I have confirmed the fix using openssh-server 1:9.6p1-3ubuntu13.9 from
noble-proposed:

First, I confirmed the bug was present on this system:

root@noble:~# cat > /etc/ssh/sshd_config.d/custom.conf << EOF
> Port 1234
> Match LocalPort 22
    PasswordAuthentication no
EOF
root@noble:~# /lib/systemd/system-generators/sshd-socket-generator .
'Match LocalPort' in configuration but 'lport' not in connection test 
specification.

Then I installed openssh-server from noble-proposed:

root@noble:~# cat > /etc/apt/sources.list.d/proposed.sources << EOF
Types: deb
URIs: http://us.archive.ubuntu.com/ubuntu/
Suites: noble-proposed
Components: main universe
Signed-By: /usr/share/keyrings/ubuntu-archive-keyring.gpg
EOF
root@noble:~# apt update && apt install -t noble-proposed openssh-server -y
Get:1 http://us.archive.ubuntu.com/ubuntu noble-proposed InRelease [265 kB]
Hit:2 http://archive.ubuntu.com/ubuntu noble InRelease                          
                            
Get:3 http://archive.ubuntu.com/ubuntu noble-updates InRelease [126 kB]         
                            
Get:4 http://archive.ubuntu.com/ubuntu noble-backports InRelease [126 kB]       
                                      
