Trying to bring up any wireless interface on a network with WPA auth fails in a very peculiar way: the interface gets correctly configured, including WPA auth, DHCP manages to get an IP, and then an error about failure to bring up wpa_supplicant causes the interface to be brought down. wpa_supplicant: /sbin/wpa_supplicant daemon failed to start run-parts: /etc/network/if-pre-up.d/wpasupplicant exited with return code 1 ifup: failed to bring up *** Debugging `ifup -v wlan=***` gives the following log: --- /etc/network/interfaces.d/***: iface *** inet dhcp test wireless essid *** dns-search *** dns-nameserver 192.168.0.2 192.168.0.1 wpa-essid *** wpa-psk *** (and several other similar ones)--- /etc/network/interfaces.d/wlan: mapping wlan0 script /usr/sbin/guessnet-ifupdown map verbose: true map syslog: true map default: none map iwscan-tries: 5 map *** *** *** *** ***--- up and down scripts installed: /etc/network/if-down.d: total 12 -rwxr-xr-x 1 root root 1015 Apr 13 2015 avahi-autoipd -rwxr-xr-x 1 root root 372 Jul 4 2016 openvpn -rwxr-xr-x 1 root root 256 Jul 20 2013 resolvconf lrwxrwxrwx 1 root root 32 Aug 8 15:59 wpasupplicant -> ../../wpa_supplicant/ifupdown.sh /etc/network/if-post-down.d: total 4 lrwxrwxrwx 1 root root 23 Oct 10 2018 avahi-daemon -> ../if-up.d/avahi-daemon lrwxrwxrwx 1 root root 29 Jan 28 2019 bridge -> /lib/bridge-utils/ifupdown.sh lrwxrwxrwx 1 root root 25 Aug 8 15:59 hostapd -> ../../hostapd/ifupdown.sh -rwxr-xr-x 1 root root 1409 Mar 24 2016 wireless-tools lrwxrwxrwx 1 root root 32 Aug 8 15:59 wpasupplicant -> ../../wpa_supplicant/ifupdown.sh /etc/network/if-pre-up.d: total 12 lrwxrwxrwx 1 root root 29 Jan 28 2019 bridge -> /lib/bridge-utils/ifupdown.sh -rwxr-xr-x 1 root root 344 Jan 28 2014 ethtool lrwxrwxrwx 1 root root 25 Aug 8 15:59 hostapd -> ../../hostapd/ifupdown.sh -rwxr-xr-x 1 root root 4191 Sep 15 2018 wireless-tools lrwxrwxrwx 1 root root 32 Aug 8 15:59 wpasupplicant -> ../../wpa_supplicant/ifupdown.sh /etc/network/if-up.d: total 72 -rwxr-xr-x 1 root root 817 Jul 20 2013 000resolvconf -rwxr-xr-x 1 root root 4359 May 29 2016 00check-network-cable -rwxr-xr-x 1 root root 4341 Oct 1 2014 00check-network-cable.dpkg-old -rwxr-xr-x 1 root root 5521 Feb 6 2018 10check-duplicate-ip -rwxr-xr-x 1 root root 3848 Feb 6 2016 10check-duplicate-ip6 -rwxr-xr-x 1 root root 4919 Feb 6 2018 20static-routes -rwxr-xr-x 1 root root 4566 Apr 10 2014 30check-gateway -rwxr-xr-x 1 root root 923 Apr 13 2015 avahi-autoipd -rwxr-xr-x 1 root root 484 Mar 6 2013 avahi-daemon -rwxr-xr-x 1 root root 1685 Sep 22 2014 ethtool -rwxr-xr-x 1 root root 4937 Aug 22 17:39 mountnfs -rwxr-xr-x 1 root root 385 Jul 4 2016 openvpn lrwxrwxrwx 1 root root 32 Aug 8 15:59 wpasupplicant -> ../../wpa_supplicant/ifupdown.sh