diff --git a/helix-term/src/application.rs b/helix-term/src/application.rs
index 43e1cdfc9..ed085749b 100644
--- a/helix-term/src/application.rs
+++ b/helix-term/src/application.rs
@@ -162,14 +162,19 @@ 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() {
-            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);
+            let mut files_it = args.files.into_iter().peekable();
+
+            // If the first file is a directory, skip it and open a picker
+            if let Some((first, _)) = files_it.next_if(|(p, _)| p.is_dir()) {
+                let picker = ui::file_picker(first, &config.load().editor);
                 compositor.push(Box::new(overlaid(picker)));
-            } else {
-                let nr_of_files = args.files.len();
-                for (i, (file, pos)) in args.files.into_iter().enumerate() {
+            }
+
+            // If there are any more files specified, open them
+            if files_it.peek().is_some() {
+                let mut nr_of_files = 0;
+                for (file, pos) in files_it {
+                    nr_of_files += 1;
                     if file.is_dir() {
                         return Err(anyhow::anyhow!(
                             "expected a path to file, found a directory. (to open a directory pass it as first argument)"
@@ -181,7 +186,7 @@ impl Application {
                         // option. If neither of those two arguments are passed
                         // in, just load the files normally.
                         let action = match args.split {
-                            _ if i == 0 => Action::VerticalSplit,
+                            _ if nr_of_files == 1 => Action::VerticalSplit,
                             Some(Layout::Vertical) => Action::VerticalSplit,
                             Some(Layout::Horizontal) => Action::HorizontalSplit,
                             None => Action::Load,
@@ -208,6 +213,8 @@ impl Application {
                 // does not affect views without pos since it is at the top
                 let (view, doc) = current!(editor);
                 align_view(doc, view, Align::Center);
+            } else {
+                editor.new_file(Action::VerticalSplit);
             }
         } else if stdin().is_tty() || cfg!(feature = "integration") {
             editor.new_file(Action::VerticalSplit);
diff --git a/helix-term/src/args.rs b/helix-term/src/args.rs
index 99ce39926..6a49889b6 100644
--- a/helix-term/src/args.rs
+++ b/helix-term/src/args.rs
@@ -17,7 +17,6 @@ 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 6411a7c5f..a62c54a40 100644
--- a/helix-term/src/main.rs
+++ b/helix-term/src/main.rs
@@ -116,16 +116,18 @@ FLAGS:
 
     setup_logging(args.verbosity).context("failed to initialize logging")?;
 
+    // Before setting the working directory, resolve all the paths in args.files
+    for (path, _) in args.files.iter_mut() {
+        *path = helix_core::path::get_canonicalized_path(path);
+    }
+
     // 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) = &args.working_directory {
         helix_loader::set_current_working_dir(path)?;
-    }
-
-    // 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()) {
+    } else if let Some((path, _)) = args.files.first().filter(|p| p.0.is_dir()) {
+        // If the first file is a directory, it will be the working directory unless -w was specified
         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() {