Subj : Tailscale
To   : All
From : Javier Sturman
Date : Wed Nov 26 2025 13:01:26


   Hello everybody!

I have two tailscale instances running, one at work, one at home. To access my internal lan from work I added a route to the box I'm running tailscale at work and use it as a gateway, the same goes for any pc at home that wants to access anything from work I add a route to my house's tailscale instance.
When I use my notebook anywhere else from home or work, using a tailscale client I can connect to any PC from work but I can't access any from my home's lan. I need to do a ssh proxy jump to a PC from work to be able to connect for e.g. to my internal nas at home. I checked the routing tables and they seem fine. The tailscale instance running at home is inside a freebsd jail and the one at work runs on a raspbery pi.

This is the routing table from the tailscala jail at home:

tailscale:/root@[14:11] # netstat -r
Routing tables

Internet:
Destination        Gateway            Flags         Netif Expire
default            10.10.20.1         UGS            eth0
10.10.1.0/24       link#10            US       tailscale0
10.10.20.0/24      link#6             U              eth0
tailscale          link#7             UHS             lo0
100.73.205.72      link#7             UH              lo0
100.74.125.58      link#10            UHS      tailscale0
100.96.41.130      link#10            UHS      tailscale0
100.97.220.87      link#10            UHS      tailscale0
100.100.100.100    link#10            UHS      tailscale0
localhost          link#7             UH              lo0


Routes for work's tailscale:
jas@jumpbox:~ $ ip route show table all
10.10.20.0/24 dev tailscale0 table 52
100.73.205.72 dev tailscale0 table 52
100.74.125.58 dev tailscale0 table 52
100.97.220.87 dev tailscale0 table 52
100.100.100.100 dev tailscale0 table 52
default via 10.10.1.150 dev enxb827ebe4c166 src 10.10.1.130 metric 202
10.10.1.0/24 dev enxb827ebe4c166 proto dhcp scope link src 10.10.1.130 metric 202
local 10.10.1.130 dev enxb827ebe4c166 table local proto kernel scope host src 10.10.1.130
broadcast 10.10.1.255 dev enxb827ebe4c166 table local proto kernel scope link src 10.10.1.130
local 100.96.41.130 dev tailscale0 table local proto kernel scope host src 100.96.41.130
local 127.0.0.0/8 dev lo table local proto kernel scope host src 127.0.0.1
local 127.0.0.1 dev lo table local proto kernel scope host src 127.0.0.1
broadcast 127.255.255.255 dev lo table local proto kernel scope link src 127.0.0.1
fd7a:115c:a1e0::53 dev tailscale0 table 52 metric 1024 pref medium
fd7a:115c:a1e0::/48 dev tailscale0 table 52 metric 1024 pref medium
::1 dev lo proto kernel metric 256 pref medium
fd7a:115c:a1e0:ab12:4843:cd96:6260:2982 dev tailscale0 proto kernel metric 256 pref medium
fe80::/64 dev enxb827ebe4c166 proto kernel metric 256 pref medium
fe80::/64 dev tailscale0 proto kernel metric 256 pref medium
local ::1 dev lo table local proto kernel metric 0 pref medium
local fd7a:115c:a1e0:ab12:4843:cd96:6260:2982 dev tailscale0 table local proto kernel metric 0 pref medium
anycast fe80:: dev enxb827ebe4c166 table local proto kernel metric 0 pref medium
anycast fe80:: dev tailscale0 table local proto kernel metric 0 pref medium
local fe80::50e9:d445:3ccf:96ae dev enxb827ebe4c166 table local proto kernel metric 0 pref medium
local fe80::61c8:7d2b:7b80:b0ba dev tailscale0 table local proto kernel metric 0 pref medium
multicast ff00::/8 dev enxb827ebe4c166 table local proto kernel metric 256 pref medium
multicast ff00::/8 dev tailscale0 table local proto kernel metric 256 pref medium

Any ideas what might be the problem?

Javier


--- GoldED+/BSD 1.1.5-b20170303-b20170303 + HPT 1.9.0 + Binkd 1.1a-115
 * Origin: FIDONODO DE JAS | ¯\_(O,O)_/¯ (86:700/10)

.