Error sending and receiving emails in Exchange 2010 and 2016 coexistence

Hi @Wandi Ding -MSFT ,

Thank you very much for your help, these are the messages it generates.

Could you please provide detailed NDR information for further troubleshooting?

NDR Ex2010

Diagnostic information for administrators:
Generating server: EX2010.contoso.com
test@contoso.com
#550 4.4.7 QUEUE.Expired; message expired ##
Original message headers:
Received: from EX2010.contoso.com ([::1]) by EX2010.contoso.com
  ([::1]) with mapi id 14.03.0513.000; Mon, 27 Nov 2023 10:55:02 -0400
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: Users Contoso <User01@contoso.com>
To: "customer@gmail.com" <customer@gmail.com>, try try
<test@contoso.com>
Subject: [Test]
Thread-Topic: test from outlook desktop
Thread-Index: AdohQaR7KnVF+6+xRRtetgPsBwNRulg==
Date: Mon, 27 Nov 2023 10:55:01 -0400
Message-ID: <44468AA3BCFDE0146ABDF10C142997EDB173677@EX2010.contoso.com>
Accept-Language: es-ES, es-ES, en-US
Content-Language: en-US
X-MS-Has-Attach: yes
*
MIME-Version: 1.0
X-Originating-IP: [200.100.1.10]

NDR Gmail

test@contoso.com
#550 4.4.7 QUEUE.Expired; message expired ##
Encabezados de mensajes originales:
Received: from mail-qt1-f173.google.com (200.100.1.1) by
 Ex2010.contoso.com (200.100.1.4) with Microsoft SMTP Server (TLS) id
 14.3.498.0; Thu, 23 Nov 2023 10:02:54 -0400
Received: by mail-qt1-f173.google.com with SMTP id
 d75a77b69052e-42033328ad0so4712481cf.0        for <test@contoso.com>;
 Thu, 23 Nov 2023 06:01:47 -0800 (PST)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
        d=gmail.com; s=20230601; t=1700748105; x=1701352905; darn=contoso.com;
        h=to:subject:message-id:date:from:mime-version:from:to:cc:subject
         :date:message-id:reply-to;
        bh=xmZtQSo0ufdrz3Htldi3iikojxvE0Fw/zKNVd24+nTs=;
        b=Y+3C1IKKvyTv1kEHyfnhu690iWlzjF9Wwkp679tpX1KMXxKLRpfOd8mtXOLGQYhyhuA
         qOC5EZHGl8GBxu9hF5maxE/IVbtq93KrEI7+XFsaaZyHJ2Nj42UKqvff1eRP+6yYvyBN
         xHpJoxxRnGNUMzpTTikSOW2BhLtT22qrYSeMA/qbdoolnpEILas8c4nhh4+frLqCRZCMKT
         BKnqM550n66+rejcTXfm77at1BnnRMr/Z7hvKU+Bg3Sjq+V25RHZs8bk3WzuZNkl1PVx
         +1MBvteJgFNfjMoAxnayUTe6W28kJuezPN+mJ4ctzehbG3kM7/Gw7b0YRNg5edsHE9/T
         br/Q==
X-Google-DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
        d=1e100.net; s=20230601; t=1700748105; x=1701352905;
        h=to:subject:message-id:date:from:mime-version:x-gm-message-state
         :from:to:cc:subject:date:message-id:reply-to;
        bh=xmZtQQSo0ufdrz3Htldi3iikojxvE0Fw/zKNVd24+nTs=;
        b=lvHJvddxMLBY5ZFyMHgR+eeV15cjnudjtJIDPdMgzJcDCmf0419UCI63QWM81sfKLM
         9mYWiqDlkOZRapTseAZnqWoQTI0Ri9e4K6RdYGToCUMGaO8HpjAHXZuC5wvEHfF57Xaf
         xpVmLVII8KuJr3GnA9LiLYiMX/d5QnPIIq8dgry86qfntSWU3DkjJtasGdTEBMz5soyr
         Eiep+JeCyhXqo+U7SAk33IJxXenSyhuLYmn2GZPI7OIwgbUc2ayjn0ZDojWbJ4Ovg5JER
         Tw0ZbfcMPKK3NHlbzMalyigBgXu0Zo9nBWdw5Sf+IMYeU+ZVfKR4VdBoNg6M89Nxamko
         bRGQ==
X-Gm-Message-State: AOJJu0YznhepKZfIvrKwR8ZpcgQGOs/7KBPy5yMHGRyQP33pLWC0E5xrQ
	ZGOQ0PrKB6KpN9Yt3sBPMoEGug8paNKUA+eCvPU54EE5
X-Google-Smtp-Source: AGHT+IHO+fdzNM8XhOXG4IwHXQQLDp7LzjGSAbdOaCM2db1WeMbqSb9kNCS/s9/cl2Z/P4LkgKbEcn/AyUiFLhdNlSqE=
X-Received: by 2002:a05:622a:7107:b0:423:9242:b15d with SMTP id
 jb7-20020a05622a710700b004239242b15dmr475398qtb.48.1700748104974; Thu, 23 Nov
 2023 06:01:44 -0800 (PST)
MIME-Version: 1.0
From: Customer <customer@gmail.com>
Date: Thu, 23 Nov 2023 10:01:31 -0400
Message-ID: <CAAEks1UDAAy31zfGb5K1dmYRNRKXb4rQC+f+rfkU+JcvRftakjxQ@mail.gmail.com>
Subject: Prueba 23/11/2023 gmail to Ex2016
To: Test User <test@contoso.com>
Content-Type: multipart/alternative; boundary="000000000000a6462b060ad246b99"
Return-Path: customer@gmail.com
Received-SPF: SoftFail (Ex2010.contoso.com: domain of transitioning
 customer@gmail.com discourages use of 200.100.1.1 as permitted sender)

