TAILMON TAILMON v1.3.0 -Aug 24, 2025- WireGuard-based Tailscale Installer, Configurator and Monitor (Available in AMTM!)

[rung]

Had an autoupdate failure last night. Repeated from command line and got the following:

[Downloading New Tailscale Binary v1.88.1]

Updating Tailscale from 1.86.2 to 1.88.1; --yes given, continuing without prompts.
Downloading "https://pkgs.tailscale.com/stable/tailscale_1.88.1_arm64.tgz"
Download size: 31587566
Get "https://dl.tailscale.com/stable/tailscale_1.88.1_arm64.tgz": dial tcp [2a09:8280:1::a:1a71]:443: connect: cannot assign requested address
[Unable to Download Tailscale Binary...Exiting]

[Email notification was sent successfully (WARNING: Router unable to reach Tailscale Repository)]

Is it trying to connect to an ipv6 addresses? Note my network is ipv4 only

 

[swejuggalo]

Had an autoupdate failure last night. Repeated from command line and got the following:

[Downloading New Tailscale Binary v1.88.1]

Updating Tailscale from 1.86.2 to 1.88.1; --yes given, continuing without prompts.
Downloading "https://pkgs.tailscale.com/stable/tailscale_1.88.1_arm64.tgz"
Download size: 31587566
Get "https://dl.tailscale.com/stable/tailscale_1.88.1_arm64.tgz": dial tcp [2a09:8280:1::a:1a71]:443: connect: cannot assign requested address
[Unable to Download Tailscale Binary...Exiting]

[Email notification was sent successfully (WARNING: Router unable to reach Tailscale Repository)]

Is it trying to connect to an ipv6 addresses? Note my network is ipv4 only

Maybe the problem is Tailscale itself. I had one device acting as exit node that insisted on trying IPv6 with failures in the logs

 

[Viktor Jaep]

Had an autoupdate failure last night. Repeated from command line and got the following:

[Downloading New Tailscale Binary v1.88.1]

Updating Tailscale from 1.86.2 to 1.88.1; --yes given, continuing without prompts.
Downloading "https://pkgs.tailscale.com/stable/tailscale_1.88.1_arm64.tgz"
Download size: 31587566
Get "https://dl.tailscale.com/stable/tailscale_1.88.1_arm64.tgz": dial tcp [2a09:8280:1::a:1a71]:443: connect: cannot assign requested address
[Unable to Download Tailscale Binary...Exiting]

[Email notification was sent successfully (WARNING: Router unable to reach Tailscale Repository)]

Is it trying to connect to an ipv6 addresses? Note my network is ipv4 only

I've got IPv6 turned off at the router level and I didn't have any issue with the autoupdate last night. I do know that the nodes use encapsulated IPv6 when they talk to each other over the tailnet/wireguard network, but that shouldn't affect downloading an update. Any google results show anything about this issue?

 

[iTyPsIDg]

Has anyone used the site-to-site configuration? I have a rental property, and I want to be able to manage the router at the property from home. I imagine site-to-site is the best way to accomplish this.

I just started using Tailscale and Tailmon a couple of days ago.

 

[ColinTaylor]

Has anyone used the site-to-site configuration? I have a rental property, and I want to be able to manage the router at the property from home. I imagine site-to-site is the best way to accomplish this.

By site to site I think you're referring to LAN to LAN. If you just want to manage the remote router (and its LAN) that's not what you want. LAN to LAN would mean the people on the remote network would have access to your home network as well. Just the basic Tailscale setup should give you the access you need (although see previous posts regarding specific issues accessing the remote router's webUI).

 

[iTyPsIDg]

By site to site I think you're referring to LAN to LAN. If you just want to manage the remote router (and its LAN) that's not what you want. LAN to LAN would mean the people on the remote network would have access to your home network as well. Just the basic Tailscale setup should give you the access you need (although see previous posts regarding issues accessing the remote router's webUI).

I have a guest network configured for renters, but fair point. Yes, the main thing now is that I want to be able to manage the rental unit's router.

I did try to go through this thread quickly, but at 15 pages, I didn't see the webUI issues. I found that if I turn Tailscale on directly on my phone, I can SSH to either router without issue using the Tailscale IP; however, if my phone is connected to one of the routers and not using Tailscale itself, I can't seem to SSH to the routers.

