Last month, we hosted our first-ever Seattle meetup and, wow. I’m still buzzing!
We had a full house 30 minutes before the event even started (shoutout to everyone who showed up early, we see you, we love you). We had pizza and custom swag, including embroidered Tailscale patches with the Seattle skyline. We also hosted a grumpy fruit mascot. It was, in a word, perfect.
Okay, maybe a few more words…
Space Needles, Sidecars, swag and slander
This wasn’t just any tech meetup it was a celebration of the people who make Tailscale what it is.
We had an awesome lineup of speakers:
- Wes Payne, co-host of Linux Unplugged, kicked things off with a look at using Tailscale Sidecars for NixOS services. Smart, sharp, and pure open source energy.
- Dan Mills, Philip Taron (one of our Tailscale Insiders), and yes, Grumpquat, Qumulo’s mascot, brought the storage love and gave us a talk on infrastructure and some hilarious learnings along the way.
- Brad Fitzpatrick from the Tailscale team closed the night by airing our dirty laundry. No, really - he shared what he wishes was different within the Tailscale product (in the most constructive, classic-Brad way possible).
The audience brought thoughtful, curious questions that sparked some of the best conversations of the night. We had so many great conversations going that we didn’t want to leave and had to be gently kicked out of the space when it was time to wrap up.
The Meetup Energy Continues
The response in Seattle has us thinking. What happened in Seattle shouldn’t stay in Seattle. Let’s do this again.
We’d love to support more Tailscale meetups around the world. If you’re interested in organizing something locally (big or small), fill out this form and let us know.
If instead you are interested in speaking at one of the Meetups we plan to host please let us know your interest here.
Now Introducing: The Tailscale Insiders 🚀
While all this was happening, something else exciting was quietly taking shape: the Tailscale Insiders program.
We opened up applications in April this year expecting maybe a few dozen replies. We got over 500. From folks running homelabs and side projects to people deploying Tailscale at massive scale inside orgs - we were floored.
In the end, we decided to start small, welcoming 17 amazing Insiders into the first cohort. When people asked us what makes the “perfect Insider,” we didn’t really have an easy answer, and that’s kind of the point. We wanted a group with diverse backgrounds, perspectives, and passions. And that’s exactly what we got.
Some Insiders are writing blogs, some speaking about Tailscale at events, some are testing early features with us, others are giving the kind of thoughtful product feedback that makes our engineers cheer (and occasionally cry, in a good way).
We’re already learning a ton, and we’re just getting started. More on what’s next soon.
Still accepting applications
While we don't have a perfect timeline on when we will accept more people into the program, we are still accepting applications that will be waitlisted.
It's well documented that folks from historically marginalized communities often hold back from applying to opportunities unless they meet every single requirement. We encourage you to break that statistic. We’re building a community that reflects a range of voices, backgrounds, and experiences.
Here is some content written by our Insiders!
🔐 Networking and Access Control
- Breaking through CGNAT with Tailscale and Caddy - Yash Garg
- Tailscale: Subnet Router & Remote Services Access - Martial Michel
- ACL example for one-way communication - caolle
- Master Tailscale ACLs for Enterprise Environments - Himanshu Mahajan
⚙️ Automation and Deployment
- Deploying Tailscale Automatically to New Proxmox VMs - Hazel Thomas
- Example systemD One-Shot Service for UDPGro Optimization - caolle
- Cloud-init + Raspberry Pi Clock Issues with Tailscale - Elliot Blackburn
🌐 Remote Management
- Remote Router Access with Tailscale - Yash Garg
Spot the Insiders on Reddit!
You’ll now find Tailscale Insiders hanging out in our Reddit community, marked with a pink ‘Tailscale Insider’ tag. These are trusted community members who love diving deep on all things Tailscale. They might share experiments, answer questions, or surface great ideas. Say hi when you see them around!
A big thanks to everyone who’s been showing up, online, IRL, and everywhere in between.
Whether you’re helping someone troubleshoot on Reddit, DMing us your wildest feature request, or just quietly building something cool with Tailscale, you are part of this.
We’re building something special together. Stay tuned and stay connected. ❤️
Natasha
Community @ Tailscale
Natasha Sawires
