diff --git a/src/common/non_utf8/path.rs b/src/common/non_utf8/path.rs
index 53f8b16..fc91b35 100644
--- a/src/common/non_utf8/path.rs
+++ b/src/common/non_utf8/path.rs
@@ -658,8 +658,16 @@ where
         } else {
             // Get the cwd as a platform path and convert to this path's encoding
             let cwd = crate::utils::current_dir()?.with_encoding();
+            let joined = cwd.join(self);
 
-            Ok(cwd.join(self).normalize())
+            if !joined.is_absolute() {
+                Err(std::io::Error::new(
+                    std::io::ErrorKind::Other,
+                    "path cannot be absolutized without ambiguity",
+                ))
+            } else {
+                Ok(joined.normalize())
+            }
         }
     }
 
diff --git a/src/windows.rs b/src/windows.rs
index f953770..f755ef8 100644
--- a/src/windows.rs
+++ b/src/windows.rs
@@ -4,3 +4,31 @@ mod utf8;
 
 pub use non_utf8::*;
 pub use utf8::*;
+
+#[cfg(feature = "std")]
+#[test]
+fn absolutize_should_fail_for_windows_path_with_drive_letter_only_prefix() {
+    let p = WindowsPath::new(r"C:something");
+    assert!(p.absolutize().is_err())
+}
+
+#[cfg(feature = "std")]
+#[test]
+fn absolutize_should_fail_for_windows_path_with_verbatim_drive_letter_only_prefix() {
+    let p = WindowsPath::new(r"\\?\C:something");
+    assert!(p.absolutize().is_err())
+}
+
+#[cfg(feature = "std")]
+#[test]
+fn absolutize_should_fail_for_windows_path_with_unc_server_only_prefix() {
+    let p = WindowsPath::new(r"\\server");
+    assert!(p.absolutize().is_err())
+}
+
+#[cfg(feature = "std")]
+#[test]
+fn absolutize_should_fail_for_windows_path_with_verbatim_unc_server_only_prefix() {
+    let p = WindowsPath::new(r"\\?\UNC\server");
+    assert!(p.absolutize().is_err())
+}