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Understanding Office
365’s Identity Solutions:
Deep Dive
Office 365 (and Azure) Identity Solutions
•

Individual / Small Business
•
•
•
•

•

No Integration Required
No Single Sign On
User logon Via Portal
No Servers on Premise

Medium Sized Business
•
•
•
•

•

No
Integration

Dirsync Tool – Perfect for Provisioning large groups of Users
No Single Sign On
User Login Via Portal
No Servers on Premise

ADFS &
Dirsync

Large Business
•
•
•
•
•

Deploy Dirsync
Implement ADFS
Users Login with WAD Credentials
Complex Server Infrastructure on Prem
Deployed as Part of a Hybrid Solution

Full Single
Sign On (SSO
Dirsync
(Provision
Only)

Hybrid
Access Control Challenges

Secure
Access for a
Wide Array
of Devices

High
Availability

Role Based
Access
Control

Customer
and Partner
Access to
Data
Support  Organizational Size Matters
The One Man Band
Small Business

Medium Size Business
Enterprise
The Four Pillars of Identity
Planning a Move to the Cloud?
• Influencing Factors:
•
•
•
•
•
•
•

Service Trials
Size of Organization
Time Constraints
Complexity of Customers Current Environment
Physical Locations
Current Identity Infrastructure.
Current IT Infrastructure. Internal / Outsourced / Hosted
Planning a Move to the Cloud?
• Influencing Factors:
•
•
•
•
•
•
•
•

Software / Hardware Issues
Network Bandwidth Issues
Security Issues
Legal & Compliance Issues
Vendor Service Level Agreement (SLA)
High Availability / Backup Issues
Resource Issues. Staff, Budget, etc!
Risk Analysis of Moving into the Cloud!
Current Identity Solution
•

No Centralized Identity Solution
•
•
•

•

Typical of a One Man Company
No Servers on Premises
Uses POP Email, Web Browser or Mobile Device

The Small Business
•
•
•
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•
•

Typically 5 to 25 Employees
Perhaps uses a Small Business Server on Premises
Are already Active Directory Users
Probably use Exchange Email
Adopt Small Scale SharePoint Usage
Probably outsource IT Support to External Consultant
Current Identity Solution
•

Medium to Enterprise level Organization
•
•
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100s or 1000s of Users
More Complex Active Directory Infrastructure
More Complex Infrastructure, Trust Relationships etc.
Probably use Exchange Email, Lotus Notes or Other On-Site
Email Solution
Probably uses Multi Factor Authentication
In house IT Support
Identity Solutions for Office 365

• Separate credential from onpremises credential
• Authentication occurs via cloud
directory service
• Password policy is stored in Office
365
• Does not require on-premises server
deployment

• Same credential as on-premises
credential
• Authentication occurs via onpremises directory service
• Password policy is stored onpremises
• Requires on-premises DirSync
server
• Requires on-premises ADFS server
Identity Architecture and Integration Options
1. No Integration
2. Directory Data Only
3. Directory and Single sign-on (SSO)
Windows Azure Active Directory

EPC Group customer
premises
Active Directory
Federation
Server 2.0
IdP

AD

Admin Portal/
PowerShell

MS Online
Directory Sync

Provisioning
platform

Office 365
Desktop Setup

SharePoint
Online

Authentication
platform

Trust

IdP

Directory
Store

Exchange
Online

Lync
Online

Office
Subscription
Services
Understanding Identities
Cloud Identity

Cloud Identity + DirSync

Federated Identity
 Large enterprise organizations with
Active Directory on-premises

 Does not require on-premises server  “Source of Authority” is on-premises
deployment
 Enables coexistence

Scenario

 Smaller organizations with or without  Medium to Large organizations with
on-premises Active Directory
Active Directory on-premises

 Single Sign-On experience

Benefits

 “Source of Authority” is on-premises
 2 Factor Authentication options

 Enables coexistence
 No Single Sign-On
 No 2 Factor Authentication options

Limitations

 No Single Sign-On
 No 2 Factor Authentication options

 Two sets of credentials to manage

 Two sets of credentials to manage

 Different password policies

 Different password policies
 Requires on-premises DirSync server
deployment

 Requires on-premises ADFS server
deployment in high availability scenario

 Requires on-premises DirSync server
deployment
Understanding Identities
Cloud Identity