And have you made any changes to the default receive connectors on Exchange 2016?

Edit Connector - Default Fronted Ex2016 -Role FrontedTransport -Scope 200.100.0.0/24 Create New connector - Ex2016 Internet - Role FrontendTransport -Scope 0.0.0.0-255.255.255.255

Use the command Get-MessageTrackingLog to view message tracking log

I don't know how to use and understand the message it generates Timestamp EventId ClientHostname ServerHostname Source ConnectorId

---

27/11/2023 10:55:02 RECEIVE Ex2010.contoso.com Ex2010 STOREDRIVER 28/11/2023 10:55:05 FAIL Ex2010 QUEUE

I use telnet to see the errors or equal (TransportRoles/Logs/FrontEnd/ProtocolLog/SmtpReceive or SmtpSend). I have the same error message.

220 Ex2010.contoso.com Microsoft ESMTP MAIL hello Ex2016.contoso.com 250 Ex2010.contoso.com Hello [200.100.1.4] mail from: user01@contoso.com 250 2.1.0 Sender OK rcpt to: test@contoso.com 250 2.1.5 Recipient OK data 354 Start mail input; end with <CRLF>.<CRLF> subject: Test Ex2010 test from telnet Ex2010 . 250 2.6.0 e6c9999f5-2876-40999-8f86-246608cc60188@Ex2010.contoso.com [InternalId=569412] Queued mail for delivery 451 4.7.0 Timeout waiting for client input Connection to the host has been lost.

could you try leaving only one MX record point to Exchange 2016 and check the result?

As long as it does not affect sending and receiving mail. My users are nervous if they don't have email.

The Test@contoso.com account is created in Ex2016, I think the problem is that it only asks in Ex2010 and does not change to ask in Ex2016 if that account exists. I don't know how to check or see if this is the problem, check the log in event viewer and it doesn't show a new error message to continue investigating

have you made any changes to the default receive connectors on Exchange 2016?

EDIT RECEIVE CONNETOR - DEFAULT FRONTEND EX2016
SCOPE  = 0.0.0.0 - 255.255.255.255  TO 200.100.0.0/24

CREATE NEW CONNECTOR - ANONYMOUS RELAY CONNECTOR
SCOPE  = 0.0.0.0 - 255.255.255.255

use the command Get-MessageTrackingLog to view message tracking log.

I don't know how to read the data to understand the error.
Timestamp           EventId ClientHostname          ServerHostname Source      ConnectorId
---------           ------- --------------          -------------- ------      -----------
27/11/2023 10:55:02 RECEIVE Ex2010.contoso.com      Ex2010        STOREDRIVER
28/11/2023 10:55:05 FAIL    Ex2010   

I use telnet more or read the SMTP logs

220 Ex2010.contoso.com Microsoft ESMTP MAIL 
hello Ex2016.contoso.com
250 Ex2010.contoso.com Hello [200.100.1.4]
mail from: user01@contoso.com
250 2.1.0 Sender OK
rcpt to: test@contoso.com
250 2.1.5 Recipient OK
data
354 Start mail input; end with <CRLF>.<CRLF>
subject: Test Ex2010 to Ex2016
test from telnet Ex2010 to Ex2016
.
250 2.6.0 <e6c9999f55-2876-40999-8f86-2466088cc60188@Ex2010.contoso.com> [InternalId=569412] Queued mail for delivery
451 4.7.0 Timeout waiting for client input
Connection to the host has been lost.

could you try leaving only one MX record point to Exchange 2016 and check the result?

If it doesn't hurt receiving and sending mail, my users are nervous if they don't have mail for a moment 😂

I think I suspect that the problem is that it only asks on the Ex2010 Server and does not make the change to Ex2016 to ask from the mailbox. I don't know how to verify if it makes the change between servers