Could not send email from local webmail

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1

I’ve just installed the free mail server in a Windows 2016 datacenter , configured my domains and created an account.

Open the webmail client on the same server where the mail server is installed.

Tried to send an email to my personal hotmail account, and received the message “The message could not be sent”.

the logs show

2020-11-09 07:56:51 +0000 08 Wisy PROCESSING:002598FB: Processing finished
2020-11-09 07:56:51 +0000 08 Wisy PROCESSING:002598FB: Shepherd thread received signal for delivery
2020-11-09 07:56:51 +0000 08 Wisy PROCESSING:002598FB: Shepherd thread finished delivery signal
2020-11-09 07:56:51 +0000 08 Wisy PROCESSING:002598FB: Start mail delivery
2020-11-09 07:56:51 +0000 08 Wisy PROCESSING:002598FB: Set mail state to SENDING
2020-11-09 07:56:51 +0000 08 Wisy PROCESSING:002598FB: Start remote delivery for 1 recipients in domain hotmail dot com
2020-11-09 07:56:51 +0000 08 Wisy PROCESSING:002598FB: Relay mail using default host:
2020-11-09 07:56:51 +0000 08 Wisy DNR:002598FB: Search MX for ‘hotmail dot com’
2020-11-09 07:56:51 +0000 08 Wisy DNR:002598FB: Sending query (1/1) to 168.63.129.16:53
2020-11-09 07:56:51 +0000 08 Wisy DNR:002598FB: ‘hotmail dot com’ found MX ‘104.47.57.161’ with priority 2 in additional section
2020-11-09 07:56:51 +0000 08 Wisy DNR:002598FB: ‘hotmail dot com’ found MX ‘104.47.56.161’ with priority 2 in additional section
2020-11-09 07:56:51 +0000 08 Wisy PROCESSING:002598FB: Relay mail: found IPv4 MX entry 104.47.56.161 for domain hotmail dot com with priority 2
2020-11-09 07:56:51 +0000 08 Wisy PROCESSING:002598FB: Relay mail: found IPv4 MX entry 104.47.57.161 for domain hotmail dot com with priority 2
2020-11-09 07:56:51 +0000 08 Wisy PROCESSING:002598FB: Use 104.47.57.161 to relay mail 2598FB for domain hotmail dot com
2020-11-09 07:56:51 +0000 08 Wisy SMTP-OUT:00000002: Relay mail 2598FB: connecting to 104.47.57.161:25
2020-11-09 07:56:51 +0000 08 Wisy SMTP-OUT:00000002: Relay mail 2598FB: connected to 104.47.57.161:25
2020-11-09 07:56:52 +0000 08 Wisy SMTP-OUT:00000002: Start sending mail 2598FB
2020-11-09 07:56:52 +0000 08 Wisy SMTP-OUT:00000002: Release mail 2598FB
2020-11-09 07:56:52 +0000 08 Wisy SMTP-OUT:00000002: Negative reply to MAIL command: 5.7.1 Unfortunately, messages from [23.101.231.125] weren’t sent. Please contact your Internet service provider since part of their network is on our block list (S3140). You can also refer your provider to mail.live dot com/mail/troubleshooting.aspx#errors. [DM6NAM11FT050.eop-nam11.prod.protection.outlook dot com]
2020-11-09 07:56:52 +0000 08 Wisy SMTP-OUT:00000002: Set recipient <my_personal@hotmail dot com> state to RELAY ERROR
2020-11-09 07:56:52 +0000 08 Wisy SMTP-OUT:00000002: Delivery attempt completed for mail 2598FB; schedule for cleanup
2020-11-09 07:56:52 +0000 08 Wisy SMTP-OUT:00000002: Set mail state to SENT
2020-11-09 07:56:52 +0000 08 Wisy PROCESSING:002598FB: Shepherd thread received signal for cleanup
2020-11-09 07:56:52 +0000 08 Wisy SMTP-OUT:00000002: Disconnected from 104.47.57.161
2020-11-09 07:56:52 +0000 08 Wisy PROCESSING:002598FB: Mail removed from queue
2020-11-09 07:56:52 +0000 08 Wisy PROCESSING:002598FB: Set mail state to REMOVED
2020-11-09 07:56:52 +0000 08 Wisy PROCESSING:002598FB: Shepherd thread finished cleanup signal
2020-11-09 07:56:56 +0000 08 Wisy JOBLOG:81000029: Finished updating mail index for user myDomain@myDomain dot com.au (1 inserts, 0 updates, 0 deletes, 0 folder deletes, 0 optimizations, 0 vacuums, 169.102400 ms)

Am I forgetting to configure anything?

2

Hello Jamal,

From the logs you have shared it is clear that the message was rejected due to presence of the IP used to send messages (23.101.231.125) into the black-lists of the remote server:

SMTP-OUT:00000002: Negative reply to MAIL command: 5.7.1 Unfortunately, messages from [23.101.231.125] weren’t sent. Please contact your Internet service provider since part of their network is on our block list (S3140). You can also refer your provider to mail.live dot com/mail/troubleshooting.aspx#errors. [DM6NAM11FT050.eop-nam11.prod.protection.outlook dot com]

Checking the presence of this IP in other DNSBL lists (here) shows it is almost “clean”.

This means that most probably the problem should be addressed by contacting Hotmail support and ask for unlinsting of that IP address (it may be difficult at is seems they have blocked an entire network range).

HTH,
Ioan

3

Hey Indeias,

Thank you for your help.
I might need to find another way to send emails from my server,

cheers!!