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WEB APPLICATION PROXY VS. TMG Ing. Ondřej Ševeček | GOPAS a.s. | MCM: Directory Services | MVP: Enterprise Security | Certified Ethical Hacker | [email protected] | www.sevecek.com |

Web Application Proxy vs. TMG

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Ing. Ondřej Ševeček | GOPAS a.s. | MCM: Directory Services | MVP: Enterprise Security | Certified Ethical Hacker | [email protected] | www.sevecek.com |. Web Application Proxy vs. TMG. Web Application Proxy. Threat Management Gateway vs. WAP. Threat Management Gateway. - PowerPoint PPT Presentation

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Page 1: Web Application Proxy vs. TMG

WEB APPLICATION PROXYVS. TMG

Ing. Ondřej Ševeček | GOPAS a.s. | MCM: Directory Services | MVP: Enterprise Security | Certified Ethical Hacker |[email protected] | www.sevecek.com |

Page 2: Web Application Proxy vs. TMG

THREAT MANAGEMENT GATEWAY VS. WAP

Web Application Proxy

Page 3: Web Application Proxy vs. TMG

Threat Management Gateway

Forward HTTP/S proxy Kerberos SSO authentication user/group based rules and logging HTTPS inspection

Reverse HTTP/S proxy TLS/SSL endpoint HTTPS inspection Basic, Forms, TLS certificate, AD FS authentication Kerberos constrained delegation

Stateful firewall IP/ICMP/TCP/UDP/GRE/AH/ESP/FTP

Page 4: Web Application Proxy vs. TMG

Web Application Proxy

Forward HTTP/S proxy Kerberos SSO authentication user/group based rules and logging HTTPS inspection

Reverse HTTP/S proxy TLS/SSL endpoint HTTPS inspection Basic, Forms, TLS certificate, AD FS authentication Kerberos constrained delegation