Federated Identity

Federated Identity

(domain joined computer)

(non-domain joined computer)

Microsoft Outlook® 2010 on Windows® 7

Sign in each session

Sign in each session

Sign in each session

Outlook 2007 on Windows 7

Sign in each session

Sign in each session

Sign in each session

Outlook 2010 or Outlook 2007 on
Windows Vista® or Windows XP

Sign in each session

Sign in each session

Sign in each session

Exchange ActiveSync®

Sign in each session

Sign in each session

Sign in each session

POP, IMAP, Microsoft Outlook for Mac
2011

Sign in each session

Sign in each session

Sign in each session

Web Experiences: Office 365 Portal /
Outlook Web App / SharePoint Online /
Office Web Apps

Sign in each browser session

No Prompt

Sign in each browser session

Sign in each SharePoint Online session

Sign in each SharePoint Online Session

Sign in each SharePoint Online Session

Lync Online

Sign in each session

No prompt

Sign in each session

Outlook for Mac 2011

Sign in each session

Sign in each session

Sign in each session

Office 2010 or Office 2007 using
SharePoint Online
Make the Solutions Workable
•
•
•
•
•
•
•

Must be Tailored to Customer Requirements
Cost Effective
Avoid Ego Driven Design Bloat!
Take into Account Future Growth
Current / Future Migration Plans
Local / National Legal / Compliance Issues
Cross Platform Integration
Understanding Identities
• Two types of Domains
• Managed Domain
• Federated Domain

• Domain ownership must be verified
• Must use publicly registered namespace (i.e. cannot use *.local, etc.)

• Options for adding new domains:
• Microsoft Online Portal
• Microsoft Online Services Module for Windows PowerShell
Understanding Identities

• Microsoft Online Portal

• Active Directory tools
• Exchange Management
Tools
• Identity management
solutions

• Microsoft Online
Services Module for
Windows PowerShell
• Remote PowerShell
Windows Active Directory
Windows Active Directory
•
•
•
•
•
•
•
•
•

Directory service implemented on MS domain networks
Introduced in Windows 2000
DCs authenticate and authorise users and computers in a domain
Assigns and enforces security policies
Deployed in a single domain nor as part of a larger forest
Can be expanded through Trust Relationships
Has both physical & logical attributes
Only one instance per domain
Active Directory uses LDAP, Kerberos, and DNS
WAD: Potential Issues
•
•
•
•

As a number of trust limitations in respect to size & complexity
Designed primarily to manage in-house networks
Protocol limitations i.e. LDAP
Customer security concerns about WAD data in cloud (closed
attributes)
• Does not natively support new cloud based protocols
• Solution: Extend AD attributes into cloud…
Windows Azure Active Directory
Windows Azure Active Directory
What is Windows Azure Active Directory?
• Customized Version of ADLDS / ADAM
• Every Office 365 Customer is an Azure
•
•
•
•

AD Tennant
Designed primarily to meet the needs
of cloud applications
Extends Customers Active Directory
into the cloud
Think of it as a Fish on a Hook!
Identity as a service: essential part of
Platform as a Service
Relationship to Windows Server AD
• On-premises and cloud Active

Directory managed as one
• Directory information synchronized

to cloud, made available to cloud
apps via roles-based access
control
• Federated authentication enables

single sign on to cloud applications
WAAD Vs WAD!

• While enterprises work to consolidate identity system on-

premises, cloud apps are fragmenting identity… again
Azure Active Directory Design Principles
The cloud design point demands capabilities that are not
part of current-day Windows Server Active Directory
• Maximize device & platform reach
• http/web/REST based protocols

• Multi-tenancy
• Customer owns directory, not Microsoft

• Optimize for availability, consistent performance, scale
• Keep it simple
To Federate or Not Too
Federate?
Protocols to Connect to Windows Azure

AD

Protocol

Purpose

Details

REST/HTTP
directory access

Create, Read, Update, Delete directory
objects and relationships

Compatible with OData V3
Authenticate with OAuth 2.0

OAuth 2.0

Service to service authentication
Delegated access

JWT token format

Open ID Connect

Web application authentication
Rich client authentication

Under investigation
JWT token format

SAML 2.0

Web application authentication

SAML 2.0 token format

WS-Federation 1.3 Web application authentication

SAML 1.1 token format
SAML 2.0 token format
JWT token format
Deploying ADFS
ADFS 2.0 & SSO Requirements
•
•
•
•
•
•
•
•

