Emails bounce when sending to an Microsoft 365 accounts

Gigas2U
Posts: 1
Joined: Fri Nov 25, 2016 9:10 am

Emails bounce when sending to an Microsoft 365 accounts

Postby Gigas2U » Fri Nov 25, 2016 9:18 am

hello

We have a issue on a mail plesk server. We can't send mails to Microsoft Servers. After 2 days of mail interchanges Microsoft said the IP is not banned and all is ok and must be a problem on our server. When we send mail to microsoft accounts we receveve the following mensaje:

----------------------------------------------------------------------------
MailEnable: Message could not be delivered to some recipients.
The following recipient(s) could not be reached:

Recipient: [SMTP:xxxxxxx@xxxxxx.xxx]
Reason: Remote SMTP Server Returned: 550 5.7.511 Access denied, banned sender[95.215.60.178]. To request removal from this list please forward this message to delist@messaging.microsoft.com. For more information please go to http://go.microsoft.com/fwlink/?LinkId=526653. AS(508)
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we have made some investigation and found that the microsoft server "requires authentication when attempting to send to a non-local e-mail address"

Report from: https://www.wormly.com/test_smtp_server
SMTP Server: 95.215.60.178
Recipient email: ejz@ngi.dk
Sender Email: administracion@instalacionesgrau.com
-----------------------------------------------------------------------------------------------
Connecting...
Connection: opening to 95.215.60.178:25, timeout=300, options=array (
)
Connection: opened
SERVER -> CLIENT: 220 ns1.gigas2u.com ESMTP MailEnable Service, Version: 9.51-- ready at 11/25/16 09:43:15
CLIENT -> SERVER: EHLO tools.wormly.com
SERVER -> CLIENT: 250-gigas2u.com [96.126.113.160], this server offers 5 extensions
250-AUTH NTLM CRAM-MD5 LOGIN
250-SIZE 40960000
250-HELP
250-AUTH=LOGIN
250 STARTTLS
CLIENT -> SERVER: STARTTLS
SERVER -> CLIENT: 220 Ready to start TLS
CLIENT -> SERVER: EHLO tools.wormly.com
SERVER -> CLIENT: 250-gigas2u.com [96.126.113.160], this server offers 4 extensions
250-AUTH NTLM CRAM-MD5 LOGIN
250-SIZE 40960000
250-HELP
250 AUTH=LOGIN
CLIENT -> SERVER: MAIL FROM:
SERVER -> CLIENT: 250 Requested mail action okay, completed
CLIENT -> SERVER: RCPT TO:
SERVER -> CLIENT: 503 This mail server requires authentication when attempting to send to a non-local e-mail address. Please check your mail client settings or contact your administrator to verify that the domain or address is defined for this server.
SMTP ERROR: RCPT TO command failed: 503 This mail server requires authentication when attempting to send to a non-local e-mail address. Please check your mail client settings or contact your administrator to verify that the domain or address is defined for this server.
CLIENT -> SERVER: QUIT
SERVER -> CLIENT: 221 Service closing TLS SSL transmission session
Connection: closed
2016-11-25 08:43:16 SMTP Error: The following recipients failed: ejz@ngi.dk: This mail server requires authentication when attempting to send to a non-local e-mail address. Please check your mail client settings or contact your administrator to verify that the domain or address is defined for this server.
Message sending failed.
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can you please assist us to find a solution to this issue?

Best Regrards
Miguel

MailEnable-Ian
Site Admin
Posts: 8220
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: Emails bounce when sending to an Microsoft 365 accounts

Postby MailEnable-Ian » Thu Dec 01, 2016 12:57 am

Hi,

From the log snippet it doesn't look like the client is authentication when trying to send the message via MailEnable. MailEnable SMTP is requiring authentication to relay and thus the reason for the error. You can:

1. Configure the client sending the message to authenticate or;
2. Add the IP of the client sending the message to the Mail Enable SMTP relay option for "Allow privileged IP's can relay" list under the "deny all - except those in the list". http://www.mailenable.com/documentation/9.0/Standard/SMTP_props_-_Relay.html
Regards,

Ian Margarone
MailEnable Support

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