A Comprehensive Guide on Bypassing Cisco Umbrella

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Cisco Umbrella is a cloud-based security platform that can be difficult to bypass, but there are a few methods that can be used. Some of these methods include using a VPN, changing your DNS settings, or using a proxy server.

What is a Cisco Umbrella?

Cisco Umbrella is a cloud-based security product designed to protect against cyber threats. Its purpose is to prevent access to filtered websites, such as social media or webmail, based on the organization’s configuration. Cisco Umbrella works with its DNS and SWG modules. The DNS module intercepts all DNS traffic and redirects it to the Umbrella DNS for filtering and logging, while the SWG module is a cloud proxy for HTTP and HTTPS traffic.

In a typical network level Umbrella deployment, pointing DNS to Umbrella alone may not be sufficient to enforce Umbrella protections. However, savvy users may attempt to bypass Umbrella by changing the DNS settings on their machines if allowed by computer policy. Therefore, it is critical to enforce DNS to Umbrella and prevent any other DNS service from being used to bypass Umbrella settings and protection. By following the recommended configuration, users will be protected against any potential threats.

Key Features and Functionality of Cisco Umbrella

Cisco Umbrella is a cloud-based cybersecurity solution that offers several key features and functionalities:

  1. DNS Filtering: Cisco Umbrella uses DNS filtering to prevent users from accessing malicious websites and threats at the DNS level, providing an additional layer of security.
  2. Web Filtering: It enforces internet usage policies and controls by filtering web traffic. This includes blocking or allowing websites based on predefined categories or custom rules.
  3. Intelligent Proxy: Umbrella includes a secure web gateway that inspects and filters HTTP/HTTPS traffic, providing real-time threat protection and data encryption.
  4. Threat Intelligence: It leverages Cisco Talos, a renowned threat intelligence team, to continuously update its threat database and block known threats.
  5. Roaming Protection: Protects users and devices outside the corporate network by routing their DNS queries through the Umbrella security infrastructure.
  6. Cloud-Delivered Security: Umbrella’s cloud-based architecture ensures scalability and high availability, making it easy to deploy and manage globally.
  7. Integration: It seamlessly integrates with other security tools and solutions, such as Cisco’s security ecosystem, for comprehensive threat protection.
  8. Reporting and Insights: Provides real-time visibility into network activity and security events, helping administrators detect and respond to threats effectively.
  9. Secure Access: Cisco Umbrella can be used to secure remote access to corporate resources, ensuring secure connectivity for remote workers.
  10. APIs and Custom Integrations: Offers APIs for custom integrations and automation, allowing organizations to tailor the solution to their specific needs.
  11. Global Data Centers: Cisco Umbrella operates data centers worldwide, minimizing latency and ensuring fast and reliable DNS and web filtering.

Reasons to Bypass Cisco Umbrella

  • Ensure Access to Restricted Websites: Cisco Umbrella is a cloud-based security product that intercepts DNS requests and proxies web traffic based on certain configurations. Some organizations use it to block access to social media or web email. However, some individuals may need access to such sites for various reasons.
  • Avoid MitM Approach: According to the analysis, when intercepting HTTPS traffic and filtering for potential issues, Cisco Umbrella uses a Man-in-the-Middle (MitM) approach to decrypt and re-encrypt the communication with a trusted certificate on the device. Although this process aims to prevent cyber threats, some may not feel comfortable with a third party having access to their sensitive information.
  • Have Better Performance: Sometimes, having a cloud-based security service like Cisco Umbrella can slow down internet traffic due to the extra layer of filtering and proxying. By bypassing it, some users may experience faster loading times for websites and smoother video streaming.
  • Test Security Measures: In some cases, network security experts may need to test the effectiveness of their own security measures and look for vulnerabilities. Bypassing Cisco Umbrella can help them identify areas where improvements can be made.
  • Not Intended to Promote Bypassing: It’s critical to remember that bypassing Cisco Umbrella without proper authorization from an organization is not recommended. The data presented is solely for analysis purposes, and it’s the responsibility of the individual to obtain permission before taking any action. The main purpose of Cisco Umbrella is to provide an extra layer of security for individuals and organizations, and it’s important to respect that.

Assessing the Risks and Legal Implications of Bypassing Cisco Umbrella

  • Cisco Umbrella is a cloud-based security product that provides protection against cyber threats by restricting access to filtered websites and inspecting HTTP and HTTPS traffic via its DNS and SWG modules, respectively. However, there are ways to bypass the restrictions and inspection, including using a firewall to restrict access to Umbrella servers and blocking specific IP addresses.
  • Bypassing Cisco Umbrella can result in risks such as exposure to malicious content and sensitive information, reduced protection against cyber threats, and potential legal implications. Since using Cisco Umbrella is often a part of an organization’s security policy, bypassing it could lead to disciplinary action and legal consequences.
  • It is important to note that intentionally bypassing Cisco Umbrella without a legitimate reason can put the organization and its employees at risk. Instead of bypassing, it is recommended to address any concerns or issues with the security policy and seek solutions within the policy framework.

Exploring Different Bypassing Techniques for Cisco Umbrella

  • Cisco Umbrella is a cloud-based security product that intercepts all domain name system (DNS) traffic and route it to the Umbrella DNS for filtering and logging, restricting access to filtered sites. Similarly, the Secure Web Gateway (SWG) intercepts HTTP and HTTPS traffic and routes it to the Umbrella proxy for inspection. However, there are ways to bypass these functionalities.
  • One way is to create a firewall rule that restricts access to Cisco Umbrella servers. This triggers deactivation on the client after a timeout and disables DNS protection. IP addresses to be blocked include the proxy and DNS and
  • Another way is to block the Cisco Umbrella proxy on the firewall rule list. Since the connection is established directly after the timeout, a website that opens multiple TCP connections requires a longer time to load than when there is a single TCP connection. This method can provide a bypass and disable DNS protection.

Furthermore, it is possible to bypass the SSL decryption and content filtering policies on an affected system. This can be done by exploiting a vulnerability in the automatic decryption process in Cisco Umbrella SWG, which uses the TLS Sever Name Indication extension of an HTTPS request to discover the domain destination. An attacker can send a crafted request over TLS from a client to an unknown or controlled URL to bypass the decryption process.

Bypassing Cisco Umbrella on Different Devices

Bypassing Cisco Umbrella DNS Proxy Firewall Restrictions can be done in various ways on different devices. Firstly, the DNS module intercepts all DNS traffic and restricts access to filtered websites like social media or web mail based on configuration. However, the DNS configuration is not altered, and HTTPS traffic is inspected with a Man-in-the-Middle (MITM) approach decrypted at the proxy end and re-encrypted using a Cisco certificate installed on the device.

 A firewall can restrict access to Cisco Umbrella servers, causing deactivation on the client after a timeout. Also, including the Cisco Umbrella proxy in the deny list of the firewall rule will work as a bypass. On Microsoft DNS servers and Bind servers, bypassing Umbrella using conditional forwarding requires adding the domain to an internal domains page on the Umbrella dashboard. Umbrella network device integrations like Cisco ASA / ISR integration have their methods of bypassing the domain from Umbrella.


Cisco Umbrella is a cloud security product that provides DNS and Proxy modules to secure and restrict web traffic. However, sometimes it may become necessary to bypass its restrictions under certain circumstances, as discussed in the following analysis. It is important to note that this analysis is solely for informational purposes, and bypassing the Cisco Umbrella should only be done with the organization’s consent and authorization.




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