diff --git a/src/Tests/NativePackerTests.cs b/src/Tests/NativePackerTests.cs
index 16caddb..d9852f3 100644
--- a/src/Tests/NativePackerTests.cs
+++ b/src/Tests/NativePackerTests.cs
@@ -84,6 +84,34 @@ public void Program_main_packs_through_the_shipped_entry_point()
         Assert.StartsWith(expected, File.ReadAllText(sha).Trim(), StringComparison.OrdinalIgnoreCase);
     }
 
+    [Fact]
+    public void Osx_rid_ignores_dsym_dwarf_also_named_ndx()
+    {
+        using var dir = new TempDir();
+        var payload = "osx-native-bytes"u8.ToArray();
+        var nupkg = RidNupkg.Write(dir.Nupkg, "osx-arm64", payload);
+
+        using (var zip = ZipFile.OpenRead(nupkg))
+        {
+            var namedNdx = zip.Entries
+                .Where(entry => Path.GetFileName(entry.FullName) == "ndx")
+                .Select(entry => entry.FullName.Replace('\\', '/'))
+                .ToArray();
+            Assert.Contains("tools/any/osx-arm64/ndx", namedNdx);
+            Assert.Contains("tools/any/osx-arm64/ndx.dSYM/Contents/Resources/DWARF/ndx", namedNdx);
+        }
+
+        var result = NativePacker.Pack(nupkg, "osx-arm64", dir.Output, "1.0.0");
+        using var file = File.OpenRead(result.ArchivePath);
+        using var gzip = new GZipStream(file, CompressionMode.Decompress);
+        using var tar = new TarReader(gzip);
+        var entry = tar.GetNextEntry(copyData: true);
+        Assert.NotNull(entry);
+        using var memory = new MemoryStream();
+        entry.DataStream!.CopyTo(memory);
+        Assert.Equal(payload, memory.ToArray());
+    }
+
     [Fact]
     public void Missing_binary_is_a_packer_error()
     {
diff --git a/src/Tests/RidNupkg.cs b/src/Tests/RidNupkg.cs
index f44321f..21ca0c9 100644
--- a/src/Tests/RidNupkg.cs
+++ b/src/Tests/RidNupkg.cs
@@ -22,6 +22,13 @@ public static string Write(string directory, string rid, byte[] payload)
         WriteEntry(zip, $"tools/any/{rid}/DotnetToolSettings.xml",
             """<?xml version="1.0" encoding="utf-8"?><DotNetCliTool />"""u8.ToArray());
         WriteEntry(zip, $"tools/any/{rid}/{Path.GetFileNameWithoutExtension(binary)}.pdb", "pdb"u8.ToArray());
+        if (rid.StartsWith("osx", StringComparison.OrdinalIgnoreCase))
+        {
+            WriteEntry(
+                zip,
+                $"tools/any/{rid}/{binary}.dSYM/Contents/Resources/DWARF/{binary}",
+                "dwarf-debug-bytes"u8.ToArray());
+        }
         WriteEntry(zip, "readme.md", "# ndx"u8.ToArray());
         return path;
     }
diff --git a/src/nativepack/NativePacker.cs b/src/nativepack/NativePacker.cs
index 8025258..201c19d 100644
--- a/src/nativepack/NativePacker.cs
+++ b/src/nativepack/NativePacker.cs
@@ -33,7 +33,7 @@ public static NativePackResult Pack(
         ArgumentException.ThrowIfNullOrWhiteSpace(version);
 
         var binaryName = BinaryFileName(rid);
-        var payload = ReadNativeBinary(nupkgPath, binaryName);
+        var payload = ReadNativeBinary(nupkgPath, rid, binaryName);
 
         Directory.CreateDirectory(outputDirectory);
 
@@ -55,7 +55,7 @@ public static NativePackResult Pack(
         return new NativePackResult(archivePath, sha256Path, sha256, binaryName);
     }
 
-    static byte[] ReadNativeBinary(string nupkgPath, string binaryName)
+    static byte[] ReadNativeBinary(string nupkgPath, string rid, string binaryName)
     {
         if (!File.Exists(nupkgPath))
         {
@@ -66,9 +66,7 @@ static byte[] ReadNativeBinary(string nupkgPath, string binaryName)
 
         using var zip = ZipFile.OpenRead(nupkgPath);
         var matches = zip.Entries
-            .Where(entry =>
-                entry.Length > 0 &&
-                string.Equals(Path.GetFileName(entry.FullName), binaryName, StringComparison.OrdinalIgnoreCase))
+            .Where(entry => IsNativeBinaryEntry(entry, binaryName))
             .ToArray();
 
         if (matches.Length == 0)
@@ -78,18 +76,44 @@ static byte[] ReadNativeBinary(string nupkgPath, string binaryName)
                 binaryName);
         }
 
-        if (matches.Length > 1)
+        var preferred = "tools/any/" + rid + "/" + binaryName;
+        var chosen = matches.FirstOrDefault(entry =>
+                PathsEqual(entry.FullName, preferred))
+            ?? (matches.Length == 1 ? matches[0] : null);
+
+        if (chosen is null)
         {
             throw new InvalidOperationException(
                 $"Multiple '{binaryName}' entries in '{nupkgPath}'.");
         }
 
-        using var stream = matches[0].Open();
+        using var stream = chosen.Open();
         using var memory = new MemoryStream();
         stream.CopyTo(memory);
         return memory.ToArray();
     }
 
+    static bool IsNativeBinaryEntry(ZipArchiveEntry entry, string binaryName)
+    {
+        if (entry.Length <= 0)
+            return false;
+
+        var path = entry.FullName.Replace('\\', '/');
+        if (path.Contains(".dSYM/", StringComparison.OrdinalIgnoreCase) ||
+            path.EndsWith(".dSYM", StringComparison.OrdinalIgnoreCase))
+        {
+            return false;
+        }
+
+        return string.Equals(Path.GetFileName(path), binaryName, StringComparison.OrdinalIgnoreCase);
+    }
+
+    static bool PathsEqual(string left, string right)
+        => string.Equals(
+            left.Replace('\\', '/').TrimStart('/'),
+            right.Replace('\\', '/').TrimStart('/'),
+            StringComparison.OrdinalIgnoreCase);
+
     static void PackZip(byte[] payload, string binaryName, string archivePath)
     {
         using var zip = ZipFile.Open(archivePath, ZipArchiveMode.Create);