How to Implement Tailscale for Distributed Companies

 

Maintaining secure and efficient network access is crucial for distributed companies. The challenge lies in balancing convenience with security, often leading organizations to seek innovative solutions. Enter Tailscale, a modern VPN solution that provides a seamless way to connect distributed teams while enhancing security and simplifying network management.

VirtualPrivateNetworks

Tailscale operates on a concept known as a mesh VPN, where devices communicate directly instead of routing traffic through a central server. This structure not only increases speed and reliability but also simplifies network configuration for remote teams. By leveraging Tailscale, businesses can build a private network accessible from anywhere in the world, effectively streamlining their digital workspace.

This article will guide you through the process of implementing Tailscale in your organization, covering everything from setting up your Tailnet to managing permissions and enhancing traffic security. Whether you’re a developer seeking better access or an IT administrator looking to streamline management, understanding Tailscale can truly transform your approach to network access.

Understanding the Basics of Tailscale

Tailscale is a secure, peer-to-peer VPN alternative that uses the open-source WireGuard protocol to create virtual mesh networks between a company’s network nodes. This technology is designed for rapid deployments and simplifies administration, making it ideal for transitioning to Zero Trust network architectures. By installing Tailscale’s client, devices generate a private/public key pair to enable encrypted peer-to-peer connections, with public keys managed by Tailscale.

Operating as a control plane, Tailscale ensures that data sessions occur outside of its network, maintaining security through end-to-end encryption. It includes NAT traversal management and uses its Designated Encryption for Packets (DERP) software for relays when direct connections face challenges. This feature set positions Tailscale as a robust solution for businesses seeking modern and secure networking options.

Creating Your Tailnet

Creating your tailnet with Tailscale is a straightforward process that enables you to establish a secure private network using the WireGuard protocol. Begin by installing the Tailscale client software on at least two devices. Once installed, log in to the Tailscale app on these devices using the same user account or authentication domain. This quickly interlinks the devices, forming your initial tailnet.

Tailscale operates atop your existing network infrastructure, ensuring that you can deploy it incrementally without modifying your current security settings. For devices that cannot have the Tailscale client installed, such as network printers, you can use subnet routers. Subnet routers integrate these devices into your tailnet, granting access without additional hardware.

To maintain control over user access and device connectivity, customize access control policies (ACLs) within the tailnet policy file. This feature allows you to define specific permissions for each user and device within your network. In just minutes, Tailscale transforms your distributed resources into a cohesive and secure network environment without the complexities of traditional VPN configurations.

Setting Up Your Devices with Tailscale

Setting up your devices with Tailscale starts by installing the Tailscale client on both the device you want to connect and the machine you intend to use. This allows for seamless access across your network. Once installed, each device is assigned its own IP address within the Tailscale network, creating a secure Wireguard connection to other devices.

Tailscale simplifies the process by eliminating the need for port forwarding, making it ideal for remote work scenarios. For complex architectures, it supports multiple devices, enabling connectivity from any place where the Tailscale client is active. This feature is particularly useful for remote users who require consistent network access without complicated setup processes.

Through the Tailscale admin interface, administrators can generate authentication keys to ensure secure connections for devices. This allows for robust access controls and enhances security within your private network. With features like the ability to establish subnet routes, administrators can facilitate easy integration with existing internal networks, optimizing network performance while maintaining tight Firewall settings.

Utilizing MagicDNS for Simplified Device Access

MagicDNS significantly enhances device accessibility within a Tailscale network by allowing users to access devices using intuitive names instead of complex IP addresses. This feature automatically utilizes OS hostnames or user-renamed device names, making communication across the network more straightforward and efficient.

Enabling MagicDNS by default is highly recommended, as it streamlines the management of multiple devices, contributing to an improved user experience. Users can easily SSH into devices using their names, such as ssh /mymachine/, thanks to the integration with Tailscale’s authentication system. This simplification reduces the complexity involved in remembering and managing IP addresses.

The MagicDNS feature also allows for easy renaming of devices within the admin console, enhancing the process of locating and organizing devices. By using recognizable names, IT administrators and remote users can ensure better accessibility and manageability across their private networks, fostering an environment of efficient operation and seamless connectivity.

Inviting Team Members and External Users

To manage team member access in Tailscale, users with email addresses matching the custom domain of your tailnet can effortlessly log in without needing an invite. This feature streamlines access for team members by leveraging the same identity provider used during tailnet creation. If you need to invite team members from outside your organization’s domain, you can do so via the admin console.

