diff --git a/src/index.js b/src/index.js
index 84e9b7a..d7d6e3c 100644
--- a/src/index.js
+++ b/src/index.js
@@ -71,7 +71,7 @@ export function resolve(pkg, entry='.', options={}) {
 		allows.add(require ? 'require' : 'import');
 		allows.add(browser ? 'browser' : 'node');
 
-		let key, tmp, isSingle=false;
+		let key, tmp, isSingle=false, longestMatch='';
 
 		for (key in exports) {
 			isSingle = key[0] !== '.';
@@ -90,18 +90,21 @@ export function resolve(pkg, entry='.', options={}) {
 
 		for (key in exports) {
 			tmp = key[key.length - 1];
-			if (tmp === '/' && target.startsWith(key)) {
-				return (tmp = loop(exports[key], allows))
-					? (tmp + target.substring(key.length))
-					: bail(name, target, 1);
+			if (key.length <= target.length && key.length > longestMatch.length && (
+				tmp === '/' && target.startsWith(key) ||
+				tmp === '*' && target.startsWith(key.slice(0, -1))
+			)) {
+				longestMatch = key;
 			}
-			if (tmp === '*' && target.startsWith(key.slice(0, -1))) {
-				// do not trigger if no *content* to inject
-				if (target.substring(key.length - 1).length > 0) {
-					return (tmp = loop(exports[key], allows))
-						? tmp.replace('*', target.substring(key.length - 1))
-						: bail(name, target, 1);
-				}
+		}
+
+		if (longestMatch) {
+			if (tmp = loop(exports[longestMatch], allows)) {
+				return (longestMatch[longestMatch.length - 1] === '/')
+					? (tmp + target.slice(longestMatch.length))
+					: tmp.replace('*', target.slice(longestMatch.length - 1));
+			} else {
+				return bail(name, target, 1);
 			}
 		}
 
diff --git a/test/resolve.js b/test/resolve.js
index dd5dc39..63f7d69 100644
--- a/test/resolve.js
+++ b/test/resolve.js
@@ -425,6 +425,33 @@ resolve('exports["./features/*"] :: with "./" key', () => {
 	fail(pkg, '.', 'foobar');
 });
 
+resolve('exports["./features/*"] :: with unsorted keys', () => {
+	let pkg = {
+		"name": "foobar",
+		"exports": {
+			"./features/*": "./features/*.js",
+			"./": "./",
+			"./features/data/*": "./features/data/*.json"
+		}
+	};
+
+	pass(pkg, './features', 'features'); // via "./"
+	pass(pkg, './features', 'foobar/features'); // via "./"
+
+	pass(pkg, './features/', 'features/'); // via "./"
+	pass(pkg, './features/', 'foobar/features/'); // via "./"
+
+	pass(pkg, './features/hello.js', 'foobar/features/hello'); // via "./features/*"
+	pass(pkg, './features/world.js', 'foobar/features/world'); // via "./features/*""
+
+	pass(pkg, './features/data/hello.json', 'foobar/features/data/hello'); // via "./features/data/*"
+	pass(pkg, './features/data/world.json', 'foobar/features/data/world'); // via "./features/data/*"
+
+	pass(pkg, './package.json', 'package.json'); // via "./"
+	pass(pkg, './package.json', 'foobar/package.json'); // via "./"
+	pass(pkg, './package.json', './package.json'); // via "./"
+});
+
 resolve('exports["./features/*"] :: conditions', () => {
 	let pkg = {
 		"name": "foobar",