300-720 Questions and Answers

Relay is the connection behavior that must be selected to properly process the messages. Relay allows Cisco ESA to accept messages from the specified source and deliver them to the intended destination, without applying any content or reputation filters.

To configure a mail flow policy with relay connection behavior on Cisco ESA, the administrator can follow these steps:

• Select Mail Policies > Mail Flow Policies and click Add Policy.
• Enter a name and description for the mail flow policy, such as Exchange Outbound.
• Under Connection Behavior, select Relay.
• Click Submit.

The other options are not valid connection behaviors to properly process the messages, because they either reject, delay, or accept the messages with content or reputation filters applied.

References: [User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway], page 6-2 and page 6-3.

Geolocation-based filtering and senderbase reputation filtering are two features of Cisco Email Security that can be added to a Sender Group to protect an organization against email threats. Geolocation-based filtering allows Cisco ESA to accept or reject connections from email servers based on their geographic location, such as country or continent. Senderbase reputation filtering allows Cisco ESA to reject or throttle connections from email servers based on their reputation score, which is calculated by Talos using sensor information from various sources.

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 5-4 and page 6-2.

According to the [Cisco Secure Email Encryption Service Add-In User Guide], you can create an encryption profile that defines the encryption settings and options for your encrypted messages[2, p. 11]. You can also create an outgoing content filter that applies the encryption profile to the messages that match certain conditions, such as having [SECURE] in the subject header[2, p. 12]. This way, you can allow users to flag the messages that require encryption by adding [SECURE] to the subject line.

The other options are not valid because:

• A. Creating an encryption profile with [SECURE] in the Subject setting and enabling encryption on the mail flow policy will not work, as the Subject setting in the encryption profile is used to specify the subject line of the encrypted message envelope, not the original message[2, p. 11].
• B. Creating an outgoing content filter with no conditions and with the Encrypt and Deliver Now action configured with [SECURE] in the Subject setting will not work, as this will encrypt all outgoing messages regardless of whether they have [SECURE] in the subject line or not[2, p. 12].
• D. Creating a DLP policy manager message action with encryption enabled and applying it to active DLP policies for outgoing mail will not work, as this will encrypt messages based on DLP rules that detect sensitive data in the message content, not based on user flags in the subject line.

To enable LDAP recipient verification on a Cisco Secure Email Gateway appliance, you need to configure the LDAP query on a listener and configure LDAP server profiles. The LDAP query specifies the criteria for matching recipient addresses against an LDAP directory. The LDAP server profile defines the connection settings and authentication credentials for accessing an LDAP server2. References = User Guide for AsyncOS 12.0 for Cisco Email Security Appliances - GD (General Deployment) - Configuring LDAP Queries [Cisco Secure Email Gateway] - Cisco

Outbreak Filters can take the action of rewriting URLs to redirect traffic to potentially harmful websites through a web security proxy. This allows the Cisco Secure Email Gateway to scan the content of the websites and block or warn the user if they are malicious or undesirable. This action can stop small-scale and nonviral attacks, such as phishing scams and malware distribution sites, that may not be detected by other filters. References: [Cisco Secure Email Gateway Administrator Guide - Configuring Outbreak Filters]

Spam Quarantine End-User Authentication Query is a query that Cisco ESA performs against an LDAP server to validate the end-user credentials during login to the End-User Quarantine.

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 10-9.

Enabling End-User Quarantine Access and pointing to an LDAP server for authentication is the action that must be taken to meet this requirement. End-User Quarantine Access is a feature that allows users to access their personal quarantine on Cisco ESA using their email address and password, without requiring an administrator account or access to Secure Email and Web Manager.

To enable End-User Quarantine Access on Cisco ESA, the administrator can follow these steps:

• Select Security Services > IronPort Anti-Spam > End User Safelist/Blocklist Settings and click Edit Settings.
• Under End User Quarantine Access, select Enable End User Quarantine Access.
• Under Authentication Server, select LDAP Server from the drop-down menu and choose an LDAP server profile from the drop-down menu.
• Click Submit.

To enable domain protection for the organization, the administrator must configure an outgoing mail policy that matches the sender and the from headers of the email. The sender header is the envelope sender address that is used by SMTP to route the email. The from header is the address that is displayed to the recipient as the source of the email. These headers are used to generate and verify a DomainKeys Identified Mail (DKIM) signature, which is a cryptographic method of validating the authenticity and integrity of an email message.

The other headers are not relevant for domain protection. The message-ID header is a unique identifier for each email message. The URL reputation header is a score that indicates the likelihood of a URL being malicious. The mail-from header is an alias for the sender header.

