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Securing Exchange 2000 Chris Weber Trustworthy Exchanges and the Art.

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1 Securing Exchange 2000 Chris Weber chris.weber@foundstone.com http://www.foundstone.com http://www.privacydefended.com Trustworthy Exchanges and the Art of doing it yourself

2 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Synopsis Focused on single backend Exchange Server with front-end OWA server Hacking Exchange Scanning Scanning Enumerating Enumerating Attacking Attacking The Exchange Application Secure Administration Secure Administration System Policies System Policies Malware Malware OWA OWA Known Vulnerabilities Known Vulnerabilities Other Fundamental Considerations IIS 5.0 IIS 5.0 Windows OS Windows OS Network Network

3 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com What is not covered A lot! Connectors and Replication Connectors and Replication Internet POP3/SMTP clients like Outlook Express Internet POP3/SMTP clients like Outlook Express Backups Backups Monitoring and status notifications Monitoring and status notifications PKI PKI

4 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Security Policy Organizational security policies should be in place to guide daily actions. Never start configuring without having a “management supported” plan in place.

5 Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Secure Network Diagram

6 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Hacking Exchange 2000 Why Hack Exchange? Learn host configuration information Learn host configuration information Learn of hidden Public Folders Learn of hidden Public Folders Glean User account names and email addresses Glean User account names and email addresses Information Gathering Network port scan Network port scan Server enumeration Server enumerationNetBIOSLDAPRPC User and configuration enumeration User and configuration enumeration LDAP with Null session NetBIOS will Null session Pilfering shares Pilfering shares Tracking logs Launching an attack Aiming for admin access Aiming for admin access

7 Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Hacking Exchange 2000 LDAP exposes Users and Public Folders hidden from the Exchange Address Lists

8 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Port Scan 172.16.2.10 995/tcp - POP/SSL 172.16.2.10 1048/tcp 172.16.2.10 1049/tcp 172.16.2.10 1053/tcp 172.16.2.10 1055/tcp 172.16.2.10 1089/tcp 172.16.2.10 1104/tcp 172.16.2.10 1107/tcp 172.16.2.10 1198/tcp 172.16.2.10 1200/tcp 172.16.2.10 1247/tcp 172.16.2.10 1249/tcp 172.16.2.10 3372/tcp 172.16.2.10 3389/tcp - MS Terminal Server 172.16.2.10 4277/tcp Scan finished at Fri Feb 22 00:55:48 2002 Scan finished at Fri Feb 22 00:55:48 2002 Time taken: 65535 ports in 318.138 secs (206.00 ports/sec) Time taken: 65535 ports in 318.138 secs (206.00 ports/sec) D:\tools>fscan -p 1-65535 -z 128 exchange FScan v1.12 - Command line port scanner. Copyright 2000 (c) by Foundstone, Inc. http://www.foundstone.com Scan started at Fri Feb 22 00:50:30 2002 Scan started at Fri Feb 22 00:50:30 2002 172.16.2.10 25/tcp - SMTP 172.16.2.10 80/tcp - HTTP 172.16.2.10 119/tcp - NNTP 172.16.2.10 135/tcp - RPC/DCE endpoint mapper 172.16.2.10 139/tcp - NetBIOS session service service 172.16.2.10 143/tcp - IMAP 172.16.2.10 443/tcp - HTTPS 172.16.2.10 445/tcp - Microsoft SMB/CIFS 172.16.2.10 563/tcp - NNTP/SSL 172.16.2.10 593/tcp - HTTP RPC endpoint mapper mapper 172.16.2.10 691/tcp - SMTP/LSA 172.16.2.10 993/tcp XGEN: TCP/UDP Ports Used By Exchange 2000 Server (Q278339)

9 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Port and Process Mappings Useful tools: FPORT.EXE (from www.foundstone.com) FPORT.EXE (from www.foundstone.com)www.foundstone.com TLIST.EXE /S (from Windows 2000 installation CD \Support directory) TLIST.EXE /S (from Windows 2000 installation CD \Support directory)

