Cisco Security. Deployment and Troubleshooting. Raymond Jett Technical Marketing Engineer, Cisco Content Security.

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1 Cisco Security Deployment and Troubleshooting Raymond Jett Technical Marketing Engineer, Cisco Content Security Cisco Secure

2 Agenda Security Deployment Devices Deployment Methods Virtual Requirements Advanced Topics Troubleshooting Basics Virtual Machines Tailing Logs Message Flows Engines 2

3 Agenda Security Deployment Devices Deployment Methods Virtual Requirements Advanced Topics Troubleshooting Basics Virtual Machines Tailing Logs Message Flows Engines 3

4 Devices Covered This presentation will cover currently sold and supported Security Appliances: Cx00 Virtual Appliances C/Mx80 Series Appliances C170 Appliance C/Mx70 Series (End of Sale) C/Mx60 Series (End of Sale) 4

5 Traffic Flow Considerations is simple. We want to be the: First hop in Last hop out There are many ways to install Security products, some better than others Traffic flow and installation connectivity will depend on your security policy needs Turn SNMP Inspection OFF on your firewalls 5

6 Ports and Protocols Typically Used Between the ESA and the Internet Inbound from Internet: TCP 25: SMTP Outbound to Internet: TCP 25: SMTP TCP 80: HTTP UDP 123: NTP TCP 443: TLS/HTTPS Internet Mail Server The complete list can be found in the ESA Configuration Guide, Appendix C 6

7 Ports and Protocols Typically Used Between the ESA and the Internal Network Inbound from internal network: TCP 22: SSH TCP 25: SMTP UDP 161: SNMP TCP 443: HTTPS Outbound to internal network: TCP 25: SMTP TCP 80: HTTP UDP 162 SNMP TCP 389: LDAP TCP/UDP 514: Syslog Internet Mail Server The complete list can be found in the ESA Configuration Guide, Appendix C 7

8 Support Tunnels Beware of Firewall Issues Support Tunnels allow TAC to connect and remotely fix issues and can be used over: TCP 22: SSH TCP 25: SMTP TCP 53: DNS TCP 80: HTTP TCP 443: HTTPS The firewall must have the desired port open AND allow for SSH to be tunneled over it. Deep inspection on non-ssh ports could block the tunnel Internet Mail Server The complete list can be found in the ESA Configuration Guide, Appendix C 8

9 ESA Installation Types There are multiple ways to configure the ESA on a network. Each has their pros and cons. Security Nightmare No protection for the inside network or outside interfaces The ESA is hardened, but this is a DO NOT DO scenario Internet Outside Inside Mail Server 9

10 ESA Installation Parallel to the Firewall Easy to Configure Security Nightmare No protection for the inside network or outside interfaces The ESA is hardened, but this is a DO NOT DO scenario Internet Outside Inside Mail Server 10

11 ESA Installation Protected Private Interface Easy to Configure Still a Security Nightmare No protection for the outside interface Internet Outside The ESA is hardened, but this is a DO NOT DO scenario Inside Mail Server 11

12 ESA Installation Protected Public Interface Public interface protected by firewall Can filter inbound and outbound related traffic No inside interface filtering Works well in smaller accounts Unprotected inside interface can cause heartburn with security teams Internet Outside Inside Mail Server 12

13 ESA Installation Single Interface System protected by firewall Simplifies firewall configuration for passing related traffic No specific routes required on the ESA. Minimizes network troubleshooting Single interface represents a possible single point of failure or bottleneck Preferred and THE most common method of installation by customers Internet Mail Server 13

14 ESA Installation Dual DMZ Interfaces Inside and outside interfaces protected by firewall Can fully filter and control inbound and outbound related traffic Offers protection of all resources Firewall represents a possible single point of failure or bottleneck Static routes required on the ESA Internet Outside Inside Mail Server 14

15 ESA Installation Large DMZ with Dual Firewalls System is well protected Allows for maximum control and isolation of traffic flowing in the DMZ Static routes required on the ESA Configure redundant firewalls for maximum uptime and to reduce single points of failure Internet Outside Inside Mail Server 15

