teleColumbus DE) block it? I tried w/ VPN still no luck. Or am I issuing the wrong openssl command?
If you do possess an outlook/hotmail/live email account, could you also try the following procedure and report whether it works? Outlook's IT support wasn't couldn't help.
Louis S.
Posted 2017-09-28T20:09:46.783
Reputation: 5
You'd be better off asking about your actual problem (sending mail being delayed) instead of trouble you're having with a specific troubleshooting strategy. However, one thought is that there's a problem with the account being used to logon or the source network has been blacklisted by Outlook.com. – I say Reinstate Monica – 2017-09-29T04:14:41.487