10 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com fport.exe FPort v1.31 - TCP/IP Process to Port Mapper Copyright 2000 by Foundstone, Inc. http://www.foundstone.com Securing the dot com world Pid Process Port Proto Path 1028 inetinfo -> 25 TCP C:\WINNT\System32\inetsrv\inetinfo.exe 1028 inetinfo -> 80 TCP C:\WINNT\System32\inetsrv\inetinfo.exe 1028 inetinfo -> 110 TCP C:\WINNT\System32\inetsrv\inetinfo.exe 1028 inetinfo -> 119 TCP C:\WINNT\System32\inetsrv\inetinfo.exe 512 svchost -> 135 TCP C:\WINNT\system32\svchost.exe 8 System -> 139 TCP 1028 inetinfo -> 143 TCP C:\WINNT\System32\inetsrv\inetinfo.exe 1028 inetinfo -> 443 TCP C:\WINNT\System32\inetsrv\inetinfo.exe 8 System -> 445 TCP 1028 inetinfo -> 563 TCP C:\WINNT\System32\inetsrv\inetinfo.exe 512 svchost -> 593 TCP C:\WINNT\system32\svchost.exe 1028 inetinfo -> 691 TCP C:\WINNT\System32\inetsrv\inetinfo.exe 1028 inetinfo -> 993 TCP C:\WINNT\System32\inetsrv\inetinfo.exe 1028 inetinfo -> 995 TCP C:\WINNT\System32\inetsrv\inetinfo.exe 264 lsass -> 1032 TCP C:\WINNT\system32\lsass.exe 264 lsass -> 1033 TCP C:\WINNT\system32\lsass.exe 600 msdtc -> 1048 TCP C:\WINNT\System32\msdtc.exe 860 MSTask -> 1049 TCP C:\WINNT\system32\MSTask.exe 1044 mad -> 1053 TCP C:\Program Files\Exchsrvr\bin\mad.exe 1044 mad -> 1055 TCP C:\Program Files\Exchsrvr\bin\mad.exe

11 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com tlist.exe /s 0 System Process 0 System Process 8 System 8 System 172 SMSS.EXE 172 SMSS.EXE 200 CSRSS.EXE 200 CSRSS.EXE 224 WINLOGON.EXE 224 WINLOGON.EXE 252 SERVICES.EXE Svcs: Alerter,Browser,Dhcp,dmserver,Dnscache,Eventlog,lanmanserver,lanmanworkstation,LmHosts,Messenger,PlugPlay,ProtectedS torage,seclogon,TrkWks,W32Time,Wmi 252 SERVICES.EXE Svcs: Alerter,Browser,Dhcp,dmserver,Dnscache,Eventlog,lanmanserver,lanmanworkstation,LmHosts,Messenger,PlugPlay,ProtectedS torage,seclogon,TrkWks,W32Time,Wmi 264 LSASS.EXE Svcs: Netlogon,NtLmSsp,PolicyAgent,SamSs 264 LSASS.EXE Svcs: Netlogon,NtLmSsp,PolicyAgent,SamSs 368 termsrv.exe Svcs: TermService 368 termsrv.exe Svcs: TermService 512 svchost.exe Svcs: RpcSs 512 svchost.exe Svcs: RpcSs 540 SPOOLSV.EXE Svcs: Spooler 540 SPOOLSV.EXE Svcs: Spooler 600 msdtc.exe Svcs: MSDTC 600 msdtc.exe Svcs: MSDTC 748 svchost.exe Svcs: EventSystem,Netman,NtmsSvc,SENS 748 svchost.exe Svcs: EventSystem,Netman,NtmsSvc,SENS 764 LLSSRV.EXE Svcs: LicenseService 764 LLSSRV.EXE Svcs: LicenseService 808 regsvc.exe Svcs: RemoteRegistry 808 regsvc.exe Svcs: RemoteRegistry 840 LOCATOR.EXE Svcs: RpcLocator 840 LOCATOR.EXE Svcs: RpcLocator 860 mstask.exe Svcs: Schedule 860 mstask.exe Svcs: Schedule 944 WinMgmt.exe Svcs: WinMgmt 944 WinMgmt.exe Svcs: WinMgmt 1000 dfssvc.exe Svcs: Dfs 1028 inetinfo.exe Svcs: IISADMIN,IMAP4Svc,NntpSvc,POP3Svc,RESvc,SMTPSVC,W3SVC 1044 MAD.EXE Svcs: MSExchangeSA 1076 mssearch.exe Svcs: MSSEARCH 1524 STORE.EXE Svcs: MSExchangeIS 1556 EMSMTA.EXE Svcs: MSExchangeMTA 2360 CSRSS.EXE Title: 2384 WINLOGON.EXE Title: NetDDE Agent 2464 rdpclip.exe Title: CB Monitor Window 2508 explorer.exe Title: Program Manager 2560 mshta.exe Title: Windows 2000 Configure Your Server 2580 svchost.exe Svcs: TapiSrv 2652 mdm.exe Title: OleMainThreadWndName 2736 CMD.EXE Title: C:\WINNT\System32\cmd.exe - tlist /s 976 notepad.exe Title: fport - Notepad 976 notepad.exe Title: fport - Notepad 768 TLIST.EXE 768 TLIST.EXE

