diff --git a/cap-primitives/src/windows/fs/open_impl.rs b/cap-primitives/src/windows/fs/open_impl.rs
index db595385..a2695e8a 100644
--- a/cap-primitives/src/windows/fs/open_impl.rs
+++ b/cap-primitives/src/windows/fs/open_impl.rs
@@ -1,4 +1,5 @@
 use crate::fs::{manually, OpenOptions};
+use std::ffi::OsStr;
 use std::path::Path;
 use std::{fs, io};
 use windows_sys::Win32::Foundation::ERROR_FILE_NOT_FOUND;
@@ -11,9 +12,9 @@ pub(crate) fn open_impl(
     // Windows reserves several special device paths. Disallow opening any
     // of them.
     // See: https://learn.microsoft.com/en-us/windows/win32/fileio/naming-a-file#naming-conventions
-    if let Some(stem) = path.file_stem() {
+    if let Some(stem) = file_prefix(path) {
         if let Some(stemstr) = stem.to_str() {
-            match stemstr.to_uppercase().as_str() {
+            match stemstr.trim_end().to_uppercase().as_str() {
                 "CON" | "PRN" | "AUX" | "NUL" | "COM0" | "COM1" | "COM2" | "COM3" | "COM4"
                 | "COM5" | "COM6" | "COM7" | "COM8" | "COM9" | "COM¹" | "COM²" | "COM³"
                 | "LPT0" | "LPT1" | "LPT2" | "LPT3" | "LPT4" | "LPT5" | "LPT6" | "LPT7"
@@ -27,3 +28,39 @@ pub(crate) fn open_impl(
 
     manually::open(start, path, options)
 }
+
+// TODO: Replace this with `Path::file_prefix` once that's stable. For now,
+// we use a copy of the code. This code is derived from
+// https://github.com/rust-lang/rust/blob/9fe9041cc8eddaed402d17aa4facb2ce8f222e95/library/std/src/path.rs#L2648
+fn file_prefix(path: &Path) -> Option<&OsStr> {
+    path.file_name()
+        .map(split_file_at_dot)
+        .and_then(|(before, _after)| Some(before))
+}
+
+// This code is derived from
+// https://github.com/rust-lang/rust/blob/9fe9041cc8eddaed402d17aa4facb2ce8f222e95/library/std/src/path.rs#L340
+#[allow(unsafe_code)]
+fn split_file_at_dot(file: &OsStr) -> (&OsStr, Option<&OsStr>) {
+    let slice = file.as_encoded_bytes();
+    if slice == b".." {
+        return (file, None);
+    }
+
+    // The unsafety here stems from converting between &OsStr and &[u8]
+    // and back. This is safe to do because (1) we only look at ASCII
+    // contents of the encoding and (2) new &OsStr values are produced
+    // only from ASCII-bounded slices of existing &OsStr values.
+    let i = match slice[1..].iter().position(|b| *b == b'.') {
+        Some(i) => i + 1,
+        None => return (file, None),
+    };
+    let before = &slice[..i];
+    let after = &slice[i + 1..];
+    unsafe {
+        (
+            OsStr::from_encoded_bytes_unchecked(before),
+            Some(OsStr::from_encoded_bytes_unchecked(after)),
+        )
+    }
+}
diff --git a/tests/windows-open.rs b/tests/windows-open.rs
index 0cb43d8c..a6c8b2bb 100644
--- a/tests/windows-open.rs
+++ b/tests/windows-open.rs
@@ -134,30 +134,43 @@ fn windows_open_special() {
     // Opening any of these should fail.
     for device in &[
         "CON", "PRN", "AUX", "NUL", "COM0", "COM1", "COM2", "COM3", "COM4", "COM5", "COM6", "COM7",
-        "COM8", "COM9", "LPT0", "LPT1", "LPT2", "LPT3", "LPT4", "LPT5", "LPT6", "LPT7", "LPT8",
-        "LPT9",
+        "COM8", "COM9", "COM¹", "COM²", "COM³", "LPT0", "LPT1", "LPT2", "LPT3", "LPT4", "LPT5",
+        "LPT6", "LPT7", "LPT8", "LPT9", "LPT¹", "LPT²", "LPT³",
     ] {
-        tmpdir.open(device).unwrap_err();
-        tmpdir.open(&format!(".\\{}", device)).unwrap_err();
-        tmpdir.open(&format!("{}.ext", device)).unwrap_err();
-        tmpdir.open(&format!(".\\{}.ext", device)).unwrap_err();
-
-        let mut options = cap_std::fs::OpenOptions::new();
-        options.write(true);
-        tmpdir.open_with(device, &options).unwrap_err();
-        tmpdir
-            .open_with(&format!(".\\{}", device), &options)
-            .unwrap_err();
-        tmpdir
-            .open_with(&format!("{}.ext", device), &options)
-            .unwrap_err();
-        tmpdir
-            .open_with(&format!(".\\{}.ext", device), &options)
-            .unwrap_err();
-
-        tmpdir.create(device).unwrap_err();
-        tmpdir.create(&format!(".\\{}", device)).unwrap_err();
-        tmpdir.create(&format!("{}.ext", device)).unwrap_err();
-        tmpdir.create(&format!(".\\{}.ext", device)).unwrap_err();
+        for suffix in &[
+            "",
+            " ",
+            ".",
+            ". ",
+            ".ext",
+            ".ext.",
+            ".ext. ",
+            ".ext ",
+            ".ext.more",
+            ".ext.more.",
+            ".ext.more ",
+            ".ext.more. ",
+            ".ext.more .",
+        ] {
+            let name = format!("{}{}", device, suffix);
+            eprintln!("testing '{}'", name);
+
+            match tmpdir.open(&name).unwrap_err().kind() {
+                std::io::ErrorKind::NotFound | std::io::ErrorKind::PermissionDenied => {}
+                kind => panic!("unexpected error: {:?}", kind),
+            }
+
+            let mut options = cap_std::fs::OpenOptions::new();
+            options.write(true);
+            match tmpdir.open_with(&name, &options).unwrap_err().kind() {
+                std::io::ErrorKind::NotFound | std::io::ErrorKind::PermissionDenied => {}
+                kind => panic!("unexpected error: {:?}", kind),
+            }
+
+            match tmpdir.create(&name).unwrap_err().kind() {
+                std::io::ErrorKind::NotFound | std::io::ErrorKind::PermissionDenied => {}
+                kind => panic!("unexpected error: {:?}", kind),
+            }
+        }
     }
 }