diff --git a/nixos/modules/services/networking/ssh/sshd.nix b/nixos/modules/services/networking/ssh/sshd.nix
index 702423ef09cd..bf2f5230c738 100644
--- a/nixos/modules/services/networking/ssh/sshd.nix
+++ b/nixos/modules/services/networking/ssh/sshd.nix
@@ -27,13 +27,11 @@ let
       mkValueString = mkValueStringSshd;
     } " ";});
 
-  configFile = settingsFormat.generate "config" cfg.settings;
-  sshconf = pkgs.runCommand "sshd.conf-validated" { nativeBuildInputs = [ validationPackage ]; } ''
+  configFile = settingsFormat.generate "sshd.conf-settings" cfg.settings;
+  sshconf = pkgs.runCommand "sshd.conf-final" { } ''
     cat ${configFile} - >$out <<EOL
     ${cfg.extraConfig}
     EOL
-
-    sshd -G -f $out
   '';
 
   cfg  = config.services.openssh;
@@ -576,6 +574,21 @@ in
         '')}
       '';
 
+    system.checks = [
+      (pkgs.runCommand "check-sshd-config"
+        {
+          nativeBuildInputs = [ validationPackage ];
+        } ''
+        ${concatMapStringsSep "\n"
+          (lport: "sshd -G -T -C lport=${toString lport} -f ${sshconf} > /dev/null")
+          cfg.ports}
+        ${concatMapStringsSep "\n"
+          (la: "sshd -G -T -C laddr=${la.addr},lport=${toString la.port} -f ${sshconf} > /dev/null")
+          cfg.listenAddresses}
+        touch $out
+      '')
+    ];
+
     assertions = [{ assertion = if cfg.settings.X11Forwarding then cfgc.setXAuthLocation else true;
                     message = "cannot enable X11 forwarding without setting xauth location";}
                   (let
diff --git a/nixos/tests/openssh.nix b/nixos/tests/openssh.nix
index 4083f5906d79..d771ffd3e0f7 100644
--- a/nixos/tests/openssh.nix
+++ b/nixos/tests/openssh.nix
@@ -52,6 +52,36 @@ in {
         };
       };
 
+    server_match_rule =
+      { ... }:
+
+      {
+        services.openssh = {
+          enable = true; listenAddresses = [ { addr = "127.0.0.1"; port = 22; } ];
+          extraConfig = ''
+            # Combined test for two (predictable) Match criterias
+            Match LocalAddress 127.0.0.1 LocalPort 22
+              PermitRootLogin yes
+
+            # Separate tests for Match criterias
+            Match User root
+              PermitRootLogin yes
+            Match Group root
+              PermitRootLogin yes
+            Match Host nohost.example
+              PermitRootLogin yes
+            Match LocalAddress 127.0.0.1
+              PermitRootLogin yes
+            Match LocalPort 22
+              PermitRootLogin yes
+            Match RDomain nohost.example
+              PermitRootLogin yes
+            Match Address 127.0.0.1
+              PermitRootLogin yes
+          '';
+        };
+      };
+
     client =
       { ... }: { };
 
@@ -114,5 +144,8 @@ in {
     with subtest("localhost-only"):
         server_localhost_only.succeed("ss -nlt | grep '127.0.0.1:22'")
         server_localhost_only_lazy.succeed("ss -nlt | grep '127.0.0.1:22'")
+
+    with subtest("match-rules"):
+        server_match_rule.succeed("ss -nlt | grep '127.0.0.1:22'")
   '';
 })