16 ESA Installation Separate Management Network Meets the most stringent customer connectivity needs Requires a larger appliance with 3 interfaces Can be done in a multi-firewall DMZ or with a single interface installation Use the route command via CLI to configure traffic flows for the extra interfaces Internet Outside Inside Mail Server Management Network Link 16

17 ESA Installation High Availability Internet Use larger appliances with RAID arrays and redundant power supplies Configure NIC Teaming to help protect against network failures L4-7 Switch Cluster the Security Appliances Use multiple security Appliances and MX records Devices can be load balanced with VIPs on a L4-7 switch Mail Server 17

18 ESA Redundancy MX Records The easiest and most common way to do redundancy Relies on the robust nature of communications on the internet If one server cannot be contacted, fail over to the next on the list Internet west.mail.company.com east.mail.company.com West Coast Mail Server East Coast Mail Server 18

19 ESA Redundancy Clustering Appliances The easiest and most common way to do redundancy Relies on the robust nature of communications on the internet If one server cannot be contacted, fail over to the next on the list Ensure the ESAs can communicate with each other and the SMA Internet West Coast Mail Server East Coast Mail Server 19

20 Virtual Architecture Currently supported on Vmware ESX/ESXi only. KVM, Hyper-V, and Xen are being investigated for future support TAC Supported on Cisco UCS hardware TAC will support ESAV running on 3 rd party hardware, but not provide support for the 3 rd party hardware platform. Cisco UCS Consolidation Automation Virtualization Other Hardware 20

21 Virtual Architecture Hardware Specifications Performance can vary greatly depending on system hardware CPU cores/speed, RAID configurations, memory bandwidth, IO bandwidth CPU and memory are not to be oversubscribed Performance testing was done on the following hardware UCS 5108 chassis with UCSB-B200-M3 blades Intel Xeon E5-2640: 6 cores, 2.5GHz clock, 15MB Cache, 1333MHz RAM speed Disks were configured at a RAID 5 level If you build your systems to meet or exceed this configuration you will have similar performance to our performance metrics Your Cisco or partner account teams can help you with sizing your solution 21

22 Virtual Architecture Separate Management Network, Consolidated Data Center Less rack space needed Lower power requirements Internet ESAv Mail Server VM Lower cooling costs Outside UCS Virtual Management Network Networks are securely separated Inside 22

23 Virtual Architecture Redundant Data Centers Migrate machines in event of a failure Internet ESAv Mail Server ESAv Mail Server Easily add additional VMs for extra mail capacity handling UCS1 UCS 2 Virtual Management Network 23

24 Advanced Topics Outbreak Filters Outbreak Filters is designed to catch day zero viral attacks and blended targeted attack messages. Detects approx. 20 different categories of threats Holds messages then releases for rescanning by the IPAS engine Can mark up message subjects to draw attention to problems Rewrite URLs to redirect to a proxy backended by our CWS product Optionally prepend a warning message to the body of the a Think before you click 24

25 Outbreak Filters Enabling Globally Enable Outbreak Filters Globally. You may need to accept the EULA. Adaptive Rules are for the Viral component Be cautious when raising the Maximum Message Size to Scan. Increment the size slowly and monitor ESA performance 25

26 Outbreak Filters Enabling Per Incoming Mail Policy Enable Outbreak Filters for each Incoming Mail Policy. The viral component is easy, but the targeted threat component is not on by default The Quarantine Threat Level is for the viral component The Other Threats is the timer for the targeted threat component 26

27 Configuring Outbreak Filters Enable Message Modification and URL Rewriting MUST be set for the targeted threat components to be active Threat Level default is 3. Raising it to a 2 or 1 makes it more aggressive in identifying threats False positives are OK with this feature as messages not caught by IPAS rule updates after quarntine timer expiration are delivered to the end user with the appropriate mark ups and changes 27

