I do not have any other interfaces in /etc/network/interfaces, besides lo.

Thanks for the tip about systemctl -l status network-manager. There is a 
difference.

I ran systemctl -l status network-manager on two boots. In both cases, the USB 
dongle was already plugged in and was not touched. The first boot, I logged 
into Mate, and the wifi connected automatically:
● NetworkManager.service - Network Manager
     Loaded: loaded (/lib/systemd/system/NetworkManager.service; enabled; 
vendor preset: enabled)
     Active: active (running) since Sat 2020-03-28 13:40:43 PDT; 8min ago
       Docs: man:NetworkManager(8)
   Main PID: 584 (NetworkManager)
      Tasks: 4 (limit: 19014)
     Memory: 16.4M
     CGroup: /system.slice/NetworkManager.service
             └─584 /usr/sbin/NetworkManager --no-daemon

Mar 28 13:41:10 raptor NetworkManager[584]: <info>  [1585428070.4504] manager: 
NetworkManager state is now CONNECTED_LOCAL
Mar 28 13:41:10 raptor NetworkManager[584]: <info>  [1585428070.4514] manager: 
NetworkManager state is now CONNECTED_SITE
Mar 28 13:41:10 raptor NetworkManager[584]: <info>  [1585428070.4515] policy: 
set 'wln' (wlx1831bf53a3a2) as default for IPv4 routing and DNS
Mar 28 13:41:10 raptor NetworkManager[584]: <info>  [1585428070.4561] device 
(wlx1831bf53a3a2): Activation: successful, device activated.
...

Now the boot where network-manager repeatedly asked for the same password:
● NetworkManager.service - Network Manager
     Loaded: loaded (/lib/systemd/system/NetworkManager.service; enabled; 
vendor preset: enabled)
     Active: active (running) since Sat 2020-03-28 13:52:45 PDT; 36s ago
       Docs: man:NetworkManager(8)
   Main PID: 584 (NetworkManager)
      Tasks: 3 (limit: 19014)
     Memory: 17.5M
     CGroup: /system.slice/NetworkManager.service
             └─584 /usr/sbin/NetworkManager --no-daemon

Mar 28 13:52:55 raptor NetworkManager[584]: <info>  [1585428775.4776] Config: 
added 'key_mgmt' value 'WPA-PSK WPA-PSK-SHA256 FT-PSK'
Mar 28 13:52:55 raptor NetworkManager[584]: <info>  [1585428775.4776] Config: 
added 'psk' value '<hidden>'
Mar 28 13:52:55 raptor NetworkManager[584]: <info>  [1585428775.4916] device 
(wlx1831bf53a3a2): supplicant interface state: disconnected -> associating
Mar 28 13:52:55 raptor NetworkManager[584]: <info>  [1585428775.7019] device 
(wlx1831bf53a3a2): supplicant interface state: associating -> 4-way handshake
Mar 28 13:52:59 raptor NetworkManager[584]: <warn>  [1585428779.7193] 
sup-iface[0x55bfd02d69f0,wlx1831bf53a3a2]: connection disconnected (reason 2)
Mar 28 13:52:59 raptor NetworkManager[584]: <info>  [1585428779.7195] device 
(wlx1831bf53a3a2): supplicant interface state: 4-way handshake -> disconnected
Mar 28 13:52:59 raptor NetworkManager[584]: <info>  [1585428779.7210] device 
(wlx1831bf53a3a2): Activation: (wifi) disconnected during association, asking 
for new key
Mar 28 13:52:59 raptor NetworkManager[584]: <info>  [1585428779.7212] device 
(wlx1831bf53a3a2): state change: config -> need-auth (reason 
'supplicant-disconnect', sys-iface-state: 'managed')
Mar 28 13:52:59 raptor NetworkManager[584]: <info>  [1585428779.8236] device 
(wlx1831bf53a3a2): supplicant interface state: disconnected -> scanning
Mar 28 13:53:02 raptor NetworkManager[584]: <info>  [1585428782.0772] device 
(wlx1831bf53a3a2): supplicant interface state: scanning -> inactive


> On Mar 28, 2020, at 12:43, Brian <a...@cityscape.co.uk> wrote:
> 

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