Configuring the outbound firewall rule to permit traffic on port 3237 is the additional action that resolves the issue. AMP file reputation is a feature that allows Cisco ESA to check files attached to messages against a cloud-based database of known malicious files and apply appropriate actions, such as block, deliver, or quarantine.

By default, AMP file reputation uses TCP port 3237 to communicate with the cloud-based database. If this port is blocked by a firewall, AMP file reputation will not work properly.

To resolve this issue, the administrator can configure the outbound firewall rule to permit traffic on port 3237 from Cisco ESA.

The other options are not valid actions to resolve the issue, because they do not affect the port used by AMP file reputation.

References: [User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway], page 7-5 and page 7-6.

The safelist/blocklist (SLBL) is a feature that allows Cisco ESA to accept or reject messages from specific email addresses or domains, based on the configuration of mail flow policies or end user preferences.

The action that provides direct access to view the SLBL on Cisco ESA is to export the SLBL to a .csv file, which can be done from the web user interface by selecting Security Services > Safelist/Blocklist and clicking Export.

The other options do not provide direct access to view the SLBL on Cisco ESA.

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 6-13 and page 6-14.

By modifying the mail policies, specifically the recipient matching criteria, you can ensure that email recipients do not match multiple policies simultaneously. When recipients in the email message belong to different domains (e.g., cisco.com and test.com), it can result in multiple policies being triggered simultaneously, leading to inconsistent delivery of emails with attachments.

DLP is for outgoing mail only and not relevant to incoming mail.

Spam threshold is a setting that determines the minimum score that a message must have to be classified as spam by Cisco ESA. The lower the threshold, the more aggressive the spam detection is.

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 6-5.

Non-final actions are actions that do not terminate the message filter evaluation, such as adding headers, setting variables, logging, etc. Final actions are actions that end the message filter evaluation and determine the fate of the message, such as accept, drop, bounce, quarantine, etc.

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 3-4.

 spam quarantine end-user authentication query is used to validate non administrative user access to the end-user quarantine via LDAP1. This query is configured in the System Administration > LDAP > LDAP Server Profile page and can be tested using the smtproutes command in the CLI1. The other queries are not related to this task. The spam quarantine alias consolidation query is used to consolidate multiple email addresses for a user into one login2. The spam quarantine external authorization query is used to authorize users to access an external spam quarantine on a separate Cisco Secure Email and Web Manager3. The local mailbox (IMAP/POP) authentication is an alternative method to authenticate users without using LDAP2.

If you store user information within LDAP directories in your network infrastructure you can configure the appliance to query your LDAP servers to accept, route, and authenticate messages. https://www.cisco.com/c/en/us/td/docs/security/esa/esa11-0/user_guide_fs/b_ESA_Admin_Guide_11_0/b_ESA_Admin_Guide_chapter_011010.html

According to the [Cisco Secure Email User Guide], Non-Viral threat detection is a feature of Outbreak Filters that detects and blocks email messages that contain non-viral threats such as phishing, fraud, or social engineering[1, p. 25]. To use this feature, you need to enable either AntiSpam or Intelligent Multi-Scan on your Cisco Secure Email Gateway, as these features provide the necessary scanning and filtering capabilities for Non-Viral threat detection[1, p. 26].

The other options are not valid because:

• A. Non-Viral threat detection does not require Antivirus or AMP enablement to properly function. Antivirus and AMP are features that detect and block email messages that contain viral threats such as malware or ransomware[1, p. 27-28].
• B. The Outbreak Filters option Graymail Header does not affect Non-Viral threat detection. Graymail Header is an option that allows you to add a header to email messages that are classified as graymail, which are messages that are not spam but may be unwanted by some recipients, such as newsletters or promotions[1, p. 25].
• D. The Outbreak Filters option URL Rewriting does not affect Non-Viral threat detection. URL Rewriting is an option that allows you to rewrite the URLs in email messages to point to a Cisco proxy server, which can scan the URLs for malicious content and redirect the users to a warning page if needed[1, p. 25].

Table Description automatically generated

Outbreak filters and antivirus are two features that can be applied to either incoming or outgoing mail policies on Cisco ESA. Outbreak filters allow Cisco ESA to detect and block messages that contain new or emerging email threats, such as viruses, worms, phishing, or spam, by using real-time updates from Talos intelligence. Antivirus allows Cisco ESA to scan messages for known viruses and malware using one or two antivirus engines (Sophos and McAfee).

