diff --git a/src/cli/pack_command.zig b/src/cli/pack_command.zig
index dc9db0f63a364d..b23e5ebaaf5f64 100644
--- a/src/cli/pack_command.zig
+++ b/src/cli/pack_command.zig
@@ -1356,10 +1356,12 @@ pub const PackCommand = struct {
                         var includes: std.ArrayListUnmanaged(Pattern) = .{};
                         defer includes.deinit(ctx.allocator);
 
+                        var path_buf: PathBuffer = undefined;
                         var files_array = _files_array;
                         while (files_array.next()) |files_entry| {
                             if (files_entry.asString(ctx.allocator)) |file_entry_str| {
-                                const parsed = try Pattern.fromUTF8(ctx.allocator, file_entry_str) orelse continue;
+                                const normalized = bun.path.normalizeBuf(file_entry_str, &path_buf, .posix);
+                                const parsed = try Pattern.fromUTF8(ctx.allocator, normalized) orelse continue;
                                 try includes.append(ctx.allocator, parsed);
                                 continue;
                             }
diff --git a/test/cli/install/bun-pack.test.ts b/test/cli/install/bun-pack.test.ts
index ac74efa8e7a6dc..482a5cc56776d9 100644
--- a/test/cli/install/bun-pack.test.ts
+++ b/test/cli/install/bun-pack.test.ts
@@ -921,7 +921,7 @@ describe("files", () => {
       write(
         join(packageDir, "package.json"),
         JSON.stringify({
-          name: "pack-files-3",
+          name: "pack-files-2",
           version: "1.2.3",
           files: ["index.js"],
         }),
@@ -932,16 +932,41 @@ describe("files", () => {
     ]);
 
     await pack(packageDir, bunEnv);
-    const tarball = readTarball(join(packageDir, "pack-files-3-1.2.3.tgz"));
+    const tarball = readTarball(join(packageDir, "pack-files-2-1.2.3.tgz"));
     expect(tarball.entries).toMatchObject([{ "pathname": "package/package.json" }, { "pathname": "package/index.js" }]);
   });
 
+  test("matches './' as the root", async () => {
+    await Promise.all([
+      write(
+        join(packageDir, "package.json"),
+        JSON.stringify({
+          name: "pack-files-3",
+          version: "1.2.3",
+          files: ["./dist", "!./subdir", "!./dist/index.js", "./////src//index.ts"],
+        }),
+      ),
+      write(join(packageDir, "dist", "index.js"), "console.log('hello ./dist/index.js')"),
+      write(join(packageDir, "subdir", "index.js"), "console.log('hello ./subdir/index.js')"),
+      write(join(packageDir, "src", "dist", "index.js"), "console.log('hello ./src/dist/index.js')"),
+      write(join(packageDir, "src", "index.ts"), "console.log('hello ./src/index.ts')"),
+    ]);
+
+    await pack(packageDir, bunEnv);
+    const tarball = readTarball(join(packageDir, "pack-files-3-1.2.3.tgz"));
+    expect(tarball.entries).toMatchObject([
+      { "pathname": "package/package.json" },
+      { "pathname": "package/dist/index.js" },
+      { "pathname": "package/src/index.ts" },
+    ]);
+  });
+
   test("recursive only if leading **/", async () => {
     await Promise.all([
       write(
         join(packageDir, "package.json"),
         JSON.stringify({
-          name: "pack-files-2",
+          name: "pack-files-4",
           version: "1.2.123",
           files: ["**/index.js"],
         }),
@@ -953,7 +978,7 @@ describe("files", () => {
     ]);
 
     await pack(packageDir, bunEnv);
-    const tarball = readTarball(join(packageDir, "pack-files-2-1.2.123.tgz"));
+    const tarball = readTarball(join(packageDir, "pack-files-4-1.2.123.tgz"));
     expect(tarball.entries).toMatchObject([
       { "pathname": "package/package.json" },
       { "pathname": "package/index.js" },