diff --git a/komorebi-core/src/lib.rs b/komorebi-core/src/lib.rs
index a7086aab..eb11b522 100644
--- a/komorebi-core/src/lib.rs
+++ b/komorebi-core/src/lib.rs
@@ -127,8 +127,10 @@ pub enum SocketMessage {
     WorkAreaOffset(Rect),
     MonitorWorkAreaOffset(usize, Rect),
     ResizeDelta(i32),
-    WorkspaceRule(ApplicationIdentifier, String, usize, usize, bool),
-    NamedWorkspaceRule(ApplicationIdentifier, String, String, bool),
+    InitialWorkspaceRule(ApplicationIdentifier, String, usize, usize),
+    InitialNamedWorkspaceRule(ApplicationIdentifier, String, String),
+    WorkspaceRule(ApplicationIdentifier, String, usize, usize),
+    NamedWorkspaceRule(ApplicationIdentifier, String, String),
     FloatRule(ApplicationIdentifier, String),
     ManageRule(ApplicationIdentifier, String),
     IdentifyObjectNameChangeApplication(ApplicationIdentifier, String),
diff --git a/komorebi/src/process_command.rs b/komorebi/src/process_command.rs
index 989c5c33..608d2d19 100644
--- a/komorebi/src/process_command.rs
+++ b/komorebi/src/process_command.rs
@@ -215,41 +215,24 @@ impl WindowManager {
                     self.set_workspace_padding(monitor_idx, workspace_idx, size)?;
                 }
             }
-            SocketMessage::WorkspaceRule(
-                _,
-                ref id,
-                monitor_idx,
-                workspace_idx,
-                apply_on_first_show_only,
-            ) => {
-                {
-                    let mut workspace_rules = WORKSPACE_RULES.lock();
-                    workspace_rules.insert(
-                        id.to_string(),
-                        (monitor_idx, workspace_idx, apply_on_first_show_only),
-                    );
-                }
-
-                self.enforce_workspace_rules()?;
+            SocketMessage::InitialWorkspaceRule(_, ref id, monitor_idx, workspace_idx) => {
+                self.handle_initial_workspace_rules(id, monitor_idx, workspace_idx)?;
             }
-            SocketMessage::NamedWorkspaceRule(
-                _,
-                ref id,
-                ref workspace,
-                apply_on_first_show_only,
-            ) => {
+            SocketMessage::InitialNamedWorkspaceRule(_, ref id, ref workspace) => {
                 if let Some((monitor_idx, workspace_idx)) =
                     self.monitor_workspace_index_by_name(workspace)
                 {
-                    {
-                        let mut workspace_rules = WORKSPACE_RULES.lock();
-                        workspace_rules.insert(
-                            id.to_string(),
-                            (monitor_idx, workspace_idx, apply_on_first_show_only),
-                        );
-                    }
-
-                    self.enforce_workspace_rules()?;
+                    self.handle_initial_workspace_rules(id, monitor_idx, workspace_idx)?;
+                }
+            }
+            SocketMessage::WorkspaceRule(_, ref id, monitor_idx, workspace_idx) => {
+                self.handle_definitive_workspace_rules(id, monitor_idx, workspace_idx)?;
+            }
+            SocketMessage::NamedWorkspaceRule(_, ref id, ref workspace) => {
+                if let Some((monitor_idx, workspace_idx)) =
+                    self.monitor_workspace_index_by_name(workspace)
+                {
+                    self.handle_definitive_workspace_rules(id, monitor_idx, workspace_idx)?;
                 }
             }
             SocketMessage::ManageRule(_, ref id) => {
@@ -1197,6 +1180,51 @@ impl WindowManager {
         tracing::info!("processed");
         Ok(())
     }
+
+    #[tracing::instrument(skip(self))]
+    fn handle_initial_workspace_rules(
+        &mut self,
+        id: &String,
+        monitor_idx: usize,
+        workspace_idx: usize,
+    ) -> Result<()> {
+        self.handle_workspace_rules(id, monitor_idx, workspace_idx, true)?;
+
+        Ok(())
+    }
+
+    #[tracing::instrument(skip(self))]
+    fn handle_definitive_workspace_rules(
+        &mut self,
+        id: &String,
+        monitor_idx: usize,
+        workspace_idx: usize,
+    ) -> Result<()> {
+        self.handle_workspace_rules(id, monitor_idx, workspace_idx, false)?;
+
+        Ok(())
+    }
+
+    #[tracing::instrument(skip(self))]
+    fn handle_workspace_rules(
+        &mut self,
+        id: &String,
+        monitor_idx: usize,
+        workspace_idx: usize,
+        initial_workspace_rule: bool,
+    ) -> Result<()> {
+        {
+            let mut workspace_rules = WORKSPACE_RULES.lock();
+            workspace_rules.insert(
+                id.to_string(),
+                (monitor_idx, workspace_idx, initial_workspace_rule),
+            );
+        }
+
+        self.enforce_workspace_rules()?;
+
+        Ok(())
+    }
 }
 
