diff --git a/nixos/modules/tasks/auto-upgrade.nix b/nixos/modules/tasks/auto-upgrade.nix
index 7028c0be444d..8bb445db9352 100644
--- a/nixos/modules/tasks/auto-upgrade.nix
+++ b/nixos/modules/tasks/auto-upgrade.nix
@@ -114,6 +114,27 @@ in
         '';
       };
 
+      rebootTriggers = lib.mkOption {
+        type = lib.types.listOf lib.types.pathInStore;
+        default = [ ];
+        description = ''
+          List of derivations that will cause an auto-reboot when changed when
+          {option}`system.autoUpgrade.allowReboot` is set to true.
+        '';
+        defaultText = lib.literalExpression ''
+          [
+            config.system.build.initialRamdisk
+            config.system.build.kernel
+            config.hardware.firmware
+            (pkgs.writeTextFile {
+              name = "kernel-params";
+              text = lib.concatStringsSep " " config.boot.kernelParams;
+            })
+          ]
+          ++ config.system.switch.inhibitors
+        '';
+      };
+
       randomizedDelaySec = lib.mkOption {
         default = "0";
         type = lib.types.str;
@@ -197,133 +218,205 @@ in
 
   };
 
-  config = lib.mkIf cfg.enable {
+  config = lib.mkMerge [
 
-    assertions = [
-      {
-        assertion = !((cfg.channel != null) && (cfg.flake != null));
-        message = ''
-          The options 'system.autoUpgrade.channel' and 'system.autoUpgrade.flake' cannot both be set.
-        '';
-      }
-      {
-        assertion = (cfg.runGarbageCollection -> config.nix.enable);
-        message = ''
-          The option 'system.autoUpgrade.runGarbageCollection = true' requires 'nix.enable = true'.
-        '';
-      }
-    ];
-
-    system.autoUpgrade.flags = (
-      if cfg.flake == null then
-        [ "--no-build-output" ]
-        ++ lib.optionals (cfg.channel != null) [
-          "-I"
-          "nixpkgs=${cfg.channel}/nixexprs.tar.xz"
+    {
+      system = {
+        autoUpgrade.rebootTriggers = [
+          config.system.build.initialRamdisk
+          config.system.build.kernel
+          config.hardware.firmware
+          (pkgs.writeTextFile {
+            name = "kernel-params";
+            text = lib.concatStringsSep " " config.boot.kernelParams;
+          })
         ]
-      else
-        [
-          "--refresh"
-          "--flake ${cfg.flake}"
-        ]
-    );
+        ++ config.system.switch.inhibitors;
 
-    systemd.services.nixos-upgrade = {
-      description = "NixOS Upgrade";
+        systemBuilderCommands = ''
+          ln -s ${config.system.build.rebootTriggers} $out/reboot-triggers
+        '';
 
-      restartIfChanged = false;
-      unitConfig.X-StopOnRemoval = false;
-      unitConfig.OnSuccess = lib.optional (
-        cfg.runGarbageCollection && config.nix.enable
-      ) "nix-gc.service";
+        build.rebootTriggers = pkgs.writeTextFile {
+          name = "reboot-triggers";
+          text = lib.concatMapStringsSep "\n" (drv: drv.outPath) config.system.autoUpgrade.rebootTriggers;
+        };
+      };
+    }
 
-      serviceConfig.Type = "oneshot";
-
-      environment =
-        config.nix.envVars
-        // {
-          inherit (config.environment.sessionVariables) NIX_PATH;
-          HOME = "/root";
+    (lib.mkIf cfg.enable {
+      assertions = [
+        {
+          assertion = !((cfg.channel != null) && (cfg.flake != null));
+          message = ''
+            The options 'system.autoUpgrade.channel' and 'system.autoUpgrade.flake' cannot both be set.
+          '';
+        }
+        {
+          assertion = (cfg.runGarbageCollection -> config.nix.enable);
+          message = ''
+            The option 'system.autoUpgrade.runGarbageCollection = true' requires 'nix.enable = true'.
+          '';
         }
-        // config.networking.proxy.envVars;
-
-      path = with pkgs; [
-        coreutils
-        gnutar
-        xz.bin
-        gzip
-        gitMinimal
-        config.nix.package.out
-        config.programs.ssh.package
       ];
 
