diff --git a/src/resolver/resolver.zig b/src/resolver/resolver.zig
index ae9562d142..b31b5f75c9 100644
--- a/src/resolver/resolver.zig
+++ b/src/resolver/resolver.zig
@@ -2877,8 +2877,8 @@ pub const Resolver = struct {
                 // because we want the output to always be deterministic
                 if (strings.startsWith(path, prefix) and
                     strings.endsWith(path, suffix) and
-                    (prefix.len >= longest_match_prefix_length and
-                    suffix.len > longest_match_suffix_length))
+                    (prefix.len > longest_match_prefix_length or
+                    (prefix.len == longest_match_prefix_length and suffix.len > longest_match_suffix_length)))
                 {
                     longest_match_prefix_length = @as(i32, @intCast(prefix.len));
                     longest_match_suffix_length = @as(i32, @intCast(suffix.len));
diff --git a/test/js/bun/resolve/bar/larger-index.js b/test/js/bun/resolve/bar/larger-index.js
new file mode 100644
index 0000000000..5837bb3bbb
--- /dev/null
+++ b/test/js/bun/resolve/bar/larger-index.js
@@ -0,0 +1,2 @@
+// this file is used in resolve.test.js
+export default {};
diff --git a/test/js/bun/resolve/resolve-test.js b/test/js/bun/resolve/resolve-test.js
index 242834b6fe..38198ef1d5 100644
--- a/test/js/bun/resolve/resolve-test.js
+++ b/test/js/bun/resolve/resolve-test.js
@@ -71,6 +71,7 @@ it("import.meta.resolve", async () => {
   expect(await import.meta.resolve("foo/bar")).toBe(join(import.meta.path, "../baz.js"));
   expect(await import.meta.resolve("@faasjs/baz")).toBe(join(import.meta.path, "../baz.js"));
   expect(await import.meta.resolve("@faasjs/bar")).toBe(join(import.meta.path, "../bar/src/index.js"));
+  expect(await import.meta.resolve("@faasjs/larger/bar")).toBe(join(import.meta.path, "../bar/larger-index.js"));
 
   // works with package.json "exports"
   expect(await import.meta.resolve("package-json-exports/baz")).toBe(
diff --git a/test/tsconfig.json b/test/tsconfig.json
index 09eecec640..248cb67477 100644
--- a/test/tsconfig.json
+++ b/test/tsconfig.json
@@ -26,7 +26,8 @@
       "node-harness": ["js/node/harness.ts"],
       "deno:harness": ["js/deno/harness.ts"],
       "foo/bar": ["js/bun/resolve/baz.js"],
-      "@faasjs/*": ["js/bun/resolve/*.js", "js/bun/resolve/*/src/index.js"]
+      "@faasjs/*": ["js/bun/resolve/*.js", "js/bun/resolve/*/src/index.js"],
+      "@faasjs/larger/*": ["js/bun/resolve/*/larger-index.js"]
     }
   },