12 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Exchange 2000 SMTP relay disabled Rights to the Mailbox Admin is DENIED access to mailboxes (by default), but easily changed Admin is DENIED access to mailboxes (by default), but easily changed “Exchange Domain Servers” group full access “Exchange Domain Servers” group full access %COMPUTERNAME%$ full access %COMPUTERNAME%$ full access No more Service Account Your LSA Secrets are safe… Your LSA Secrets are safe… Some Security related changes from 5.5 to 2000

13 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Security Checklist: http://www.microsoft.com/technet/treeview/defau lt.asp?url=/technet/security/tools/w2ksvrcl.asp Disable unnecessary services and ports Disable unnecessary services and ports Enable Auditing Enable Auditing Rename local Admin account and enable a strong password Rename local Admin account and enable a strong password ACL and monitor critical Registry keys ACL and monitor critical Registry keys Watch event logs for failed login attempts Exchange 2000 Secure Administration – Lock it down

14 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Exchange 2000 Administrative Roles Exchange Administrator Exchange Administrator Exchange Full Administrator Exchange Full Administrator Exchange View Only Administrator Exchange View Only Administrator XADM: How to Get Service Account Access to All Mailboxes in Exchange 2000 (Q262054) http://support.microsoft.com/default.aspx?scid=kb;en- us;Q262054 XADM: How to Get Service Account Access to All Mailboxes in Exchange 2000 (Q262054) http://support.microsoft.com/default.aspx?scid=kb;en- us;Q262054 Delegation Wizard Use to add/edit Admin roles Use to add/edit Admin roles Secure Administration - Roles

15 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Exchange 2000 XADM: Enhancing the Security of Exchange 2000 for the Exchange Domain Servers Group (Q313807) The All-Powerful Exchange Domain Servers Group

16 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Registry Hack To show the security tab in System Manager To show the security tab in System ManagerHKCU\Software\Microsoft\Exchange\ExAdmin Value: ShowSecurityPage Date: 1 (REG_DWORD) XADM: Security Tab Not Available on All Objects in System Manager (Q259221) XADM: Security Tab Not Available on All Objects in System Manager (Q259221) Exchange 2000 Secure Administration – Security Permissions Page

17 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Exchange 2000 Security of Shares Tracking Logs: %COMPUTERNAME%.log Contain user information such as email addresses and usernames. Tracking Logs: %COMPUTERNAME%.log Contain user information such as email addresses and usernames. EVERYONE or Authenticated Users can read by default EVERYONE or Authenticated Users can read by default Securing File Shares

