diff --git a/helix-term/src/application.rs b/helix-term/src/application.rs
index fabd0fa4..43e1cdfc 100644
--- a/helix-term/src/application.rs
+++ b/helix-term/src/application.rs
@@ -162,8 +162,7 @@ impl Application {
             // Unset path to prevent accidentally saving to the original tutor file.
             doc_mut!(editor).set_path(None);
         } else if !args.files.is_empty() {
-            let first = &args.files[0].0; // we know it's not empty
-            if first.is_dir() {
+            if args.open_cwd {
                 // NOTE: The working directory is already set to args.files[0] in main()
                 editor.new_file(Action::VerticalSplit);
                 let picker = ui::file_picker(".".into(), &config.load().editor);
diff --git a/helix-term/src/args.rs b/helix-term/src/args.rs
index 6a49889b..99ce3992 100644
--- a/helix-term/src/args.rs
+++ b/helix-term/src/args.rs
@@ -17,6 +17,7 @@ pub struct Args {
     pub log_file: Option<PathBuf>,
     pub config_file: Option<PathBuf>,
     pub files: Vec<(PathBuf, Position)>,
+    pub open_cwd: bool,
     pub working_directory: Option<PathBuf>,
 }
 
diff --git a/helix-term/src/main.rs b/helix-term/src/main.rs
index 8db5f310..6411a7c5 100644
--- a/helix-term/src/main.rs
+++ b/helix-term/src/main.rs
@@ -76,7 +76,7 @@ FLAGS:
         helix_loader::default_log_file().display(),
     );
 
-    let args = Args::parse_args().context("could not parse arguments")?;
+    let mut args = Args::parse_args().context("could not parse arguments")?;
 
     helix_loader::initialize_config_file(args.config_file.clone());
     helix_loader::initialize_log_file(args.log_file.clone());
@@ -118,10 +118,14 @@ FLAGS:
 
     // NOTE: Set the working directory early so the correct configuration is loaded. Be aware that
     // Application::new() depends on this logic so it must be updated if this changes.
-    if let Some((path, true)) = args.files.first().map(|(path, _)| (path, path.is_dir())) {
+    if let Some(path) = &args.working_directory {
         helix_loader::set_current_working_dir(path)?;
-    } else if let Some(path) = &args.working_directory {
+    }
+
+    // If the first file is a directory, it will be the working directory and a file picker will be opened
+    if let Some((path, _)) = args.files.first().filter(|p| p.0.is_dir()) {
         helix_loader::set_current_working_dir(path)?;
+        args.open_cwd = true; // Signal Application that we want to open the picker on "."
     }
 
     let config = match Config::load_default() {
diff --git a/helix-term/tests/test/helpers.rs b/helix-term/tests/test/helpers.rs
index e6762baf..112b5e35 100644
--- a/helix-term/tests/test/helpers.rs
+++ b/helix-term/tests/test/helpers.rs
@@ -320,6 +320,14 @@ impl AppBuilder {
     }
 
     pub fn build(self) -> anyhow::Result<Application> {
+        if let Some(path) = &self.args.working_directory {
+            bail!("Changing the working directory to {path:?} is not yet supported for integration tests");
+        }
+
+        if let Some((path, _)) = self.args.files.first().filter(|p| p.0.is_dir()) {
+            bail!("Having the directory {path:?} in args.files[0] is not yet supported for integration tests");
+        }
+
         let mut app = Application::new(self.args, self.config, self.syn_conf)?;
 
         if let Some((text, selection)) = self.input {