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SEC 318 SEC 318 Guerilla Security – Securing Guerilla Security – Securing Exchange 2000 and 2003 Exchange 2000 and 2003 Infrastructures Infrastructures Fred Baumhardt and Rab Thynne Fred Baumhardt and Rab Thynne Senior and Partner Strategy Senior and Partner Strategy Consultant Consultant Microsoft UK Microsoft UK

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Page 1: Guerilla Security

SEC 318SEC 318Guerilla Security – Securing Guerilla Security – Securing Exchange 2000 and 2003 Exchange 2000 and 2003 InfrastructuresInfrastructures

Fred Baumhardt and Rab ThynneFred Baumhardt and Rab Thynne

Senior and Partner Strategy ConsultantSenior and Partner Strategy Consultant

Microsoft UKMicrosoft UK

Page 2: Guerilla Security

Why do we call this Guerilla

• Guerilla as a type of warfare is exactly what we face in Internet Security

• Expect attacks from anywhere, with any device, at any time, from the inside

• Defences must be built exactly the same way, good monitoring, competent security forces, and ruthless execution of security policy on attackers

Page 3: Guerilla Security

Session Overview

• Core Security Concepts applied to Exchange

• The Exchange Server Security Model

• Implementing End to End Exchange Security • Implications of Client Selection

• Securing Client/Server to Server Communications

• Network Layer Security

• Exchange Host Server Security

• Questions


Page 4: Guerilla Security

The Big Picture

• Exchange is an Infrastructure product – ergo: it is only as secure as the infrastructure

• So design of Supporting Infra is critical :• DMZ design• DCs and their configuration• DNS infrastructure• Server Build• Management and Operations

Page 5: Guerilla Security

Internet Security Roots and Mail

• Lets be honest – from a security perspective: IPv4 Sucks – not designed for Security

• Internet used to require Sec clearance to use – physical access was restricted – no need for protocol security

• Resistance to Nuclear attack was more important than protecting traffic as people on the network were trusted

• TCP/IP was thus designed without security in mind – added as a bolt-on- SMTP has almost none

• SMTP takes anonymous un-authenticated messages from the dirty world and puts them into heart of your network

• No one thought mail storage would be mission critical


Page 6: Guerilla Security

Core Security Concepts applied to Exchange• The OS is only one component of security AND

Firewalls are not a Panacea• Getting into the bank branch doesn’t mean you get

into the vault• In the real world security relies on multiple things.

It should also do this in the IT world• People and Process• Internal and Edge Technologies • Management and Operations

• Securing your Exchange system is securing your core systems – there is no silver bullet wizard


Page 7: Guerilla Security

Your Attack Sources for Comms

• Answer: Everyone – inside and out

• The majority of attacks originate internally• Corporate espionage

• People with Inside knowledge

• Your Users playing with stuff they don’t understand

• Externally…could be anyone• “Script kiddies” armed with widely accessible


• More serious attackers– fun or profit

Page 8: Guerilla Security

Exchange Comms Architecture

Front End BackendFirewallPotentialFirewall

Mail Server

Internal Clients

Internal Net

TCP80, TCP443 for Web

TCP80 TCP443 encapsulating RPC

TCP25 for inbound and outbound mail

TCP25 in/outTCP443 InTCP80 In


Too many to list (see slide)



C, G

C, K





Depends on Auth Status


Page 9: Guerilla Security

Internal DMZ Firewall Ports

• TCP 80 for HTTP 143 for IMAP 110 for POP 25 for SMTP • 691 for Link State Algorithm routing protocol • TCP/UDP port 389 for LDAP to Directory Service • TCP port 3268 for LDAP to Global Catalog Server • TCP/UDP port 88 for Kerberos authentication • TCP/UDP port 53 - DNS• TCP port 135 - RPC endpoint mapper • TCP ports 1024+ - RPC service ports (unless DC and

Exchange Restricted)• If you use IPSec between the front-end and back-end,

open the appropriate ports. If the policy you configure only uses AH, you do not need to allow ESP, and vice versa.

