Stairway to Heaven: Best Practices for Hybrid Deployments

www.ENowSoftware.com

Michael Van Horenbeeck, Exchange MVP, MCM

Michael Van Horenbeeck

• Microsoft Certified Solutions Master: Messaging

• Exchange Server MVP

• Microsoft Certified Trainer

• Co-author of “Exchange 2013 Cookbook”, regular speaker at various international events (Microsoft Exchange Conference, Exchange Connections) and regular contributor to “The UC Architects” and michaelvh.wordpress.com

What you will learn

• What are the challenges involved with migrating to the cloud and what can you do about them?

• What tools can you use for deploying hybrid environment?

• How does a typical hybrid deployment unfold?

• What are some tips for managing a Hybrid Deployment?

When you do not plan your migration to the cloud, things go wrong.

When things go wrong, your email system will be disrupted.

When your email system is disrupted, your CIO gets embarrassed.

When your CIO gets embarrassed, you lose your job.

When you lose your job, you have to cancel your family vacation to Disney.

Don’t cancel your family vacation! Prepare for your migration to the cloud!

Deployment Challenges…

Planning

ExchangeLotus Notes

GmailYahoo

...

Source

LargeMedium

Small

Size

DirSyncBulk Provisioning

Manual

Provisioning

On-Premises(Single Sign-On)

On-Cloud

Identity Management

Planning

• What Source?• Tooling?

– Office 365 Migration tools?– 3rd party tools needed?– PST Export/Import?– Hybrid deployment?

• Can influence migration path– e.g. Exchange 2003 -> Office 365

IMAP migration

Cutover migration

Staged

migratio

n

Hybrid

Exchange 5.5 X

Exchange 2000 X

Exchange 2003 X X X X

Exchange 2007 X X X X

Exchange 2010 X X X

Notes/Domino X

GroupWise X

Other X

What?

• What date are you moving?• How large is the data?• Where is it located?• Can you reduce the amount of data?

• Infrastructure• How much bandwidth do you have available?

• Provisioning

• It’s no longer only about Exchange. Many different teams are involved:– Active Directory– Networking– Exchange– …

Many moving parts…

ImplementationNavigating your way through the migration

16

ACTIVE DIRECTORY

OFFICE 365 TENANT

EXCHANGE ONLINE TENANT

MICROSOFT DATA CENTER INTERNET PERIMETERNETWORK

INTERNAL NETWORK

EXCHANGE ON-PREM ORG.

AZURE AD

ADFSPROXY

ADFS

ACTIVE DIRECTORY

DIRSYNCSERVER

EXCHANGE 2013(CAS)ORGANIZATIONAL RELATIONSHIP

EXCHANGE 2013(MBX)

ONLINE PROTECTION

HYBRID MAIL FLOW

SMTP

EXCHANGE ONLINE

AUTHENTICATION SERVICE

EXTERNAL USER(O365)

SYNC

HTTP(S)

HTTPS

HTTPS

OWA USER(O365)

HTTPS

MAIL FLOW

AUTHENTICATION

SYNCHRONIZATION

APP. ACCESS (HTTP(S))

INTERNAL USER(O365)

EXCHANGE USER

HTTPS

INTERNAL OWA USER(O365)

Hybrid Architecture

Office 365 (v 2010) Office 365 (v 2013)w/ On-Prem 2010

Office 365 (v 2013)w/ On-Prem 2013

Exchange 2003 SP2 (X) (X)

Exchange 2007 SP2/SP3 (X) (X)

Exchange 2007 SP3 Urx (X) (X) (X)

Exchange 2010 SP1 X

Exchange 2010 SP2 X

Exchange 2010 SP3 X X X

Exchange 2013 N/A X

(X) = supported w/ dependencies X = supported

Supported Topologies

Decisions, decisions, decisions

• High Availability?• ADFS• DirSync• Hybrid Exchange environment?

• Executing the migration:• Pilot?• Deciding who gets in first• Cross-premises permissions

“The Internet”

DeployExchange

1.

ConfigureSSO (optional)

2.

Setup DirSync

3.

Configure Certificates

4.

Configure WebServices

5.

Run Hybrid Configuration Wizard

6.

ConfigureMX Records

MX

7.

Deployment Process

Validating the deployment

• Is the environment ‘ready’?

• Is Exchange configured properly?

• Is everyone properly trained?

Visit: bit.ly/ExchangeTools for information on what tools you can use to validate your deployment

ExchangeOn-Prem

“The Internet”

ExchangeOnline

(Office 365)

MRS

Admin

Hybrid Mailbox Moves

Tips for living in the cloud

Managing hybrid deployments

• New challenges:• Lots of moving pieces• What do you have to monitor?• How to monitor cloud components?

• Complexity & lack of experience can become a problem

Common Issues

• Certificates• Expired• Not from a trusted source• Missing/Wrong subject (alternative) name

• Single Sign-On not functioning

• Free/Busy not working properly

• Peers not recognized as “internal”

• Outlook-related (e.g. missing updates)

Troubleshooting steps

• Hybrid Configuration Log Files

• Review Federation Information

• Review OrganizationRelationShips

• Troubleshoot connection issues

Mailscape for Exchange Online

• Award Winning Software• Used in over 50 countries• Named Best Exchange Reporting tool for 3 years.

• Monitoring Hybrid Deployments since 2012, including:

• ADFS, DirSync, Office365 connections

• Gain visibility into Office 365, with over 30 reports, including:

• Mailbox stats, Auditing, Mobile Devices, License reporting.

Thank Youwww.ENowSoftware.com