Hybrid Deployment - Architecture Overview Common Issues and Misconceptions Moving Mailboxes: The Good, the Bad the Ugly Keeping ADFS Alive DirSync / AADSync / AADConnect / Password Synchronization Monitoring in a Hybrid Deployment

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”

6. HybridArchitecture

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

11. DEMO
Troubleshooting Directory Synchronization

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)

13. DEMO
Troubleshooting AD FS

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)

16. How Federation works (MFG)

17. DEMO
Troubleshooting Exchange Federation Issues

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

22. Thank you!
www.enowsoftware.com