Get:5 http://security.ubuntu.com/ubuntu noble-security InRelease [126 kB]
Get:6 http://archive.ubuntu.com/ubuntu noble/universe amd64 Packages [15.0 MB]
Get:7 http://us.archive.ubuntu.com/ubuntu noble-proposed/main amd64 Packages 
[206 kB]   
Get:8 http://us.archive.ubuntu.com/ubuntu noble-proposed/main Translation-en 
[54.1 kB]            
Get:9 http://us.archive.ubuntu.com/ubuntu noble-proposed/main amd64 Components 
[13.8 kB]                              
Get:10 http://us.archive.ubuntu.com/ubuntu noble-proposed/main amd64 c-n-f 
Metadata [3768 B]                  
Get:11 http://us.archive.ubuntu.com/ubuntu noble-proposed/universe amd64 
Packages [472 kB]                    
Get:12 http://us.archive.ubuntu.com/ubuntu noble-proposed/universe 
Translation-en [62.9 kB]                           
Get:13 http://us.archive.ubuntu.com/ubuntu noble-proposed/universe amd64 
Components [46.7 kB]                         
Get:14 http://us.archive.ubuntu.com/ubuntu noble-proposed/universe amd64 c-n-f 
Metadata [10.7 kB]                     
Get:15 http://security.ubuntu.com/ubuntu noble-security/main amd64 Packages 
[668 kB]                                  
Get:16 http://archive.ubuntu.com/ubuntu noble/universe Translation-en [5982 kB]
Get:17 http://archive.ubuntu.com/ubuntu noble/universe amd64 Components [3871 
kB]                
Get:18 http://archive.ubuntu.com/ubuntu noble/universe amd64 c-n-f Metadata 
[301 kB]               
Get:19 http://archive.ubuntu.com/ubuntu noble/multiverse amd64 Packages [269 
kB]                
Get:20 http://archive.ubuntu.com/ubuntu noble/multiverse Translation-en [118 
kB]           
Get:21 http://archive.ubuntu.com/ubuntu noble/multiverse amd64 Components [35.0 
kB]            
Get:22 http://archive.ubuntu.com/ubuntu noble/multiverse amd64 c-n-f Metadata 
[8328 B]               
Get:23 http://archive.ubuntu.com/ubuntu noble-updates/main amd64 Packages [916 
kB]               
Get:24 http://archive.ubuntu.com/ubuntu noble-updates/main Translation-en [206 
kB]       
Get:25 http://archive.ubuntu.com/ubuntu noble-updates/main amd64 Components 
[151 kB]   
Get:26 http://archive.ubuntu.com/ubuntu noble-updates/universe amd64 Packages 
[1036 kB]  
Get:27 http://archive.ubuntu.com/ubuntu noble-updates/universe Translation-en 
[260 kB]
Get:28 http://archive.ubuntu.com/ubuntu noble-updates/universe amd64 Components 
[364 kB]
Get:29 http://archive.ubuntu.com/ubuntu noble-updates/universe amd64 c-n-f 
Metadata [19.9 kB]
Get:30 http://archive.ubuntu.com/ubuntu noble-updates/restricted amd64 Packages 
[753 kB] 
Get:31 http://archive.ubuntu.com/ubuntu noble-updates/restricted Translation-en 
[150 kB]
Get:32 http://security.ubuntu.com/ubuntu noble-security/main Translation-en 
[128 kB]   
Get:33 http://archive.ubuntu.com/ubuntu noble-updates/restricted amd64 
Components [212 B]               
Get:34 http://archive.ubuntu.com/ubuntu noble-updates/multiverse amd64 Packages 
[30.1 kB]
Get:35 http://archive.ubuntu.com/ubuntu noble-updates/multiverse Translation-en 
[5884 B]           
Get:36 http://archive.ubuntu.com/ubuntu noble-updates/multiverse amd64 
Components [940 B]               
Get:37 http://archive.ubuntu.com/ubuntu noble-updates/multiverse amd64 c-n-f 
Metadata [552 B]
Get:38 http://archive.ubuntu.com/ubuntu noble-backports/main amd64 Components 
[208 B]  
Get:39 http://security.ubuntu.com/ubuntu noble-security/main amd64 Components 
[9004 B]                  
Get:40 http://security.ubuntu.com/ubuntu noble-security/universe amd64 Packages 
[822 kB]
Get:41 http://archive.ubuntu.com/ubuntu noble-backports/main amd64 c-n-f 
Metadata [112 B]
Get:42 http://archive.ubuntu.com/ubuntu noble-backports/universe amd64 Packages 
[14.2 kB]       
Get:43 http://archive.ubuntu.com/ubuntu noble-backports/universe Translation-en 
[12.1 kB]   
Get:44 http://archive.ubuntu.com/ubuntu noble-backports/universe amd64 
Components [19.9 kB]
Get:45 http://archive.ubuntu.com/ubuntu noble-backports/universe amd64 c-n-f 
Metadata [1104 B]      
Get:46 http://archive.ubuntu.com/ubuntu noble-backports/restricted amd64 
Components [212 B]
Get:47 http://archive.ubuntu.com/ubuntu noble-backports/restricted amd64 c-n-f 
Metadata [116 B]
Get:48 http://archive.ubuntu.com/ubuntu noble-backports/multiverse amd64 
Components [212 B]
Get:49 http://archive.ubuntu.com/ubuntu noble-backports/multiverse amd64 c-n-f 
Metadata [116 B]  
Get:50 http://security.ubuntu.com/ubuntu noble-security/universe Translation-en 
[177 kB]       
Get:51 http://security.ubuntu.com/ubuntu noble-security/universe amd64 
Components [51.9 kB]
Get:52 http://security.ubuntu.com/ubuntu noble-security/universe amd64 c-n-f 
Metadata [13.5 kB]
Get:53 http://security.ubuntu.com/ubuntu noble-security/restricted amd64 
Packages [719 kB]
Get:54 http://security.ubuntu.com/ubuntu noble-security/restricted 
Translation-en [143 kB]
Get:55 http://security.ubuntu.com/ubuntu noble-security/restricted amd64 
Components [212 B]
Get:56 http://security.ubuntu.com/ubuntu noble-security/multiverse amd64 
Packages [26.2 kB]
Get:57 http://security.ubuntu.com/ubuntu noble-security/multiverse 
Translation-en [4892 B]
Get:58 http://security.ubuntu.com/ubuntu noble-security/multiverse amd64 
Components [208 B]
Get:59 http://security.ubuntu.com/ubuntu noble-security/multiverse amd64 c-n-f 
Metadata [356 B]
Fetched 33.8 MB in 5s (7207 kB/s)                              
Reading package lists... Done
Building dependency tree... Done
Reading state information... Done
All packages are up to date.
Reading package lists... Done
Building dependency tree... Done
Reading state information... Done
The following additional packages will be installed:
  openssh-client openssh-sftp-server
Suggested packages:
  keychain libpam-ssh monkeysphere ssh-askpass molly-guard
The following packages will be upgraded:
  openssh-client openssh-server openssh-sftp-server
3 upgraded, 0 newly installed, 0 to remove and 33 not upgraded.
Need to get 1452 kB of archives.
After this operation, 7168 B disk space will be freed.
Get:1 http://us.archive.ubuntu.com/ubuntu noble-proposed/main amd64 
openssh-sftp-server amd64 1:9.6p1-3ubuntu13.9 [37.3 kB]
Get:2 http://us.archive.ubuntu.com/ubuntu noble-proposed/main amd64 
openssh-server amd64 1:9.6p1-3ubuntu13.9 [509 kB]
Get:3 http://us.archive.ubuntu.com/ubuntu noble-proposed/main amd64 
openssh-client amd64 1:9.6p1-3ubuntu13.9 [905 kB]
Fetched 1452 kB in 0s (6137 kB/s)      
Preconfiguring packages ...
(Reading database ... 37213 files and directories currently installed.)
Preparing to unpack .../openssh-sftp-server_1%3a9.6p1-3ubuntu13.9_amd64.deb ...
Unpacking openssh-sftp-server (1:9.6p1-3ubuntu13.9) over (1:9.6p1-3ubuntu13.8) 
...
Preparing to unpack .../openssh-server_1%3a9.6p1-3ubuntu13.9_amd64.deb ...
Unpacking openssh-server (1:9.6p1-3ubuntu13.9) over (1:9.6p1-3ubuntu13.8) ...
Preparing to unpack .../openssh-client_1%3a9.6p1-3ubuntu13.9_amd64.deb ...
Unpacking openssh-client (1:9.6p1-3ubuntu13.9) over (1:9.6p1-3ubuntu13.8) ...
Setting up openssh-client (1:9.6p1-3ubuntu13.9) ...
Setting up openssh-sftp-server (1:9.6p1-3ubuntu13.9) ...
Setting up openssh-server (1:9.6p1-3ubuntu13.9) ...
'Match LocalPort' in configuration but 'lport' not in connection test 
specification.
Processing triggers for man-db (2.12.0-4build2) ...
Processing triggers for ufw (0.36.2-6) ...
Scanning processes...                                                           
                                       

