Email Routing in a Hybrid Deployment for O365

What is it ?

If you are migrating your emails to #Office365 and for any reason if you required by your business to route your email via on-premises network infrastructure, this how you want to do this.

Note:
Don’t place any servers, services, or devices between your on-premises Exchange servers and Office 365 that process or modify SMTP traffic. Secure mail flow between your on-premises Exchange organization and Office 365 depends on information contained in messages sent between the organization. Firewalls that allow SMTP traffic on TCP port 25 through without modification are supported. If a server, service, or device processes a message sent between your on-premises Exchange organization and Office 365, this information is removed. If this happens, the message will no longer be considered internal to your organization and will be subject to anti-spam filtering, transport and journal rules, and other policies that may not apply to it.

JAN 14 2020 -One year from today Exchange Server 2010 will no longer be supported

Jan 14 2020 – One year from today Exchange Server 2010 will no longer be supported.

What does end of support mean?

Exchange Server, like almost all Microsoft products, has a support lifecycle during which we provide new features, bug fixes, security fixes, and so on. This lifecycle typically lasts for 10 years from the date of the product’s initial release, and the end of this lifecycle is known as the product’s end of support. When Exchange 2010 reaches its end of support on January 14, 2020, Microsoft will no longer provide:

  • Technical support for problems that may occur
  • Bug fixes for issues that are discovered and that may impact the stability and usability of the server
  • Security fixes for vulnerabilities that are discovered and that may make the server vulnerable to security breaches
  • Time zone updates

Your installation of Exchange 2010 will continue to run after this date. However, due to the changes and risks listed above, we strongly recommend that you migrate from Exchange 2010 as soon as possible.

What are my options?

We’ve [Exchange PG] created a page (https://aka.ms/Exchange2010EndOfSupport) where we outline options, but in order to stay supported you essentially can;

  • Migrate all mailboxes to Office 365 and remove all Exchange 2010 servers by Jan 2020, making sure any on-premises servers used for administration purposes are on a supported version.
  • Go Hybrid with Office 365, remove all Exchange 2010 servers by Jan 2020 and make sure any on-premises servers are on a supported version.
  • Stay On-Premises and upgrade to a newer version of Exchange Server.

Clearly we think moving to Exchange Online and Office 365 is a good idea. We really do believe that’s where you’ll get access to the most secure and productive software with the lowest TCO. But over and above all of that, and in relation to the subject of this post – it gets you out of the upgrade business. If you migrate fully to Office 365 you really don’t need to worry about these big bang version migrations any more. You just have to make sure you keep a much smaller number of on-prem servers up to date, and you’re good.

If you do want to stay on-premises don’t forget that you cannot upgrade directly from Exchange 2010 on-premises to Exchange Server 2019. You can upgrade to Exchange 2013 or 2016 directly from Exchange 2010 and we recommend you upgrade to Exchange 2016 if you have the choice. It will give you a longer support lifecycle and more features. Given how similar 2013 and 2016 are from a migration standpoint, it’s also just as easy to go to 2016 as it is 2013. So, upgrade to Exchange 2016, and then you have the option to go to 2019 if you want to.

What if I need help?

If you have a complex deployment, or if you just don’t have the time or skills you might need some help. That’s fine, there are plenty of ways to get help.

If you’re migrating to Office 365, you might be eligible to use our Microsoft FastTrack service. FastTrack provides best practices, tools, and resources to make your migration to Office 365 as seamless as possible. Best of all, you’ll have a real support engineer that will walk you through your migration, from planning and design all the way to migrating your last mailbox. If you want to know more about FastTrack, take a look at Microsoft FastTrack.

If you run into any problems during your migration to Office 365 and you aren’t using FastTrack, or you are migrating to a newer version of Exchange Server, we’re still here to help. Here are some resources you can use:

You might choose to engage a partner to help too. We have a great number of partners with deep skills in Exchange, and we’re sure one of them will be able to help you. Start your search here – https://www.microsoft.com/en-us/solution-providers/home

So What Now?

What now? You need to get started if you haven’t already. Time really does fly and Jan 14th2020 is only a year away.

Tick Tock.

Transport routing in Exchange hybrid deployments

What is centralized transport?

If you already have heavily invested in your on-premise mail gateways and other infrastructure and you plan on moving to Office 365, Exchange Hybrid is the way to go in a long haul. When you have Exchange 2016 configured for Hybrid Setup with Office this where it come. 

So Why Centralized Transport?

It all depends on your business requirements, and if you don’t then you are good with regular setup routing via Office 365 , let’s cloud manage it for you. IF YOU DO HAVE such as regulatory and compliance requirements and even for other purpose where you want you emails MUST  route through your on-premises infrastructure then you need to configure it this way. In this video I will walk you over how does it really work.

Route mail through the on-premises organization for both on-premises and Exchange Online organizations

Outbound Messages from on-premises to Internet recipients

Exchange 2013/2016 Installation will be BLOCKED If?

Yes this will happen in Jun ’18 release of Exchange cumulative update and after that If your system does not meet requirements which included .NET Framework 4.7.1 it would not allow to you install either exchange 2013 or Exchange 2016.

So make sure in the next few months you do testing in your lab environment and make sure it goes through you change management process (if any) and get the system ready. This is major update. At this point it not clear how or what will happen if you have existing Exchange 2013/2016 without .NET Framework 4.7.1 and new Servers installed after June ’18 with .NET 4.7.1.

I will update this post as soon as I hear back from Exchange product team, till then stay tuned.

Exchange Team Blog

https://blogs.technet.microsoft.com/exchange/2017/12/19/released-december-2017-quarterly-exchange-updates/

Recent Release

KB articles that describe the fixes in each release are available as follows:

Reminder for Hybrid

In hybrid deployments where Exchange is deployed on-premises and in the cloud, or who are using Exchange Online Archiving (EOA) with their on-premises Exchange deployment are required to deploy the most current (e.g., 2013 CU19, 2016 CU8) or the prior (e.g., 2013 CU18, 2016 CU7) Cumulative Update release.

Hybrid free/busy lookups fail between Exchange Server 2016 CU8 and O365

Microsoft has identified a condition where Free/Busy lookups from On-Premises to O365 in a hybrid configuration may fail.

 

Symptoms

After you install Microsoft Exchange Server 2016 Cumulative Update 8 (CU8), free/busy queries from Microsoft Office 365 users to on-premises mailboxes in hybrid environments fail if the cloud mailboxes are not archive-enabled.

Cauase

This problem occurs because of a known issue that affects OAuth connectivity in Exchange Sever 2016 CU8.

Workaround

To work around this issue, create personal archive mailboxes for each cloud mailbox.

Status

This problem is scheduled to be fixed in Microsoft Exchange Server 2016 Cumulative Update 9 (CU9). For a supported fix for CU8, contact Microsoft Support.