diff --git a/src/rules/expectRule.ts b/src/rules/expectRule.ts
index 99cc14de..d1478de0 100644
--- a/src/rules/expectRule.ts
+++ b/src/rules/expectRule.ts
@@ -298,7 +298,12 @@ function getExpectTypeFailures(
 
 			const actual = checker.typeToString(type, /*enclosingDeclaration*/ undefined, ts.TypeFormatFlags.NoTruncation);
 			if (actual !== expected) {
-				unmetExpectations.push({ node, expected, actual });
+				console.log("!!!", actual);
+				const actualSorted = fixupType(actual);
+				if (actualSorted !== expected) {
+					console.log("???", actualSorted);
+					unmetExpectations.push({ node, expected, actual });
+				}
 			}
 
 			typeAssertions.delete(line);
@@ -308,6 +313,27 @@ function getExpectTypeFailures(
 	}
 }
 
+function fixupType(s: string): string {
+	// Don't mess up `{ a: number | string }` into `string } | { a: number`
+	if (/[\<\(\[\{]/.test(s)) {
+		return s;
+	}
+	return fixupUnions(s);
+}
+
+function fixupUnions(s: string): string {
+	const splitter = " | ";
+	return s.split(splitter).map(fixupIntersections).sort().join(splitter);
+}
+
+function fixupIntersections(s: string): string {
+	if (s.startsWith("(") && s.endsWith(")")) {
+		return `(${fixupIntersections(s.slice(1, s.length - 1))})`;
+	}
+	const splitter = " & ";
+	return s.split(splitter).sort().join(splitter);
+}
+
 function lineOfPosition(pos: number, sourceFile: SourceFile): number {
 	return sourceFile.getLineAndCharacterOfPosition(pos).line;
 }
diff --git a/test/dt-header/wrong/types/bad-url-username/index.d.ts.lint b/test/dt-header/wrong/types/bad-url-username/index.d.ts.lint
index 91b3d985..0ac32c82 100644
--- a/test/dt-header/wrong/types/bad-url-username/index.d.ts.lint
+++ b/test/dt-header/wrong/types/bad-url-username/index.d.ts.lint
@@ -1,5 +1,5 @@
 // Type definitions for dt-header 1.0
 // Project: https://github.com/bobby-headers/dt-header
 // Definitions by: Jane Doe <https://github.com/jane doe>
-                                                    ~ [Error parsing header. Expected: '>']
+                            ~ [Error parsing header. Expected: /\<https\:\/\/github\.com\/([a-zA-Z\d\-]+)\>/]
 // Definitions: https://github.com/DefinitelyTyped/DefinitelyTyped
diff --git a/test/dt-header/wrong/types/bad-url/index.d.ts.lint b/test/dt-header/wrong/types/bad-url/index.d.ts.lint
index c71501e1..35f39b1a 100644
--- a/test/dt-header/wrong/types/bad-url/index.d.ts.lint
+++ b/test/dt-header/wrong/types/bad-url/index.d.ts.lint
@@ -1,5 +1,5 @@
 // Type definitions for dt-header 1.0
 // Project: https://github.com/bobby-headers/dt-header
 // Definitions by: Jane Doe <https://github.org/janedoe>
-                            ~                            [Error parsing header. Expected: '<https://github.com/']
+                            ~ [Error parsing header. Expected: /\<https\:\/\/github\.com\/([a-zA-Z\d\-]+)\>/]
 // Definitions: https://github.com/DefinitelyTyped/DefinitelyTyped
diff --git a/test/expect/expectType.ts.lint b/test/expect/expectType.ts.lint
index 2b830753..24c72118 100644
--- a/test/expect/expectType.ts.lint
+++ b/test/expect/expectType.ts.lint
@@ -18,3 +18,17 @@ declare function f(
 
 // Test that we never truncate types.
 f; // $ExpectType (one: number, two: [number, number], three: [number, number, number], four: [number, number, number, number]) => number
+
+// Test that a union could be either exactly what tsc output, or a sorted version of that.
+declare const x: "foo" | "bar";
+x; // $ExpectType "foo" | "bar"
+x; // $ExpectType "bar" | "foo"
+
+type A = { a: number };
+type B = { b: number };
+type C = { c: number };
+
+// Test that we don't try to sort nested unions.
+declare class Generic<T> {}
+declare const generic: Generic<string | number>;
+generic; // $ExpectType Generic<string | number>