Stateful firewall IP/ICMP/TCP/UDP/GRE/AH/ESP/FTP

Page 5: Web Application Proxy vs. TMG

HTTP/S Client

TMG forward proxyHTTP/SServer

TMGProxy

DCHTTP/SClient

HTTP/SClient

NATHTTP/SClient

Page 6: Web Application Proxy vs. TMG

Exchange

OWA

TMG/WAP reverse proxyBrowserHTTP/S Client

TMG

DCWeb

CRM

SharePoint

GUIHTTP/S Client

NAT

TLS Cert

TLS Cert

TLS Cert

TLS Cert

Page 7: Web Application Proxy vs. TMG

Exchange

OWA

Perimeter authentication+ auth. forwarding Browser

HTTP/S Client

TMG

DCWeb

CRM

SharePoint

GUIHTTP/S Client

NAT

Page 8: Web Application Proxy vs. TMG

TLS client certificate authentication

TLS session establishes first Without client certificate no HTTP

inside No password guessing Certificates mapped to user accounts

Page 9: Web Application Proxy vs. TMG

REMOTE ACCESS COMPAREDWeb Application Proxy

Page 10: Web Application Proxy vs. TMG

Network Access Technologies VPN

SMB/SQL/LDAP/DCOM sensitive to RTT Remote Desktop

no clipboard, no file proliferation limited malware surface

802.1x WiFi or Ethernet no encryption, authorization only

DirectAccess GPO managed IPSec tunnel over IPv6

Web Application Proxy HTTPS reverse proxy for web applications

Page 11: Web Application Proxy vs. TMG

RDP

VPN ScenarioVPN

Client

VPN Gatewa

y

DC FSSQL

RADIUS

NATSharePoint

Page 12: Web Application Proxy vs. TMG

RDP

DA ScenarioDA

Client

DA Server

DC FSSQL

RADIUS

NATSharePoint

Page 13: Web Application Proxy vs. TMG

WksWks

RDP

RDP ScenarioRDP

Client

RDP Gatewa

y

DC FSSQL

RADIUS

NATSharePoint

Wks

Page 14: Web Application Proxy vs. TMG

RDP

802.1x WiFi Scenario

WiFiClient

DC FSSQL

RADIUS

WiFi AP

SharePoint

Page 15: Web Application Proxy vs. TMG

RDP

802.1x Ethernet Scenario

Wks

DC FSSQL

RADIUS

Switch

SharePoint Wks

Printer

Page 16: Web Application Proxy vs. TMG

AD FS Proxy

Exchange

WAP ScenarioWeb

Browser or GUI client

Web Application Proxy

DC

Web

Lync

AD FS

NAT

SharePoint

Page 17: Web Application Proxy vs. TMG

VPN ComparedProtocol Transport Client RRAS Server

Server Requirements

PPTP TCP 1723IP GRE

MS-DOS and newer NT 4.0 and newer -

-

L2TPUDP 500, 4500IP ESP

NT 4.0, 98and newer 2000 and

newer

IPSec certificatepublic namePublic IPIPSec machine

certificate

SSTP TCP 443TLS

Vista/2008 and newer 2008 and

newerTLS certificatepublic name-

IKEv2UDP 500, 4500IP ESP

7/2008 R2 and newer 2008 R2 and

newer

IPSec certificatepublic namePublic IP

IPSec machine certificate

Page 18: Web Application Proxy vs. TMG

VPN Compared

Protocol Transport Client RRAS ServerServer Requirements

RD Gateway

TCP 443TLS

RDP Client 6.0and newer 2008 and

newerTLS certificatepublic name

-

DirectAccess

IPSec insideIPv6 insideTCP 443 TLSor Teredo/6-to-4

7/2008 R2 EntepriseIPv6 enabled, GPO 2012 and

newer

IPSec certificateTLS certificatepublic nameIPSec machine

certificate

Web Application Proxy

HTTPSweb browserGUI web client (office)

2012 R2 and newer WAP and AD FS server

TLS certificatepublic nameTLS certificate for AD FS public name

Page 19: Web Application Proxy vs. TMG

WEB APPLICATION PROXYWeb Application Proxy

Page 20: Web Application Proxy vs. TMG

AD FS Proxy

Names and certificatesWeb

Browser or GUI client

Web Application Proxy

DC

AD FS

SharePoint

http://intranet

https://adfs.gopas.cz

https://adfs.gopas.cz

https://intranet.gopas.cz

NAT

Page 21: Web Application Proxy vs. TMG

AD FS Proxy

Service accountsWeb

Browser or GUI client

Web Application Proxy

DC

AD FS

SharePoint

sp-intranet-web

Network Service

svc-adfs

Network Service

NAT

Page 22: Web Application Proxy vs. TMG

AD FS Proxy

Windows authenticationwith passwords - overview Web

Browser or GUI client

Web Application Proxy

DC

AD FS

SharePoint

Forms

BasicPOST

Cookie

NAT

Kerberos

Exchange

Page 23: Web Application Proxy vs. TMG

AD FS Proxy

Windows authenticationwith passwords - #1 Web

Browser or GUI client

Web Application Proxy

DC

AD FS

SharePoint

Exchange

NAT

Redirect 307

Page 24: Web Application Proxy vs. TMG

AD FS Proxy

Windows authenticationwith passwords - #2 Web

Browser or GUI client

Web Application Proxy

DC

AD FS

SharePoint

Exchange

Forms

BasicPOST

NAT

Page 25: Web Application Proxy vs. TMG

AD FS Proxy

Windows authenticationwith passwords - #3 Web

Browser or GUI client

Web Application Proxy

DC

AD FS

SharePoint

Exchange

NAT

Claims

ClaimsRedirect

302

Page 26: Web Application Proxy vs. TMG

AD FS Proxy

Windows authenticationwith passwords - #4 Web

Browser or GUI client

Web Application Proxy

DC

AD FS

SharePoint

Exchange

NAT

Claims

Kerberos

Cookie

Page 27: Web Application Proxy vs. TMG

AD FS Proxy

Windows authenticationwith passwords - #5 Web

Browser or GUI client

Web Application Proxy

DC

AD FS

SharePoint

Exchange

NAT200 OK

200 OK

CookieCookie

Page 28: Web Application Proxy vs. TMG

AD FS Proxy

Windows authenticationwith TLS client certificate Web

Browser or GUI client

Web Application Proxy

DC

AD FS

SharePoint

Cookie

NAT

TLS Client Certificate

Kerberos

Exchange

TLS Client Certificate

TCP 49443

TCP 49443

Page 29: Web Application Proxy vs. TMG

AD FS Proxy

Claims authenticationWeb

Browser or GUI client

Web Application Proxy

DC

AD FS

SharePoint

Forms

Cookie NAT

Claims

Exchange

BasicPOST

TLS Client Certificate

CookieClaims

Page 30: Web Application Proxy vs. TMG

LONG JOURNEY?Web Application Proxy

Page 31: Web Application Proxy vs. TMG

Long journey yet?

Basic only with pass-through deprecated since AD FS 2.0 no Basic fallback (GUI clients)

No selection intranet/extranet No persistent cookies

always the web page regardless of client (GUI) AD FS native support since Exchange 2013

SP1 AD FS native support since SharePoint 2010

no WebDAV support No inspection