diff --git a/packages/safe-ds-lang/src/language/typing/safe-ds-type-checker.ts b/packages/safe-ds-lang/src/language/typing/safe-ds-type-checker.ts
index 87d4962aa..3e4b21d2e 100644
--- a/packages/safe-ds-lang/src/language/typing/safe-ds-type-checker.ts
+++ b/packages/safe-ds-lang/src/language/typing/safe-ds-type-checker.ts
@@ -75,7 +75,8 @@ export class SafeDsTypeChecker {
         // Handle union types
         if (type instanceof UnionType) {
             return type.types.every((it) => this.isSubtypeOf(it, other, options));
-        } else if (other instanceof UnionType) {
+        } else if (other instanceof UnionType && !(type instanceof LiteralType)) {
+            // For literal types the quantifiers would be the wrong way around
             return other.types.some((it) => this.isSubtypeOf(type, it, options));
         }
 
@@ -264,17 +265,21 @@ export class SafeDsTypeChecker {
                 return true;
             }
 
-            return type.constants.every((constant) => this.constantIsSubtypeOfClassType(constant, other, options));
+            return type.constants.every((constant) => this.constantIsSubtypeOf(constant, other, options));
         } else if (other instanceof LiteralType) {
             return type.constants.every((constant) =>
                 other.constants.some((otherConstant) => constant.equals(otherConstant)),
             );
+        } else if (other instanceof UnionType) {
+            return type.constants.every((constant) =>
+                other.types.some((it) => this.constantIsSubtypeOf(constant, it, options)),
+            );
         } else {
             return false;
         }
     }
 
-    private constantIsSubtypeOfClassType(constant: Constant, other: ClassType, options: TypeCheckOptions): boolean {
+    private constantIsSubtypeOf(constant: Constant, other: Type, options: TypeCheckOptions): boolean {
         const classType = this.typeComputer().computeClassTypeForConstant(constant);
         return this.isSubtypeOf(classType, other, options);
     }
diff --git a/packages/safe-ds-lang/tests/language/typing/type checker/isSubOrSupertypeOf.test.ts b/packages/safe-ds-lang/tests/language/typing/type checker/isSubOrSupertypeOf.test.ts
index fdda32898..6c145f42b 100644
--- a/packages/safe-ds-lang/tests/language/typing/type checker/isSubOrSupertypeOf.test.ts	
+++ b/packages/safe-ds-lang/tests/language/typing/type checker/isSubOrSupertypeOf.test.ts	
@@ -508,6 +508,11 @@ const basic = async (): Promise<IsSubOrSupertypeOfTest[]> => {
             type2: factory.createUnionType(coreTypes.String),
             expected: false,
         },
+        {
+            type1: factory.createLiteralType(new IntConstant(1n), new StringConstant('')),
+            type2: factory.createUnionType(coreTypes.Int, coreTypes.String),
+            expected: true,
+        },
         // Literal type to other
         {
             type1: factory.createLiteralType(), // Empty literal type