Windows Server 2008 or Windows Server 2008 R2
Windows Server 2012 (2.1)
PowerShell V3
Web Server (IIS)
.Net 3.5 SP1
Windows Identity Foundation
Publicly registered domain name
SSL Certificate for Hybrid Deployment
Understanding SAML Authentication Into the
Cloud
Customer

Microsoft Online Services

Active Directory

AD FS 2.0

Logon (SAML 1.1) Token
UPN:user@contoso.com
ServerUser ID: ABC123
Source

Authentication platform
Auth Token
UPN:user@contoso.com
Unique ID: 254729

`

Client
(joined to CorpNet)

Exchange Online or
SharePoint Online
Walkthrough
Access Control Using ADFS Client Endpoints
ADFS Claim Types
• Launch ADFS 2.0

•
•

•
•

Management Console,
browse to Claims Provider
Trusts, and Edit Claim
Rules…
Add new rule
Select “Pass through or
filter an incoming claim”
template
Provide rule name and type
Repeat for all 5 claim types
Issuance Authorization Rule
• Launch ADFS 2.0

Management Console,
browse to Relying Party
Trusts, and Edit Claim
Rules…
• Add new Issuance
Authorization Rule
• Select “Send claims using a
custom rule” template
• Add rule name and custom
rule syntax
Cloud Provisioning
WAAD Provisioning
• Manual
• Simple Web based user interface
• Bulk import of user
• Best for small customers

• Scriptable
• PowerShell module for windows
• Programmable New REST based API
• Limited attribute set/object types

• Automated
• Directory Synchronization with delta
• Full fidelity of attributes and object types
• Optimized for large object sets
What is Dirsync?
(Azure Active Directory Sync Tool )

• Enables Simple & Rich Coexistence
• Provisions objects in Office 365 with same email
addresses as the objects in the on-premises environment
• Provides a unified Global Address List experience
between on-premises and Office 365
• Objects hidden from the GAL on-premises are also hidden from the

GAL in Office 365

• Enables coexistence for Exchange
• Works in both simple and hybrid deployment scenarios

• Enabler for mail routing between on-premises and Office

365 with a shared domain namespace
• Enables coexistence for Microsoft Lync
Dirsync Implementation Options
1 Way Sync from AD to Cloud
• Provisions users, DLs, Security Groups and contacts
• Can move to 2 Way Sync later
• on-premises master for all objects and properties

2 Way Sync from AD to Cloud and Cloud to AD
• Required for Hybrid Deployments e.g. co-existence
•
•
•
•

with Exchange online and Exchange on-premises
Cannot move back to 1 way sync
Cloud becomes master for certain properties (safe
senders, mail co-existence, UM)
Password Sync Option
Password Syncing is 1 way. Users that have
Password Sync enabled are required to change their
passwords on premises in an AD connected machine.
Dirsync Password Synchronization
• No longer requires ADFS to provide SSO
• Does not sync plaintext passwords
• Dirsync syncs hashes of hashes of your user's passwords
greatly reducing the risk of a password leaking
• You don't need to install any new software on your DCs or
reboot DCs
• Users don't need to change passwords
• Password Syncing is 1 way. Users that have Password
Sync enabled are required to change their passwords on
premises in an AD connected machine.
• “In my opinion not as secure as ADFS”
Dirsync: Synchronization Schedule
• Default is Every 3 Hours
• “Start-OnlineCoexistenceSync” cmdlet can manually force a manual sync
• Synchronization can be re-scheduled here!
1. First navigate to the following directory on your DirSync Server. C:Program

2.
3.
4.

5.

FilesMicrosoft Online Directory Sync
Locate service executable that is used to run the DirSync scheduleLocate the
following lines within the Microsoft.Online.DirSync.Scheduler.exe.config file:
<add key="SyncTimeInterval" value="3:00:0" />
Edit the time within this file to reduce the sync schedule; for example to reduce
the time to every 30 minutes use the following values: <add
key="SyncTimeInterval" value="0:30:0" />
Finally open the Services console (Start>Run>Services.msc) and restart the
Microsoft Online Services Directory Synchronization Service.

