diff --git a/modules/services/aerospace/default.nix b/modules/services/aerospace/default.nix
index 531e7b220..56315fa66 100644
--- a/modules/services/aerospace/default.nix
+++ b/modules/services/aerospace/default.nix
@@ -3,13 +3,34 @@
   lib,
   pkgs,
   ...
-}:
-
-let
+}: let
   cfg = config.services.aerospace;
-
   format = pkgs.formats.toml { };
-  configFile = format.generate "aerospace.toml" cfg.settings;
+  filterAttrsRecursive = pred: set:
+    lib.listToAttrs (
+      lib.concatMap (
+        name: let
+          v = set.${name};
+        in
+          if pred v
+          then [
+            (lib.nameValuePair name (
+              if lib.isAttrs v
+              then filterAttrsRecursive pred v
+              else if lib.isList v
+              then
+                (map (i:
+                  if lib.isAttrs i
+                  then filterAttrsRecursive pred i
+                  else i) (lib.filter pred v))
+              else v
+            ))
+          ]
+          else []
+      ) (lib.attrNames set)
+    );
+  filterNulls = filterAttrsRecursive (v: v != null);
+  configFile = format.generate "aerospace.toml" (filterNulls cfg.settings);
 in
 
 {
@@ -17,7 +38,7 @@ in
     services.aerospace = with lib.types; {
       enable = lib.mkEnableOption "AeroSpace window manager";
 
-      package = lib.mkPackageOption pkgs "aerospace" { };
+      package = lib.mkPackageOption pkgs "aerospace" {};
 
       settings = lib.mkOption {
         type = submodule {
@@ -30,14 +51,14 @@ in
             };
             after-login-command = lib.mkOption {
               type = listOf str;
-              default = [ ];
+              default = [];
               description = "Do not use AeroSpace to run commands after login. (Managed by launchd instead)";
             };
             after-startup-command = lib.mkOption {
               type = listOf str;
-              default = [ ];
+              default = [];
               description = "Add commands that run after AeroSpace startup";
-              example = [ "layout tiles" ];
+              example = ["layout tiles"];
             };
             enable-normalization-flatten-containers = lib.mkOption {
               type = bool;
@@ -72,23 +93,100 @@ in
               description = "Default orientation for the root container.";
             };
             on-window-detected = lib.mkOption {
-              type = listOf str;
-              default = [ ];
-              description = "Commands to run every time a new window is detected.";
+              type = types.listOf (types.attrsOf types.anything);
+              default = [];
+              type = listOf (submodule {
+                options = {
+                  "if" = lib.mkOption {
+                    type = submodule {
+                      options = {
+                        app-id = lib.mkOption {
+                          type = nullOr str;
+                          default = null;
+                          description = "The application ID to match (optional).";
+                        };
+                        workspace = lib.mkOption {
+                          type = nullOr str;
+                          default = null;
+                          description = "The workspace name to match (optional).";
+                        };
+                        window-title-regex-substring = lib.mkOption {
+                          type = nullOr str;
+                          default = null;
+                          description = "Substring to match in the window title (optional).";
+                        };
+                        app-name-regex-substring = lib.mkOption {
+                          type = nullOr str;
+                          default = null;
+                          description = "Regex substring to match the app name (optional).";
+                        };
+                        during-aerospace-startup = lib.mkOption {
+                          type = nullOr bool;
+                          default = null;
+                          description = "Whether to match during aerospace startup (optional).";
+                        };
+                      };
+                    };
+                    default = {};
+                    description = "Conditions for detecting a window.";
+                  };
+                  check-further-callbacks = lib.mkOption {
+                    type = nullOr bool;
+                    default = null;
+                    description = "Whether to check further callbacks after this rule (optional).";
+                  };
+                  run = lib.mkOption {
+                    type = oneOf [str (listOf str)];
+                    example = ["move-node-to-workspace m" "resize-node"];
+                    description = "Commands to execute when the conditions match (required).";
+                  };
+                };
+              });
+              default = [];
+              example = [
+                {
+                  "if" = {
+                    app-id = "Another.Cool.App";
+                    workspace = "cool-workspace";
+                    window-title-regex-substring = "Title";
+                    app-name-regex-substring = "CoolApp";
+                    during-aerospace-startup = false;
+                  };
+                  check-further-callbacks = false;
+                  run = ["move-node-to-workspace m" "resize-node"];
+                }
+              ];
+              description = "Commands to run every time a new window is detected with optional conditions.";
+            };
+            workspace-to-monitor-force-assignment = lib.mkOption {
+              type = attrsOf (oneOf [int str (listOf str)]);
+              default = { };
+              description = ''
+                Map workspaces to specific monitors.
+                Left-hand side is the workspace name, and right-hand side is the monitor pattern.
+              '';
+              example = {
+                "1" = 1; # First monitor from left to right.
+                "2" = "main"; # Main monitor.
+                "3" = "secondary"; # Secondary monitor (non-main).
+                "4" = "built-in"; # Built-in display.
+                "5" = "^built-in retina display$"; # Regex for the built-in retina display.
+                "6" = ["secondary" "dell"]; # Match first pattern in the list.
+              };
             };
             on-focus-changed = lib.mkOption {
               type = listOf str;
-              default = [ ];
+              default = [];
               description = "Commands to run every time focused window or workspace changes.";
             };
             on-focused-monitor-changed = lib.mkOption {
               type = listOf str;
-              default = [ "move-mouse monitor-lazy-center" ];
+              default = ["move-mouse monitor-lazy-center"];
               description = "Commands to run every time focused monitor changes.";
             };
             exec-on-workspace-change = lib.mkOption {
               type = listOf str;
-              default = [ ];
+              default = [];
               example = [
                 "/bin/bash"
                 "-c"
@@ -106,7 +204,7 @@ in
             };
           };
         };
-        default = { };
+        default = {};
         example = lib.literalExpression ''
           {
             gaps = {
@@ -140,16 +238,16 @@ in
           message = "AeroSpace started at login is managed by home-manager and launchd instead of itself via this option.";
         }
         {
-          assertion = cfg.settings.after-login-command == [ ];
+          assertion = cfg.settings.after-login-command == [];
           message = "AeroSpace will not run these commands as it does not start itself.";
         }
       ];
-      environment.systemPackages = [ cfg.package ];
+      environment.systemPackages = [cfg.package];
 
