Can't connect to XRDP from Windows to Ubuntu

Hi there!

I have two machines running Tailscale.

  • (1) odroid

  • (2) Dell Laptop

I have a xrdp server running on odroid that I can connect when in the same lan (at home).
When using Tailscale, I’m unable to connect to xrdp.

My ufw status is the following:
Status: active

To Action From


22/tcp ALLOW Anywhere
41641/udp ALLOW Anywhere
3478/udp ALLOW Anywhere
443 ALLOW Anywhere
3389 ALLOW Anywhere
41641/udp (v6) ALLOW Anywhere (v6)
3478/udp (v6) ALLOW Anywhere (v6)
443 (v6) ALLOW Anywhere (v6)
3389 (v6) ALLOW Anywhere (v6)

Using tcpdump on odroid, I can see the machines talking to each other:

sudo tcpdump port 3389 and ‘(tcp-syn|tcp-ack)!=0’

10:47:29.643571 IP odroid.ms-wbt-server > 100.125.39.35.52689: Flags [S.], seq 1215152845, ack 2289217118, win 29200, options [mss 1460,nop,nop,sackOK,nop,wscale 7], length 0
10:47:37.843933 IP odroid.ms-wbt-server > 100.125.39.35.52689: Flags [S.], seq 1215152845, ack 2289217118, win 29200, options [mss 1460,nop,nop,sackOK,nop,wscale 7], length 0
10:47:53.971938 IP odroid.ms-wbt-server > 100.125.39.35.52689: Flags [S.], seq 1215152845, ack 2289217118, win 29200, options [mss 1460,nop,nop,sackOK,nop,wscale 7], length 0


Using netstat on windows, I can see it sending syn packets:

netstat -aon 1 | findstr /R “3389 | 3389”
TCP 0.0.0.0:3389 0.0.0.0:0 LISTENING 1380
TCP [::]:3389 [::]:0 LISTENING 1380
UDP 0.0.0.0:3389 : 1380
UDP [::]:3389 : 1380


xrdp service is up and running on odroid

sudo systemctl status xrdp
● xrdp.service - xrdp daemon
Loaded: loaded (/lib/systemd/system/xrdp.service; enabled; vendor preset: enabled)
Active: active (running) since Wed 2022-09-28 10:44:11 -03; 14min ago
Docs: man:xrdp(8)
man:xrdp.ini(5)
Process: 725809 ExecStartPre=/bin/sh /usr/share/xrdp/socksetup (code=exited, status=0/SUCCESS)
Process: 725818 ExecStart=/usr/sbin/xrdp $XRDP_OPTIONS (code=exited, status=0/SUCCESS)
Main PID: 725819 (xrdp)
Tasks: 1 (limit: 3832)
Memory: 1.4M
CGroup: /system.slice/xrdp.service
└─725819 /usr/sbin/xrdp

Sep 28 10:44:10 odroid xrdp[725818]: (725818)(548439130128)[INFO ] address [0.0.0.0] port [3389] mode 4
Sep 28 10:44:10 odroid xrdp[725818]: (725818)(548439130128)[INFO ] listening to port 3389 on 0.0.0.0
Sep 28 10:44:10 odroid xrdp[725818]: (725818)(548439130128)[INFO ] xrdp_listen_pp done
Sep 28 10:44:10 odroid xrdp[725818]: (725818)(548439130128)[DEBUG] Closed socket 7 (AF_INET 0.0.0.0:3389)
Sep 28 10:44:10 odroid systemd[1]: xrdp.service: Can’t open PID file /run/xrdp/xrdp.pid (yet?) after start: Operation not permitted
Sep 28 10:44:11 odroid systemd[1]: Started xrdp daemon.
Sep 28 10:44:12 odroid xrdp[725819]: (725819)(548439130128)[INFO ] starting xrdp with pid 725819
Sep 28 10:44:12 odroid xrdp[725819]: (725819)(548439130128)[INFO ] address [0.0.0.0] port [3389] mode 4
Sep 28 10:44:12 odroid xrdp[725819]: (725819)(548439130128)[INFO ] listening to port 3389 on 0.0.0.0
Sep 28 10:44:12 odroid xrdp[725819]: (725819)(548439130128)[INFO ] xrdp_listen_pp done


Firewall is disabled in Windows

Any thoughts on how to solve this issue?

Thanks!