Stairway to Heaven: Best Practices for Hybrid Deployments (Exchange + Office 365)

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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?

What tools can you use for monitoring & reporting on a hybrid deployment?

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Stairway to Heaven: Best Practices for Hybrid Deployments (Exchange + Office 365)

  1. 1. Stairway to Heaven: Best Practices for Hybrid Deployments www.ENowSoftware.com Michael Van Horenbeeck, Exchange MVP, MCM
  2. 2. 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
  3. 3. 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?
  4. 4. When you do not plan your migration to the cloud, things go wrong.
  5. 5. When things go wrong, your email system will be disrupted.
  6. 6. When your email system is disrupted, your CIO gets embarrassed.
  7. 7. When your CIO gets embarrassed, you lose your job.
  8. 8. When you lose your job, you have to cancel your family vacation to Disney.
  9. 9. Don’t cancel your family vacation! Prepare for your migration to the cloud!
  10. 10. Deployment Challenges…
  11. 11. Planning Exchange Lotus Notes Gmail Yahoo ... Source Large Medium Small Size DirSync Bulk Provisioning Manual Provisioning On-Premises (Single Sign-On) On-Cloud Identity Management
  12. 12. 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 IMAPmigration Cutovermigration Stagedmigration 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
  13. 13. 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
  14. 14. • It’s no longer only about Exchange. Many different teams are involved: – Active Directory – Networking – Exchange – … Many moving parts…
  15. 15. Implementation Navigating your way through the migration
  16. 16. ACTIVE DIRECTORY OFFICE 365 TENANT EXCHANGE ONLINE TENANT MICROSOFT DATA CENTER INTERNET PERIMETER NETWORK INTERNAL NETWORK EXCHANGE ON-PREM ORG. AZURE AD ADFS PROXY ADFS ACTIVE DIRECTORY DIRSYNC SERVER 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) 16 Hybrid Architecture
  17. 17. 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
  18. 18. Decisions, decisions, decisions • High Availability? • ADFS • DirSync • Hybrid Exchange environment? • Executing the migration: • Pilot? • Deciding who gets in first • Cross-premises permissions
  19. 19. “The Internet” Deploy Exchange 1. Configure SSO (optional) 2. Setup DirSync 3. Configure Certificates 4. Configure WebServices 5. Run Hybrid Configuration Wizard 6. Configure MX Records MX 7. Deployment Process
  20. 20. 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
  21. 21. Exchange On-Prem “The Internet” Exchange Online (Office 365) MRS Admin Hybrid Mailbox Moves
  22. 22. Tips for living in the cloud
  23. 23. 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
  24. 24. 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)
  25. 25. Troubleshooting steps • Hybrid Configuration Log Files • Review Federation Information • Review OrganizationRelationShips • Troubleshoot connection issues
  26. 26. 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.
  27. 27. Thank You www.ENowSoftware.com

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