diff --git a/crates/nu-cli/src/cli.rs b/crates/nu-cli/src/cli.rs
index 0a07c33e42..9391cfd026 100644
--- a/crates/nu-cli/src/cli.rs
+++ b/crates/nu-cli/src/cli.rs
@@ -641,8 +641,43 @@ async fn process_line(
                         && which::which(name).is_err()
                         && args.list.is_empty()
                     {
-                        ctx.shell_manager.set_path(name.to_string());
-                        return LineResult::Success(line.to_string());
+                        // Here we work differently if we're in Windows because of the expected Windows behavior
+                        #[cfg(windows)]
+                        {
+                            if name.ends_with(':') {
+                                // This looks like a drive shortcut. We need to a) switch drives and b) go back to the previous directory we were viewing on that drive
+                                // But first, we need to save where we are now
+                                let current_path = ctx.shell_manager.path();
+
+                                let split_path: Vec<_> = current_path.split(':').collect();
+                                if split_path.len() > 1 {
+                                    ctx.windows_drives_previous_cwd
+                                        .lock()
+                                        .insert(split_path[0].to_string(), current_path);
+                                }
+
+                                let name = name.to_uppercase();
+                                let new_drive: Vec<_> = name.split(':').collect();
+
+                                if let Some(val) =
+                                    ctx.windows_drives_previous_cwd.lock().get(new_drive[0])
+                                {
+                                    ctx.shell_manager.set_path(val.to_string());
+                                    return LineResult::Success(line.to_string());
+                                } else {
+                                    ctx.shell_manager.set_path(name.to_string());
+                                    return LineResult::Success(line.to_string());
+                                }
+                            } else {
+                                ctx.shell_manager.set_path(name.to_string());
+                                return LineResult::Success(line.to_string());
+                            }
+                        }
+                        #[cfg(not(windows))]
+                        {
+                            ctx.shell_manager.set_path(name.to_string());
+                            return LineResult::Success(line.to_string());
+                        }
                     }
                 }
             }
diff --git a/crates/nu-cli/src/context.rs b/crates/nu-cli/src/context.rs
index b2ff0c7188..5d9909611d 100644
--- a/crates/nu-cli/src/context.rs
+++ b/crates/nu-cli/src/context.rs
@@ -82,6 +82,9 @@ pub struct Context {
     pub current_errors: Arc<Mutex<Vec<ShellError>>>,
     pub ctrl_c: Arc<AtomicBool>,
     pub(crate) shell_manager: ShellManager,
+
+    #[cfg(windows)]
+    pub windows_drives_previous_cwd: Arc<Mutex<std::collections::HashMap<String, String>>>,
 }
 
 impl Context {
@@ -102,15 +105,33 @@ impl Context {
 
     pub(crate) fn basic() -> Result<Context, Box<dyn Error>> {
         let registry = CommandRegistry::new();
-        Ok(Context {
-            registry: registry.clone(),
-            host: Arc::new(parking_lot::Mutex::new(Box::new(
-                crate::env::host::BasicHost,
-            ))),
-            current_errors: Arc::new(Mutex::new(vec![])),
-            ctrl_c: Arc::new(AtomicBool::new(false)),
-            shell_manager: ShellManager::basic(registry)?,
-        })
+
+        #[cfg(windows)]
+        {
+            Ok(Context {
+                registry: registry.clone(),
+                host: Arc::new(parking_lot::Mutex::new(Box::new(
+                    crate::env::host::BasicHost,
+                ))),
+                current_errors: Arc::new(Mutex::new(vec![])),
+                ctrl_c: Arc::new(AtomicBool::new(false)),
+                shell_manager: ShellManager::basic(registry)?,
+                windows_drives_previous_cwd: Arc::new(Mutex::new(std::collections::HashMap::new())),
+            })
+        }
+
+        #[cfg(not(windows))]
+        {
+            Ok(Context {
+                registry: registry.clone(),
+                host: Arc::new(parking_lot::Mutex::new(Box::new(
+                    crate::env::host::BasicHost,
+                ))),
+                current_errors: Arc::new(Mutex::new(vec![])),
+                ctrl_c: Arc::new(AtomicBool::new(false)),
+                shell_manager: ShellManager::basic(registry)?,
+            })
+        }
     }
 
     pub(crate) fn error(&mut self, error: ShellError) {