What was the reason for removing the same-domain grouping during delivery?
Problem reported by Terry Mann - 5/4/2026 at 1:48 PM
Submitted
In the recent past, SM was changed so that it now delivers multiple recipients of the same external domain individually.  Previously, same-domain recipients were properly grouped into one session.  However, it now has to make a connection, authenticate, send the message and disconnect for each recipient.  The disadvantages are obvious but what is the advantage to making this change?
Derek Curtis Replied
Employee Post
We didn't make any changes to how we send, especially with regards to grouping. We do still group recipients by their external domain. 

Where are you seeing this? In the logs? May be worthwhile to open a ticket with our team so we can dig into it a bit. 
Derek Curtis
CCO
SmarterTools Inc.
Terry Mann Replied
Thanks Derek.  The delivery log clearly shows that this is happening.
[26B-31876DCA-0017] Delivery Recipient Grouping
Tony Scholz Replied
Employee Post
Hello Terry, 

I wanted to follow up on our investigation into the issue. We discovered the reason behind the messages being sent as individual sessions instead of being grouped by domain. Since this change was made several years ago, I couldn’t pinpoint the exact time or the reason behind it. However, based on the changes made, I believe it’s related to the reliability of message delivery. 

The issue is with the addition of three new headers that could be applied: X-ForwardingAddress, X-OriginalSender, and X-Forwarded-To. These are applied in four places: 

1. Alias expansion
2. User-level forwarding
3. Content filter forwarding
4. Gateway spam reroute

This is by design — it allows the destination to know the forwarding chain. Since these headers are unique to each message, they all get their own SMTP session. 
Tony Scholz
Lead Network/System Administrator
SmarterTools Inc.
Douglas Foster Replied
This is unfortunate.   It would be desirable to delay replicating the message until there is a need to do so.

However, one easy fix is to eliminate the unnecessary disconnect-reconnect that occurs between each recipient of a multiple-recipient message.   The time lost seems to be only about a quarter of a second, but it also breaks FIFO sequencing.   The downstream server sees the secondary recipient(s) as subsequent to every parallel stream that may have been started while the first recipient was being transmitted.

The net result of both problems is that the secondary recipients are excessively delayed by spam filtering.

Here is a sanitized extract of the disconnect and reconnect log entries:

RSP: 250 HELP
CMD: MAIL FROM:<sendinguser@sendingdomain> SIZE=4942
RSP: 250 Sender <sendinguser@sendingdomain> OK
CMD: RCPT TO:<user1@mydomain.com>
RSP: 250 Recipient <user1@mydomain.com> OK
CMD: DATA
RSP: 354 Start mail input; end with <CRLF>.<CRLF>
RSP: 250 Ok: queued as A4693AC0065

********** start of wasted effort **********

CMD: QUIT
RSP: 221 server2.example.com Goodbye server.example.com, closing connection
Sending remote mail to: user2@mydomain.com
Initiating connection to 192.168.1.203
Connecting to 192.168.1.203:25 (Id: 3)
Connection to 192.168.1.203:25 from 192.168.1.119:55413 succeeded (Id: 3)
RSP: 220 server2.example.com ESMTP (493ac9a54b921d242e0b077fa5020003)
CMD: EHLO server.example.com
RSP: 250-server2.example.com Hello server.example.com [192.168.1.119], pleased to meet you
RSP: 250-SIZE 51300000
RSP: 250-STARTTLS
RSP: 250-PIPELINING
RSP: 250-8BITMIME
RSP: 250 HELP
CMD: STARTTLS
RSP: 220 Ready to start TLS
CMD: EHLO server.example.com
RSP: 250-server2.example.com Hello server.example.com [192.168.1.119], pleased to meet you
RSP: 250-SIZE 51300000
RSP: 250-PIPELINING
RSP: 250-8BITMIME
RSP: 250 HELP

********** end of wasted effort **********

CMD: MAIL FROM:<sendinguser@sendingdomain> SIZE=4942
RSP: 250 Sender <sendinguser@sendingdomain> OK
CMD: RCPT TO:<user2@mydomain.com>
RSP: 250 Recipient <user2@mydomain.com> OK

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