Note: This post is not meant to hate on Tailscale or its members. It’s just my own thoughts about my experience being an Insider. I am not going to share any of the people’s names I interacted with nor our private chats.

Tailscale is an amazing product. I have been using it for almost 4 years and I can’t go back to the traditional Wireguard setup. I really don’t have anything negative to say about the product itself.

I am generally a person that likes to socialize online, specifically chat and sometimes argue with strangers about things I am interested in. I like joining the communities of the projects I use and that’s what I did with Tailscale. I had been interested in becoming an insider for a long time but unfortunately my original application didn’t get accepted. However after a random chat with one of their Community Managers, I got in the Insider program.

The Insider program was cool, a lot of cool people that were actually interested in helping you try out new Tailscale features. Genuinely a fun experience. Unfortunately due to my other projects I didn’t have time to contribute code but I did try to help as much as possible by testing out new features and providing feedback.

One day, Tailscale released their border0 integration (quite a cool product) and announced their free trial waitlist. Sounded cool, so I went to sign-up and noticed something weird. The sign-up form had the following note in the bottom:

By continuing, I agree to receive news, offers, information about Tailscale products and services, and invitations to surveys, webinars and events from Tailscale. You can unsubscribe at any time. For more information, please see our Privacy Policy.

Now, I am generally not a crazy privacy advocate, but I was surprised since I have only seen such practices being utilized by less trusted companies in order to achieve some cheap advertising. Turns out that under GDPR Article 7 paragraph 4 this small note may be illegal. The GDPR states:

When assessing whether consent is freely given, utmost account shall be taken of whether, inter alia, the performance of a contract, including the provision of a service, is conditional on consent to the processing of personal data that is not necessary for the performance of that contract.

Which in other words means that if a company is forcing you to share your personal data to get access to a service and that data is not needed by the company to provide you that service, then the company essentially forces you to either agree to the advertising or prohibits you from using the service.

Now for Tailscale, I trust that they are an honest company and that they would use the email only for their own marketing but, since they link their privacy policy, they can very much state that they may share the data with whoever they want (not saying they do, but that doesn’t mean that it’s not possible).

First instinct was to let them know about it, so I shared the following messages in their new border0 channel:

1. form text quote I get the marketing part but to be honest I would like for this to be a checkbox.
2. 1. It’s a bit…sneaky?

What I didn’t expect was getting messaged by a moderator. The moderator instead of focusing on the feedback, focused on the word “sneaky” stating that it violates the Insider CoC and that it can reputational harm for Tailscale. I couldn’t really believe what I was reading because…why would I want to cause any kind of damage to Tailscale? There are a lot of ways to make such a small issue a big fuss and actually cause reputational harm, but my message wasn’t that.

I generally text in a very lax style and my messages never intend to be harsh or aggressive, just more to the fun side (maybe I should start using /s more). In any case, I answered to the moderator that I of course don’t intend to cause any damage to Tailscale - why would I be an Insider if that was my plan? - but at the same time I don’t believe that simply sharing my feedback publicly is bad. Sure, I am an Insider, but that doesn’t say anything about me. I don’t work at Tailscale, I am not part of their staff, I am just a guy with a badge that happens to try out new features faster than others. Never got a reply so I thought that it was just a bad day for the moderator and left it there.

In the following days I received a message from one of their Community Managers saying that I had been removed from their Insider program because my idea of an Insider didn’t align with theirs…what? This message caught me off guard, I never expected this to escalate to such level for a simple feedback message. Is that really a basis to remove someone from an Insider program? Is sharing our opinion publicly suddenly bad because we have a stupid badge next to our purple name? Are we supposed to praise Tailscale for their every move and do damage control for free? These are the questions I asked the responsible Community Manager but I unfortunately never got an answer.

The saddest thing is not that I got removed from the Insider program, but rather that they didn’t even fix the issue. Raised the issue on 2026-06-25 and to this day (2026-07-04) they haven’t changed a single thing. These are not the kind of issues you let collect dust for weeks, especially when the law might be involved.

This isn’t a post targeting the Community Manager or the moderator but rather it criticizes the way the entire Insider program works. We shouldn’t focus on the way feedback is being communicated (as long as its purpose is not to cause harm) but rather on the feedback itself. Just because we get access to an Insider program doesn’t mean we lose the right to communicate our thoughts publicly.