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 6-16 and page 7-2.

Forged Email Detection is a feature that allows Cisco ESA to detect and block messages that spoof the display names of internal senders in the From header, such as executives or managers, to trick recipients into opening malicious or fraudulent emails. To configure this feature, two steps are required:

• Configure a content dictionary with friendly names of internal senders that should not appear in the From header of external messages, such as Alpha Beta or John Smith.
• Configure a filter to use the Forged Email Detection rule and dictionary, which will compare the display name in the From header of incoming messages with the entries in the content dictionary, and apply the configured action if a match is found.

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 9-8.

Bounce Verification is a feature that mitigates denial of service attacks on Cisco ESA. A denial of service attack is an attempt to overwhelm a system or network with excessive traffic or requests, rendering it unavailable or slow for legitimate users. Bounce Verification prevents Cisco ESA from accepting bounce messages that are not generated by itself or by trusted hosts, reducing the load on the system and preventing backscatter spam.

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 5-8.

A benefit of implementing URL filtering on the ESA is that it provides URL reputation protection. URL filtering uses SenderBase, a web-based service that collects information about URLs and domains from various sources, to assign a reputation score and a category to each URL. Based on these attributes, you can configure content or message filters to take actions on messages containing malicious or undesirable URLs.

References: User Guide for AsyncOS 12.0 for Cisco Email Security Appliances - GD (General Deployment), Chapter: Protecting Against Malicious or Undesirable URLs, Section: URL-Related Protections and Controls

Modify Subject is an additional option that should be used to help the end users be aware of the elevated risk of interacting with these messages. Modify Subject allows the administrator to add a prefix or suffix to the message subject, such as “[SPF Fail]”, to indicate that the message has failed the SPF verification and may be fraudulent or spoofed.

The other options are not valid additional options to help the end users be aware of the elevated risk of interacting with these messages, because they do not affect the message subject or provide any warning to the end users.

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 8-7 and page 8-8.

Secure unsubscribe option for end users. Mimicking an unsubscribe option is a popular phishing technique. For this reason, the end users are generally wary of clicking unknown unsubscribe links. For such scenarios, the cloud-based Unsubscribe Service extracts the original unsubscribe URI, checks the reputation of the URI, and then performs the unsubscribe process on behalf of the end user. This protects end users from malicious threats masquerading as unsubscribe links. https://www.cisco.com/c/en/us/td/docs/security/esa/esa14-2-1/User_Guide/b_ESA_Admin_Guide_14-2-1/b_ESA_Admin_Guide_12_1_chapter_01110.html#id_101033

spf-status is the section of the filter that must be modified to correct this behavior. spf-status is a condition that determines whether a message matches the content filter rule based on the result of SPF verification, such as pass, fail, neutral, etc.

The content filter in the exhibit has a spf-status condition set to “Pass”, which means that it will match messages that passed SPF verification and apply the action of “Quarantine”. This is the opposite of what the network engineer intended to do.

To correct this behavior, the network engineer can modify the spf-status condition to “Fail”, which means that it will match messages that failed SPF verification and apply the action of “Quarantine”.

The other options are not valid sections of the filter that must be modified to correct this behavior, because they do not affect the spf-status condition.

References: [User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway], page 8-3 and page 8-4.

spf-status is the section of the filter that must be modified to correct this behavior. spf-status is a condition that determines whether a message matches the content filter rule based on the result of SPF verification, such as pass, fail, neutral, etc.

The content filter in the exhibit has a spf-status condition set to “Pass”, which means that it will match messages that passed SPF verification and apply the action of “Quarantine”. This is the opposite of what the network engineer intended to do.

To correct this behavior, the network engineer can modify the spf-status condition to “Fail”, which means that it will match messages that failed SPF verification and apply the action of “Quarantine”.

The other options are not valid sections of the filter that must be modified to correct this behavior, because they do not affect the spf-status condition.

References: [User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway], page 8-3 and page 8-4.

• System: This is the default list of trusted certificate authorities that is provided by Cisco and updated automatically. It contains the certificates of well-known and widely used certificate authorities, such as VeriSign, Thawte, and GoDaddy.
• Custom: This is the list of additional certificate authorities that you can add manually or import from a file. It allows you to trust certificates that are issued by your own or third-party certificate authorities that are not included in the system list.

 in the spam quarantine section, you can configure settings for access to the spam quarantine, and by default, HTTP uses port 82 and HTTPS uses port 83.

