1. Autodiscover is Hero of Exchange Motherland!
Jeff Guillet, MVP | MCSM | CISSP

2. Why is Autodiscover Important?
Autodiscover is more than just a convenience
Required for EWS, availability, OOF
Required by Mac for Outlook
Used by scripts and applications
Used by auto-mapping
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3. What does it do for me?
You have no choice – you might get mail to work, but Availability, OOF, EWS, etc. won’t work without it.
Autodiscover provides Outlook with several key pieces of information:
Outlook Anywhere also includes SSL requirement and Certificate Principal Name
Display Name
Server/Outlook Anywhere End Point/RPC CAS
Alias
Availability Service URL
OOF URL
AOB URL or Location
Unified Messaging URL, if appropriate
OWA URL
ECP URL
Authentication Package
Alternate Mailboxes
Archive Access
Public Folder Access
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4. How does it work? Autodiscover is a web service
Authenticated client posts web request
Autodiscover service returns XML response
Response comes from mailbox server and is dynamic, based on client and location
Configures Outlook or mobile client
Configures URLs for each service based on location
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5. Autodiscover Requirements
Internally, Exchange publishes an SCP during setup
Externally, you need the following to get it working:
Enable Outlook Anywhere
SSL Certificates
Configure URLs for each service
Publish URLs in external DNS
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6. How do Clients Connect to Autodiscover?
Authentication
Assumes username + domain portion of the user’s primary SMTP address (SMTP domain)
Otherwise uses Outlook's Auto Account Setup or prompts for logon ID
Domain password
Best practice: Match logon ID to address
Password policy implications
Denials of Service
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7. Autodiscover 2010 Internal Architecture
The XML request contains a reference to a schema as the first part of the opening <Autodiscover> XML tag
xmlns=
xmlns=
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8. Autodiscover 2013 Internal Architecture
The XML request contains a reference to a schema as the first part of the opening <Autodiscover> XML tag
xmlns=
xmlns=
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9. Anatomy of an Autodiscover Response
Schema (outlook or mobilesync)
User Information
Account Information
Alias
Protocols:
EXCH, EXPR, EXHTTP, WEB and sometimes mapiHttp
Encryption
Authentication
URLs
Alternative Mailboxes
Public Folder Information
Exchange 2007\2010: EXCH = Internal Outlook provider; EXPR = External Outlook provider
Exchange 2013\2016: EXCH = EWS; EXPR = EWS; EXHTTP = Both, Internal then External
WEB = URL for Outlook Web Access
EXPR = Exchange HTTP protocol for OA (web services)
EXHTTP =
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10. Outlook Anywhere 2010 Response
Exchange Availability Service
OOF
OAB, and below that is UM
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11. Outlook Anywhere 2010 Response
4. Protocol – in this case Outlook Anywhere
5. RPC Proxy server
6. Encryption requirement
7. Type of authentication – mutual means AutoD service uses cert, and user uses password
8. Certificate Principal Name (msstd) – server name (5) must match
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12. MAPI over HTTP Response
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13. MAPI over HTTP Response
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14. How Does Internal Outlook Connect to Autodiscover?
Internal Autodiscover (domain-based)
Service Connection Point (SCP)
AD site-based
First server in AD site
SSL encrypted, so FQDNs and certs matter!
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15. How Does External Outlook Connect to Autodiscover?
External Autodiscover (everywhere else)
Publish Autodiscover URL in DNS
A record
CNAME record
SRV record
SSL encrypted, so FQDNs and certs matter!
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16. Outlook Order of Operations
SCP lookup
HTTPS root domain query
HTTPS Autodiscover domain query
Local XML file
HTTP redirect method
SRV record query
Cached URL in the Outlook profile (new for Outlook 2010 version and later versions)
Direct Connect to Office 365 (new for Outlook 2016 version and later versions)
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17. Mobile Devices Only once (usually) during initial config
Different customized response
HTTP Error 451 redirect does not use Autodiscover
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18. What Makes Outlook Contact Autodiscover?
On Outlook startup
Periodically on a background thread
Default every 1 hour
TTL setting (in hours) using Set-OutlookProvider
If connection to Exchange server fails (failover or migration)
Outlook for Mac requires Autodiscover for normal operation
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19. Publishing Autodiscover
Internal Publishing
SCP
Edit with Set-ClientAccessServer -AutoDiscoverServiceInternalUri
Best practice is to use the load balanced namespace for all servers
External Publishing
A records
CNAME records
SRV records
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20. Autodiscover Coexistence
Autodiscover URL should always point to latest version
2013 CAS can up-level proxy to 2016
Exchange 2007 coexistence
Client  CAS2013/16  MBX2013/16
EX2013/16 delivers Exchange 2007 XML for the correct AD site.
Exchange 2010 coexistence
Client  CAS2013 (proxy)  CAS2010  MBX2010
Hybrid autodiscover should always point on-prem
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21. Autodiscover Testing Exchange Remote Connectivity Analyzer (ExRCA)
Microsoft Connectivity Analyzer
Outlook Test AutoConfiguration
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22. Demo
Outlook Test Autodiscover, ExRCA, Connectivity tool. Show local logs in C:\Users\Jeff\AppData\Local\Microsoft\Outlook\16

23. Autodiscover Gotchas
Registry or GPO settings cause Autodiscover to misbehave
Ensure autodiscover.domain.com is on your certificate or use a wildcard
Set each SCP to the load balanced name on your certificate
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24. Set-AutodiscoverSCP Script
Prevents Outlook security warnings when building new Exchange servers
Copies the SCP to the new AD object
Copies all virtual directory URLs to the new server
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25. Autodiscover Tips Beware of bare domain lookups in hosted environments
Use Set-AutodiscoverSCP.ps1 for new servers
Match UPNs to addresses
Reconfigure automapping
Troubleshooting from Outlook (logs)
Only use A records, but if you have to use SRV make sure they're consistent
Bare domain lookups may be problematic if it has a cert on it. (expired, android).
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