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Hybrid Exchange 2010 SP3 Office 365

Posted on 2016-09-06
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Last Modified: 2016-09-26
Hi there,

we`re planning to implement a hybrid deployment of Exchange2010 SP3 (on premise) and Office 365.
I read a lot about Hybrid configuration wizard and found some information about mail flow.
In our case the current on premise mail-flow is as follows:

Domain:
 test.de (located at a hosting-provider)
Internal AD-Domain: test.local
MX for Domain test.de: IP of the mail cluster of a hosting provider

Incoming Mail-flow:
Mails from the internet get delivered to mailboxes that are hosted at the hosting provider.
The on-premise Exchange pulls E-Mails via POP3 (PopCon) and delivers the mail to on premise Exchange-Mailboxes.

Outgoing Mail-Flow:
The on premise Exchange sends outgoing mail via a sending connector that uses the hosting-provider as a smarthost.

Now I would like to configure a hybrid environment with Office365:
- MX should still point to do hosting providers mail cluster and mail should be delivered to the mailboxes there until all mailboxes have been moved to Office365
- Internal mail flow should work correctly between on premise and Office 365

Where I stuck planning is the place in the wizard, where it asks me for a public IP adress and FQDN of my on premise exchange (because I don`t have one yet) and where I have to decide the mail flow path.

How do I have to publish my on premise Exchange (Which ports?)?
If I choose "Route all Internet-bound messages through you on-premise Exchange....":
Will my incoming (Pop3-Pull) and outgoing (SmartHost) mail flow still work?

Looking forward to your suggestions!

Thanks in advance!
Roland
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Question by:Systemadministration
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Mahesh earned 250 total points (awarded by participants)
ID: 41787255
Try by providing hosting provider IP and public DNS hostname, however your hosting provider will not support MRS proxy protocol if he is not running Exchange and MRS Proxy is required onpremise (which is nothinbg but your onpremise CAS servers) for mailbox movement

How do I have to publish my on premise Exchange (Which ports?)?
 If I choose "Route all Internet-bound messages through you on-premise Exchange....":
 Will my incoming (Pop3-Pull) and outgoing (SmartHost) mail flow still work?

You just need to publish your CAS server (With MRS proxy Component enabled) on internet and allow TCP 443 from internet and same should be provided in Hybrid wizard
https://technet.microsoft.com/en-us/library/ee732395(v=exchg.141).aspx

Your incoming mailflow should still work via hosting provider

Now if you choose "Route all internet bound messages through onpremise server" it means user with mailbox in O365 can send mail to internet but it will 1st forwarded / relayed to onpremise Exchange server via connector and from onpremise exchange it will be passed on to internet - this is requirement by some organizations

So in short, your mailflow would continue to work from hosting provider > onpremise Exchange for incoming and from onpremise > hosting provider for outgoing.

 You need to try or log the call with Microsoft O365 support

Mahesh.
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by:Systemadministration
ID: 41787337
Hi Mahesh,

thanks for your answer. I think I will try it in our lab environment.
I have no problem publishing my on premise CAS server, so I don`t even need to try providing the hosting provider`s DNS hostname, right?

Many thanks!
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by:Mahesh
Mahesh earned 250 total points (awarded by participants)
ID: 41787394
However for Hybrid wizard to send / foward mail to your onpremise exchange, you do need O365 connector which should point to hosting provider IP over TCP 25 port

Normally Hybrid wizard forward / send email traffic to your Hub Transport server which is published on internet, in your case it is hosting provider server, Hybrid wizard automatically detect hub servers but I don't think in your case it will detect automatically and hence I suggest you test this with Lab

Better you test this scenario as per below modern post which would give you answers
https://blogs.technet.microsoft.com/exchange/2016/02/17/office-365-hybrid-configuration-wizard-for-exchange-2010/

I have done few Hybrid setup but in those case my CAS and HUB is already published on internet
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by:Jian An Lim
Jian An Lim earned 250 total points (awarded by participants)
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my major concern is the PopCon configuration you have.
by default, if you move your mailbox to Office 365, PopCon will break immediately hence no users will receive email upon switch over.


I will probably create a blank mailbox on office 365 then do a quick switch and  move active users to office 365 with blank mailbox and change over the MX record.

If you think blank mailbox is not acceptable, you might want to look at migrationwiz quick switch
https://community.bittitan.com/kb/Pages/How%20do%20I%20configure%20a%20Quick%20Switch%20migration.aspx

It will cost a bit but it will be a better experience if you plan it correctly.
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by:Jian An Lim
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OP did not return. solution has been provided.
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