39
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•

Best Bets and Next
Choose Correct 365 Solution
Steps
Product V.s. Service
Clean House
SSO or not to SSO?
Read the Planning Guides
Region V.s. Compliance!
Get your DNS Correct
Watch out for Expiring SSL Certs
Beware the Deleted Domain Issue

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Understanding Office 365’s Identity Solutions: Deep Dive - EPC Group

  • 2. Office 365 (and Azure) Identity Solutions • Individual / Small Business • • • • • No Integration Required No Single Sign On User logon Via Portal No Servers on Premise Medium Sized Business • • • • • No Integration Dirsync Tool – Perfect for Provisioning large groups of Users No Single Sign On User Login Via Portal No Servers on Premise ADFS & Dirsync Large Business • • • • • Deploy Dirsync Implement ADFS Users Login with WAD Credentials Complex Server Infrastructure on Prem Deployed as Part of a Hybrid Solution Full Single Sign On (SSO Dirsync (Provision Only) Hybrid
  • 3. Access Control Challenges Secure Access for a Wide Array of Devices High Availability Role Based Access Control Customer and Partner Access to Data
  • 4. Support Organizational Size Matters The One Man Band Small Business Medium Size Business Enterprise
  • 5. The Four Pillars of Identity
  • 6. Planning a Move to the Cloud? • Influencing Factors: • • • • • • • Service Trials Size of Organization Time Constraints Complexity of Customers Current Environment Physical Locations Current Identity Infrastructure. Current IT Infrastructure. Internal / Outsourced / Hosted
  • 7. Planning a Move to the Cloud? • Influencing Factors: • • • • • • • • Software / Hardware Issues Network Bandwidth Issues Security Issues Legal & Compliance Issues Vendor Service Level Agreement (SLA) High Availability / Backup Issues Resource Issues. Staff, Budget, etc! Risk Analysis of Moving into the Cloud!
  • 8. Current Identity Solution • No Centralized Identity Solution • • • • Typical of a One Man Company No Servers on Premises Uses POP Email, Web Browser or Mobile Device The Small Business • • • • • • Typically 5 to 25 Employees Perhaps uses a Small Business Server on Premises Are already Active Directory Users Probably use Exchange Email Adopt Small Scale SharePoint Usage Probably outsource IT Support to External Consultant
  • 9. Current Identity Solution • Medium to Enterprise level Organization • • • • • • 100s or 1000s of Users More Complex Active Directory Infrastructure More Complex Infrastructure, Trust Relationships etc. Probably use Exchange Email, Lotus Notes or Other On-Site Email Solution Probably uses Multi Factor Authentication In house IT Support
  • 10. Identity Solutions for Office 365 • Separate credential from onpremises credential • Authentication occurs via cloud directory service • Password policy is stored in Office 365 • Does not require on-premises server deployment • Same credential as on-premises credential • Authentication occurs via onpremises directory service • Password policy is stored onpremises • Requires on-premises DirSync server • Requires on-premises ADFS server
  • 11. Identity Architecture and Integration Options 1. No Integration 2. Directory Data Only 3. Directory and Single sign-on (SSO) Windows Azure Active Directory EPC Group customer premises Active Directory Federation Server 2.0 IdP AD Admin Portal/ PowerShell MS Online Directory Sync Provisioning platform Office 365 Desktop Setup SharePoint Online Authentication platform Trust IdP Directory Store Exchange Online Lync Online Office Subscription Services
  • 12. Understanding Identities Cloud Identity Cloud Identity + DirSync Federated Identity  Large enterprise organizations with Active Directory on-premises  Does not require on-premises server  “Source of Authority” is on-premises deployment  Enables coexistence Scenario  Smaller organizations with or without  Medium to Large organizations with on-premises Active Directory Active Directory on-premises  Single Sign-On experience Benefits  “Source of Authority” is on-premises  2 Factor Authentication options  Enables coexistence  No Single Sign-On  No 2 Factor Authentication options Limitations  No Single Sign-On  No 2 Factor Authentication options  Two sets of credentials to manage  Two sets of credentials to manage  Different password policies  Different password policies  Requires on-premises DirSync server deployment  Requires on-premises ADFS server deployment in high availability scenario  Requires on-premises DirSync server deployment
