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1 Single Sign-On Showdown ADFS vs Pass-Through Authentication Max Fritz Solutions Architect SADA Systems #ITDEVCONNECTIONS

2 Azure AD Identity Sync & Auth Timeline DirSync becomes Azure AD Sync 2013 Password Hash Sync added to AAD Sync 2015 Azure AD Sync becomes Azure AD Connect Introduces Health engine 2017 msds- ConsistencyGuid as source anchor Pass Through Authentication introduced Seamless SSO introduced DirSync introduced for identity synchronizat ion

3 Azure AD Authentication Methods Today Cloud Only Identity Password Hash Synchronization Pass-through Authentication Federated (ADFS) 3 rd Party Federated Identities exist only in AAD Authentication handled by AAD Identities synced to AAD Authentication handled by AAD Identities synced to AAD Authentication handled by local AD Identities synced to AAD Authentication handled by local AD Identities synced to AAD Authentication handled by third-party

4 Azure AD Authentication Methods Today Password Hash Synchronization Identities synced to AAD Authentication handled by AAD Pass-through Authentication Identities synced to AAD Authentication handled by local AD Federated (ADFS) Identities synced to AAD Authentication handled by local AD

5 Azure AD Authentication Methods Today Password Hash Synchronization Identities synced to AAD Authentication handled by AAD Pass-through Authentication Identities synced to AAD Authentication handled by local AD Federated (ADFS) Identities synced to AAD Authentication handled by local AD Identity Synchronization through Azure AD Connect

6 Sidebar: What is Azure AD Connect? Application installed on a Windows machine within your environment Integrates local Active Directory with Azure Active Directory Sync engine based on Microsoft Identity Manager (shared codebase) Uses a local SQL server for sync database (can be separate SQL server) Includes a monitoring component: Azure AD Connect Health Free for all Azure AD customers (so just free ) Can manage ADFS installations

7 Azure AD Connect is required for all authentication methods we will cover today We will not demo installation or basic configuration of AADC today, however AADC will be a part of some demos

8 Authentication Methods: How we will rank Ease of Implementation Security Customization Options Available Features Usability Maintenance & Reliability

9 Scoreboard Password Sync + Seamless SSO PTA + Seamless SSO ADFS (2019) Ease of Implementation Security Customizations Features Usability Maintenance & Reliability Score

10 Password Hash Synchronization

11 Password Hash Synchronization Involves syncing hashed passwords to Azure AD Relies on Azure AD Connect Passwords synced every 2 minutes Authentication is completely cloud based

12 Password Hash Sync Authentication Identity delta sync every 30 minutes Azure AD # AADC request MD4 password hashes from DC via MS-DRSR replication protocol (every 2 min) DC encrypts password in an MD5 envelope and sends to AADC AADC Decrypts MD5 hash and expands MD4 hash to 64 bytes AADC adds a 10-byte salt to MD4 hash, and converts to SHA256 hash (using PBKDF2 function) SHA256 hash is sent to Azure AD over SSL # On Premises

13 Password Hash Sync Authentication Identity delta sync every 30 minutes # # Azure AD User attempts to sign in to app Session redirected to Azure AD for sign in User provides credentials to Azure AD Azure AD applies MD4+salt+PBKDF2+SHA256 process, and validates resulting hash against stored hash Azure AD completes sign in If successful, user is granted access to the app On Premises

14 Password Hash Sync Considerations Locked out local accounts are not properly reflected in AAD Disabled local accounts will not be disabled in AAD until an AADC sync cycle (can be manually triggered) MD4 hashes are notoriously easy to crack, and MD5 is not much harder Extra SHA-2 encryption makes the hash much harder to decrypt Extra hashing technically makes this more secure than local AD credentials Allows for leaked credential reports from MS if AAD P1 licensing is in place Remember, Microsoft does not get your passwords. They only receive a triple hashed password. Required for use of Azure AD Domain Services

15 Pass-through Authentication

16 Pass-through Authentication (PTA) Relies on Azure AD Connect and PTA (AuthN) Agents Agents can be installed on multiple servers for high availability First agent is on the Azure AD Connect server Additional agents can be deployed via script or manually Networking: only requires outbound communication on 80, 443, and 8080 [for reporting status to AAD] (no inbound ports to open) Requires Server 2013 R2 or later

17 Pass-through Authentication Identity delta sync every 30 minutes 1 2 Azure AD User attempts to sign in to app Session redirected to Azure AD for sign in User provides credentials to Azure AD Azure AD produces encrypted passwords (1 for each PTA agent registered, using public key for the agent) and places them onto the Service Bus for the tenant PTA Agent retrieves validation request (persistent connection) and decrypts password using private key PTA Agent attempts credential validation against Domain Controller 1 2 PTA Agents On Premises

18 Pass-through Authentication Identity delta sync every 30 minutes Azure AD DC provides result to PTA agent (success/failure/expired) PTA agent sends result to Azure AD via mutually authenticated HTTPS channel Azure AD completes sign in If successful, user is granted access to the app 2 1 PTA Agents On Premises