 

[ColinTaylor]

I have a guest network configured for renters, but fair point. Yes, the main thing now is that I want to be able to manage the rental unit's router.

I did try to go through this thread quickly, but at 15 pages, I didn't see the webUI issues. I found that if I turn Tailscale on directly on my phone, I can SSH to either router without issue using the Tailscale IP; however, if my phone is connected to one of the routers and not using Tailscale itself, I can't seem to SSH to the routers.

We'd need more information on how Tailscale is installed on the remote system. Is it installed on an Asus router (via tailmon?). If so, is this router the internet gateway device? What Tailscale options are you using?

 

[iTyPsIDg]

Yes, I have a RT-AX86U running Tailmon at the rental and an RT-AX86U Pro running Tailmon at home. Here is a screenshot from the rental router (I'm currently onsite at the rental).

The LAN on the home router is 192.168.60.0/24.

 

[ColinTaylor]

I found that if I turn Tailscale on directly on my phone, I can SSH to either router without issue using the Tailscale IP; however, if my phone is connected to one of the routers and not using Tailscale itself, I can't seem to SSH to the routers.

Sorry, I think I may have missed the point here. Are you only concerned with SSH access to the router and not HTTP/S?

Regarding the connection working when your phone's Tailscale client is enabled but not when it's disabled - that's not something I'd considered as personally I would use a Tailscale client.

 

[iTyPsIDg]

Sorry, I think I may have missed the point here. Are you only concerned with SSH access to the router and not HTTP/S?

Regarding the connection working when your phone's Tailscale client is enabled but not when it's disabled - that's not something I'd considered as personally I would use a Tailscale client.

I would prefer both, but can live with just SSH (non-standard port).

I was hoping that the client running on both routers would allow me to connect from either network to the other. I'm setting up a new NAS now as well (on my home network), and was hoping I could use the NAS from anywhere with Tailscale (and from the main network on the rental router by only having Tailscale on the routers).

I hope I'm explaining this well.

I think maybe I need to set up some routes, but I'm really not sure. It seems like that may be the first step for me.

 

[ColinTaylor]

I would prefer both, but can live with just SSH (non-standard port).

I was hoping that the client running on both routers would allow me to connect from either network to the other. I'm setting up a new NAS now as well (on my home network), and was hoping I could use the NAS from anywhere with Tailscale (and from the main network on the rental router by only having Tailscale on the routers).

I hope I'm explaining this well.

I think maybe I need to set up some routes, but I'm really not sure. It seems like that may be the first step for me.

OK so this would indeed be a site to site setup as you want full access to each LAN in both directions.

This is not something I've tried myself and have no way of testing such a thing. At a minimum both routers would need to have --advertise-routes=<CIDR> --snat-subnet-routes=false --accept-routes set (and the corresponding permissions enabled in the Tailscale web console). Have a look at the documentation here.

 

[iTyPsIDg]

OK so this would indeed be a site to site setup as you want full access to each LAN in both directions.

This is not something I've tried myself and have no way of testing such a thing. At a minimum both routers would need to have --advertise-routes=<CIDR> --snat-subnet-routes=false --accept-routes set (and the corresponding permissions enabled in the Tailscale web console). Have a look at the documentation here.

It sounds like what I thought should be relatively simple may actually be complicated, so I think the best bet is to run Tailscale on whatever device I want to use.

That said, I would like to be able to access my NAS behind my main router running Tailscale from any client that is directly running Tailscale. I need to wait for the hard drives to arrive so I can see if that part is an issue. I would hope that as long as I'm advertising routes it should just work.

 

[rung]

I've got IPv6 turned off at the router level and I didn't have any issue with the autoupdate last night. I do know that the nodes use encapsulated IPv6 when they talk to each other over the tailnet/wireguard network, but that shouldn't affect downloading an update. Any google results show anything about this issue?

I tried again just now and it failed with a new error: "server misbehaving" referencing my isp dns address. So, as a shot in the dark, I enabled MagicDNS up in the web config area, tried a manual update, and it worked! I don't know what MagicDNS is, but I guess I need it.