300-209 Security Implementing Cisco Secure Mobility Solutions (SIMOS) Practice Questions
Prepare for 300-209 with more than an answer.
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- v1Version 1 240 questions Locked
- 300-209Legacy Security Implementing Cisco Secure Mobility Solutions (SIMOS) 289 questions Current
- Exam fee
- $300 USD
- Level
- Professional
- Valid for
- 3 years
Domains covered on the exam 3
- Secure Communications32%
- Troubleshooting, Monitoring and Reporting Tools38%
- Secure Communications Architectures30%
- 1
A network security engineer needs to configure a clientless SSL VPN on a Cisco ASA. The goal is to rewrite URLs for an internal web server,
http://intranet.local, so they are accessible to external users via the ASA's portal. Which configuration snippet correctly achieves this URL rewriting?! Snippet A url-list REWRITE_URLS url http://intranet.local/* ! Snippet B clientless-rewrite rewrite-rule REWRITE_URLS "http://intranet.local" "/internal" ! Snippet C webvpn smart-tunnel list REWRITE_URLS http://intranet.local ! Snippet D group-policy GP-SSL attributes webvpn url-list value REWRITE_URLS url-entry enableShow answer details
Correct answer: C
To configure basic URL entry for a Clientless SSL VPN portal, you define a URL list and then enable it within the
webvpnsection of a group policy. Snippet D shows the correct method: defining the list of URLs (which would be configured separately like in Snippet A, but that part is implied) and then enabling theurl-entryfeature under the group policy'swebvpnattributes. The ASA's content rewriting engine then automatically handles the necessary transformations for the links specified in the list. - 2
A new DMVPN spoke is unable to register with the hub. The engineer runs
debug crypto isakmpon the spoke and sees the message%CRYPTO-4-IKMP_NO_SA: IKE message from [hub_ip_address] has no SA and is not an initialization offer. The hub configuration is using a dynamic crypto map. What is the most likely cause of this error?Show answer details
Correct answer: D
The error message 'no SA and is not an initialization offer' indicates that the spoke is sending an IKE initiation packet, but the hub is unable to respond correctly. In a DMVPN setup where the hub has a dynamic crypto map and spokes have dynamic public IPs, the hub must have a route back to the spoke's public (NBMA) address to send the IKE reply. This is often a default route pointing to the internet. Without this reverse route, the hub receives the IKE packet but drops the reply, leading the spoke to timeout and display this error.
- 3
A project requires implementing a VPN solution that preserves the original IP header of packets to support a legacy application that is sensitive to NAT and tunneling overhead. The underlying network is a private MPLS cloud, and the goal is to encrypt all traffic between sites without altering the existing IP routing scheme. Which Cisco VPN technology is specifically designed for this use case?
Show answer details
Correct answer: C
Group Encrypted Transport VPN (GETVPN) is the ideal solution for this scenario. Its key feature is the ability to encrypt traffic while preserving the original source and destination IP headers. This is because it uses a variation of IPsec Transport Mode rather than Tunnel Mode. This makes it transparent to the underlying routing infrastructure (like MPLS) and compatible with applications that rely on the original IP addresses, QoS markings, and multicast. DMVPN and FlexVPN use Tunnel Mode, which encapsulates the original packet inside a new IP header, changing the packet structure.
- 4
A security audit of a Cisco ASA remote access VPN revealed that the
anyconnect-essentialslicense is being used. A new requirement is to implement endpoint posture checks using the HostScan module. Which action must be taken to enable this functionality?Show answer details
Correct answer: C
Cisco AnyConnect licensing is tiered. The
AnyConnect Essentialslicense provides basic VPN functionality only. Advanced features like endpoint posture assessment (HostScan), clientless SSL VPN, and Suite B cryptography require theAnyConnect Apexlicense. Therefore, to enable HostScan, the administrator must purchase and apply an Apex license to the ASA. - 5
An engineer is deploying a large-scale FlexVPN network. What is the primary role of a virtual-template interface in this type of deployment?
