Been using WWIPStuff for years and recently my small company was gobbled by a larger one. I had my O365 set up to allow relaying of emails from my external IP and was able to send with no issues. The new parent company does not want to allow this and has had me using smtp.mailgun.org to send through. This requires me to send authentication username and passwords. I am passing the necessary info the WWIPStuf, but I am receiving a "530 5.7.0 Authentication required" when I send from my company's server. However, if I run the same code from my laptop, I CAN send.
I have my own private mail server, so I pointed to it in an attempt see what might be happening. When the code fails, it is due to a HELO
This is the log from the failed attempt (helo):
Session 01221256; child 0001
Accepting SMTP connection from ##.##.##.##:20010 to 192.168.1.3:366
Location Screen says connection is from United States, North America
--> 220 mail.myserver.com ESMTP Mon, 01 Nov 2021 06:39:45 -0400
<-- helo MyServer.office.mydomain.com
--> 250 mail.mymailserver.com Hello PX-DC01.office.mydomain.com [##.##.##.##], pleased to meet you
<-- mail from: <root@mymailserver.com>
Performing PTR lookup (##.##.##.##.IN-ADDR.ARPA)
* D=##.##.##.##.IN-ADDR.ARPA TTL=(57) PTR=[##-##-##-##-static.hfc.comcastbusiness.net]
* D=##-##-##-##-static.hfc.comcastbusiness.net TTL=(57) A=[##.##.##.##]
---- End PTR results
Performing IP lookup ( MyServer.office.mydomain.com)
* DNS server reports domain name unknown
---- End IP lookup results
--> 530 5.7.0 Authentication required
root@mymailserver.com may not send mail from 23.25.118.82 (IP Shield)
Connection closed
SMTP session terminated (Bytes in/out: 70/196)
----------
This is the log from the successful send (ehlo):
Session 01221393; child 0001
Accepting SMTP connection from ##.##.##.##:20016 to 192.168.1.3:366
Location Screen says connection is from United States, North America
220 mail.mymailserver.com ESMTP Mon, 01 Nov 2021 08:18:56 -0400
<-- ehlo MyServer.office.mydomain.com
--> 250-mail.mymailserver.com Hello MyServer.office.mydomain.com [##.##.##.##], pleased to meet you
--> 250-ETRN
--> 250-AUTH LOGIN CRAM-MD5 PLAIN
--> 250-8BITMIME
--> 250-ENHANCEDSTATUSCODES
--> 250-STARTTLS
--> 250-ATRN
--> 250 SIZE
<-- auth login
--> 334 VXNlcm5hbWU6
<-- cm9vdEBwZmRzb2Z0d2FyZS5jb20=
--> 334 UGFzc3dvcmQ6
<-- ******
Authenticating root@mymailserver.com...
Authenticated as root@mymailserver.com
--> 235 2.7.0 Authentication successful
<-- mail from: <root@mymailserver.com>
--> 250 2.1.0 Sender OK
<-- RCPT TO: <matt@pfdsoftware.com>
--> 250 2.1.5 Recipient OK
<-- DATA
--> 354 Enter mail, end with <CRLF>.<CRLF>
Message size: 284 bytes
Passing message through AntiVirus (Size: 284)...
* Message is clean (no viruses found) scanned by (Cyren AV) (ClamAV)
---- End AntiVirus results
Message creation successful: c:\mdaemon\queues\inbound\md5001000839922.msg
--> 250 2.6.0 Ok, message saved
<-- quit
--> 221 2.0.0 See ya in cyberspace
SMTP session successful (Bytes in/out: 461/494)
----------
I ma using an older version of WWIPStuff, but I am trying to determine why I am see these results. Can anyone tell me what determines the HELO vs EHLO when sending? I have looked through the documentation, but if it is there, I am missing it.
thanks matt
Your version of wwIPStuff must be very old. EHelo is esmtp which requires authentication etc.
That old version of wwIPstuff isn't going to work with O365 as it doesn't support secure TLS communication. You need a newer version of wwSmtp - which is the successor to wwIPStuff. Same interface but support for a lot more features.
It's part of West Wind Internet and Client Tools which supersedes wwIPStuff and there's an upgrade path.
Here's more info on how to use it:
+++ Rick ---
Rick, Thanks for the reply, I have ordered the upgrade.
Your tools have been a great help for me over the years, thanks! matt
Hey Rick,
I just wanted to drop you a note of thanks. The latest tools are just great. The cLogFile is huge and my problem is solved.
Your tools are great and they have been a huge help to me over the years.
Thanks much for all your work. Matt Cummings