  • 13. Understanding Identities Cloud Identity Federated Identity Federated Identity (domain joined computer) (non-domain joined computer) Microsoft Outlook® 2010 on Windows® 7 Sign in each session Sign in each session Sign in each session Outlook 2007 on Windows 7 Sign in each session Sign in each session Sign in each session Outlook 2010 or Outlook 2007 on Windows Vista® or Windows XP Sign in each session Sign in each session Sign in each session Exchange ActiveSync® Sign in each session Sign in each session Sign in each session POP, IMAP, Microsoft Outlook for Mac 2011 Sign in each session Sign in each session Sign in each session Web Experiences: Office 365 Portal / Outlook Web App / SharePoint Online / Office Web Apps Sign in each browser session No Prompt Sign in each browser session Sign in each SharePoint Online session Sign in each SharePoint Online Session Sign in each SharePoint Online Session Lync Online Sign in each session No prompt Sign in each session Outlook for Mac 2011 Sign in each session Sign in each session Sign in each session Office 2010 or Office 2007 using SharePoint Online
  • 14. Make the Solutions Workable • • • • • • • Must be Tailored to Customer Requirements Cost Effective Avoid Ego Driven Design Bloat! Take into Account Future Growth Current / Future Migration Plans Local / National Legal / Compliance Issues Cross Platform Integration
  • 15. Understanding Identities • Two types of Domains • Managed Domain • Federated Domain • Domain ownership must be verified • Must use publicly registered namespace (i.e. cannot use *.local, etc.) • Options for adding new domains: • Microsoft Online Portal • Microsoft Online Services Module for Windows PowerShell
  • 16. Understanding Identities • Microsoft Online Portal • Active Directory tools • Exchange Management Tools • Identity management solutions • Microsoft Online Services Module for Windows PowerShell • Remote PowerShell
  • 18. Windows Active Directory • • • • • • • • • Directory service implemented on MS domain networks Introduced in Windows 2000 DCs authenticate and authorise users and computers in a domain Assigns and enforces security policies Deployed in a single domain nor as part of a larger forest Can be expanded through Trust Relationships Has both physical & logical attributes Only one instance per domain Active Directory uses LDAP, Kerberos, and DNS
  • 19. WAD: Potential Issues • • • • As a number of trust limitations in respect to size & complexity Designed primarily to manage in-house networks Protocol limitations i.e. LDAP Customer security concerns about WAD data in cloud (closed attributes) • Does not natively support new cloud based protocols • Solution: Extend AD attributes into cloud…
  • 20. Windows Azure Active Directory
  • 21. Windows Azure Active Directory
  • 22. What is Windows Azure Active Directory? • Customized Version of ADLDS / ADAM • Every Office 365 Customer is an Azure • • • • AD Tennant Designed primarily to meet the needs of cloud applications Extends Customers Active Directory into the cloud Think of it as a Fish on a Hook! Identity as a service: essential part of Platform as a Service
  • 23. Relationship to Windows Server AD • On-premises and cloud Active Directory managed as one • Directory information synchronized to cloud, made available to cloud apps via roles-based access control • Federated authentication enables single sign on to cloud applications
  • 24. WAAD Vs WAD! • While enterprises work to consolidate identity system on- premises, cloud apps are fragmenting identity… again
  • 25. Azure Active Directory Design Principles The cloud design point demands capabilities that are not part of current-day Windows Server Active Directory • Maximize device & platform reach • http/web/REST based protocols • Multi-tenancy • Customer owns directory, not Microsoft • Optimize for availability, consistent performance, scale • Keep it simple
  • 26. To Federate or Not Too Federate?
  • 27. Protocols to Connect to Windows Azure AD Protocol Purpose Details REST/HTTP directory access Create, Read, Update, Delete directory objects and relationships Compatible with OData V3 Authenticate with OAuth 2.0 OAuth 2.0 Service to service authentication Delegated access JWT token format Open ID Connect Web application authentication Rich client authentication Under investigation JWT token format SAML 2.0 Web application authentication SAML 2.0 token format WS-Federation 1.3 Web application authentication SAML 1.1 token format SAML 2.0 token format JWT token format
