diff --git a/crates/assistant2/src/context_picker/file_context_picker.rs b/crates/assistant2/src/context_picker/file_context_picker.rs
index a96d0f986cacade1a98fbf84681df40c5a8fae9e..8dca313fd2f2bce291d43602f08023c83160425b 100644
--- a/crates/assistant2/src/context_picker/file_context_picker.rs
+++ b/crates/assistant2/src/context_picker/file_context_picker.rs
@@ -321,10 +321,7 @@ pub fn render_file_context_entry(
 
     let added = context_store.upgrade().and_then(|context_store| {
         if is_directory {
-            context_store
-                .read(cx)
-                .includes_directory(path)
-                .map(FileInclusion::Direct)
+            context_store.read(cx).includes_directory(path)
         } else {
             context_store.read(cx).will_include_file_path(path, cx)
         }
diff --git a/crates/assistant2/src/context_store.rs b/crates/assistant2/src/context_store.rs
index e4ef3da196d2ce2ce171cb593e0ba1748e554ffc..b9af3c1ce59e955f135edb612c8f83b754753077 100644
--- a/crates/assistant2/src/context_store.rs
+++ b/crates/assistant2/src/context_store.rs
@@ -180,14 +180,15 @@ impl ContextStore {
             return Task::ready(Err(anyhow!("failed to read project")));
         };
 
-        let already_included = if let Some(context_id) = self.includes_directory(&project_path.path)
-        {
-            if remove_if_exists {
-                self.remove_context(context_id);
+        let already_included = match self.includes_directory(&project_path.path) {
+            Some(FileInclusion::Direct(context_id)) => {
+                if remove_if_exists {
+                    self.remove_context(context_id);
+                }
+                true
             }
-            true
-        } else {
-            false
+            Some(FileInclusion::InDirectory(_)) => true,
+            None => false,
         };
         if already_included {
             return Task::ready(Ok(()));
@@ -509,8 +510,12 @@ impl ContextStore {
         None
     }
 
-    pub fn includes_directory(&self, path: &Path) -> Option<ContextId> {
-        self.directories.get(path).copied()
+    pub fn includes_directory(&self, path: &Path) -> Option<FileInclusion> {
+        if let Some(context_id) = self.directories.get(path) {
+            return Some(FileInclusion::Direct(*context_id));
+        }
+
+        self.will_include_file_path_via_directory(path)
     }
 
     pub fn included_symbol(&self, symbol_id: &ContextSymbolId) -> Option<ContextId> {