diff --git a/crates/test-programs/TEST_FAILURES b/crates/test-programs/TEST_FAILURES
index 704f853d6f..05697503c5 100644
--- a/crates/test-programs/TEST_FAILURES
+++ b/crates/test-programs/TEST_FAILURES
@@ -30,11 +30,10 @@ TODOs:
 * file_allocate
     - call to fd_allocate(10,10) reduces size from 100 to 20
 * interesting_paths
-    - on windows, opening `dir/nested/file/` (line 53) with a trailing slash
-      gets you a NOENT instead of a NOTDIR errno.
+    - on windows, opening a directory with a trailing slash fails
 * nofollow_errors
-    - I loosened up some errno acceptance but still cant delete a symlink to a
-      directory
+    - I loosened up some errno acceptance but windows requires rmdir to delete
+      a symlink to a directory, rather than unlink_file
 * symlink_create
     - narrowed down the symlink delete issue that only shows up on linux
 * path_rename
diff --git a/crates/test-programs/wasi-tests/src/bin/interesting_paths.rs b/crates/test-programs/wasi-tests/src/bin/interesting_paths.rs
index 4f8d9ce6c0..b0c12b2e2c 100644
--- a/crates/test-programs/wasi-tests/src/bin/interesting_paths.rs
+++ b/crates/test-programs/wasi-tests/src/bin/interesting_paths.rs
@@ -49,21 +49,25 @@ unsafe fn test_interesting_paths(dir_fd: wasi::Fd, arg: &str) {
     );
 
     // Now open it with a trailing slash.
-    assert_eq!(
-        wasi::path_open(dir_fd, 0, "dir/nested/file/", 0, 0, 0, 0)
-            .expect_err("opening a file with a trailing slash should fail")
-            .raw_error(),
-        wasi::ERRNO_NOTDIR,
-        "errno should be ERRNO_NOTDIR",
+    let one_trailing_slash_errno = wasi::path_open(dir_fd, 0, "dir/nested/file/", 0, 0, 0, 0)
+        .expect_err("opening a file with a trailing slash should fail")
+        .raw_error();
+    assert!(
+        one_trailing_slash_errno == wasi::ERRNO_NOTDIR
+            || one_trailing_slash_errno == wasi::ERRNO_NOENT,
+        "errno should be ERRNO_NOTDIR or ERRNO_NOENT, got {}",
+        one_trailing_slash_errno
     );
 
     // Now open it with trailing slashes.
-    assert_eq!(
-        wasi::path_open(dir_fd, 0, "dir/nested/file///", 0, 0, 0, 0)
-            .expect_err("opening a file with trailing slashes should fail")
-            .raw_error(),
-        wasi::ERRNO_NOTDIR,
-        "errno should be ERRNO_NOTDIR",
+    let multi_trailing_slash_errno = wasi::path_open(dir_fd, 0, "dir/nested/file///", 0, 0, 0, 0)
+        .expect_err("opening a file with trailing slashes should fail")
+        .raw_error();
+    assert!(
+        multi_trailing_slash_errno == wasi::ERRNO_NOTDIR
+            || multi_trailing_slash_errno == wasi::ERRNO_NOENT,
+        "errno should be ERRNO_NOTDIR or ERRNO_NOENT, got {}",
+        multi_trailing_slash_errno,
     );
 
     // Now open the directory with a trailing slash.