When I talk to Tailscale users online, at conferences, or in the wild, I hear lots of different stories of how they got started with the service. In some cases, Tailscale enabled them to do something they’d never realized was possible. In others, they had some existing legacy VPN solution and were starting to really run into the rough edges of it.
Nobody talks to more users in those two camps than Chris, our director of new business sales. In a recent blog post, Chris distills some of the business challenges and pain points that teams face before kicking off an evaluation of Tailscale. Sometimes it’s exciting news, like growing business operations (🎉). Sometimes it’s tending to team members getting grumpy with legacy VPN performance problems (😡).
If any of those sound familiar, you may be interested in an upcoming free, no-pitch webinar about migrating to Tailscale. You’ll find more info about upcoming events, alongside our regular updates and community links, in this month’s edition of the newsletter.
👉 We’d love to hear your thoughts on Tailscale. Filling out this feedback form helps us build a better product for you and other users.
Product Updates
Video: Prometheus monitoring for Tailscale clients
Network administrators can now monitor devices in their Tailscale network using Prometheus and our new client metrics feature, which provides connection data in a standard and ingestible format. That combination brings enterprise-grade visibility to your tailnet, making it easy to track performance, spot trends, and set up alerts.
Maintain security for your Tailscale secrets with GitHub
We’ve rolled out a secret scanning integration between Tailscale and GitHub, the world’s largest source code host. This collaborative effort marks our fourth secret scanning partnership established as part of continual efforts to secure customers’ tailnets.
Tailscale patterns from the field: Real-world enterprise use cases
In the second part of the two-part series introduced above, Chris walks through patterns that he’s seen from customers actually deploying Tailscale. Of course every user has different needs, but over time, and after talking to lots of customers, some general categories emerge.
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Community Highlights
Simon Willison: “Using a Tailscale exit node with GitHub Actions”
As an entry in his TIL series documenting things he’s learned, Simon Willison blogged about how to route traffic from a GitHub Action runner through an exit node running on an Apple TV in his home network.
Apple @ Work Podcast: “Catching up with Tailscale CEO Avery Pennarun”
Avery sat down with Bradley from 9 to 5 Mac’s Apple @ Work podcast to talk about how Tailscale compares to legacy VPNs, and a new MDM integration for fleets of Apple devices.
TidBITS: “Tailscale Gives You Remote Access to Your LAN from Anywhere”
A hat trick on the Apple-related community links today! In this article for the venerable TidBITS, Glenn Fleishman talks about how he has come to use Tailscale to fill in the gaps left by the sunset of Back to My Mac.
Upcoming webinars and workshops
Replace Your Legacy VPN with Tailscale
March 5, 2025
Join our monthly webinar series to discover how Tailscale modernizes networking by addressing the limitations of legacy VPNs. We’ll explore key challenges, the right time to switch, and how Tailscale simplifies Zero Trust networking. We will also review guidance on planning a smooth migration for your organization.
Ask a Tailscale Expert
March 4, 2025
Join the Tailscale Solutions Engineer team for our interactive monthly office hours series. Our team will rotate through demos for new and existing features and answer common technical questions.
JIT Network Access: Demo and Q&A
Just-in-time (JIT) Network Access is an API-first solution to provide temporary, time-bound, and audited elevated access to resources within your Tailscale network (tailnet). Join Alex and Allen as they demo how to use our API to set up Just-in-time access and then answer your questions.
See all upcoming and on-demand webinars
Tailscale IRL
The Tailscale team is hitting the road! Come see us IRL at any of the upcoming following industry events:
Scale22X
Pasedena, CA | March 6-9
Come say hi! We are at booth #219 and our own Alex Kretzschmar, who you know from YouTube, is giving us a talk titled "Access self-hosted services securely from anywhere" Saturday, March 8 at 3:45pm in Room 105.
DevOps Live
London, UK | March 12-13
DevOps Days Chicago
Chicago, IL | March 19
KubeCon + CloudNativeCon EU
London, UK | April 1-4
RSAC Conference
San Fransisco, CA | April 28 - May 1
🚀Are you building something cool or exciting using Tailscale? We love hearing about how our customers use Tailscale for their personal setups or at the workplace. We want to share these examples with the broader Tailscale community. If interested, fill out this form, and we will share your experience in an upcoming newsletter.
Parker Higgins
