diff --git a/src/hook_env.rs b/src/hook_env.rs
index 78cbec5628..d448c620ef 100644
--- a/src/hook_env.rs
+++ b/src/hook_env.rs
@@ -64,11 +64,15 @@ pub fn should_exit_early(watch_files: impl IntoIterator<Item = WatchFilePattern>
     true
 }
 
-pub fn dir_change() -> Option<(PathBuf, PathBuf)> {
+pub fn dir_change() -> Option<(Option<PathBuf>, PathBuf)> {
     match (&*env::__MISE_DIR, &*dirs::CWD) {
         (Some(old), Some(new)) if old != new => {
             trace!("dir change: {:?} -> {:?}", old, new);
-            Some((old.clone(), new.clone()))
+            Some((Some(old.clone()), new.clone()))
+        }
+        (None, Some(new)) => {
+            trace!("dir change: None -> {:?}", new);
+            Some((None, new.clone()))
         }
         _ => None,
     }
diff --git a/src/hooks.rs b/src/hooks.rs
index 03b274a165..a9f829deda 100644
--- a/src/hooks.rs
+++ b/src/hooks.rs
@@ -65,7 +65,7 @@ pub fn run_one_hook(ts: &Toolset, hook: Hooks) {
                 if !new.starts_with(&root) {
                     continue;
                 }
-                if old.starts_with(&root) {
+                if old.is_some_and(|old| old.starts_with(&root)) {
                     continue;
                 }
             }
@@ -74,7 +74,7 @@ pub fn run_one_hook(ts: &Toolset, hook: Hooks) {
                 if new.starts_with(&root) {
                     continue;
                 }
-                if !old.starts_with(&root) {
+                if old.is_some_and(|old| !old.starts_with(&root)) {
                     continue;
                 }
             }
@@ -110,7 +110,7 @@ fn execute(ts: &Toolset, root: &Path, hook: &Hook) -> Result<()> {
         "MISE_PROJECT_ROOT".to_string(),
         root.to_string_lossy().to_string(),
     );
-    if let Some((old, _new)) = hook_env::dir_change() {
+    if let Some((Some(old), _new)) = hook_env::dir_change() {
         env.insert(
             "MISE_PREVIOUS_DIR".to_string(),
             old.to_string_lossy().to_string(),