Administrators can navigate to the Users page in the admin console to invite external users. Options include sending an invite through email or copying an invite link. This flexibility is ideal for contractors or partners who are not part of your organization’s domain, ensuring they have the necessary access. Implementing external invites also aids in maintaining a secure network while expanding user capability.

To enhance user access and management, setting up MagicDNS is recommended within your tailnet. MagicDNS simplifies network navigation by providing auto-generated hostnames and reducing dependency on external DNS servers, thereby improving the overall experience for all users.

Configuring Exit Nodes for Enhanced Security

To configure an Exit Node in Tailscale for enhanced security, begin by accessing the admin console to select and enable the desired device as an Exit Node. This setup allows network traffic to route through the chosen device, offering secure Internet access, especially on untrusted Wi-Fi networks. Ensure that traffic is routed through reliable devices to maintain security.

Implementing Access Controls is crucial to enforcing security policies within your private network. By default, Tailscale allows all users to access all connected devices, so customizing Access Controls is essential to apply the principle of least privilege. This confines users to their devices and designated Exit Nodes, reducing potential threats.

Enhance your security management by modifying Tailscale’s Access Control List (ACL). You can add specific rules that grant or deny network traffic based on security needs. This fine-tuning allows you to restrict access to only necessary devices and users, safeguarding the network while preserving functionality. Configuring these settings ensures a robust security posture, minimizing the risks associated with compromised devices while enhancing user experience.

Implementing Subnet Routing for Network Expansion

Implementing subnet routing with Tailscale is an efficient way for distributed companies to expand their network without installing the Tailscale client on every device. By enabling subnet routes via the Tailscale web admin console, users can ensure seamless communication between different nodes and existing resources like printers. This feature supports incremental deployment, allowing companies to gradually integrate subnet routes across various offices or data centers, which facilitates a smooth transition to a hub-and-spoke or multi-hub VPN setup.

Managing subnet conflicts is crucial when deploying Tailscale across devices with overlapping IP ranges. Users should select unique CIDR ranges for each subnet to avoid network issues. In addition, regional routing enhances subnet router capabilities by advertising identical routes from routers in various regions. This optimization ensures that users can access resources more efficiently, improving network performance and availability. By carefully planning the expansion, companies can maintain existing configurations while also supporting future growth.

Managing Permissions with Access Control Lists (ACLs)

Tailscale’s Access Control Lists (ACLs) provide a structured way to manage permissions for users and devices within a tailnet. By default, the ACLs are open, but once configured, they shift to a deny-by-default stance. This setup demands that administrators explicitly grant access, enhancing security for fully remote operations.

The ACL configuration is crafted in a user-friendly variant of JSON. This format is manageable for admins and allows them to effectively outline who can access which specific resources, down to precise IP addresses and port levels. As a result, ACLs facilitate fine-grained traffic flow between systems and services, ensuring secure and efficient remote work environments.

With Tailscale, admins can customize permissions to suit organizational needs. This includes establishing specific permissions for both users and devices, ensuring that only authorized individuals have access to necessary resources. The flexibility of ACLs in Tailscale ensures that distributed companies can maintain high levels of security and control while supporting a seamless remote work experience.

Enhancing Traffic Security with Tailscale

Tailscale utilizes zero-trust architecture and the WireGuard protocol to establish secure peer-to-peer VPN tunnels. This setup enhances traffic security by reducing traditional configuration complexities. Implementing Tailscale allows distributed companies to enforce traffic rules, ensuring that all sensitive service traffic is securely channeled and unauthorized access risks are minimized.

Tailscale’s App Connectors facilitate simplified IP allowlisting for SaaS tools. This ensures that attackers must not only acquire credentials but also be within the Tailnet for access. Additionally, integration with logging solutions supports extended log retention, assisting in identifying slow-developing security threats and improving compliance.

Regional routing capabilities introduced by Tailscale increase high availability for subnet routers, ensuring secure connectivity across regions while maintaining stringent security. This functionality is crucial for distributed companies looking to optimize network traffic security across their private networks. By simplifying VPN access and providing robust access controls, Tailscale enhances the user experience while safeguarding against potential security threats.

Monitoring and Logging Network Activities

Tailscale provides a robust solution for monitoring and logging network activities within distributed companies. Each connection made within the Tailscale network is logged both on the source and destination nodes. This dual logging enhances audit capabilities and makes any tampering with logs easily detectable.

