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Difficult login on windows #509

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opened 2025-12-29 02:19:19 +01:00 by adam · 5 comments
adam commented 2025-12-29 02:19:19 +01:00
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Originally created by @iszhi on GitHub (May 14, 2023).

Whenever I restarted my PC, I need spend hours to login my headscale server with tailscale client on my Windows PC.
I"m using the commend tailscale login --login-server https://my server.com:443 in the CMD. However, The response takes hours, and maybe days, I don't. What I did in the past is to restart the tailscale service, then try again, try again. Maybe uninstall tailscale, and install it again. and try again, try again. I don't remember how many times I tried. In the end, sometimes, I'm luck, I succeed, sometimes not. I don't know what's the problem.

Originally created by @iszhi on GitHub (May 14, 2023). Whenever I restarted my PC, I need spend hours to login my headscale server with tailscale client on my Windows PC. I"m using the commend tailscale login --login-server https://my server.com:443 in the CMD. However, The response takes hours, and maybe days, I don't. What I did in the past is to restart the tailscale service, then try again, try again. Maybe uninstall tailscale, and install it again. and try again, try again. I don't remember how many times I tried. In the end, sometimes, I'm luck, I succeed, sometimes not. I don't know what's the problem.
adam added the bug label 2025-12-29 02:19:19 +01:00
adam closed this issue 2025-12-29 02:19:19 +01:00
adam commented 2025-12-29 02:19:19 +01:00
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@luizvaz commented on GitHub (May 17, 2023):

I was facing the same issue.
Watching the logs, I found that the Headscale server was receiving the request correctly.
But it sent back the wrong address to the Windows client request.

After fixing the config file, everything started to work:
image

I used the following steps on Windows client

  • CMD as Admin
  • close Tailscale client
  • net stop Tailscale
  • delete the %appdata% local\tailscale folder
  • net start Tailscale
  • tailscale logout
  • tailscale up --accept-routes --login-server=https://<SERVER_URL>/ --unattended

Add the node using the key part to the WebUI or using the console command:
headscale nodes register --user USER --key nodekey:2ceb1d687ae8adaa9f3d1cd530a076cdfbfb8fd30ca87ebd78ea409d1e9e5360

For now, the log goes to the syslog file on the server.
You can watch it by using tail -f /var/log/syslog

@luizvaz commented on GitHub (May 17, 2023): I was facing the same issue. Watching the logs, I found that the Headscale server was receiving the request correctly. But it sent back the wrong address to the Windows client request. After fixing the config file, everything started to work: ![image](https://github.com/juanfont/headscale/assets/691612/a096e114-13a8-42d2-ae57-a2fcb87e3c53) I used the following steps on Windows client - `CMD `as Admin - close Tailscale client - `net stop Tailscale` - delete the %appdata% local\tailscale folder - `net start Tailscale` - `tailscale logout` - `tailscale up --accept-routes --login-server=https://<SERVER_URL>/ --unattended` Add the node using the key part to the WebUI or using the console command: `headscale nodes register --user USER --key nodekey:2ceb1d687ae8adaa9f3d1cd530a076cdfbfb8fd30ca87ebd78ea409d1e9e5360` For now, the log goes to the syslog file on the server. You can watch it by using `tail -f /var/log/syslog`
adam commented 2025-12-29 02:19:20 +01:00
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@iszhi commented on GitHub (May 17, 2023):

@luizvaz Thanks for the suggestions, but actually it didn't work for me. I cannot find any log about my windows client on my headscale server. And, after I clean up my client on my windows by following your suggestion, it still didn't work.

Actually, I think my server configuration is OK, because I also have another PC(ubuntu) at my home, and my Android phone and my Android Pad. All of the other devices works fine with my headscale server, only I cannot make it running on windows.

Or accurately I can not always promise I can run it on windows. Sometimes I can succeed without any reason, sometimes failed also without any reason.

I'm not an expert. I don't know how to debug it. Or are you interested in teaching me how to debug on my windows?

@iszhi commented on GitHub (May 17, 2023): @luizvaz Thanks for the suggestions, but actually it didn't work for me. I cannot find any log about my windows client on my headscale server. And, after I clean up my client on my windows by following your suggestion, it still didn't work. Actually, I think my server configuration is OK, because I also have another PC(ubuntu) at my home, and my Android phone and my Android Pad. All of the other devices works fine with my headscale server, only I cannot make it running on windows. Or accurately I can not always promise I can run it on windows. Sometimes I can succeed without any reason, sometimes failed also without any reason. I'm not an expert. I don't know how to debug it. Or are you interested in teaching me how to debug on my windows?
adam commented 2025-12-29 02:19:20 +01:00
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@juanfont commented on GitHub (May 17, 2023):

Hi :)

This is user support, please use our Discord channel.

@juanfont commented on GitHub (May 17, 2023): Hi :) This is user support, please use our Discord channel.
adam commented 2025-12-29 02:19:20 +01:00
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@wtdry commented on GitHub (Jan 16, 2024):

For Windows users, if you have multiple network adapters and cannot login, try temporarily disabling all other network adapters except the one you get the internet connection.

@wtdry commented on GitHub (Jan 16, 2024): For Windows users, if you have multiple network adapters and cannot login, try temporarily disabling all other network adapters except the one you get the internet connection.
adam commented 2025-12-29 02:19:20 +01:00
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@iszhi commented on GitHub (Jan 16, 2024):

@wtdry This may be a solution. I'll try it later.

@iszhi commented on GitHub (Jan 16, 2024): @wtdry This may be a solution. I'll try it later.
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