• UDP port 500 – • RPC over HTTP can reduce this 600-2 and 593


Page 10: Guerilla Security

Exchange Defence-in-DepthOrchestration • Perimeter Defences: Packet

Filtering, Stateful Inspection of Packets, Intrusion Detection

• Network Defences: VLAN Access Control Lists, Internal Firewall, Auditing, Intrusion Detection

• Host Defences: Server Hardening, Host Intrusion Detection, IPSec Filtering, Auditing

• Application Defences: AV, Content Scanning, Layer 7 (URL) Switching Source, Secure IIS, Secure Exchange

• Data and Resources: ACLs on PFs, Correct mail permissions, Data, Relay Permissions

Data & Resources

Application Defences

Host Defences

Network Defences

Perimeter Defences


me P





Page 11: Guerilla Security

Connection StrategiesMethod Experience Complexity Security

POP3/IMAP4 via SSL with SMTP

Basic Medium/ High


OWA via SSL with ISA

Moderate Low Full

VPN – PPTPv2 Full High Full

Secure RPC with ISA

Full Medium Full

RPC over HTTP Full Medium/Low Full in

None Out

Page 12: Guerilla Security


• Uses SSL to secure POP or IMAP connection

• Does not authenticate at front end

• Requires SMTP at front-end to send mail OR separate SMTP relay (watch for relay spam)

• Removes much of the rich functionality

• Public Folder access can be tricky

• Don’t enable unless you absolutely have to


Page 13: Guerilla Security

OWA via SSL with ISA

• OWA is lightweight and available anywhere• Not totally functional but close• No Offline facility – but great usability

• SSL is an easy and proven security tool• Can be terminated at ISA with Feature Pack• Only used to Front-end server – not FE-BE in 2000 –

2003 can use Kerberos for delegation• Pre-authentication with ISA is very strong


Page 14: Guerilla Security

Protecting HTTPS for OWA

Traditional Traditional firewallfirewall

Traditional Traditional firewallfirewall

OWA OWA OWA OWA clientclientclientclient

Web server prompts for Web server prompts for authentication — any authentication — any

Internet user can access Internet user can access this promptthis prompt


SSL tunnels through SSL tunnels through traditional firewalls traditional firewalls

because it is encrypted…because it is encrypted…

……which allows viruses which allows viruses and worms to pass and worms to pass

through undetected…through undetected…

……and infect internal servers!and infect internal servers!

ISA Server with ISA Server with Feature Pack 1Feature Pack 1ISA Server with ISA Server with Feature Pack 1Feature Pack 1

Basic authentication delegationBasic authentication delegation

ISA Server pre-authenticates ISA Server pre-authenticates users, eliminating multiple users, eliminating multiple

dialog boxes and only allowing dialog boxes and only allowing valid traffic throughvalid traffic through

URLScan for ISA ServerURLScan for ISA Server




ISA Server can ISA Server can decrypt and inspect decrypt and inspect

SSL trafficSSL traffic

inspected traffic can be sent to the internal inspected traffic can be sent to the internal server re-encrypted or in the clear.server re-encrypted or in the clear.

URLScan for URLScan for ISA ServerISA Server

URLScan for ISA Server can stop URLScan for ISA Server can stop Web attacks at the network edge, Web attacks at the network edge,

even over encrypted SSLeven over encrypted SSL



Page 15: Guerilla Security

VPN Inbound

• Dedicated HW/SW VPN infrastructure• Requires opening of ports for VPN and

authentication• Provides Full and Rich Network Access• Can be costly for enterprises to


• RPC over HTTP can reduce need – also secure RPC publishing with ALF


Page 16: Guerilla Security

Using ISA for RPC Publishing

• ISA Can Securely Publish RPC• Opens 135 and listens (can block by source)

• Only Allows Specific UUID for Outlook (configurable)

• Dynamically Port Filters subsequent connections

• Can require Encrypted RPC only

• Outlook can have full functionality without VPN


Page 17: Guerilla Security

RPC server RPC server (Exchange)(Exchange)RPC server RPC server (Exchange)(Exchange)

RPC client RPC client (Outlook)(Outlook)

RPC client RPC client (Outlook)(Outlook)

Service UUID Port

Exchange {12341234-1111… 4402

AD replication {01020304-4444… 3544

MMC {19283746-7777… 9233

RPC services grab random RPC services grab random high ports when they start, high ports when they start,

server maintains tableserver maintains table

RPC – Outlook to ExchangeRPC 101


Client connects to Client connects to portmapper on server portmapper on server

(port 135/tcp)(port 135/tcp)Client knows UUID Client knows UUID of service it wantsof service it wants


Client accesses Client accesses application over application over

learned portlearned port

Client asks, “What Client asks, “What port is associated port is associated with my UUID?”with my UUID?”

