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Troubleshooting Exchange Hybrid Deployments
www.enowsoftware.com
Michael Van Horenbeeck
• Exchange Server MVP & MCSM
• Director of Product Research at
ENow Software
• Active in the industry for the
past 13 years
• Frequent speaker at
international conferences
• Blogs at www.vanhybrid.com
• Member of The UC Architects
podcast
Agenda
• Hybrid deployment – architecture overview
• Common issues and misconceptions
• Moving mailboxes: the good, the bad and the ugly
• Keeping ADFS alive
• DirSync / AADSync / AADConnect / Password Synchronization
• Monitoring in a hybrid deployment
• Q&A
Hybrid Deployment
Components of a Hybrid deployment (Architecture Overview)
What is a hybrid deployment?
“Two distinct cross-premises Exchange organizations, combined to ‘act’
as a single organization through a series of customizations in both
environments”
HybridArchitecture
Hybrid Building Blocks
Federation
• Free/Busy
• Mailtips
• Message Tracking
• eDiscovery
• …
DirSync
• Unified GAL
• X500 (Mailbox
Moves)
• Online Archiving
Secure Transport
• TLS encryption
• Header Preservation
• Cert-based security
• Centralized mail
flow
Mailbox Moves
• Mailbox Replication
Service (MRS)
• Online Moves
• Fast / Reliable
Common issues & misconceptions
DirSync
• Not synchronizing…at all.
• Synchronizing but is having issues with a subset of
accounts due to:
• Duplicates
• Illegal characters (corrupted items etc…)
• Attributes not written back properly
How DirSync works
DirSync
Active Directory
METAVERSE
DEMO
Troubleshooting Directory Synchronization
Active Directory Federation Services
• Error messages can be cryptic…
• Troubleshooting is not easy
• You only have “half” of the story
• Different authentication flows
• 3rd party tooling needed to help figuring out what
happen(s)(ed)
DEMO
Troubleshooting AD FS
Troubleshooting AD FS Summary
• Not easy
• Use tools like e.g. Fiddler
• Enable Debug Logging in Event Viewer
• Pair AD FS Proxy w/ ADFS for easier troubleshooting
• Understanding different authentication flows is important
Exchange Federation
• Many components to take a look at
• Microsoft Federation Gateway trust
• Organization Relationship (local)
• Organization Relationship (remote)
• Domain Federation Information
• Autodiscover
• OAUTH (‘new’ since Exchange 2013 CU5)
How Federation works (MFG)
DEMO
Troubleshooting Exchange Federation Issues
Avoid Troubleshooting
Why monitoring makes sense in a clouded world…
Monitoring Exchange Hybrid
• Change in monitoring paradigm:
• It’s no longer about the server(s), rather about the service!
• Allows you to identify faster where the problem is located:
• proactively communicate to your user base (and management)
• Faster resolution time in case problem is caused on-prem
• Escalate issues to support earlier
• No need to “wait” for updated dashboard
What components do I need to monitor?
• Directory Synchronization
• Identity Federation (if applicable)
• Exchange Federation
• Mail Flow
• Certificates
• Connectivity
Featured as Messaging and Unified
Communications Award Finalist
About ENow Software
Download Mailscape
for Exchange Online
Free Trial
http://bit.ly/Mailscape-Hybrid
Thank you!
www.enowsoftware.com

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Troubleshooting Exchange Hybrid Deployments

  • 1. Troubleshooting Exchange Hybrid Deployments www.enowsoftware.com
  • 2. Michael Van Horenbeeck • Exchange Server MVP & MCSM • Director of Product Research at ENow Software • Active in the industry for the past 13 years • Frequent speaker at international conferences • Blogs at www.vanhybrid.com • Member of The UC Architects podcast
  • 3. Agenda • Hybrid deployment – architecture overview • Common issues and misconceptions • Moving mailboxes: the good, the bad and the ugly • Keeping ADFS alive • DirSync / AADSync / AADConnect / Password Synchronization • Monitoring in a hybrid deployment • Q&A
  • 4. Hybrid Deployment Components of a Hybrid deployment (Architecture Overview)
  • 5. What is a hybrid deployment? “Two distinct cross-premises Exchange organizations, combined to ‘act’ as a single organization through a series of customizations in both environments”
  • 7. Hybrid Building Blocks Federation • Free/Busy • Mailtips • Message Tracking • eDiscovery • … DirSync • Unified GAL • X500 (Mailbox Moves) • Online Archiving Secure Transport • TLS encryption • Header Preservation • Cert-based security • Centralized mail flow Mailbox Moves • Mailbox Replication Service (MRS) • Online Moves • Fast / Reliable
  • 8. Common issues & misconceptions
  • 9. DirSync • Not synchronizing…at all. • Synchronizing but is having issues with a subset of accounts due to: • Duplicates • Illegal characters (corrupted items etc…) • Attributes not written back properly
  • 10. How DirSync works DirSync Active Directory METAVERSE
  • 12. Active Directory Federation Services • Error messages can be cryptic… • Troubleshooting is not easy • You only have “half” of the story • Different authentication flows • 3rd party tooling needed to help figuring out what happen(s)(ed)
  • 14. Troubleshooting AD FS Summary • Not easy • Use tools like e.g. Fiddler • Enable Debug Logging in Event Viewer • Pair AD FS Proxy w/ ADFS for easier troubleshooting • Understanding different authentication flows is important
  • 15. Exchange Federation • Many components to take a look at • Microsoft Federation Gateway trust • Organization Relationship (local) • Organization Relationship (remote) • Domain Federation Information • Autodiscover • OAUTH (‘new’ since Exchange 2013 CU5)
  • 18. Avoid Troubleshooting Why monitoring makes sense in a clouded world…
  • 19. Monitoring Exchange Hybrid • Change in monitoring paradigm: • It’s no longer about the server(s), rather about the service! • Allows you to identify faster where the problem is located: • proactively communicate to your user base (and management) • Faster resolution time in case problem is caused on-prem • Escalate issues to support earlier • No need to “wait” for updated dashboard
  • 20. What components do I need to monitor? • Directory Synchronization • Identity Federation (if applicable) • Exchange Federation • Mail Flow • Certificates • Connectivity Featured as Messaging and Unified Communications Award Finalist
  • 21. About ENow Software Download Mailscape for Exchange Online Free Trial http://bit.ly/Mailscape-Hybrid

Editor's Notes

  1. http://social.technet.microsoft.com/wiki/contents/articles/24544.how-to-avoid-syncing-accidental-deletes-to-the-cloud-directory.aspx