 pub fn read_commands_uds(wm: &Arc<Mutex<WindowManager>>, stream: UnixStream) -> Result<()> {
diff --git a/komorebic/src/main.rs b/komorebic/src/main.rs
index 335d56f7..ddf914d2 100644
--- a/komorebic/src/main.rs
+++ b/komorebic/src/main.rs
@@ -515,6 +515,28 @@ gen_application_target_subcommand_args! {
     IdentifyBorderOverflowApplication,
 }
 
+#[derive(Parser, AhkFunction)]
+struct InitialWorkspaceRule {
+    #[clap(value_enum)]
+    identifier: ApplicationIdentifier,
+    /// Identifier as a string
+    id: String,
+    /// Monitor index (zero-indexed)
+    monitor: usize,
+    /// Workspace index on the specified monitor (zero-indexed)
+    workspace: usize,
+}
+
+#[derive(Parser, AhkFunction)]
+struct InitialNamedWorkspaceRule {
+    #[clap(value_enum)]
+    identifier: ApplicationIdentifier,
+    /// Identifier as a string
+    id: String,
+    /// Name of a workspace
+    workspace: String,
+}
+
 #[derive(Parser, AhkFunction)]
 struct WorkspaceRule {
     #[clap(value_enum)]
@@ -525,9 +547,6 @@ struct WorkspaceRule {
     monitor: usize,
     /// Workspace index on the specified monitor (zero-indexed)
     workspace: usize,
-    #[clap(short, long)]
-    /// Only apply once on first app load
-    apply_on_first_show_only: bool,
 }
 
 #[derive(Parser, AhkFunction)]
@@ -538,9 +557,6 @@ struct NamedWorkspaceRule {
     id: String,
     /// Name of a workspace
     workspace: String,
-    #[clap(short, long)]
-    /// Only apply once on first app load
-    apply_on_first_show_only: bool,
 }
 
 #[derive(Parser, AhkFunction)]
@@ -927,6 +943,12 @@ enum SubCommand {
     /// Add a rule to always manage the specified application
     #[clap(arg_required_else_help = true)]
     ManageRule(ManageRule),
+    /// Add a rule to associate an application with a workspace on first show
+    #[clap(arg_required_else_help = true)]
+    InitialWorkspaceRule(InitialWorkspaceRule),
+    /// Add a rule to associate an application with a named workspace on first show
+    #[clap(arg_required_else_help = true)]
+    InitialNamedWorkspaceRule(InitialNamedWorkspaceRule),
     /// Add a rule to associate an application with a workspace
     #[clap(arg_required_else_help = true)]
     WorkspaceRule(WorkspaceRule),
@@ -1453,27 +1475,33 @@ fn main() -> Result<()> {
         SubCommand::ManageRule(arg) => {
             send_message(&SocketMessage::ManageRule(arg.identifier, arg.id).as_bytes()?)?;
         }
-        SubCommand::WorkspaceRule(arg) => {
+        SubCommand::InitialWorkspaceRule(arg) => {
             send_message(
-                &SocketMessage::WorkspaceRule(
+                &SocketMessage::InitialWorkspaceRule(
                     arg.identifier,
                     arg.id,
                     arg.monitor,
                     arg.workspace,
-                    arg.apply_on_first_show_only,
                 )
                 .as_bytes()?,
             )?;
         }
+        SubCommand::InitialNamedWorkspaceRule(arg) => {
+            send_message(
+                &SocketMessage::InitialNamedWorkspaceRule(arg.identifier, arg.id, arg.workspace)
+                    .as_bytes()?,
+            )?;
+        }
+        SubCommand::WorkspaceRule(arg) => {
+            send_message(
+                &SocketMessage::WorkspaceRule(arg.identifier, arg.id, arg.monitor, arg.workspace)
+                    .as_bytes()?,
+            )?;
+        }
         SubCommand::NamedWorkspaceRule(arg) => {
             send_message(
-                &SocketMessage::NamedWorkspaceRule(
-                    arg.identifier,
-                    arg.id,
-                    arg.workspace,
-                    arg.apply_on_first_show_only,
-                )
-                .as_bytes()?,
+                &SocketMessage::NamedWorkspaceRule(arg.identifier, arg.id, arg.workspace)
+                    .as_bytes()?,
             )?;
         }
         SubCommand::Stack(arg) => {