28 Advanced Topics URL Reputation and Filtering Included in the Outbreak Filters policy and introduced in AsyncOS 8.5.x; Outbreak Filters and IPAS use web reputation components to target more spam Enable URL filtering globally to enable it in IPAS and Outbreak Filters automatically. Whitelist can be created to bypass scanning for specific domains at a global level 28

29 Configuring URL Category Filtering URL Category Condition Introduced in 8.5.x, this new Content Filter Condition lets you filter URLs by category Enforce Acceptable Use Policies for the web on incoming Any action available in Content Filters can be taken on the messages: Drop, Quarantine, BCC, etc. A whitelist can be used to bypass specific URLs at this level 29

30 Configuring URL Category Action Actions to Take on URLs A new Content Filter Action lets you take specific actions on URLs by category: Defang, Redirect to the Cisco Security Proxy, or Replace the URL with a text message for users. These actions can be performed on all messages or unsigned to keep from breaking message signatures A whitelist can be used to bypass specific URLs at this level 30

31 Filtering URLs by Reputation Introduced in 8.5.x, this new Content Filter Condition lets you take specific actions on URLs by raw URL reputation scoring: If you wish to broaden the Malicious category using a Custom Range, do so slowly and deliver the messages to a quarantine until you are satisfied with the results. A whitelist can be used to bypass specific URLs at this level Any CF Action can be taken based on URL Reputation Conditions 31

32 Filtering URLs by Reputation Actions to Take on Reputation Introduced in 8.5.x, this new Content Filter Action lets you take specific actions on URLs by raw URL reputation scoring: Defang, Redirect, or Replace the URL with a text message Replicate any Custom Range from CF Conditions here A whitelist can be used to bypass specific URLs at this level 32

33 Advanced Topics DKIM DomainKeys Identified Mail In a nutshell: senders sign outgoing messages which recipients can verify Helps avoid spoofing of messages Transparent: Does not affect receiving of messages if not used by recipients Public keys published by sender in DNS Keys checked upon receipt, configure in Mail Flow Policies Use Content Filters to control messages based on results 33

34 DKIM DomainKeys Identified Mail DKIM Verification includes: Pass: This message was signed by DKIM. These should be delivered Neutral: The message was not signed by DKIM. These should be delivered TempError: There was a temporary error during DNS lookups. These should be delivered PermError: An unrecoverable error occurred during verification. These should be delivered HardFail: The signature is not vaild for this message. These should be quarantined or dropped None: Verification was not tempted as the MFP for the message has DKIM Verification disabled 34

35 Advanced Topics SPF Sender Policy Framework Senders publish a list of systems used for sending Helps avoid spoofing of messages Transparent: Does not affect receiving of messages if not used by recipients List is published by sender in DNS Ends with?all, ~all, or -all IP/hostnames checked upon receipt of message. Configure in Mail Flow Policies Use Content Filters to control messages based on results 35

36 SPF Sender Policy Framework SPF Verification includes: None: The domain does not have an SPF record. These should be delivered Pass: The IP address of the sender is included in the SPF record. These should be delivered Neutral: The IP address of the sender matches a host mechanism with the? prefix. These should be delivered SoftFail: The IP address of the sender is not listed in the SPF record. Because of the ~all at the end of the record, you shouldn t drop these but you may want to quarantine or mark up before delivery. Fail: The IP address of the sender is not listed in the SPF record. These should be quarantined or dropped TempError: There was a temporary error during DNS lookups. These should be delivered PermError: An unrecoverable error occurred during verification. These should be delivered 36

37 Shortcomings SPF and DKIM There are shortcomings with DKIM and SPF that made it difficult to implement You must decide what to do with messages that fail checks Do you know all the systems you have that send ? What about third parties sending on your behalf? Targeted messages from cousin domains could be signed No feedback from recipients on message disposition 37

38 DMARC Domain-Based Message Authentication, Reporting & Conformance DMARC addresses many of the shortcomings with DKIM and SPF Senders publish DKIM records in DNS telling recipients how to process messages purported to come from them Recipients can automatically send reports to the senders By tying DKIM and SPF together, DMARC has gained rapid acceptance by financial, e-commerce, and other business segments plagued by spoofed s Only one test (DKIM or SPF) needs to pass for DMARC checks to pass 38

