Also, re-reading this revealed the bug has slightly changed:

Note this time around, the password seems to re-appear in the GUI after
being entered - however, it's not stored in the conf file, and I'm
promoted to enter it upon reboot, so it's now:

  - storing it somewhere (maybe somewhere preferrable to a globally readable 
file!)
  - and then not using it upon reboot.


After entering it in the conf file, it started working again, upon reboot.

Note that this version has been updated to:

root@stuart:/etc/pam.d# apt list network-manager
Listing... Done
network-manager/xenial-updates,now 1.2.2-0ubuntu0.16.04.3 amd64 
[installed,automatic]


So it's getting better, but not there yet.

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You received this bug notification because you are a member of Desktop
Packages, which is subscribed to network-manager in Ubuntu.
https://bugs.launchpad.net/bugs/1643737

Title:
  Network Manager doesn't use 802.1x password entered in GUI

Status in network-manager package in Ubuntu:
  Confirmed

Bug description:
  This is a bug that seems to constantly re-surface across multiple
  versions in Ubuntu, and I've seen it in other distributions as well.

  Scenario:
    I want to enable 802.1x on a wired (*not* wireless), ethernet connection. I 
enter my identity, my computer cert, my ca cert, my private key file, and my 
password for my private key. 

  What doesn't work:
  I confirm the password works by using openssl. NetworkManager does not save 
the password. When I am asked to re-enter it, the connection fails. I look in 
syslog, and it complains about the private key password being blank.

  Workaround:
  Open the file:

  /etc/NetworkManager/system-connections/[Your network connection]
  Example:
  $> vim /etc/NetworkManager/system-connections/Wired\ connection\ 1

  Add the field:
  private-key-password=[your password]

  Example:
  private-key-password=UtterlyPointlessGloballyReadableStoredInPlaintextPassword

  Save the file.

  Attempt to re-connect. (and it worked for me).
  Look in Network Manager UI, the password seems to now be stored.

  Expected behavior:
  Entering the password in the GUI works (i.e, it is saved to the file, or at 
least used temporarily when connecting, either way - the latter would be more 
secure)

  Additionally, this whole thing is pretty lame, because Network Manager
  restricts you to using an encrypted private key, but this is dumb,
  because the password is then stored in a globally readable file in
  plaintext. Or you can decide to not save a password, and enter every
  time in a gui that fails to use the password you type in.

  ProblemType: Bug
  DistroRelease: Ubuntu 16.04
  Package: network-manager 1.2.0-0ubuntu0.16.04.3
  ProcVersionSignature: Ubuntu 4.4.0-31.50-generic 4.4.13
  Uname: Linux 4.4.0-31-generic x86_64
  ApportVersion: 2.20.1-0ubuntu2.1
  Architecture: amd64
  CurrentDesktop: Unity
  Date: Mon Nov 21 17:52:44 2016
  IfupdownConfig:
   # interfaces(5) file used by ifup(8) and ifdown(8)
   auto lo
   iface lo inet loopback
  InstallationDate: Installed on 2016-11-21 (0 days ago)
  InstallationMedia: Ubuntu 16.04.1 LTS "Xenial Xerus" - Release amd64 
(20160719)
  IpRoute:
   default via 10.0.50.1 dev eno1  proto static  metric 100 
   10.0.50.0/23 dev eno1  proto kernel  scope link  src 10.0.50.207  metric 100 
   10.0.254.32 via 10.0.50.1 dev eno1  proto dhcp  metric 100 
   169.254.0.0/16 dev eno1  scope link  metric 1000
  IwConfig:
   lo        no wireless extensions.
   
   eno1      no wireless extensions.
  NetworkManager.state:
   [main]
   NetworkingEnabled=true
   WirelessEnabled=true
   WWANEnabled=true
  RfKill:
   
  SourcePackage: network-manager
  UpgradeStatus: No upgrade log present (probably fresh install)
  nmcli-con:
   NAME                UUID                                  TYPE            
TIMESTAMP   TIMESTAMP-REAL                   AUTOCONNECT  AUTOCONNECT-PRIORITY  
READONLY  DBUS-PATH                                   ACTIVE  DEVICE  STATE     
 ACTIVE-PATH                                        
   Wired connection 1  fcbffec0-f9e4-4405-acfa-1cd80dec7362  802-3-ethernet  
1479779500  Mon 21 Nov 2016 05:51:40 PM PST  yes          4294966297            
no        /org/freedesktop/NetworkManager/Settings/0  yes     eno1    activated 
 /org/freedesktop/NetworkManager/ActiveConnection/0
  nmcli-dev:
   DEVICE  TYPE      STATE      DBUS-PATH                                  
CONNECTION          CON-UUID                              CON-PATH              
                             
   eno1    ethernet  connected  /org/freedesktop/NetworkManager/Devices/0  
Wired connection 1  fcbffec0-f9e4-4405-acfa-1cd80dec7362  
/org/freedesktop/NetworkManager/ActiveConnection/0 
   lo      loopback  unmanaged  /org/freedesktop/NetworkManager/Devices/1  --   
               --                                    --
  nmcli-nm:
   RUNNING  VERSION  STATE      STARTUP  CONNECTIVITY  NETWORKING  WIFI-HW  
WIFI     WWAN-HW  WWAN    
   running  1.2.0    connected  started  full          enabled     enabled  
enabled  enabled  enabled

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