       launchd.user.agents.aerospace = {
         command =
           "${cfg.package}/Applications/AeroSpace.app/Contents/MacOS/AeroSpace"
-          + (lib.optionalString (cfg.settings != { }) " --config-path ${configFile}");
+          + (lib.optionalString (cfg.settings != {}) " --config-path ${configFile}");
         serviceConfig = {
           KeepAlive = true;
           RunAtLoad = true;
diff --git a/tests/services-aerospace.nix b/tests/services-aerospace.nix
index 28688c461..088c92d95 100644
--- a/tests/services-aerospace.nix
+++ b/tests/services-aerospace.nix
@@ -21,6 +21,32 @@ in
       alt-k = "focus up";
       alt-l = "focus right";
     };
+    on-window-detected = [
+      {
+        "if" = {
+          app-id = "Another.Cool.App";
+          during-aerospace-startup = false;
+        };
+        check-further-callbacks = false;
+        run = "move-node-to-workspace m";
+      }
+      {
+        "if".app-name-regex-substring = "finder|calendar";
+        run = "layout floating";
+      }
+      {
+        "if".workspace = "1";
+        run = "layout h_accordion";
+      }
+    ];
+    workspace-to-monitor-force-assignment = {
+        "1" = 1;
+        "2" = "main";
+        "3" = "secondary";
+        "4" = "built-in";
+        "5" = "^built-in retina display$";
+        "6" = [ "secondary" "dell" ];
+    };
   };
 
   test = ''
@@ -43,5 +69,24 @@ in
     grep 'alt-j = "focus down"' $conf
     grep 'alt-k = "focus up"' $conf
     grep 'alt-l = "focus right"' $conf
+
+    grep 'check-further-callbacks = false' $conf
+    grep 'run = "move-node-to-workspace m"' $conf
+    grep 'app-id = "Another.Cool.App"' $conf
+    grep 'during-aerospace-startup = false' $conf
+
+    grep 'run = "layout floating"' $conf
+    grep 'app-name-regex-substring = "finder|calendar"' $conf
+    (! grep 'window-title-regex-substring' $conf)
+    
+    grep 'workspace = "1"' $conf
+    grep 'run = "layout h_accordion"' $conf
+
+    grep '1 = 1' $conf
+    grep '2 = "main"' $conf
+    grep '3 = "secondary"' $conf
+    grep '4 = "built-in"' $conf
+    grep '5 = "^built-in retina display$"' $conf
+    grep '6 = \["secondary", "dell"\]' $conf
   '';
 }