diff --git a/macos/Sources/Features/App Intents/NewTerminalIntent.swift b/macos/Sources/Features/App Intents/NewTerminalIntent.swift
index 35f53169f..67d1a9676 100644
--- a/macos/Sources/Features/App Intents/NewTerminalIntent.swift	
+++ b/macos/Sources/Features/App Intents/NewTerminalIntent.swift	
@@ -74,7 +74,7 @@ struct NewTerminalIntent: AppIntent {
         // If we were given a working directory then open that directory
         if let url = workingDirectory?.fileURL {
             let dir = url.hasDirectoryPath ? url : url.deletingLastPathComponent()
-            config.workingDirectory = dir.path(percentEncoded: false)
+            config.workingDirectory = dir.pathWithoutTrailingSlash
         }
 
         // Parse environment variables from KEY=VALUE format
diff --git a/macos/Sources/Features/Services/ServiceProvider.swift b/macos/Sources/Features/Services/ServiceProvider.swift
index aa5ab7c8a..5f51c9ed4 100644
--- a/macos/Sources/Features/Services/ServiceProvider.swift
+++ b/macos/Sources/Features/Services/ServiceProvider.swift
@@ -59,7 +59,7 @@ class ServiceProvider: NSObject {
 
         for url in directoryURLs {
             var config = Ghostty.SurfaceConfiguration()
-            config.workingDirectory = url.path(percentEncoded: false)
+            config.workingDirectory = url.pathWithoutTrailingSlash
 
             switch target {
             case .window:
diff --git a/macos/Sources/Helpers/Extensions/URL+Extension.swift b/macos/Sources/Helpers/Extensions/URL+Extension.swift
new file mode 100644
index 000000000..1e5090111
--- /dev/null
+++ b/macos/Sources/Helpers/Extensions/URL+Extension.swift
@@ -0,0 +1,9 @@
+import Foundation
+import System
+
+extension URL {
+    /// The decoded path with trailing separators removed, except for the root path.
+    var pathWithoutTrailingSlash: String {
+        FilePath(path(percentEncoded: false)).string
+    }
+}
diff --git a/macos/Tests/URLTests.swift b/macos/Tests/URLTests.swift
new file mode 100644
index 000000000..f3f0ec151
--- /dev/null
+++ b/macos/Tests/URLTests.swift
@@ -0,0 +1,25 @@
+import Foundation
+import Testing
+@testable import Ghostty
+
+struct URLTests {
+    @Test func pathWithoutTrailingSlash() {
+        let url = URL(string: "file:///tmp/example/")!
+        #expect(url.pathWithoutTrailingSlash == "/tmp/example")
+    }
+
+    @Test func pathWithoutMultipleTrailingSlashes() {
+        let url = URL(string: "file:///tmp/example///")!
+        #expect(url.pathWithoutTrailingSlash == "/tmp/example")
+    }
+
+    @Test func pathWithoutTrailingSlashDecodesPath() {
+        let url = URL(string: "file:///tmp/example%20directory/")!
+        #expect(url.pathWithoutTrailingSlash == "/tmp/example directory")
+    }
+
+    @Test func pathWithoutTrailingSlashPreservesRoot() {
+        let url = URL(string: "file:///")!
+        #expect(url.pathWithoutTrailingSlash == "/")
+    }
+}