# Avery Pennarun on Reddit (u/apenwarr)

Part of Founders and CEOs on Reddit, researched with Autumn (https://www.autumn.ai) from public sources. Updated 2026-11-07. Interactive version: https://www.autumn.ai/resources/founders-on-reddit/avery-pennarun

Avery Pennarun: Co-founder and CEO of Tailscale.

- Reddit account: [u/apenwarr](https://www.reddit.com/user/apenwarr/) (Personal account)
- How we know it's theirs: ["Tailscalar" flair from r/Tailscale's moderators, who flair Tailscale staff](https://www.reddit.com/r/Tailscale/comments/ie21y8/)
- Where they post, in the records we retrieved: r/Tailscale (21), r/programming (2), r/PleX (1)
- Known activity in the posts we found: 2011 to 2026
- Wikipedia: https://en.wikipedia.org/wiki/Tailscale

## Moments

### u/apenwarr in r/Tailscale, Aug 13, 2020 · Owned it

Replying to the post "Any plans for affordable family plan ?".

> [tailscale employee here] Yeah, we realize our pricing for friends-and-family use is pretty wrong. It's not that we're so bad at pricing, but rather that the software core doesn't make collaboration very easy yet, so we can't launch the plans we want. A flawed temporary workaround for this is to share a single login between multiple people's devices. ACLs also work in the Solo plan we we intend to continue allowing that.
>
> Stay tuned for something that makes a lot more sense. Our goal was never to try to extract tons of profit from home users. We just don't have a family-friendly underlying domain model working yet. Working on it!

Full thread: https://www.reddit.com/r/Tailscale/comments/i7x0x1/any_plans_for_affordable_family_plan/g1as9wc/ · 8 points as of Nov 7, 2026

### u/apenwarr in r/Tailscale, Jun 12, 2020 · The why

Replying to the post "hello.ipn.dev security".

> Actually the reason for the auto-added server on new network is to prevent a chicken-and-egg problem: after you install just one node, how do you know it's workng? If you install two nodes and they can't talk to each other, how do you know which one (or both) is broken?
>
> hello.ipn.dev helps with those questions, even if it's just a pingable server. But ping is hard to do on iOS or Android, and even on other OSes it requires people to drop to the command line, which can be tough, so we added an https server you can visit from a browser. And then we had to make the https server respond with something, so we added a (go-based) irc server kind of as a joke. (You can also connect using a regular irc client, which is another important test: most BeyondCorp-style products cannot proxy non-http traffic like irc.) More on testing with hello.ipn.dev here: https://tailscale.com/kb/1030/next-steps
>
> The irc server seems to have gotten misconstrued as a tech support mechanism lately, which isn't ideal (since we're a small team and can't monitor it full time), so we'll probably aim to shut it down and redirect people to freenode. But on the other hand, some users like it so we're hesitant to shut it down.
>
> Anyway, other commenters are correct that it's ACLed to not allow outgoing connections; it makes a good demo of a "one way" node. Nevertheless, users who are concerned about keeping their network private should remove the test node from their network, as described here: https://tailscale.com/kb/1073/hello-ipn-dev
>
> -- Avery@Tailscale

Full thread: https://www.reddit.com/r/Tailscale/comments/h79gmr/helloipndev_security/fumdx2f/ · 3 points as of Nov 7, 2026

### u/apenwarr in r/Tailscale, Aug 6, 2020 · Behind the scenes

Replying to the post "Tailscale is down?".

> Hmm, we aren't aware of any reason tailscale.com should have appeared down earlier today. We had one downtime incident for about an hour last weekend (our first! Postmortem coming soon). The reliability is generally pretty high.
>
> One thing we're proud of in the tailscale architecture is even if our public web site and login servers have outages, your network itself should keep being able to communicate, because the data is exchanged point-to-point. (The only part that wouldn't work during server downtime is adding new nodes, changing permissions, etc.) Obviously this doesn't excuse server downtime, but it's nice to have multiple layers of protection.

Full thread: https://www.reddit.com/r/Tailscale/comments/i4kpbq/tailscale_is_down/g0j29zr/ · 6 points as of Nov 7, 2026