-      script =
-        let
-          nixos-rebuild = "${config.system.build.nixos-rebuild}/bin/nixos-rebuild";
-          date = "${pkgs.coreutils}/bin/date";
-          readlink = "${pkgs.coreutils}/bin/readlink";
-          shutdown = "${config.systemd.package}/bin/shutdown";
-          upgradeFlag = lib.optional (cfg.channel == null && cfg.upgrade) "--upgrade";
-        in
-        if cfg.allowReboot then
-          ''
-            ${nixos-rebuild} boot ${toString (cfg.flags ++ upgradeFlag)}
-            booted="$(${readlink} /run/booted-system/{initrd,kernel,kernel-modules})"
-            built="$(${readlink} /nix/var/nix/profiles/system/{initrd,kernel,kernel-modules})"
-
-            ${lib.optionalString (cfg.rebootWindow != null) ''
-              current_time="$(${date} +%H:%M)"
-
-              lower="${cfg.rebootWindow.lower}"
-              upper="${cfg.rebootWindow.upper}"
-
-              if [[ "''${lower}" < "''${upper}" ]]; then
-                if [[ "''${current_time}" > "''${lower}" ]] && \
-                   [[ "''${current_time}" < "''${upper}" ]]; then
-                  do_reboot="true"
-                else
-                  do_reboot="false"
-                fi
-              else
-                # lower > upper, so we are crossing midnight (e.g. lower=23h, upper=6h)
-                # we want to reboot if cur > 23h or cur < 6h
-                if [[ "''${current_time}" < "''${upper}" ]] || \
-                   [[ "''${current_time}" > "''${lower}" ]]; then
-                  do_reboot="true"
-                else
-                  do_reboot="false"
-                fi
-              fi
-            ''}
-
-            if [ "''${booted}" = "''${built}" ]; then
-              ${nixos-rebuild} ${cfg.operation} ${toString cfg.flags}
-            ${lib.optionalString (cfg.rebootWindow != null) ''
-              elif [ "''${do_reboot}" != true ]; then
-                echo "Outside of configured reboot window, skipping."
-            ''}
-            else
-              ${shutdown} -r +1
-            fi
-          ''
+      system.autoUpgrade.flags = (
+        if cfg.flake == null then
+          [ "--no-build-output" ]
+          ++ lib.optionals (cfg.channel != null) [
+            "-I"
+            "nixpkgs=${cfg.channel}/nixexprs.tar.xz"
+          ]
         else
-          ''
-            ${nixos-rebuild} ${cfg.operation} ${toString (cfg.flags ++ upgradeFlag)}
-          '';
+          [
+            "--refresh"
+            "--flake ${cfg.flake}"
+          ]
+      );
 
-      startAt = cfg.dates;
+      systemd.services.nixos-upgrade = {
+        description = "NixOS Upgrade";
 
-      after = [ "network-online.target" ];
-      wants = [ "network-online.target" ];
-    };
+        restartIfChanged = false;
+        unitConfig.X-StopOnRemoval = false;
+        unitConfig.OnSuccess = lib.optional (
+          cfg.runGarbageCollection && config.nix.enable
+        ) "nix-gc.service";
 