The logging service is designed to stream data in real time from each node, reducing the risk of local log tampering to just milliseconds. By collecting metadata about the internal mesh network, it ensures user privacy by not recording personal or Internet usage data.

These logs can be seamlessly integrated into your Security Information & Event Management (SIEM) system, offering a comprehensive monitoring solution. This integration allows businesses to closely monitor network traffic and activities, enhancing overall network security and performance. The ability to monitor activities asynchronously strengthens oversight and ensures the network’s integrity.

Use Cases for Developers Utilizing Tailscale

Tailscale is a powerful tool for developers who need to connect multiple devices without the hassle of port forwarding. By installing the Tailscale client on the desired devices, developers can quickly establish a secure private network, facilitating remote access to internal systems from any location. This capability is particularly beneficial for accessing diverse resources hosted on various cloud platforms.

One of Tailscale’s standout features is its support for incremental deployments. Developers can start with a small-scale proof of concept and gradually expand their network, ensuring minimal disruption to existing infrastructure. This flexibility allows companies to adopt and adapt Tailscale at their own pace.

Moreover, Tailscale’s exit-node service is an effective alternative to traditional VPN solutions. Companies can replace multiple personal VPNs with a limited number of compute instances configured as VPN endpoints. These instances can be strategically placed to optimize network performance and provide consistent Internet access across different geographic locations. Here are the key use cases:

  1. Secure Remote Access to Cloud Resources
  2. Incremental Network Expansion
  3. Replacement of Multiple VPN Solutions

By leveraging Tailscale, developers can enhance collaboration and productivity while maintaining robust security for their distributed networks.

Tailscale for IT Administrators: Streamlining Management

Tailscale is a powerful tool for IT administrators aiming to streamline the management of private networks using the WireGuard protocol. By allowing devices to connect directly and securely, Tailscale facilitates the management of network traffic without the complexities common in traditional VPNs. This simplifies setting up a private network, making it accessible even to those with limited technical expertise.

A standout feature is Tailscale’s ability to integrate with platforms like Axiom, enhancing network visibility and security. This integration streams audit and network flow logs, providing detailed insights into network activity useful for monitoring purposes. The architecture of Tailscale supports seamless scalability, enabling admins to add users and modify access controls without impacting the network infrastructure.

Each device runs a Tailscale client, which connects to a centralized coordination server. This setup creates a mesh network, ensuring efficient communication between endpoints. Such an arrangement not only improves network performance but also supports remote access for users, allowing secure file sharing over local networks. By managing communications effectively, Tailscale reduces dependency on slower external Internet connections, improving user experience.

Personal Use Cases of Tailscale in Remote Access

Tailscale is an effective tool for personal remote access by creating a secure, peer-to-peer VPN without the need for traditional port forwarding. Users can connect to their office computers or home devices by installing the Tailscale client on both the local machine and the remote device they aim to access. This setup ensures seamless connectivity, allowing users to manage files and applications from different locations.

The platform supports diverse use cases, from simple device access to complex connections across global networks. With Tailscale, users can handle on-premises resources and cloud applications with ease, all within a virtual mesh network. The integration with WireGuard protocol provides encrypted connections, enhancing security and privacy for remote access activities. This is particularly beneficial for personal users who require a robust yet straightforward solution for accessing their devices across various networks.

Key benefits include:

  • Secure Remote Access: Encryption via WireGuard enhances privacy.
  • Seamless Connectivity: No need for complex port forwarding steps.
  • Versatility: Manage devices across different networks, improving user experience.

In summary, Tailscale eases the challenges of accessing remote devices, ensuring personal users can maintain productivity and security from anywhere.

Troubleshooting Common Problems with Tailscale

Troubleshooting common problems with Tailscale involves leveraging its robust features for managing device connections. By acting as a control plane, Tailscale enables devices to locate each other even when real IP addresses vary, simplifying connectivity issue resolution. Its zero-trust networking model supports incremental deployments, allowing you to add devices one at a time, which helps in pinpointing and fixing specific issues efficiently.

When facing network connectivity problems, Tailscale manages NAT traversal to navigate environments with restrictive network settings. This capability aids in resolving connection issues by ensuring devices can communicate without extensive manual configuration. If persistent problems occur, Tailscale can automatically switch to its own network of relays, providing a fallback option that maintains connectivity.

Tailscale’s foundation on WireGuard, an open-source technology, enhances transparency and invites community support, making it easier to diagnose and address unique problems. This transparency ensures that troubleshooting can be both collaborative and systematic. By utilizing these features, network administrators can effectively troubleshoot and improve network performance in distributed company environments.

