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Paulsiso-0904 avatar image
Paulsiso-0904 asked ·

Installed new Exchange 2016 mailbox server into 2010 environment w/2010 Edge. Test account from 2016 will not send/receive externally.

I recently completed an installation of Exchange 2016 mailbox server into an Exchange 2010 environment, which includes one 2010 mailbox server and one 2010 Edge Transport server.

I created a test account on the 2016 database and tested the send/receive connectivity. I was able to send internally, but for external mail, it's hangs in the queue. Error below.



Diagnostic information for administrators:
Generating server: Exchange2016.domain.local
Receiving server: edgesync - default-first-site-name to internet (2xx.xx.xx.xx)
example@gmail.com
Server at edgesync - default-first-site-name to internet (2xx.xx.xx.xx) returned '400 4.4.7 Message delayed'
10/21/2020 10:43:36 AM - Server at edgesync - default-first-site-name to internet (2xx.xx.xx.xx) returned '451 4.4.397 Error communicating with target host. -> 421 4.2.1 Unable to connect -> SocketTimedout: Socket error code 10060'
Original message headers:
Received: from Exchange2016.domain.local (192.168.xx.xxx) by
Exchange2016.domain.local (192.168.xx.xxx) with Microsoft SMTP Server
(version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256) id
15.1.2106.2; Wed, 21 Oct 2020 02:46:10 -0400
Received: from Exchange2016.domain.local ([::1]) by
Exchange2016.domain.local ([::1]) with mapi id 15.01.2106.002; Wed, 21
Oct 2020 02:46:10 -0400

office-exchange-server-administrationoffice-exchange-server-connectivityoffice-exchange-server-mailflowoffice-excel-itpro
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Paulsiso-0904 avatar image
Paulsiso-0904 answered ·

The Resolution:

So I followed everyone's advice to resubscribe the Edge Subscription and so I did, using the Edge 2010 and Exchange 2010 mailbox. Tested it and got the same error. This is not to say that this wasn't required, it very well may have, it's just that I also needed to create a Firewall rule to allow the Exchange 2016 mailbox server to see the Edge 2010 and vice versa. Once the bidirectional FW rule was enabled, I was able to send/receive to external recipients using a test mailbox from the Exchange 2016 mailbox server. Thank you all for your assistance and expertise.

Paul S.

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AndyDavid avatar image
AndyDavid answered ·

You have to re-subscribe an Edge Subscription whenever you add or remove Mailbox servers in the AD site.
https://docs.microsoft.com/en-us/exchange/architecture/edge-transport-servers/edge-subscriptions?view=exchserver-2019

Also, I would suggest following the docs and bring up an Exchange 2016 Edge and subscribe that

https://practical365.com/exchange-server/exchange-server-2016-migration-mail-flow-cutover/

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Thank you AndyDavid. Should I re-subscribe the Edge Subscription on just the Exchange 2010 mailbox server, or on both 2010 and 2016 mailbox servers?

0 Votes 0 · ·

Subscriptions are to the entire AD site, not to mailbox servers.

I would bring up a 2016 Edge server as well.

1 Vote 1 · ·

I see. So it doesn't matter which server I use to re-subscribe the Edge server? Yes, I will bring up the 2016 Edge servers once it has been cleared by the Security Team and will subscribe that as well.

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LydiaZhou-MSFT avatar image
LydiaZhou-MSFT answered ·

@Paulsiso-0904

Agree with AndyDavid. When we add a Mailbox server, the new Mailbox server doesn't automatically participate in EdgeSync synchronization. So we have to resubscribe the Edge Transport server to AD. For your reference: Add or Remove a Mailbox server.

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Just checking in to see if above information was helpful. If you have any questions or need further help on this issue, please feel free to post back.


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1 Vote 1 · ·

Any updates so far?
Does re-subscribing the Edge Transport server work for you? Please let us know if you would like further assistance.


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1 Vote 1 · ·

Yesterday, I was given the green light to re-subscribe the Edge subscription. So I went ahead and re-subscribe the Edge 2010 server using the Exchange 2010 mailbox server. Same result. I was able to send/receive to internal/external recipients using a Exchange 2010 mailbox, but when I to send an external email using a test account mailbox created on the Exchange 2016 mailbox, I get the same "Delayed delivery" notification:

0 Votes 0 · ·

Just to clarify, the Edge 2016 server has not been subscribed yet. Not sure if this will have any impact on mail flow.

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WiegmannNiklas-7178 avatar image
WiegmannNiklas-7178 answered ·

Hi,

just found your articel becuase I came to the same problem.

I re subscribed and mail flow is working from the new mailboxserver 2016 aswell.

however wenn I run test-edgesubscription on the old 2010 mailboxserver it states failed.
when I run test-edgsubscription on the new 2016server it states successfully.

Is this normal behavior in 2010/2016 mix?

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Yes,
https://docs.microsoft.com/en-us/exchange/architecture/edge-transport-servers/edge-subscriptions?view=exchserver-2019

In Exchange 2016 organizations, if you also have Exchange 2010 Hub Transport servers in the subscribed Active Directory site, Exchange 2016 Mailbox servers will always take precedence and perform the replication.

1 Vote 1 · ·

great, thanks a lot for the quick respond :)

1 Vote 1 · ·
Paulsiso-0904 avatar image Paulsiso-0904 WiegmannNiklas-7178 ·

Hey WiegmannNiklas -

Were you able to fix the issue by subscribing the new Edge 2016 server, or did you resubscibe the Edge 2010 server?

Thanks

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