diff --git a/komorebi/src/process_event.rs b/komorebi/src/process_event.rs
index f2a4db0b..d545ef1a 100644
--- a/komorebi/src/process_event.rs
+++ b/komorebi/src/process_event.rs
@@ -329,7 +329,8 @@ impl WindowManager {
                 }
 
                 if proceed {
-                    let behaviour = self.window_container_behaviour;
+                    let behaviour =
+                        self.window_container_behaviour(focused_monitor_idx, focused_workspace_idx);
                     let workspace = self.focused_workspace_mut()?;
                     let workspace_contains_window = workspace.contains_window(window.hwnd);
                     let monocle_container = workspace.monocle_container().clone();
@@ -399,10 +400,12 @@ impl WindowManager {
                     .monitor_idx_from_current_pos()
                     .ok_or_else(|| anyhow!("cannot get monitor idx from current position"))?;
 
-                let new_window_behaviour = self.window_container_behaviour;
+                let focused_monitor_idx = self.focused_monitor_idx();
+                let focused_workspace_idx = self.focused_workspace_idx().unwrap_or_default();
+                let window_container_behaviour =
+                    self.window_container_behaviour(focused_monitor_idx, focused_workspace_idx);
 
                 let workspace = self.focused_workspace_mut()?;
-
                 let focused_container_idx = workspace.focused_container_idx();
                 let new_position = WindowsApi::window_rect(window.hwnd())?;
                 let old_position = *workspace
@@ -519,7 +522,7 @@ impl WindowManager {
                             // Here we handle a simple move on the same monitor which is treated as
                             // a container swap
                         } else {
-                            match new_window_behaviour {
+                            match window_container_behaviour {
                                 WindowContainerBehaviour::Create => {
                                     match workspace.container_idx_from_current_point() {
                                         Some(target_idx) => {
diff --git a/komorebi/src/window_manager.rs b/komorebi/src/window_manager.rs
index 53a0e026..d2cf2203 100644
--- a/komorebi/src/window_manager.rs
+++ b/komorebi/src/window_manager.rs
@@ -303,6 +303,24 @@ impl WindowManager {
         StaticConfig::reload(pathbuf, self)
     }
 
+    pub fn window_container_behaviour(
+        &self,
+        monitor_idx: usize,
+        workspace_idx: usize,
+    ) -> WindowContainerBehaviour {
+        if let Some(monitor) = self.monitors().get(monitor_idx) {
+            if let Some(workspace) = monitor.workspaces().get(workspace_idx) {
+                return if workspace.containers().is_empty() {
+                    WindowContainerBehaviour::Create
+                } else {
+                    self.window_container_behaviour
+                };
+            }
+        }
+
+        WindowContainerBehaviour::Create
+    }
+
     #[tracing::instrument(skip(self))]
     pub fn watch_configuration(&mut self, enable: bool) -> Result<()> {
         let config_pwsh = HOME_DIR.join("komorebi.ps1");
diff --git a/komorebi/src/workspace.rs b/komorebi/src/workspace.rs
index 44982143..672bd61f 100644
--- a/komorebi/src/workspace.rs
+++ b/komorebi/src/workspace.rs
@@ -748,6 +748,9 @@ impl Workspace {
             self.focus_previous_container();
         } else {
             container.load_focused_window();
+            if let Some(window) = container.focused_window() {
+                window.focus(false)?;
+            }
         }
 
         Ok(())