hm Ok, in this case, the problem was the suffix actually:

root@mantic:/etc/NetworkManager/system-connections# nmcli con load 
/etc/NetworkManager/system-connections/UPTOWN.guests
Could not load file '/etc/NetworkManager/system-connections/UPTOWN.guests'
root@mantic:/etc/NetworkManager/system-connections# mv 
/etc/NetworkManager/system-connections/UPTOWN.guests 
/etc/NetworkManager/system-connections/UPTOWN
root@mantic:/etc/NetworkManager/system-connections# nmcli con load 
/etc/NetworkManager/system-connections/UPTOWN
root@mantic:/etc/NetworkManager/system-connections# nmcli con show
NAME            UUID                                  TYPE      DEVICE
netplan-enp5s0  e1419a5e-5e1d-3fff-a17c-b2fc6d2cef99  ethernet  enp5s0
lo              e71fd408-7b42-49a1-af17-072edc915266  loopback  lo
UPTOWN.guests   491fa5c8-68ef-4140-8679-dca422f5c262  wifi      --
root@mantic:/etc/NetworkManager/system-connections#

It's considering the .guests a bad extension as far as I can see. Only
removing the .guests makes it loadable. So we shouldn't load only
.nmconnection files.

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https://bugs.launchpad.net/bugs/2039503

Title:
  package network-manager 1.44.2-1ubuntu1 failed to install/upgrade:
  installed network-manager package post-installation script subprocess
  returned error exit status 10

Status in network-manager package in Ubuntu:
  New
Status in network-manager source package in Mantic:
  New

Bug description:
  lunar to mantic upgrade, exciting to see output from network-manager
  postinst migrating connections to /etc/netplan one by one.  But then:

  Error: 491fa5c8-68ef-4140-8679-dca422f5c262 - no such connection profile.
  dpkg: error processing package network-manager (--configure):
   installed network-manager package post-installation script subprocess 
returned error exit status 10

  That UUID appears in a file /etc/NetworkManager/system-
  connections/UPTOWN.guests that hasn't been touched since 2015.

  Contents of the file were:

  [connection]
  id=UPTOWN.guests
  uuid=491fa5c8-68ef-4140-8679-dca422f5c262
  type=wifi

  [wifi]
  ssid=UPTOWN.guests
  mode=infrastructure
  mac-address=E0:9D:31:09:84:54

  [ipv6]
  method=auto

  [ipv4]
  method=auto

  
  I've removed it from disk and the migration continued to completion.

  Then I got another failure on:

  [connection]
  id=belkin.1e4.guests
  uuid=2c77e512-f3e3-4238-b401-c94559cc6db0
  type=802-11-wireless

  [802-11-wireless]
  ssid=belkin.1e4.guests
  mode=infrastructure
  mac-address=00:24:D7:1F:EA:20

  [ipv6]
  method=auto

  [ipv4]
  method=auto

  Is it unhappy because of the . in the names?

  ProblemType: Package
  DistroRelease: Ubuntu 23.10
  Package: network-manager 1.44.2-1ubuntu1
  ProcVersionSignature: Ubuntu 6.2.0-34.34-generic 6.2.16
  Uname: Linux 6.2.0-34-generic x86_64
  NonfreeKernelModules: zfs zunicode zavl icp zcommon znvpair
  ApportVersion: 2.27.0-0ubuntu5
  Architecture: amd64
  CasperMD5CheckResult: unknown
  Date: Mon Oct 16 16:12:43 2023
  ErrorMessage: installed network-manager package post-installation script 
subprocess returned error exit status 10
  InstallationDate: Installed on 2019-12-23 (1393 days ago)
  InstallationMedia: Ubuntu 19.10 "Eoan Ermine" - Release amd64 (20191017)
  NetworkManager.state:
   [main]
   NetworkingEnabled=true
   WirelessEnabled=true
   WWANEnabled=true
  Python3Details: /usr/bin/python3.11, Python 3.11.6, python3-minimal, 3.11.4-5
  PythonDetails: N/A
  RebootRequiredPkgs: Error: path contained symlinks.
  RelatedPackageVersions:
   dpkg 1.22.0ubuntu1
   apt  2.7.3
  SourcePackage: network-manager
  Title: package network-manager 1.44.2-1ubuntu1 failed to install/upgrade: 
installed network-manager package post-installation script subprocess returned 
error exit status 10
  UpgradeStatus: Upgraded to mantic on 2023-10-16 (0 days ago)
  nmcli-nm:
   RUNNING  VERSION  STATE      STARTUP  CONNECTIVITY  NETWORKING  WIFI-HW  
WIFI     WWAN-HW  WWAN    
   running  1.44.2   connected  started  full          enabled     enabled  
enabled  missing  enabled

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