-    systemd.timers.nixos-upgrade = {
-      timerConfig = {
-        RandomizedDelaySec = cfg.randomizedDelaySec;
-        FixedRandomDelay = cfg.fixedRandomDelay;
-        Persistent = cfg.persistent;
+        serviceConfig.Type = "oneshot";
+
+        environment =
+          config.nix.envVars
+          // {
+            inherit (config.environment.sessionVariables) NIX_PATH;
+            HOME = "/root";
+          }
+          // config.networking.proxy.envVars;
+
+        path = with pkgs; [
+          coreutils
+          gnutar
+          xz.bin
+          gzip
+          gitMinimal
+          config.nix.package.out
+          config.programs.ssh.package
+          config.system.build.nixos-rebuild
+          config.systemd.package
+        ];
+
+        script =
+          let
+            upgradeFlag = lib.optional (cfg.channel == null && cfg.flake == null) "--upgrade";
+          in
+          if cfg.allowReboot then
+            # bash
+            ''
+              echo "Running nixos-rebuild boot..."
+              new_configuration="$(
+                # For some reason we still get a newline here in the journal between the
+                # nixos-rebuild stderr output and us echoing the store path that was
+                # printed on stdout.
+                # This might have to do with the particular way in which systemd handles
+                # stdout/stderr, they are unix sockets and not normal streams.
+                store_path="$(nixos-rebuild boot ${toString (cfg.flags ++ upgradeFlag)})"
+                echo "$store_path" >&2
+                echo "$store_path"
+              )"
+              if [ -z "$new_configuration" ]; then
+                echo "Looks like nixos-rebuild failed... Aborting"
+                exit 1
+              fi
+              echo "New configuration is $new_configuration"
+              switch_to_new_configuration="$new_configuration"/bin/switch-to-configuration
+
+              ${lib.optionalString (cfg.rebootWindow != null) # bash
+                ''
+                  current_time="$(date +%H:%M)"
+
+                  lower="${cfg.rebootWindow.lower}"
+                  upper="${cfg.rebootWindow.upper}"
+
+                  if [[ "''${lower}" < "''${upper}" ]]; then
+                    if [[ "''${current_time}" > "''${lower}" ]] && [[ "''${current_time}" < "''${upper}" ]]; then
+                      do_reboot="true"
+                    else
+                      do_reboot="false"
+                    fi
+                  else
+                    # lower > upper, so we are crossing midnight (e.g. lower=23h, upper=6h)
+                    # we want to reboot if cur > 23h or cur < 6h
+                    if [[ "''${current_time}" < "''${upper}" ]] || [[ "''${current_time}" > "''${lower}" ]]; then
+                      do_reboot="true"
+                    else
+                      do_reboot="false"
+                    fi
+                  fi
+                ''
+              }
+
+              booted_triggers="$(realpath /run/booted-system)/reboot-triggers"
+              booted_triggers_sha="$(
+                if [ -f "$booted_triggers" ]; then
+                  sha256sum - < "$booted_triggers"
+                else
+                  echo 'none'
+                fi
+              )"
+
+              new_triggers="$(realpath "$new_configuration")/reboot-triggers"
+              new_triggers_sha="$(
+                if [ -f "$new_triggers" ]; then
+                  sha256sum - < "$new_triggers"
+                else
+                  echo 'none'
+                fi
+              )"
+
+              ${lib.optionalString (cfg.operation == "switch") # bash
+                ''
+                  echo "Running switch-to-configuration check..."
+                  if "$switch_to_new_configuration" check; then
+                    echo "Checking reboot triggers..."
+                    if [ "$new_triggers_sha" == "$booted_triggers_sha" ]; then
+                      echo "Switching into the new generation..."
+                      "$switch_to_new_configuration" ${cfg.operation}
+                      exit 0
+                    fi
+                  fi
+                ''
+              }
+              ${lib.optionalString (cfg.rebootWindow != null) # bash
+                ''
+                  if [ "''${do_reboot}" != true ]; then
+                    echo "Outside of configured reboot window, skipping."
+                    exit 0
+                  fi
+                ''
+              }
+              echo "Scheduling a reboot to activate the new generation"
+              systemctl reboot --when="+2min"
+            ''
+          else
+            # bash
+            ''
+              nixos-rebuild ${cfg.operation} ${toString (cfg.flags ++ upgradeFlag)}
+            '';
+
+        startAt = cfg.dates;
+
+        after = [ "network-online.target" ];
+        wants = [ "network-online.target" ];
       };
-    };
-  };
 
+      systemd.timers.nixos-upgrade = {
+        timerConfig = {
+          RandomizedDelaySec = cfg.randomizedDelaySec;
+          FixedRandomDelay = cfg.fixedRandomDelay;
+          Persistent = cfg.persistent;
+        };
+      };
+    })
+
+  ];
 }