No services need to be restarted.

No containers need to be restarted.

No user sessions are running outdated binaries.

No VM guests are running outdated hypervisor (qemu) binaries on this
host.

Finally, I ran the test again to confirm the fix:

root@noble:~# /lib/systemd/system-generators/sshd-socket-generator .
root@noble:~# cat ssh.socket.d/addresses.conf 
# Automatically generated by sshd-socket-generator

[Socket]
ListenStream=
ListenStream=1234
root@noble:~# apt policy openssh-server
openssh-server:
  Installed: 1:9.6p1-3ubuntu13.9
  Candidate: 1:9.6p1-3ubuntu13.9
  Version table:
 *** 1:9.6p1-3ubuntu13.9 100
        100 http://us.archive.ubuntu.com/ubuntu noble-proposed/main amd64 
Packages
        100 /var/lib/dpkg/status
     1:9.6p1-3ubuntu13.8 500
        500 http://archive.ubuntu.com/ubuntu noble-updates/main amd64 Packages
        500 http://security.ubuntu.com/ubuntu noble-security/main amd64 Packages
     1:9.6p1-3ubuntu13 500
        500 http://archive.ubuntu.com/ubuntu noble/main amd64 Packages

-- 
You received this bug notification because you are a member of Ubuntu
Bugs, which is subscribed to Ubuntu.
https://bugs.launchpad.net/bugs/2076023

Title:
  Failed to apply 'Match' directive in sshd_config with sshd-socket-
  generator

To manage notifications about this bug go to:
https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/2076023/+subscriptions


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