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I know I'm not supposed to run do-release-upgrade in WSL, but I did it anyway. The upgrade itself went without errors, but any attempt to run sudo returns:

sudo: no tty present and no askpass program specified

The output of ls -l /dev as a regular user:

ls: cannot access 'lxss': Operation not permitted

ls: random: Invalid argument

ls: tty: Invalid argument

ls: tty0: Invalid argument

total 0

drwxr-xr-x 2 root     root      0 Aug 15 19:27 block

lrwxrwxrwx 1 root     root     13 Aug 15 19:27 fd -> /proc/self/fd

crw------- 1 root     root   0, 0 Aug 15 19:32 kmsg

c????????? ? ?        ?         ?            ? lxss

crw-rw-rw- 1 root     root   1, 3 Dec 31  1969 null

crw-rw-rw- 0 root     tty    5, 2 Aug 15 19:28 ptmx

drwxr-xr-x 0 root     root      0 Aug 15 19:27 pts

crw-rw-rw- 1 root     root   1, 8 Aug 15 19:32 random

lrwxrwxrwx 1 root     root      8 Aug 15 19:27 shm -> /run/shm

lrwxrwxrwx 1 root     root     15 Aug 15 19:27 stderr -> /proc/self/fd/2

lrwxrwxrwx 1 root     root     15 Aug 15 19:27 stdin -> /proc/self/fd/0

lrwxrwxrwx 1 root     root     15 Aug 15 19:27 stdout -> /proc/self/fd/1

crw--w---- 0 me tty  136, 0 Dec 31  1969 tty

crw-rw-rw- 1 root     tty    4, 0 Aug 15  2016 tty0

crw------- 1 me tty    4, 1 Aug 15  2016 tty1

crw-rw-rw- 1 root     root   1, 9 Aug 15 19:32 urandom

crw-rw-rw- 1 root     root   0, 0 Aug 15 19:32 zero

Running as root(using lxrun.exe/setdefaultuser) returns the same thing.

I know I can just reinstall Ubuntu, but I'm still curious as to what might be causing the problem and if there's an easy fix.

Oh- and date returns Mon Aug 15 19:45:49 DST 2016, like it should.

What might help as an alternative to downloading older packages:

• Log in as Root, via lxrun /setdefaultuser root, or (if you have not upgraded yet) sudo su
  


• Set a password for the Root user via passwd
  

Now you can always switch to root by simply using su root and entering the password you have set, without having to toggle the default user via lxrun.

As an alternative, you can prevent sudo from requiring a password at all, as mentioned in several answers here:

To prevent sudo from asking a password at all, you can add the following line at the end of your /etc/sudoers file (use visudo as root to edit the file)

<username> ALL=(ALL) NOPASSWD: ALL

Be advised, this will cause sudo to no longer ask for a password at all, when executing any Sudo command. If you want to limit the programs that can be used using sudo, add the full path to the binaries (comma separated) instead of the final ALL, eg.:

<username> ALL=(ALL) NOPASSWD: /usr/sbin/cron, /usr/sbin/visudo

Found a solution here:

From cmd:

lxrun /setdefaultuser root

From bash as root:

wget http://mirrors.kernel.org/ubuntu/pool/main/s/sudo/sudo_1.8.9p5-1ubuntu1.1_amd64.deb

wget http://mirrors.kernel.org/ubuntu/pool/main/p/procps/procps_3.3.9-1ubuntu2_amd64.deb

wget http://mirrors.kernel.org/ubuntu/pool/main/s/strace/strace_4.8-1ubuntu5_amd64.deb

dpkg -i sudo_1.8.9p5-1ubuntu1.1_amd64.deb

dpkg -i procps_3.3.9-1ubuntu2_amd64.deb

dpkg -i strace_4.8-1ubuntu5_amd64.deb

Don't forget to set your non-root default user after your done!

lxrun /setdefaultuser <your user>

From cmd:

ubuntu config --default-user root

To run WSL in the current Windows command prompt

ubuntu.exe

To see the last three users added to the Ubuntu system

tail -3 /etc/passwd

To change the password for user01

passwd user01

To exit WSL

exit