Comparing Tailscale with Traditional VPN Solutions

Tailscale’s peer-to-peer mesh networking is a modern approach compared to the traditional hub-and-spoke topology of conventional VPN solutions. This design offers rapid deployments and simplified administration, reducing the complexity often associated with VPN setups. Traditional VPNs, requiring centralized network traffic routing, can face bottlenecks, unlike Tailscale’s decentralized model which enhances network performance.

The cost-effectiveness of Tailscale is notable, as it can be free for particular use cases, making it ideal for users needing occasional VPN access. Traditional VPN services usually charge monthly fees, which can add up over time. Tailscale’s use of the open-source WireGuard protocol enhances security through encrypted peer-to-peer connections, ensuring better privacy than many standard VPNs.

Trust levels with traditional VPNs are high, as users must rely on the service provider. Tailscale shifts control to the user, minimizing trust dependency. Additionally, Tailscale allows remote access to resources like self-hosted servers without exposing the entire private network, addressing privacy concerns. This ability to fine-tune access controls is beneficial for distributed companies relying on remote users and personal devices.

Benefits of Adopting Tailscale for Distributed Teams

Tailscale enables distributed teams to create a secure private network that seamlessly connects devices across different locations. By offering a streamlined approach to remote access, it eliminates complex hardware setups and configurations, making it an ideal solution for teams working remotely or spread out geographically. Its zero-trust architecture ensures secure communications even under varying network conditions.

Integrating Tailscale with Axiom allows users to extend log retention, crucial for identifying security threats and fulfilling compliance requirements. The visibility provided by streaming audit and network flow logs gives teams a comprehensive view of their network activity, enhancing oversight and improving network performance.

Here are some key benefits of Tailscale for distributed teams:

  • Secure Private Network: Enables encrypted peer-to-peer connections within a mesh network.
  • Zero Trust Architecture: Enhances security and simplifies user authentication.
  • Ease of Use: No need for complex VPN setups; accessible through any Internet connection.
  • Comprehensive Visibility: Integration with Axiom for detailed audit logs and network monitoring.
  • Cost-effective: Eliminates expensive hardware, manageable with a low user per month fee.

These features make Tailscale a powerful tool for distributed teams, ensuring efficient and secure collaboration across networks.

Conclusion: Transforming Network Access with Tailscale

In conclusion, Tailscale offers a transformative approach to network access for distributed companies by leveraging a zero-trust mesh VPN system. It simplifies the setup and management of secure connections across diverse environments, including on-premises infrastructure, cloud services, and personal devices. By utilizing the WireGuard protocol, Tailscale ensures that network traffic remains encrypted and secure, significantly reducing the risks associated with compromised devices and public IP address exposures.

Companies can implement Tailscale incrementally, allowing for a gradual transition to zero-trust architecture. This flexibility promotes easier adoption and minimizes operational disruptions. Tailscale’s features, such as controllable log retention and seamless integration with existing security systems, offer improved network visibility and enhanced analysis through SIEM systems. These capabilities are crucial for compliance, security audits, and optimizing network performance.

Overall, Tailscale redefines how organizations approach remote access and internal network security. It enhances user experience by streamlining VPN server configurations, exit node features, and remote user authentication. By focusing on protecting network integrity and simplifying administration, Tailscale empowers distributed workforces to securely access resources with minimal latency and maximal efficiency.

More Information and Help

For more detailed assistance on how to implement Tailscale for your distributed company, consider reaching out to MicroSolved. They can provide valuable insights into the use cases, configuration, and Access Control Lists (ACLs) necessary for optimizing Tailscale networks.

To get in touch with MicroSolved, you can email them at info@microsolved.com or call 614.351.1237. Their team can guide you through vital components such as user authentication, setting up subnet routes, and managing your network traffic. Whether you’re looking to improve your VPN access, refine Exit Node configurations, or enhance your internal networks, MicroSolved is ready to help.

Remember to use their expertise to ensure your network performance remains robust and secure, catering to both remote users and those needing private network solutions. By engaging with them, you can alleviate concerns about potentially compromised devices. For a detailed consultation and support, contact MicroSolved today.

 

 

*MSI does not resell any products. We have no financial relationship with Tailscale. * AI tools were used as a research assistant for this content.

