Tailscale

Raised as a usability problem by 47 people on Hacker News over 8 years (2019–2026), in 35 threads.

People raised many different problems with Tailscale, but no single problem has yet been raised by 3 people in 3 different months and threads.

Unreviewed issues were grouped by machine: Claude Haiku labelled each comment as a usability complaint, named what it's about and summed up the problem in a line, and a small model grouped similar problems. Nobody has checked them by hand. Expect mistakes.

The newest 47 complaints

Internal services have huge delays and poor bandwidth, with no clear way to debug2026-10-12
Login forces confusing hardware-key and QR workarounds on the user's own phone2026-09-18
Recipients must install an app, create an account, and be added manually before accessing media2026-09-10
Interface is complicated and hard to figure out2026-07-29
Links randomly break over time because of how the service handles URLs2026-05-09
Passkey login can't make the owner of a GitHub-created tailnet, leaving stuck duplicate users2026-04-05
Launching the app from Applications shows only a menu bar icon, with no window to use2026-04-03
Menu bar icon can be hidden behind the notch on first launch, so users may not find the app2026-04-03
App is only reachable from the menu bar icon, with no regular window2026-04-03
Background connectivity app pops up intrusive windows and a complex menu bar detail card2026-04-02
Notch hides the menu bar icons, so users can't reach them2026-04-02
Quitting the configuration app unexpectedly also stops the Tailscale service2026-04-02
User couldn't tell the app wanted browser-based auth and couldn't find a config file2026-02-18
Button is disconnected from its modal and placed in a nonstandard location2026-02-18
Typing the Tailscale address autocompletes to the unrelated Tailwind site2026-01-08
Interface is sometimes tiring to use, especially search, and some decisions are counterintuitive2025-10-04
Hard to troubleshoot when something breaks outside the default setup2025-07-27
Devices unexpectedly require re-authentication and break workflows, with no way to disable expiry2025-06-12
Netfilter rules make the Linux routing table useless, so debugging forwarding is a nightmare2025-04-15
Setting up mobile clients for a custom control server is fiddly because the option is hidden2025-04-10
No alerts or tooling to diagnose subnet routing breakage or DERP fallback2025-04-08
Drains iPhone battery so badly while connected in background that it's unusable2025-04-04
CLI is limited and forces sharing the network stack with the service2024-12-26
Recent versions add so much latency that connections become unusable2024-10-24
Cannot enable SSH on a Mac when using the GUI app2024-09-08
Invited machine appears in admin console but cannot be pinged2024-07-26
Silently fails to start when a subnet address ends in 02023-01-18
Tunnels disappear until the UI is launched and manually reactivated2023-01-18
Client app doesn't show that the new Windows version is available2022-11-21
Text is light grey on white, so code sections are illegible2022-11-21
Docs don't say whether the client needs root, so user can't tell if it works without root2022-11-18
App drains battery or misbehaves, so user must toggle it off manually2022-11-18
Cannot switch users quickly or connect to multiple networks at once2022-10-20
Lack of email/password sign-in made setup take six months2022-10-20
Cannot run a normal VPN alongside Tailscale without adding latency via exit node2022-10-13
Asks for home/work/public network choice on every reboot2022-09-30
Same query returns different results each time, and an unclear 403 tailnet error appears2022-09-30
Tapping listed machines has confusing, unexpected behavior on mobile2022-08-15
Restricting SSH to Tailscale needs hand-coded firewall rules; documentation lacks the needed information2022-06-22
Unclear how browser login relates to the device being added; confusing sign-in chain2022-06-22
Requires using a browser for authentication, which the commenter finds horrible to use2022-06-22
On mobile, setup requires exchanging keys back and forth over a different medium, too complex for lay people2022-05-04
Configuring a custom control server is undocumented and hard to find2021-09-18
Can't find an easy way to migrate account or reliably clear settings remotely2021-08-02
Sessions expire by default, so things silently stop working unexpectedly2021-06-13
Can't find an Exit button; unclear how to close the application2020-03-23
Repeated reCAPTCHA verification after already entering email and confirming, creating unnecessary hoops2019-12-07