Hmm, what I had used 'succesfully' was apprently pure chance that it did work that boot.
Apparently it is still the broken, and the cause has to be found within the systemd I guess. With the information of this bug: https://trac.transmissionbt.com/ticket/5421 Everything 'seems to be right' in /etc/systemd/system/multi-user.target.wants/transmission-daemon.service but still transmission-daemon is not able to reliable bind to the ip address. ** Bug watch added: Transmission Trac #5421 https://trac.transmissionbt.com/ticket/5421 -- You received this bug notification because you are a member of Desktop Packages, which is subscribed to transmission in Ubuntu. https://bugs.launchpad.net/bugs/1261192 Title: Incorrect start on condition in upstart script for transmission-daemon Status in transmission package in Ubuntu: Confirmed Bug description: Release: Ubuntu Server 13.10 x86_64 Package: transmission-daemon 2.82 After the system is booted transmission-daemon is not contactable on port 9091 using transmission-remote or the web interface. The daemon is however started and uploading/downloading. After the daemon is restarted everything works correctly. The 'start on' condition (in /etc/init/transmission-daemon.conf) currently reads as follows: start on (filesystem and net-device-up IFACE=lo) i.e. start after both the filesystem and loopback adapter are available. The transmission-daemon binds to 0.0.0.0:9091 on start up in order to listen for remote procedure calls and as such should wait for an adapter other than the loopback adapter to be available. The line should read as follows: start on (filesystem and net-device-up IFACE!=lo) PS At least I think that's what's going on (and this change has resolved my problem)... To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/transmission/+bug/1261192/+subscriptions -- Mailing list: https://launchpad.net/~desktop-packages Post to : desktop-packages@lists.launchpad.net Unsubscribe : https://launchpad.net/~desktop-packages More help : https://help.launchpad.net/ListHelp