 

3 Essential Tips for Enhancing Site-to-Site VPN Security

 

Site-to-site VPNs are a crucial tool for securing communication between different network locations. To ensure the utmost security for your VPN connections, consider implementing these three key suggestions:

1. Select Strong Secrets or Secure Certificates

The foundation of any secure site-to-site VPN is the authentication mechanism. Opt for strong pre-shared keys or secure digital certificates when configuring your VPN. Using weak passwords or keys can leave your VPN vulnerable to attacks. Remember, a strong password should be lengthy, complex, and incorporate a mix of letters, numbers, and special characters. Alternatively, employing secure certificates provides an added layer of protection as they are difficult to intercept or guess.

2. Implement Modern, Peer-Reviewed Cryptography

Ensure that your site-to-site VPN employs modern encryption protocols have been rigorously reviewed by the security community. Protocols like IKEv2/IPsec are popular choices that offer robust encryption and authentication mechanisms. Peer-reviewed cryptography guarantees that the algorithms have undergone extensive scrutiny and are less likely to contain vulnerabilities or backdoors. Currently, AES is the suggested cryptographic mechanism for most VPNs. DES and 3DES should be eliminated wherever possible.

3. Create Proper Firewall Rules or ACLs

Managing traffic over your VPN connection is essential for maintaining a secure network environment. Utilize firewall rules or Access Control Lists (ACLs) to carefully regulate data flow between connected sites. You can prevent unauthorized access and potential breaches by explicitly defining what types of traffic are permitted and denied. Regularly review and update these rules to adapt to changing security requirements.

In Conclusion

Enhancing your site-to-site VPN’s security involves strong authentication, robust encryption, and intelligent traffic management. By selecting strong secrets or certificates, implementing modern cryptography, and creating well-defined firewall rules, you can significantly bolster the security of your VPN connections. Securing your network is an ongoing process, so staying updated on the latest security practices and adapting your configurations is essential.

Implement these tips today to build a resilient and secure site-to-site VPN that safeguards sensitive data and ensures seamless communication between your network locations.

 

* Just to let you know, we used some AI tools to gather the information for this article, and we polished it up with Grammarly to make sure it reads just right!

 

The Mixed Up World of Hola VPN

Have you heard about, or maybe you use, the “free” services of Hola VPN?

This is, of course, a VPN, in that it routes your traffic over a “protected” network, provides some level of privacy to users and can be used to skirt IP address focused restrictions, such as those imposed by streaming media systems and television suppliers. There are a ton of these out there, but Hola is interesting for another reason.

That other reason is that it turns the client machine into “exit nodes” for a paid service offering by the company:

In May 2015, Hola came under criticism from 8chan founder Frederick Brennan after the site was reportedly attacked by exploiting the Hola network, as confirmed by Hola founder Ofer Vilenski. After Brennan emailed the company, Hola modified its FAQ to include a notice that its users are acting as exit nodes for paid users of Hola’s sister service Luminati. “Adios, Hola!”, a website created by nine security researchers and promoted across 8chan, states: “Hola is harmful to the internet as a whole, and to its users in particular. You might know it as a free VPN or “unblocker”, but in reality it operates like a poorly secured botnet – with serious consequences.”[23]

In this case, you may be getting a whole lot more than you bargained for when you grab and use this “free” VPN client. As always, your paranoia should vary and you should carefully monitor any new software or tools you download – since they may not play nice, be what you thought, or be outright malicious. 

I point this whole debacle out, just to remind you, “free” does not always mean without a cost. If you don’t see a product, you are likely THE PRODUCT… Just something to keep in mind as you wander the web… 

Until next time, stay safe out there!

The iPad as a VPN Client

Today was my first real chance to try out the iPad as a VPN client in a critical situation. I needed an essential file for a client in a real hurry. We were about 50 miles from the office and a physical return with the file wasn’t possible. Even worse, it was stored on an encrypted vault volume on my personal backup system, so none of my engineers could assist me, since they lack credentials for that box.
Thankfully, I had my iPad with me. I had already set up a VPN connection for my device, but hadn’t yet tested it. The good news is that it worked perfectly! I was able to quickly create a VPN tunnel back to my network and then SSH into my vault. Once there, I could effortlessly arrange for a file transfer to my client in a secure manner. I even piped a VNC connection over the tunnel using iTeleport and could interact with the GUI nearly as easily as on a laptop.
All in all, it was a great save and made an excellent real world use case for the iPad in my work flow. Have you had any other big successes with the iPad in your security work? If so, drop a comment and tell us about it. I look forward to reading about it!