diff --git a/macos/Sources/Features/Services/ServiceProvider.swift b/macos/Sources/Features/Services/ServiceProvider.swift
index 9bf46fcf9..fd3e8e9cc 100644
--- a/macos/Sources/Features/Services/ServiceProvider.swift
+++ b/macos/Sources/Features/Services/ServiceProvider.swift
@@ -42,10 +42,21 @@ class ServiceProvider: NSObject {
         // to their directories because that's the only thing we can open.
         let directoryURLs = Set(
             pathURLs.map { url -> URL in
-                url.hasDirectoryPath ? url : url.deletingLastPathComponent()
+                /// We check file system resources here because
+                /// NSURL doesn't append `/` when reading string contents from pasteboard
+                ///     ```
+                ///     NSURL(pasteboardPropertyList: "/System/Library".propertyList(), ofType: .fileURL)?.hasDirectoryPath
+                ///     ```
+                let isDirectory = (try? url.resourceValues(forKeys: [.isDirectoryKey]))?.isDirectory ?? url.hasDirectoryPath
+                return isDirectory ? url : url.deletingLastPathComponent()
             }
         )
 
+        guard !directoryURLs.isEmpty else {
+            error.pointee = Self.errorNoString
+            return
+        }
+
         for url in directoryURLs {
             var config = Ghostty.SurfaceConfiguration()
             config.workingDirectory = url.path(percentEncoded: false)