On 2021-11-29 3:20 p.m., Bill Cole via mailop wrote:
On 2021-11-29 at 16:57:54 UTC-0500 (Mon, 29 Nov 2021 13:57:54 -0800)
Michael Peddemors via mailop <mich...@linuxmagic.com>
is rumored to have said:

On 2021-11-29 6:57 a.m., Larry M. Smith via mailop wrote:
On 11/24/2021, Michael Peddemors via mailop wrote:
CONN: 40.107.96.87 -> 25 GeoIP = [US] PTR = mail-sn1anam02on2087.outbound.protection.outlook.com OS = Windows NT kernel

Returning 250 ok [qp 3539411] for data
QUIT command received, args:

And then it terminates the connection, SSL collapses, without waiting for the remote mail server to acknowledge the QUIT.

I get it that they 'might' think that closing when 'they are done' and we gave a 250ok on the DATA, and they sent the QUIT.. I don't know, thinking to shave a few milliseconds off of the connection, but the RFC is pretty clear that a QUIT .. AND .. and acknowlegement is part of RFC.

Comments? (And no, there is zero lag before they terminate)

If I understand you correctly;

When sending mail, *.outbound.protection.outlook.com appears to send DATA, terminate via <CRLF>.<CRLF>, wait for a response, then issue QUIT immediately followed by a TCP FIN packet.

Operationally, I don't think it makes a difference.  RFC pedantics? Maybe.  Does the receiving system advertise the Pipelining SMTP Service Extension?.. Does setting/un-setting that response to EHLO make a difference to outlook.com's behavior?  If so, does and/or should RFC2920 allow for QUIT->TCP FIN?

No, Pipeline is not advertised, the RFC's say that when you send a command, if you are NOT using pipelining, you need to wait for a response, and that includes the QUIT.. wait for the receiving system to send an OK in this respect, not only does it satisfy RFC's but also helps differentiate from the many spamming systems that terminate as quickly as they can to reduce overhead when spamming.

Review the precise wording of https://datatracker.ietf.org/doc/html/rfc5321#section-4.1.1.10

SHOULD in RFCs is stronger than it is in casual use, but it is still SHOULD, not MUST.

SMTP clients of all sorts have done this (and worse, e.g. just FIN after getting a 250 at end-of-data) for at least 3 decades. I don't see how it could possibly be useful at this late date to try to enforce that SHOULD which only exists for a human sense of elegance and tradition. The "polite" pattern doesn't serve any functional purpose at QUIT, because there's no ambiguity for either side if the reply is simply lost. Even if QUIT is never sent and the client just sends a FIN packet after its last message is acknowledged, the only ambuiguity is that the server doesn't know whether the client failed in some way or was just finished sending messages, and that's not something a server should usually care about.



For anyone not familiar with the passage..

Bill is 'technically' correct on this point..

4.1.1.10.  QUIT (QUIT)

   This command specifies that the receiver MUST send a "221 OK" reply,
   and then close the transmission channel.

   The receiver MUST NOT intentionally close the transmission channel
   until it receives and replies to a QUIT command (even if there was an
   error).  The sender MUST NOT intentionally close the transmission
   channel until it sends a QUIT command, and it SHOULD wait until it
   receives the reply (even if there was an error response to a previous
   command).

(And yes Bill, we do see the odd system sending a FIN without even a QUIT, and it is more complicated when the remote end tears down the SSL connection before QUIT)

It does sound like you are arguing for dropping QUIT altogether, but the protocol was designed for robustness, and there is a reason for the general use of COMMAND/ACKNOWLEGEMENT.

However, he is missing that earlier in the same RFC we see.. (Notice the MUST NOT, which over reaches the later SHOULD)

3.8.  Terminating Sessions and Connections

   An SMTP connection is terminated when the client sends a QUIT
   command.  The server responds with a positive reply code, after which
   it closes the connection.

   An SMTP server MUST NOT intentionally close the connection under
   normal operational circumstances (see Section 7.8) except:

   o  After receiving a QUIT command and responding with a 221 reply.

   o  After detecting the need to shut down the SMTP service and
      returning a 421 response code.  This response code can be issued
      after the server receives any command or, if necessary,
      asynchronously from command receipt (on the assumption that the
      client will receive it after the next command is issued).

   o  After a timeout, as specified in Section 4.5.3.2, occurs waiting
      for the client to send a command or data.

   In particular, a server that closes connections in response to


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