diff --git a/modules/juce_core/files/juce_File.cpp b/modules/juce_core/files/juce_File.cpp
index ce076d85fa..e6ed109022 100644
--- a/modules/juce_core/files/juce_File.cpp
+++ b/modules/juce_core/files/juce_File.cpp
@@ -103,6 +103,11 @@ static String removeEllipsis (const String& path)
     return path;
 }
 
+bool File::isRoot() const
+{
+    return fullPath.isNotEmpty() && *this == getParentDirectory();
+}
+
 String File::parseAbsolutePath (const String& p)
 {
     if (p.isEmpty())
diff --git a/modules/juce_core/files/juce_File.h b/modules/juce_core/files/juce_File.h
index 35d5749d6c..8f18d99f1b 100644
--- a/modules/juce_core/files/juce_File.h
+++ b/modules/juce_core/files/juce_File.h
@@ -120,6 +120,14 @@ public:
     */
     bool isDirectory() const;
 
+    /** Checks whether the path of this file represents the root of a file system,
+        irrespective of its existance.
+
+        This will return true for "C:", "D:", etc on Windows and "/" on other
+        platforms.
+    */
+    bool isRoot() const;
+
     /** Returns the size of the file in bytes.
 
         @returns    the number of bytes in the file, or 0 if it doesn't exist.
diff --git a/modules/juce_gui_basics/native/juce_win32_FileChooser.cpp b/modules/juce_gui_basics/native/juce_win32_FileChooser.cpp
index 9497499998..728a4c6d36 100644
--- a/modules/juce_gui_basics/native/juce_win32_FileChooser.cpp
+++ b/modules/juce_gui_basics/native/juce_win32_FileChooser.cpp
@@ -164,7 +164,7 @@ void FileChooser::showPlatformDialog (Array<File>& results, const String& title_
     auto parentDirectory = currentFileOrDirectory.getParentDirectory();
 
     // Handle nonexistent root directories in the same way as existing ones
-    if (currentFileOrDirectory.isDirectory() || parentDirectory == currentFileOrDirectory)
+    if (currentFileOrDirectory.isDirectory() || currentFileOrDirectory.isRoot())
     {
         info.initialPath = currentFileOrDirectory.getFullPathName();
     }