diff --git a/komorebi-bar/src/komorebi.rs b/komorebi-bar/src/komorebi.rs
index a16db58c1..4c60e05a3 100644
--- a/komorebi-bar/src/komorebi.rs
+++ b/komorebi-bar/src/komorebi.rs
@@ -83,14 +83,6 @@ impl From<&KomorebiConfig> for Komorebi {
             if let Some(configuration_switcher) = &value.configuration_switcher {
                 let mut configuration_switcher = configuration_switcher.clone();
                 for (_, location) in configuration_switcher.configurations.iter_mut() {
-                    if let Ok(expanded) = std::env::var("KOMOREBI_CONFIG_HOME") {
-                        *location = location.replace("$Env:KOMOREBI_CONFIG_HOME", &expanded);
-                    }
-
-                    if let Ok(expanded) = std::env::var("USERPROFILE") {
-                        *location = location.replace("$Env:USERPROFILE", &expanded);
-                    }
-
                     *location = dunce::simplified(&PathBuf::from(location.clone()))
                         .to_string_lossy()
                         .to_string();
diff --git a/komorebi/src/static_config.rs b/komorebi/src/static_config.rs
index 8bc09cef6..1ca3633a5 100644
--- a/komorebi/src/static_config.rs
+++ b/komorebi/src/static_config.rs
@@ -934,7 +934,34 @@ impl StaticConfig {
 
     pub fn read(path: &PathBuf) -> Result<Self> {
         let content = std::fs::read_to_string(path)?;
-        let value: Self = serde_json::from_str(&content)?;
+        let mut value: Self = serde_json::from_str(&content)?;
+
+        if let Some(path) = &mut value.app_specific_configuration_path {
+            *path = resolve_home_path(&*path)?;
+        }
+
+        if let Some(monitors) = &mut value.monitors {
+            for m in monitors {
+                for w in &mut m.workspaces {
+                    if let Some(path) = &mut w.custom_layout {
+                        *path = resolve_home_path(&*path)?;
+                    }
+
+                    if let Some(map) = &mut w.custom_layout_rules {
+                        for path in map.values_mut() {
+                            *path = resolve_home_path(&*path)?;
+                        }
+                    }
+                }
+            }
+        }
+
+        if let Some(bar_configurations) = &mut value.bar_configurations {
+            for path in bar_configurations {
+                *path = resolve_home_path(&*path)?;
+            }
+        }
+
         Ok(value)
     }
 
@@ -944,8 +971,7 @@ impl StaticConfig {
         incoming: Receiver<WindowManagerEvent>,
         unix_listener: Option<UnixListener>,
     ) -> Result<WindowManager> {
-        let content = std::fs::read_to_string(path)?;
-        let mut value: Self = serde_json::from_str(&content)?;
+        let mut value = Self::read(path)?;
         value.apply_globals()?;
 
         let listener = match unix_listener {
@@ -1024,8 +1050,7 @@ impl StaticConfig {
     }
 
     pub fn postload(path: &PathBuf, wm: &Arc<Mutex<WindowManager>>) -> Result<()> {
-        let content = std::fs::read_to_string(path)?;
-        let value: Self = serde_json::from_str(&content)?;
+        let value = Self::read(path)?;
         let mut wm = wm.lock();
 
         if let Some(monitors) = value.monitors {
@@ -1092,8 +1117,7 @@ impl StaticConfig {
     }
 
     pub fn reload(path: &PathBuf, wm: &mut WindowManager) -> Result<()> {
-        let content = std::fs::read_to_string(path)?;
-        let mut value: Self = serde_json::from_str(&content)?;
+        let mut value = Self::read(path)?;
 
         value.apply_globals()?;
 
diff --git a/komorebic/src/main.rs b/komorebic/src/main.rs
index 139ad10f6..248cf6b83 100644
--- a/komorebic/src/main.rs
+++ b/komorebic/src/main.rs
@@ -1517,26 +1517,15 @@ fn main() -> Result<()> {
 
                 println!("Found komorebi.json; this file can be passed to the start command with the --config flag\n");
 
-                if let Ok(config) = &parsed_config {
-                    if let Some(asc_path) = config.get("app_specific_configuration_path") {
-                        let mut normalized_asc_path = asc_path
-                            .to_string()
-                            .replace(
-                                "$Env:USERPROFILE",
-                                &dirs::home_dir().unwrap().to_string_lossy(),
-                            )
-                            .replace('"', "")
-                            .replace('\\', "/");
-
-                        if let Ok(komorebi_config_home) = std::env::var("KOMOREBI_CONFIG_HOME") {
-                            normalized_asc_path = normalized_asc_path
-                                .replace("$Env:KOMOREBI_CONFIG_HOME", &komorebi_config_home)
-                                .replace('"', "")
-                                .replace('\\', "/");
+                if let Ok(config) = StaticConfig::read(&static_config) {
+                    match config.app_specific_configuration_path {
+                        None => {
+                            println!("Application specific configuration file path has not been set. Try running 'komorebic fetch-asc'\n");
                         }
-
-                        if !Path::exists(Path::new(&normalized_asc_path)) {
-                            println!("Application specific configuration file path '{normalized_asc_path}' does not exist. Try running 'komorebic fetch-asc'\n");
+                        Some(path) => {
+                            if !Path::exists(Path::new(&path)) {
+                                println!("Application specific configuration file path '{}' does not exist. Try running 'komorebic fetch-asc'\n", path.display());
+                            }
                         }
                     }
                 }
@@ -2042,26 +2031,8 @@ if (!(Get-Process whkd -ErrorAction SilentlyContinue))
                     let mut config = StaticConfig::read(config)?;
                     if let Some(display_bar_configurations) = &mut config.bar_configurations {
                         for config_file_path in &mut *display_bar_configurations {
-                            let mut normalized = config_file_path
-                                .to_string_lossy()
-                                .to_string()
-                                .replace(
-                                    "$Env:USERPROFILE",
-                                    &dirs::home_dir().unwrap().to_string_lossy(),
-                                )
-                                .replace('"', "")
-                                .replace('\\', "/");
-
-                            if let Ok(komorebi_config_home) = std::env::var("KOMOREBI_CONFIG_HOME")
-                            {
-                                normalized = normalized
-                                    .replace("$Env:KOMOREBI_CONFIG_HOME", &komorebi_config_home)
-                                    .replace('"', "")
-                                    .replace('\\', "/");
-                            }
-
                             let script = r"Start-Process 'komorebi-bar' '--config CONFIGFILE' -WindowStyle hidden"
-                            .replace("CONFIGFILE", &normalized);
+                            .replace("CONFIGFILE", &config_file_path.to_string_lossy());
 
                             match powershell_script::run(&script) {
                                 Ok(_) => {