Show answer details
Correct answer: B
In FlexVPN and other dynamic VPN technologies, a virtual-template interface serves as a blueprint. It is not an active interface itself but holds the configuration (e.g., IP address negotiation, IPsec profile, QoS policies) that should be applied to each VPN session. When a new spoke or client connects, the router dynamically creates a
Virtual-Accessinterface for that specific session, cloning all the configuration parameters from theVirtual-Template. This allows for scalable and consistent configuration of thousands of dynamic tunnels. - 6
A network administrator is troubleshooting a Cisco AnyConnect SSL VPN where users are unable to access internal web servers via FQDN but can access them via IP address. The split-tunneling policy is correctly configured to include the internal DNS server's subnet. The ASA configuration includes the command
split-dns DefaultDNS. What is the most likely cause of this issue?Show answer details
Correct answer: B
The
split-dnscommand requires a list of domain names. When a client needs to resolve a name matching a domain in this list, the query is sent through the tunnel to the corporate DNS server. The commandsplit-dns DefaultDNSis not a valid configuration; it should be followed by a domain name, for example,split-dns value internal.company.com. Without the specific domain list, the AnyConnect client will continue to use its local DNS server, failing to resolve internal FQDNs. - 7
During a GETVPN deployment, a new Group Member (GM) fails to register with the Key Server (KS). The administrator observes 'GDOI registration failed' messages on the GM. The pre-shared key for ISAKMP Phase 1 is confirmed to be correct. Which two of the following are potential causes for this registration failure? (Select TWO)
Show answer details
Correct answer: A, C
GETVPN uses the GDOI protocol, which is encapsulated in UDP over port 848. If an access control list on the KS or any intermediate device blocks this traffic from the GM, the registration process will fail.
The group identity number is a critical parameter that must match between the KS and GM. It is used to associate the GM with the correct GDOI group. A mismatch will cause the KS to reject the registration request.
- 8
A consultant is designing a FlexVPN solution to replace a legacy DMVPN network. A key requirement is to use IKEv2 with certificate-based authentication and to dynamically assign spoke-specific IP addresses from a local pool on the hub. Which configuration block is essential on the FlexVPN hub to achieve this?
Show answer details
Correct answer: B
In a FlexVPN IKEv2 server (hub) configuration, the
crypto ikev2 profileis the central component. It ties together authentication (certificates), authorization (AAA), and the configuration template for dynamic tunnels (virtual-template). The AAA server or local pool is then configured to provide IP addresses and other attributes to authenticated spokes, which are applied via the virtual-access interface cloned from the virtual-template. - 9
True or False: In a Cisco ASA Clientless SSL VPN deployment, enabling Java-based port forwarding is necessary to provide remote users with access to internal applications that use a static TCP port, such as an SSH or Telnet server.
Show answer details
Correct answer: A
True. Clientless SSL VPN primarily provides access to web-based resources. To access non-web applications that use specific TCP ports (like SSH on port 22 or Telnet on port 23), port forwarding must be configured. This feature uses a Java applet that is downloaded to the client's browser to map a local port on the client's machine to the internal application's IP address and port, tunneling the traffic through the SSL VPN session.
- 10
An engineer is configuring a site-to-site IPsec VPN tunnel between two Cisco IOS routers and needs to ensure that if the primary encryption or hash algorithm is compromised, the overall security of the session keys is not affected. Which IKEv1 feature must be enabled to achieve this?
Show answer details
Correct answer: C
Perfect Forward Secrecy (PFS) ensures that a session key derived from a set of long-term keys will not be compromised if one of the long-term keys is compromised in the future. In IPsec, this is achieved by forcing a new Diffie-Hellman exchange to generate fresh, unrelated keys for each new security association (SA) rekey, typically during IKE Phase 2. This prevents an attacker who compromises a router's private key from decrypting previously captured VPN traffic.