18 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Disable unnecessary services and protocols For both Exchange and Windows For both Exchange and Windows Do you need POP3? IMAP? HTTP? Do you need POP3? IMAP? HTTP? Do you need the Alerter service? Messenger? DHCP client? Do you need the Alerter service? Messenger? DHCP client? Exchange 2000 Secure Administration - TURN OFF WHAT YOU DON’T NEED

19 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Exchange 2000 System Policies Server policy Server policy Mailbox policy Mailbox policy Public Folder policy Public Folder policy System Policies

20 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Use SMTP content filter for Internet email Use a separate host or a firewall for SMTP relay Use a separate host or a firewall for SMTP relay Catch incoming/outgoing malware elsewhere, and relieve your Exchange server of the load Catch incoming/outgoing malware elsewhere, and relieve your Exchange server of the load Virus protection in the Information Store Well, some viruses originate within, so you still need protection. Well, some viruses originate within, so you still need protection. Several server based virus scanners will protect (i.e. MailSecurity by GFI, Trend Micro, Sybari Antigen, NAI GroupShield) Several server based virus scanners will protect (i.e. MailSecurity by GFI, Trend Micro, Sybari Antigen, NAI GroupShield) Virus protection on the client Exchange 2000 Malware - Virus, trojan and worm protection

21 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Exchange and Outlook Prevent scripts and Active content from running on your user’s workstations Set the Security Zone in Outlook to “Restricted Sites” – under Tools > Options > Security Set the Security Zone in Outlook to “Restricted Sites” – under Tools > Options > Security Keep up-to-date with latest MS Outlook and Internet Explorer patches and security hotfixes Malware – Protection in Outlook

22 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Outlook Web Access General OWA security Lock down IIS Lock down IIS Security checklists http://www.microsoft.com/technet/treeview/default.asp?u rl=/technet/security/tools/tools.asp http://www.microsoft.com/technet/treeview/default.asp?u rl=/technet/security/tools/tools.asp http://www.microsoft.com/technet/treeview/default.asp?u rl=/technet/security/tools/tools.aspIISLock.exe Definitely use SSL Definitely use SSL Decide on Front-end vs. Back-end model Must read: http://www.microsoft.com/Exchange/techinfo/deployment/2000/E2 KFrontBack.asp Decide on Front-end vs. Back-end model Must read: http://www.microsoft.com/Exchange/techinfo/deployment/2000/E2 KFrontBack.asp http://www.microsoft.com/Exchange/techinfo/deployment/2000/E2 KFrontBack.asp http://www.microsoft.com/Exchange/techinfo/deployment/2000/E2 KFrontBack.asp Front-End server Isolate it even in the DMZ (it should only communicate with the Exchange BE server and an AD DC) Intranet Firewall between Front End and Back End Intranet Firewall between Front End and Back End Use STATIC RPC ports: http://support.microsoft.com/support/kb/articles/q224/1/96.asp Use STATIC RPC ports: http://support.microsoft.com/support/kb/articles/q224/1/96.asp http://support.microsoft.com/support/kb/articles/q224/1/96.asp Installation and Design Considerations

23 Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Secure Network Diagram

24 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Firewalls Internet firewall DENY ALL incoming and outgoing DENY ALL incoming and outgoing Allow only what you need! For example: Allow only what you need! For example: Incoming from Internet Allow: TCP port 443 (HTTPS) TCP port 25 (SMTP) TCP/UDP port 53 (DNS) Outgoing Allow: Only established connectionsIntranet Assign static RPC ports to the Exchange Server Assign static RPC ports to the Exchange Server DMZ firewall DENY ALL incoming and outgoin Allow only what you need! For example: Incoming from DMZ Allow: TCP port 80 (HTTP) TCP/UDP port 88 (Kerberos) TCP/UDP port 53 TCP/UDP port 389 (LDAP) TCP port 3268 (GC) TCP port 135 (endpoing mapper) TCP port 1025 (optional RPC static port) TCP port 445 (SMB/CIFS) Outgoing Allow: Only established connections DENY everything. Only allow what you need!