According to the [Cisco Secure Email User Guide], you can create a text resource of type Disclaimer Template and use the code view option to insert HTML code into the text box. Then, you can use this text resource in a content filter to prepend or append the HTML message to the email body[1, p. 15-16].

The other options are not valid because:

• A. Creating a text resource type of Disclaimer Template and pasting the HTML code into the text box without changing to code view will not work, as the HTML code will be treated as plain text and not rendered properly[1, p. 15].
• C. Creating a text resource type of Notification Template and pasting the HTML code into the text box will not work, as Notification Templates are used for sending notifications to senders or recipients, not for modifying the email body[1, p. 17].
• D. Creating a text resource type of Notification Template and changing to code view to paste the HTML code into the text box will not work, as Notification Templates are used for sending notifications to senders or recipients, not for modifying the email body[1, p. 17].

To use DKIM for outbound email, the administrator must export the DNS TXT record from the Cisco Secure Email Gateway and provide it to the DNS registrar of the domain. This will allow the recipient servers to verify the DKIM signature of the email by querying the DNS record of the sender domain. References: [Cisco Secure Email Gateway Administrator Guide - Configuring DKIM Signing]

The PVO cannot be enabled and shows this type of error message.

Unable to proceed with Centralized Policy, Virus and Outbreak Quarantines

configuration as host1 and host2 in Cluster have content filters / DLP actions

available at a level different from the cluster Level.

The error message can indicate that one of the hosts does not have a DLP feature key applied and DLP is disabled. The solution is to add the missing feature key and apply DLP settings identical as on the host that has the feature key applied. This feature key inconsistency might have the same effect with Outbreak Filters, Sophos Antivirus, and other feature keys.

https://www.cisco.com/c/en/us/support/docs/security/email-security-appliance/118026-technote-esa-00.html

If the assigned certificate under one of the IP interfaces is modified, then the HTTPS traffic when connecting to the web user interface of the Cisco Secure Email Gateway will be impacted. The administrator must ensure that the certificate is valid and trusted by the browser or client that is used to access the web user interface. Otherwise, the connection may fail or generate a warning message. References: [Cisco Secure Email Gateway Administrator Guide - Configuring Certificates]

Content filters are rules that allow Cisco ESA to perform actions on messages based on predefined or custom conditions, such as headers, envelope, body, attachments, etc.

The two primary components of content filters are:

• Conditions, which are the criteria that determine whether a message matches a content filter rule or not, such as message size, sender address, attachment type, etc.
• Actions, which are the operations that Cisco ESA performs on a message if it matches the conditions of a content filter rule, such as deliver, drop, quarantine, encrypt, etc.

The other options are not primary components of content filters on Cisco ESA.

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 8-3 and page 8-4.

All users with administrator privileges can change spam quarantine settings and view and manage messages in the spam quarantine. You do not need to configure spam quarantine access for administrator users.

If you configure access to the spam quarantine for users with the following roles, they can view, release, and delete messages in the spam quarantine:

-Operator

-Read-only operator

-Help desk user

-Guest

-Custom user roles that have spam quarantine privileges

These users cannot access spam quarantine settings.

https://www.cisco.com/c/en/us/td/docs/security/esa/esa14-0/user_guide/b_ESA_Admin_Guide_14-0/b_ESA_Admin_Guide_12_1_chapter_0100000.html?bookSearch=true#con_1624156

Undesirable URL protection is a feature that allows Cisco ESA to detect and block messages that contain URLs that lead to malicious or unwanted websites, such as phishing, malware, or adult content sites. To enable this feature, outbreak filters and antispam scanning must be enabled on Cisco ESA.

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 6-17.

Load balancing and failover are two configurations that can be used on multiple LDAP servers to connect with Cisco ESA. Load balancing means that Cisco ESA will distribute the LDAP queries among the available LDAP servers in a round-robin fashion, improving the performance and efficiency of the LDAP queries. Failover means that Cisco ESA will switch to another LDAP server if the current one is unavailable or unresponsive, ensuring the continuity and reliability of the LDAP queries.

References: User Guide for AsyncOS 15.0 for Cisco Secure Email Gateway, page 10-8.

You can enter multiple host names to configure the LDAP servers for failover or load-balancing. Separate multiple entries with commas.

If the assigned certificate under one of the IP interfaces is modified, then the HTTPS traffic when connecting to the web user interface of the Cisco Secure Email Gateway will be impacted. The administrator must ensure that the certificate is valid and trusted by the browser or client that is used to access the web user interface. Otherwise, the connection may fail or generate a warning message. References: [Cisco Secure Email Gateway Administrator Guide - Configuring Certificates]