39 Configuring DMARC Enable DKIM and SPF Verification in each Mail Flow Policy no need to create the Content Filters Global settings such as bypassing verification for s with specific headers must be configured. Additional contact information mailbox should not be a real user. These are being harvested by spammers. 39

40 DMARC Domain-Based Message Authentication, Reporting & Conformance Different DMARC Verification Profiles can be configured for each Mail Flow Policy Set the Message Action for Reject to reject the message and give a 550 message back to the sender Choose the quarantine to place quarantined messages in TempFail and PermFail messages should be accepted. 40

41 Sending Messages Using DKIM, SPF, and DMARC Is beyond the scope for this presentation, but it requires configuration on and off of the ESA: Creating DKIM, SPF, and DMARC records in DNS Creating DKIM signing keys and Domain Signing Profiles on the ESA Enable DKIM Signing on the RELAYED MFP 41

42 Use Caution When Creating Your SPF Record Do not use the all unless you know ALL of the senders sending on your behalf. Amazon.com uses the all. When is the last time you saw spoofed on that domain? Allow third parties to relay through a set of ESAs from specific IP addresses. Cisco IT does this. You are limited to 10 recursions when doing SPF record queries Do not use hostnames. Use IP addresses and save FQDNs for includes Keep your record <512 bytes in size You re using DNS queries. When you pass 512 bytes it s a TCP connection instead of UDP and many networks filter TCP 53 42

43 Additional Resources For DKIM, SPF, and DMARC Check an SPF record: More information on DKIM: Check a DMARC record: 43

44 Agenda Security Deployment Devices Deployment Methods Virtual Requirements Advanced Topics Troubleshooting Virtual Machines Basics Tailing Logs Message Flows Engines 44

45 Troubleshooting Virtual machine considerations Licensing Cloning Mixed Clusters with HW Appliances All Systems: Testing Communications Using mail_logs 45

46 Licensing Virtual Machines are licensed differently than hardware devices Licensed by VLN ID Use showlicense CLI command to get the VLN ID License is loaded via the CLI using the loadlicense command o FTP the license to the appliance OR paste the file data into the terminal program 46

47 Licensing Malformed License Error The default program for opening XML on Windows is Internet Explorer. When copying the license from IE and pasting into the ESAV, you will receive an error: Malformed License: Invalid XML, could not parse Don t open the file with IE. Use a text editor such as Wordpad Example of opening a license file with IE 47

48 Cloning Virtual Machines Cloning the ESAV should be done before you deploy it. Cloning a configured system will forcefully expire any licenses on the new machine Additional steps are required if cloning a configured system: Licenses must be reinstalled Messages in queues must be delivered first or cleared before cloning Network settings must be changed Quarantines must be cleared Message Tracking and reporting data must be deleted UCS 48

49 Mixed Clusters Virtual and Hardware Appliances Virtual ESA uses a different manifest server than the hardware appliances ESAV: update-manifests.sco.cisco.com:443 ESA: update-manifests.ironport.com:443 If you are joining virtual appliances with physical appliances in the same cluster this setting will be overwritten on the virtual appliances If mixing clusters you can: Create a Group Level configuration for the virtual appliances update setting Use Machine Level update settings to have the correct Dynamic Host settings for the virtual appliances 49

50 Testing Communications The Basics From the CLI, use ping to test communications on then off the subnet. If you can ping the default gateway try to ping a system on the internet or the internal network Internet If pinging to these networks fail check your firewall rules and route rules for traffic If pinging by hostname fails, check DNS Mail Server 50

51 Testing Communications The Basics From the CLI, use nslookup to test DNS If you cannot connect on port 53 check your DNS and/or firewall rules Use a domain name and choose the type of query to do. For querying MX records for a domain, choose query type 4 51

52 Testing Communications The Basics From the CLI, use telnet to test communications off the subnet to ensure port 80 is open. Internet If you cannot connect on port 80 check your firewall rules If a proxy is required, set it on the ESA: UI under Security Services > Service Updates CLI using updateconfig Mail Server 52