Server matches UUID to Server matches UUID to the current port…the current port…


Portmapper responds Portmapper responds with the port and closes with the port and closes

the connectionthe connection


• Due to the random nature of RPC, this is not feasible over the Internet• All 64,512 high ports & port 135 must be opened on

traditional firewalls..

Page 18: Guerilla Security

Securing the Front Side• Exchange 2000 SP2+ doesn’t require RPC for DSAccess from

Front-end to Backend; However….• RPC is still required for IIS authentication (OWA), POP-IMAP

• Exchange DMZ Tradeoff: is it better to• Allow RPC packets from the DMZ inward, or• IPSec Tunnel through Firewall (Bypass it), (no NAT Firewalls)• Allow anonymous requests from the FE to the BE?

Swiss Cheesed orSwiss Cheesed orBypassed FirewallBypassed Firewall


Stateful PacketStateful PacketFiltering FirewallFiltering Firewall

Front End Front End ServerServer



Back End Back End ServerServer

RPC and/or Defined PortRPC and/or Defined PortHTTP (TCP80)HTTP (TCP80)


Page 19: Guerilla Security

Best Practice for the Front Side

• A Flat DMZ Design

• ISA layer 7 switching (OWA) or RPC filtration (Outlook)

• No Firewalls between front-end and backend servers

• Front-end and backend servers authenticate clients

• IPSec if required between front-end and backend

Exchange ServerExchange Server


Stateful PacketStateful PacketFilteringFilteringFirewallFirewall

Application Application Filtering Filtering Firewall (ISA Firewall (ISA Server)Server)

TCP 80: HTTPTCP 80: HTTPInternetInternet



Page 20: Guerilla Security

Is This Less Secure ?

• Same numbers of firewalls to defeat

• RPC or tunnelling can negate firewalls anyway

• Attacks come at Data Layer

• This is a shift in thinking as Firewalls move up the stack and switches start port filtering


Page 21: Guerilla Security

Secure Networking


Redundant Routers

ISA Firewalls



DC + Infrastructure

NIC teams/2 switches





Intrusion Detection Intrusion Detection Intrusion Detection

First Tier Firewalls

URL Filtering for OWARPC Termination for Outlook

Switches Implement VLANs and Control Inter-VLAN Traffic like Firewalls do


Page 22: Guerilla Security

Client Security from Internet

• Every time you connect into a network you extend the security perimeter

• RPC Publishing and VPN both require great care at the client

• Harden your clients on the Internet or hackers will attack clients and ride the VPN

• Require RPC encryption for Outlook• Client Based IDS systems

Page 23: Guerilla Security

General Member Server Hardening

• Role-based Hardening• OU Structure to hold

FE-BE servers by role

• Security Templates from Exchange Security Operations Guide

• AD is a great Security Tool





BaselineDC Policy

BaselineServer Policy

OWA Front-end










Page 24: Guerilla Security

IIS Lockdown Changes

• File ACLs-denies relevant permissions on home directory

• Also sets ACL on (ExchDirectory)\ExchWeb

• Denies execute access to all system utilities, such as cmd.exe, in the c:\winnt\system32 folder.

