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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.
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