53 Testing Communications The Basics From the CLI, use telnet to test communications off the subnet to ensure port 25 is open to the internet and to your internal server. Use standard SMTP commands to manually send a message: helo mail from: rcpt to: data End the message with a period on a blank line then use the SMTP command quit to end the session 53

54 Testing Communications LDAP From the CLI, use telnet to test communications off the subnet to ensure port 389 is open to your internal LDAP server. If you are having problems with queries try the free Softerra LDAP Browser m?download=browser 54

55 Tailing Logs Using mail_logs From the CLI, use tail mail_logs to watch what is happening when you send test messages through the ESA This command will display the tail of any log you choose. use the tail command by itself and the system will list the 27 logs available 55

56 Searching Logs Using findevent From the CLI, use findevent to search logs for specific messages 56

57 Searching Logs Using grep From the CLI, use grep to search logs for specific messages If you don t know the log name, use grep without any parameters to use it interactively 57

58 Troubleshooting Mail Delivery RAT Entries and SMTP Routes If your mail_logs show problems delivering mail to the correct location, ensure you have an SMTP Route for each RAT entry. The RAT entries signify I accept incoming for these domains and the SMTP Route tells the ESA where to deliver that mail. 58

59 Troubleshooting Message Flows TLS Messages Use the tlsverify CLI command to verify against a domain to ensure TLS is working properly 59

60 Troubleshooting Message Flows What s in Queue? Use the showrecipients CLI command to see what is currently in queue or the Delivery Status report on the UI to see if messages are still in the queue 60

61 Troubleshooting Message Flows Anti-Spam Scanning Did a spam get through? How do you determine the cause? Examine the headers in your client and look for the IPAS header: X-IronPort-Anti-Spam-Filtered: true The X-IronPort-Anti-Spam-Result header value is valuable to TAC for investigation 61

62 Troubleshooting Message Flows Anti-Spam Scanning Look in Message Tracking for: Sender Group per-recipient policy CASE verdicts Outbreak Filters verdict Are any of the items missing? 62

63 Troubleshooting Message Flows Sender Groups Sender Groups are important in tracking down sources of spam as they can be set to bypass anti-spam scanning An example of this is the TRUSTED Mail Flow Policy used by the WHITELIST Sender Group 63

64 Marketing Message Detection When Spam is Not Spam A large number of end-user spam complaints come from aggressive marketers who use Opt-Out messaging techniques. Their messages conform to Can-SPAM and other legal requirements. Marketing Message Detection is off by default. Turn it on to address these messages Options are Deliver, Drop, Spam Quarantine, or Bounce 64

65 Is IPAS Updating Properly? The Anti-Spam engine in the ESA regularly communicates and checks for updates to the engines, databases, and rules. This can be checked under Security Services > IronPort Anti-Spam Click Update Now, or use the CLI command antispamupdate ironport force You can run the tail updater_logs CLI command to watch for errors in updating 65

66 Is Anti-Virus Updating Properly? Similar to Anti-Spam, the Anti-Virus engine in the ESA regularly communicates and checks for updates to the engines, databases, and rules. This can be checked under Security Services > Sophos or Security Services > McAfee Click Update Now, or use the CLI command antivirusupdate force You can run the tail updater_logs CLI command to watch for errors in updating 66

67 One Last Item Submitting Missed Spam Missed spam must be submitted in the proper format for us to be able to process it. Send as an RFC 822 compliant attachment Spam: Phish: Non-Spam: Marketing: Use our free Outlook or Lotus Notes plug-in to make reporting easier For Thunderbird use the 3 rd party MailSentry IronPort Spam Reporter 1.4 or newer 67

68 Resources White Papers: Catch More Spam: Fine-Tune Your Security Appliance Higher Education: Combining Features for Defense Outbreak Filters: Software: Security Plug-in for Outlook (7.3.x) and Lotus Notes (7.1.x) Security Products: and 68

69 Questions? 69

70 70

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