  • 29. ADFS 2.0 & SSO Requirements • • • • • • • • Windows Server 2008 or Windows Server 2008 R2 Windows Server 2012 (2.1) PowerShell V3 Web Server (IIS) .Net 3.5 SP1 Windows Identity Foundation Publicly registered domain name SSL Certificate for Hybrid Deployment
  • 30. Understanding SAML Authentication Into the Cloud Customer Microsoft Online Services Active Directory AD FS 2.0 Logon (SAML 1.1) Token UPN:user@contoso.com ServerUser ID: ABC123 Source Authentication platform Auth Token UPN:user@contoso.com Unique ID: 254729 ` Client (joined to CorpNet) Exchange Online or SharePoint Online
  • 31. Walkthrough Access Control Using ADFS Client Endpoints
  • 32. ADFS Claim Types • Launch ADFS 2.0 • • • • Management Console, browse to Claims Provider Trusts, and Edit Claim Rules… Add new rule Select “Pass through or filter an incoming claim” template Provide rule name and type Repeat for all 5 claim types
  • 33. Issuance Authorization Rule • Launch ADFS 2.0 Management Console, browse to Relying Party Trusts, and Edit Claim Rules… • Add new Issuance Authorization Rule • Select “Send claims using a custom rule” template • Add rule name and custom rule syntax
  • 35. WAAD Provisioning • Manual • Simple Web based user interface • Bulk import of user • Best for small customers • Scriptable • PowerShell module for windows • Programmable New REST based API • Limited attribute set/object types • Automated • Directory Synchronization with delta • Full fidelity of attributes and object types • Optimized for large object sets
  • 36. What is Dirsync? (Azure Active Directory Sync Tool ) • Enables Simple & Rich Coexistence • Provisions objects in Office 365 with same email addresses as the objects in the on-premises environment • Provides a unified Global Address List experience between on-premises and Office 365 • Objects hidden from the GAL on-premises are also hidden from the GAL in Office 365 • Enables coexistence for Exchange • Works in both simple and hybrid deployment scenarios • Enabler for mail routing between on-premises and Office 365 with a shared domain namespace • Enables coexistence for Microsoft Lync
  • 37. Dirsync Implementation Options 1 Way Sync from AD to Cloud • Provisions users, DLs, Security Groups and contacts • Can move to 2 Way Sync later • on-premises master for all objects and properties 2 Way Sync from AD to Cloud and Cloud to AD • Required for Hybrid Deployments e.g. co-existence • • • • with Exchange online and Exchange on-premises Cannot move back to 1 way sync Cloud becomes master for certain properties (safe senders, mail co-existence, UM) Password Sync Option Password Syncing is 1 way. Users that have Password Sync enabled are required to change their passwords on premises in an AD connected machine.
  • 38. Dirsync Password Synchronization • No longer requires ADFS to provide SSO • Does not sync plaintext passwords • Dirsync syncs hashes of hashes of your user's passwords greatly reducing the risk of a password leaking • You don't need to install any new software on your DCs or reboot DCs • Users don't need to change passwords • Password Syncing is 1 way. Users that have Password Sync enabled are required to change their passwords on premises in an AD connected machine. • “In my opinion not as secure as ADFS”
  • 39. Dirsync: Synchronization Schedule • Default is Every 3 Hours • “Start-OnlineCoexistenceSync” cmdlet can manually force a manual sync • Synchronization can be re-scheduled here! 1. First navigate to the following directory on your DirSync Server. C:Program 2. 3. 4. 5. FilesMicrosoft Online Directory Sync Locate service executable that is used to run the DirSync scheduleLocate the following lines within the Microsoft.Online.DirSync.Scheduler.exe.config file: <add key="SyncTimeInterval" value="3:00:0" /> Edit the time within this file to reduce the sync schedule; for example to reduce the time to every 30 minutes use the following values: <add key="SyncTimeInterval" value="0:30:0" /> Finally open the Services console (Start>Run>Services.msc) and restart the Microsoft Online Services Directory Synchronization Service. 39
  • 40. • • • • • • • • • Best Bets and Next Choose Correct 365 Solution Steps Product V.s. Service Clean House SSO or not to SSO? Read the Planning Guides Region V.s. Compliance! Get your DNS Correct Watch out for Expiring SSL Certs Beware the Deleted Domain Issue