These are the versions of the exchange servers: Exchange 2016 CU23 - 15.1 Build (2507.6) Exchange 2010 SP3 - 14.3.0513 Build(123.4) The problem is sending and receiving emails in Exchange 2016. Creating the send and receive connector in Ex2016: Send Receive Message Ex2010 Internet OK Internet Ex2010 OK Ex2016 Internet 4.4.7 Queue Expired Internet Ex2016 4.4.7 Queue Expired Ex2010 Ex2016 4.4.7 Queue Expired Ex2016 Ex2010 OK Without connector to send and by default receive in Ex2016: Send Receive message Ex2010 Internet OK Internet Ex2010 OK Ex2016 Internet OK Internet Ex2016 4.4.7 Queue Expired Ex2010 Ex2016 4.4.7 Queue Expired Ex2016 Ex2010 OK Perform tests with Microsoft Remote Connectivity Analyzer . The test mail arrives and passes the tests.Also with Chektls and without problems Reading on the internet, there are more problems in Ex2010 , I was thinking if this problem is corrected by recreating the connectors as done in Exchange 2003 - 2010 Reviewing the RND message in a little detail, I realize that it only checks the message in Ex2010 and does not ask in Ex2016 if the mailbox exists. I have created test mailboxes on both servers and I can access them in OWA, that is where I have these problems sending and receiving emails Ex2010 in 10 MX Ex2010.contoso.com Ex2016 in 20 MX Ex2016.contoso.com

Hello Luis Alberto, Welcome to our forum! Did you see the error code “4.4.7 Queue Expired” in the queue viewer? If so, is there any more information included which might be helpful for further investigation? Could you please provide detailed NDR information for further troubleshooting? And have you made any changes to the default receive connectors on Exchange 2016? In addition, it is recommended that you use the command Get-MessageTrackingLog to view message tracking log to see if there is any information that can help pinpoint the problem. Get-TransportService|Get-MessageTrackingLog -MessageSubject <subject> -Sender <mailbox address> -Recipients <mailbox address> |ft timestamp,EventID,ClientHostname,ServerHostname,Source,ConnectorID -autosize Besides, noted that you are now having two MX records pointed to both Exchange 2010 and Exchange 2016, could you try leaving only one MX record point to Exchange 2016 and check the result? If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment". Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

It sounds like the Mail scanner is not configured to allow the 2016 server to send through it. Does sending through the 2016 server generate an NDR? If so, what is the exact error?

Error sending and receiving emails in Exchange 2010 and 2016 coexistence

Luis Alberto 101

These are the versions of the exchange servers:

Exchange 2016 CU23 - 15.1 Build (2507.6)

Exchange 2010 SP3 - 14.3.0513 Build(123.4)

The problem is sending and receiving emails in Exchange 2016.

Creating the send and receive connector in Ex2016:

Send	Receive	Message
Ex2010	Internet	OK
Internet	Ex2010	OK
Ex2016	Internet	4.4.7 Queue Expired
Internet	Ex2016	4.4.7 Queue Expired
Ex2010	Ex2016	4.4.7 Queue Expired
Ex2016	Ex2010	OK

Without connector to send and by default receive in Ex2016:

Send	Receive	message
Ex2010	Internet	OK
Internet	Ex2010	OK
Ex2016	Internet	OK
Internet	Ex2016	4.4.7 Queue Expired
Ex2010	Ex2016	4.4.7 Queue Expired
Ex2016	Ex2010	OK

Perform tests with Microsoft Remote Connectivity Analyzer. The test mail arrives and passes the tests.Also with Chektls and without problems

Reading on the internet, there are more problems in Ex2010, I was thinking if this problem is corrected by recreating the connectors as done in Exchange 2003 - 2010

Reviewing the RND message in a little detail, I realize that it only checks the message in Ex2010 and does not ask in Ex2016 if the mailbox exists. I have created test mailboxes on both servers and I can access them in OWA, that is where I have these problems sending and receiving emails

Ex2010 in 10 MX Ex2010.contoso.com

Ex2016 in 20 MX Ex2016.contoso.com

2 answers

Wandi Ding -MSFT 2,970 Reputation points Microsoft Vendor

2023-11-28T08:04:46.5933333+00:00
Hello Luis Alberto,

Welcome to our forum!

Did you see the error code “4.4.7 Queue Expired” in the queue viewer? If so, is there any more information included which might be helpful for further investigation? Could you please provide detailed NDR information for further troubleshooting? And have you made any changes to the default receive connectors on Exchange 2016?

In addition, it is recommended that you use the command Get-MessageTrackingLog to view message tracking log to see if there is any information that can help pinpoint the problem.

Get-TransportService|Get-MessageTrackingLog -MessageSubject <subject> -Sender <mailbox address> -Recipients <mailbox address> |ft timestamp,EventID,ClientHostname,ServerHostname,Source,ConnectorID -autosize

Besides, noted that you are now having two MX records pointed to both Exchange 2010 and Exchange 2016, could you try leaving only one MX record point to Exchange 2016 and check the result?

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.
Please sign in to rate this answer.
Luis Alberto 101 Reputation points

2023-11-28T20:11:47.64+00:00

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.

Server autodiscover Mx Priority

Ex2010 contoso.com Ex2010.contoso.com 10

Ex2016 contoso.com Ex2016.contoso.com 20

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

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Luis Alberto 101 Reputation points

2023-11-28T22:01:37.14+00:00

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 😂

SERVER MX Priority

Ex2010 Ex2010.contoso.com 10

Ex2016 Ex2016.contoso.com 20

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

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Wandi Ding -MSFT 2,970 Reputation points Microsoft Vendor

2023-11-30T07:43:02.99+00:00

Thank you for providing detailed information. You mentioned that you changed the Default Fronted Ex2016 and have you tested the mail flow before changing it? Is there any problem?

In addition, please confirm whether you have changed the Default connector on Ex16. If so, it is recommended that you try to restore it to the default. If the problem still exists, it is recommended that you rebuild all default receive connectors in 16. For more information, please refer to: Recreatedefault receive connectors in Exchange Server - ALI TAJRAN(Please Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.)

Wandi Ding -MSFT 2,970 Reputation points Microsoft Vendor

2023-12-05T08:32:50.2866667+00:00

Hi, just want to confirm that whether your issue has been resolved, and do you have any questions about the information provided?
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Amit Singh 4,986 Reputation points

2023-11-29T05:33:53.16+00:00

It sounds like the Mail scanner is not configured to allow the 2016 server to send through it.

Does sending through the 2016 server generate an NDR? If so, what is the exact error?
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Error sending and receiving emails in Exchange 2010 and 2016 coexistence

2 answers

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Server	autodiscover	Mx	Priority
Ex2010	contoso.com	Ex2010.contoso.com	10
Ex2016	contoso.com	Ex2016.contoso.com	20