• Changes by IISLockdown can be overwritten by Group Policy

Page 25: Guerilla Security

Front-end OWA Server Hardening

• Run IISLockdown w/ Template for Exchange; see Q309508 • Removes all unnecessary script mappings Vdirs, and applications

• Disables password change (HTR) – so hide in UI to avoid confusion (Q297121)

• Configure URLScan• Blocks special characters, extensions and canonicalisation .. ./ \ % &

• DSAccess uses RPC to contact Netlogon for authentication• Limit RPC ports on all DC’s & allow this through the internal firewall• Use ISA to securely publish RPC from FE in the DMZ to BE if


• Use MetaEdit to change the SMTP banner• Run EDSLock to lockdown folder and mailbox store group access• Dismount the Mailbox Store and delete the Public Folder Store


Page 26: Guerilla Security

Front-end OWA Server Hardening

• Disable the following Exchange Services• Exchange IMAP4, POP3

• Exchange Information Store

• Microsoft Search

• Exchange Event, Site Replication Service

• Exchange Management, Exchange MTA

• Disable all other unnecessary services – Messenger, Alerter, etc. Network Bindings

Page 27: Guerilla Security

Front End OWA Server Hardening

• Ensure the following are enabled• Exchange Routing Engine

• IPSEC Policy Agent

• RPC Locator

• IIS Admin Service

• World Wide Web Publishing Service

Page 28: Guerilla Security

Backend Server Hardening

• Enabled Exchange Services• Information Store• Exchange Management• Exchange Management Instrumentation • Exchange System Attendant • Exchange Routing Engine

• Disabled Exchange Services• IMAP4• POP• Exchange Event Service (If E2K only)• Exchange Site Replication Service (If E2K only)• Exchange MTA Stacks (If E2K only and no X.400)

Page 29: Guerilla Security

Backend Server Hardening• Exchange Required O/S Services

• WWW Service (OWA comms)• IIS Admin Service (Exchange Routing)• SMTP• RPC Locator (DC comms)• IPSEC Policy Agent

• System Attendant Depends on• Event Log• NTLM Security Support Provider• RPC• RPC Locator• Server• Workstation

Page 30: Guerilla Security

Generic Exchange Server Hardening

• Filesystem ACLs

Directory Old ACL New ACLApplied toSubdirectories?


Everyone: Full Domain Admins: Full Local System: Full



Everyone: Full Domain Admins: Full Local System: Full



Everyone:Full Everyone: Full Yes


Page 31: Guerilla Security

Business Continuity

• Security planning also needs to cover breaches

• Think through disaster recovery strategy

• Backup and Recovery Strategy critical

• Critical Incident Management Procedure

Page 32: Guerilla Security

Physical Server Access

• Physical Infrastructure access must be strictly controlled

• Access to Domain Controllers can cripple networks in seconds

• We often find mission critical machines under desks

Page 33: Guerilla Security

Additional Security Protection

• Antivirus applications are critical to exchange

• SMTP Screening software is becoming increasingly important

• Content Blocking – Appropriate E-mails

Page 34: Guerilla Security

Maintaining Security

• Microsoft Baseline Security Analyzer• V1.2 Scans Exchange and Windows

• Software Update Services – simplified patch management and control – free tool

• Not enterprise focused tools – SMS 2003 is better option

• Use Group Policy to enforce configuration


Page 35: Guerilla Security

Top 10 Ways to Get Secure

1. Implement the Security Operations Guides for Windows and Exchange

2. Use MBSA to identify missing patches

3. Implement IISLockdown based on role

4. Secure Infrastructure Assets

5. Use the EDSLock script to restrict groups


Page 36: Guerilla Security

Top 10 Ways To Get Secure

6. Get adequate antivirus protection for servers and desktops

7. Use perimeter SMTP scanning

8. Automate Patch Management

9. Use SSL, IPsec, and MAPI encryption where appropriate

10.Plan your response to an intrusion before it happens

Page 37: Guerilla Security

Exchange Security Resources

• Exchange Security Operations Guide

• Windows Security Operations Guide

• NSA Security Guides

• Microsoft Systems Architecture – EDC-IDC

• Microsoft Operations Framework


Page 38: Guerilla Security

Other Links

• Exchange 2000 – EDS Lockdown

• Exchange Library

• Exchange Security

Page 39: Guerilla Security

In Closing…

• Thanks for coming!• Feel free to send comments or feedback

[email protected][email protected]

• PLEASE fill out your evaluations!


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© 2003 Microsoft Corporation. All rights reserved.This presentation is for informational purposes only. MICROSOFT MAKES NO WARRANTIES, EXPRESS OR IMPLIED, IN THIS SUMMARY.