25 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Exchange 2000 Vulnerabilities * February 2002 * MS02-003 : Exchange 2000 System Attendant Incorrectly Sets Remote Registry Permissions http://archives.neohapsis.com/archives/vendor/2002-q1/0023.html MS02-003 : Exchange 2000 System Attendant Incorrectly Sets Remote Registry Permissions MS02-003 : Exchange 2000 System Attendant Incorrectly Sets Remote Registry Permissions September 2001 MS01-049 : Deeply-nested OWA Request Can Consume Server CPU Availability MS01-049 : Deeply-nested OWA Request Can Consume Server CPU Availability MS01-049 : Deeply-nested OWA Request Can Consume Server CPU Availability August 2001 MS01-043 : NNTP Service in Windows NT 4.0 and Windows 2000 Contains Memory Leak MS01-043 : NNTP Service in Windows NT 4.0 and Windows 2000 Contains Memory Leak MS01-043 : NNTP Service in Windows NT 4.0 and Windows 2000 Contains Memory Leak July 2001 MS01-041 : Malformed RPC Request Can Cause Service Failure MS01-041 : Malformed RPC Request Can Cause Service Failure MS01-041 : Malformed RPC Request Can Cause Service Failure June 2001 MS01-030 : Incorrect Attachment Handling in Exchange OWA Can Execute Script MS01-030 : Incorrect Attachment Handling in Exchange OWA Can Execute Script MS01-030 : Incorrect Attachment Handling in Exchange OWA Can Execute Script March 2001 MS01-014 : Malformed URL Can Cause Service Failure in IIS 5.0 and Exchange 2000 MS01-014 : Malformed URL Can Cause Service Failure in IIS 5.0 and Exchange 2000 MS01-014 : Malformed URL Can Cause Service Failure in IIS 5.0 and Exchange 2000 November 2000 MS00-088 : Exchange User Account Vulnerability MS00-088 : Exchange User Account Vulnerability MS00-088 : Exchange User Account Vulnerability

26 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com The Windows OS Security is a pyramid Exchange security depends on the OS security Follow checklists and best practices available from www.microsoft.com/security as well as many third parties like SANS (www.sans.org) Follow checklists and best practices available from www.microsoft.com/security as well as many third parties like SANS (www.sans.org) www.microsoft.com/securitywww.sans.org www.microsoft.com/securitywww.sans.org Ensure new OS and Exchange installs are hardened before placed into production Ensure new OS and Exchange installs are hardened before placed into production Don’t let unnecessary services and software run! Don’t let unnecessary services and software run! Keep up-to-date on latest MS Service Packs and security hotfixes Keep up-to-date on latest MS Service Packs and security hotfixes The FOUNDATION of Exchange

27 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com Exchange 2000 SMTP replication in clear text!!! Use IPSec with encryption parameters to protect this traffic Use IPSec with encryption parameters to protect this traffic Public Folders EVERYONE group can add new folders by default EVERYONE group can add new folders by default Event Sinks XCCC: Script Host Sink Is Not Registered on Exchange 2000 Server by Default (Q264995) XCCC: Script Host Sink Is Not Registered on Exchange 2000 Server by Default (Q264995) http://www.outlookexchange.com/articles/glenscales/ wssevtar.asp by Glen Scales http://www.outlookexchange.com/articles/glenscales/ wssevtar.asp by Glen Scales http://www.outlookexchange.com/articles/glenscales/ wssevtar.asp http://www.outlookexchange.com/articles/glenscales/ wssevtar.asp Additional Thoughts

28 Ask a Question Now! Click on the left portion of your screen. Securing Microsoft Exchange 2000 Chris.Weber@Foundstone.com References Exchange http://www.microsoft.com/exchange http://www.microsoft.com/security http://www.slipstick.com http://www.msexchange.org http://www.labmice.net IPSec http://www.securityfocus.com/infocus/1519

29 The End Securing Exchange 2000 Chris Weber chris.weber@foundstone.com http://www.foundstone.com http://www.privacydefended.com Ask a Question Now!

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