diff --git a/komorebi-core/src/config_generation.rs b/komorebi-core/src/config_generation.rs
index f2c6fe8e..2fd97dc3 100644
--- a/komorebi-core/src/config_generation.rs
+++ b/komorebi-core/src/config_generation.rs
@@ -89,8 +89,36 @@ impl ApplicationConfigurationGenerator {
         Ok(serde_yaml::to_string(&cfgen)?)
     }
 
-    pub fn generate_ahk(content: &str) -> Result<Vec<String>> {
-        let mut cfgen = Self::load(content)?;
+    fn merge(base_content: &str, override_content: &str) -> Result<Vec<ApplicationConfiguration>> {
+        let base_cfgen = Self::load(base_content)?;
+        let override_cfgen = Self::load(override_content)?;
+
+        let mut final_cfgen = base_cfgen.clone();
+
+        for entry in override_cfgen {
+            let mut replace_idx = None;
+            for (idx, base_entry) in base_cfgen.iter().enumerate() {
+                if base_entry.name == entry.name {
+                    replace_idx = Option::from(idx);
+                }
+            }
+
+            match replace_idx {
+                None => final_cfgen.push(entry),
+                Some(idx) => final_cfgen[idx] = entry,
+            }
+        }
+
+        Ok(final_cfgen)
+    }
+
+    pub fn generate_ahk(base_content: &str, override_content: Option<&str>) -> Result<Vec<String>> {
+        let mut cfgen = if let Some(override_content) = override_content {
+            Self::merge(base_content, override_content)?
+        } else {
+            Self::load(base_content)?
+        };
+
         cfgen.sort_by(|a, b| a.name.cmp(&b.name));
 
         let mut lines = vec![
diff --git a/komorebic.lib.sample.ahk b/komorebic.lib.sample.ahk
index 86b58948..8b498bbd 100644
--- a/komorebic.lib.sample.ahk
+++ b/komorebic.lib.sample.ahk
@@ -304,8 +304,8 @@ AhkLibrary() {
     Run, komorebic.exe ahk-library, , Hide
 }
 
-AhkAppSpecificConfiguration(path) {
-    Run, komorebic.exe ahk-app-specific-configuration %path%, , Hide
+AhkAppSpecificConfiguration(path, override_path) {
+    Run, komorebic.exe ahk-app-specific-configuration %path% %override_path%, , Hide
 }
 
 FormatAppSpecificConfiguration(path) {
diff --git a/komorebic/src/main.rs b/komorebic/src/main.rs
index 893e0aa3..5361626c 100644
--- a/komorebic/src/main.rs
+++ b/komorebic/src/main.rs
@@ -422,22 +422,18 @@ struct Unsubscribe {
     named_pipe: String,
 }
 
-macro_rules! gen_application_specific_configuration_subcommand_args {
-    // SubCommand Pattern
-    ( $( $name:ident ),+ $(,)? ) => {
-        $(
-            #[derive(clap::Parser, derive_ahk::AhkFunction)]
-            pub struct $name {
-                /// YAML file from which the application-specific configurations should be loaded
-                path: String,
-            }
-        )+
-    };
+#[derive(Parser, AhkFunction)]
+struct AhkAppSpecificConfiguration {
+    /// YAML file from which the application-specific configurations should be loaded
+    path: String,
+    /// Optional YAML file of overrides to apply over the first file
+    override_path: Option<String>,
 }
 
-gen_application_specific_configuration_subcommand_args! {
-    AhkAppSpecificConfiguration,
-    FormatAppSpecificConfiguration,
+#[derive(Parser, AhkFunction)]
+struct FormatAppSpecificConfiguration {
+    /// YAML file from which the application-specific configurations should be loaded
+    path: String,
 }
 
 #[derive(Parser)]
@@ -1165,7 +1161,16 @@ fn main() -> Result<()> {
         }
         SubCommand::AhkAppSpecificConfiguration(arg) => {
             let content = fs::read_to_string(resolve_windows_path(&arg.path)?)?;
-            let lines = ApplicationConfigurationGenerator::generate_ahk(&content)?;
+            let lines = if let Some(override_path) = arg.override_path {
+                let override_content = fs::read_to_string(resolve_windows_path(&override_path)?)?;
+
+                ApplicationConfigurationGenerator::generate_ahk(
+                    &content,
+                    Option::from(override_content.as_str()),
+                )?
+            } else {
+                ApplicationConfigurationGenerator::generate_ahk(&content, None)?
+            };
 
             let mut generated_config = HOME_DIR.clone();
             generated_config.push("komorebi.generated.ahk");