19 Pass-through Authentication Considerations Locked and Disabled local accounts are respected Supports alternate login IDs Fully supports Azure AD conditional access Since sign in request are still process through AAD (as opposed to redirected) Requires Modern Authentication* Supports alternate login IDs Supports AAD Smart Lockout (prevents brute force attacks) Does not support leaked credential reports Not available in GCC at this time

20 Pass-through Authentication Demo

21 Seamless Single Sign-on

22 Seamless Single Sign-On Provides single sign on capabilities to domain joined machines Compatible with Password Hash Sync or PTA Requirements: OS: Windows 7+ or Mac OS X, domain joined (to local AD) Browsers: IE 10+, Chrome, Safari*, Firefox* Does not support Edge at this time 1 URL needs to be added to Intranet Zone (via group policy) Ability to register non-windows 10 devices with Azure AD

23 Seamless SSO Authentication (browser based) User attempts to sign in to app from domain joined machine Session redirected to Azure AD for sign in* User provides username to Azure AD* Azure AD challenges browser to provide a Kerberos ticket Browser requests a ticket from local AD for the AZUREADSSOACC computer account AD returns ticket to browser encrypted with computer account s secret Browser forward Kerberos ticket to Azure AD Azure AD decrypts ticket, identifies user, and returns token If successful, user is granted access to the app Azure AD On Premises

24 Seamless Single Sign-On Considerations Opportunistic: If Seamless SSO fails, sign-in experience falls back to regular behavior Sign-out supported: Allows users to sign in with other credentials if desired Requires Modern Authentication Creates a computer account in the local AD named AZUREADSSOACC Kerberos decryption key of this account, if compromised, could be used to generate Kerberos tickets for any user in the forest Recommendation is to manually rollover key every 30 days (automated method coming soon) Only works when devices are on the local network

25 Seamless Single Sign-on Demo

26 Active Directory Federation Services

27 Active Directory Federation Services (2019) Requires Azure AD Connect for identity sync Also can help manage the ADFS farm Requires a minimum of 2 servers (1 Federation and 1 Proxy), recommended minimum of 4 Allows for sign in with more alternative methods samaccountname, Certificate, Smart-Card, Windows Hello for Business, 3 rd party MFA, etc Supports Extranet lockout & extranet smart lockout policies Supports banned IP lists Deep login screen customization Supports Windows Integrated Authentication

28 ADFS Authentication

29 ADFS Recommended Deployment using Azure

30 ADFS Considerations Limited support for Azure AD Conditional Access However additional support for custom conditional access via ADFS claim rules Large investment of on-premises (or cloud) infrastructure, including DMZ deployment Requires valid third party certificate Supports Alternate Login ID Does not support Azure AD Identity protection Unless password hash is enabled as a backup*

31 Active Directory Federation Services Demo

32 Migrating from ADFS to PTA Demo

33 Back to the Scoreboard! Password Sync + Seamless SSO PTA + Seamless SSO ADFS (2019) Ease of Implementation Security Customizations Features Usability Maintenance & Reliability Score

34 Ease of Implementation Password Sync + Seamless SSO PTA + Seamless SSO ADFS 2019 Wizard based install and configuration Wizard based initial install and configuration Minimum of 4 servers required GPO required for Seamless SSO Agent deployment manual or script based Wizard based configuration of basic features GPO required for Seamless SSO Manual configuration for many items

35 Security Password Sync + Seamless SSO PTA + Seamless SSO ADFS 2019 Triple hashed passwords synced to the cloud Authentication remains on premises Authentication remains on premises

36 Customizations Password Sync + Seamless SSO PTA + Seamless SSO ADFS 2019 Limited login screen customization Limited login screen customization Detailed login screen customizations available with CSS Intermediate rule customizations and transformations Intermediate rule customizations and transformations Advanced rule customizations and transformations

37 Features Password Sync + Seamless SSO PTA + Seamless SSO ADFS 2019 Supports all Azure AD features Supports most Azure AD features Limited support for Azure AD features SSO support for most clients SSO support for most clients SSO support for more clients Lack of support for instant account lockouts and expirations Support for alternate login methods

38 Usability Password Sync + Seamless SSO PTA + Seamless SSO ADFS 2019 Simple end user experience, consistent with other Azure AD experiences Simple end user experience, consistent with other Azure AD experiences End user experience depends on customizations

39 Maintenance & Reliability Password Sync + Seamless SSO PTA + Seamless SSO ADFS 2019 Can go down with minimal impact At least 1 PTA agent must be available at all times At least 1 Federation and 1 Proxy server must be available at all times Seamless SSO requires manual Kerberos rollover No automated failover Seamless SSO requires manual Kerberos rollover Agents can go on existing servers, avoiding additional maintenance Requires certificate renewal More servers required for maintenance

40 Scoreboard Results Password Sync + Seamless SSO PTA + Seamless SSO ADFS (2019) Ease of Implementation Security Customizations Features Usability Maintenance & Reliability Score

41 WINNER! Pass-through Authentication!

42 Taking a closer look Everyone s environment is different, and the winner will be different from everyone The takeaway is that you should carefully consider your authentication method based on your organization s priorities It s not too late to change your method

43 Thank you!

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