diff --git a/modules/swagger-core/src/test/java/io/swagger/v3/core/converting/SwaggerSerializerTest.java b/modules/swagger-core/src/test/java/io/swagger/v3/core/converting/SwaggerSerializerTest.java
index 491c40f380..81095f4e6d 100644
--- a/modules/swagger-core/src/test/java/io/swagger/v3/core/converting/SwaggerSerializerTest.java
+++ b/modules/swagger-core/src/test/java/io/swagger/v3/core/converting/SwaggerSerializerTest.java
@@ -5,6 +5,7 @@
 import io.swagger.v3.core.matchers.SerializationMatchers;
 import io.swagger.v3.core.oas.models.Person;
 import io.swagger.v3.core.util.Json;
+import io.swagger.v3.core.util.JsonAssert;
 import io.swagger.v3.core.util.OutputReplacer;
 import io.swagger.v3.core.util.ResourceUtils;
 import io.swagger.v3.oas.models.Components;
@@ -172,7 +173,7 @@ public void writeSpecWithParameterReferences() throws IOException {
 
         final String swaggerJson = Json.mapper().writeValueAsString(swagger);
         final OpenAPI rebuilt = Json.mapper().readValue(swaggerJson, OpenAPI.class);
-        assertEquals(Json.pretty(rebuilt), Json.pretty(swagger));
+        JsonAssert.assertJsonEquals(Json.mapper(), Json.pretty(rebuilt), Json.pretty(swagger));
     }
 
     @Test
diff --git a/modules/swagger-core/src/test/java/io/swagger/v3/core/roundtrip/ComprehensiveRoundTripTest.java b/modules/swagger-core/src/test/java/io/swagger/v3/core/roundtrip/ComprehensiveRoundTripTest.java
index 36c2b3c770..e2ae0ea6a6 100644
--- a/modules/swagger-core/src/test/java/io/swagger/v3/core/roundtrip/ComprehensiveRoundTripTest.java
+++ b/modules/swagger-core/src/test/java/io/swagger/v3/core/roundtrip/ComprehensiveRoundTripTest.java
@@ -3,6 +3,7 @@
 import com.fasterxml.jackson.databind.JsonNode;
 import com.fasterxml.jackson.databind.ObjectMapper;
 import io.swagger.v3.core.util.Json;
+import io.swagger.v3.core.util.JsonAssert;
 import io.swagger.v3.core.util.Json31;
 import io.swagger.v3.core.util.ResourceUtils;
 import io.swagger.v3.core.util.Yaml;
@@ -70,7 +71,7 @@ public void testRoundTrip30Json() throws IOException {
         String jsonAgain = Json.pretty(deserializedOpenAPI);
         
         // Compare JSON strings
-        assertEquals(json, jsonAgain, "JSON round-trip failed");
+        JsonAssert.assertJsonEquals(Json.mapper(), json, jsonAgain, "JSON round-trip failed");
     }
     
     /**
@@ -106,7 +107,7 @@ public void testRoundTrip30Yaml() throws IOException {
         String yamlAgain = Yaml.pretty(deserializedOpenAPI);
         
         // Compare YAML strings
-        assertEquals(yaml, yamlAgain, "YAML round-trip failed");
+        JsonAssert.assertJsonEquals(Yaml.mapper(), yaml, yamlAgain, "YAML round-trip failed");
     }
     
     /**
@@ -148,7 +149,7 @@ public void testRoundTrip31Json() throws IOException {
         String jsonAgain = Json31.pretty(deserializedOpenAPI);
         
         // Compare JSON strings
-        assertEquals(json, jsonAgain, "JSON round-trip failed");
+        JsonAssert.assertJsonEquals(Json31.mapper(), json, jsonAgain, "JSON round-trip failed");
     }
     
     /**
@@ -190,7 +191,7 @@ public void testRoundTrip31Yaml() throws IOException {
         String yamlAgain = Yaml31.pretty(deserializedOpenAPI);
         
         // Compare YAML strings
-        assertEquals(yaml, yamlAgain, "YAML round-trip failed");
+        JsonAssert.assertJsonEquals(Yaml31.mapper(), yaml, yamlAgain, "YAML round-trip failed");
     }
     
     /**
@@ -242,7 +243,7 @@ public void testComplexRoundTrip31() throws IOException {
         String jsonAgain = Json31.pretty(deserializedOpenAPI);
         
         // Compare JSON strings
-        assertEquals(json, jsonAgain, "JSON round-trip failed");
+        JsonAssert.assertJsonEquals(Json31.mapper(), json, jsonAgain, "JSON round-trip failed");
     }
     
     /**
@@ -276,7 +277,7 @@ public void testBooleanSchemaRoundTrip() throws IOException {
         String jsonAgain = Json31.pretty(deserializedOpenAPI);
         
         // Compare JSON strings
-        assertEquals(json, jsonAgain, "JSON round-trip failed");
+        JsonAssert.assertJsonEquals(Json.mapper(), json, jsonAgain, "JSON round-trip failed");
     }
     
     /**
@@ -307,7 +308,7 @@ public void testNullValuesRoundTrip() throws IOException {
         String jsonAgain = Json31.pretty(deserializedOpenAPI);
         
         // Compare JSON strings
-        assertEquals(json, jsonAgain, "JSON round-trip failed");
+        JsonAssert.assertJsonEquals(Json.mapper(), json, jsonAgain, "JSON round-trip failed");
     }
     
     /**
@@ -350,14 +351,7 @@ public void testRealWorldRoundTrip31() throws IOException {
         String yamlAgain = Yaml31.pretty(deserializedOpenAPI);
         
         // Compare YAML strings (normalize whitespace)
-        assertEquals(normalizeWhitespace(serializedYaml), normalizeWhitespace(yamlAgain), "YAML round-trip failed");
-    }
-    
-    /**
-     * Helper method to normalize whitespace in YAML strings for comparison
-     */
-    private String normalizeWhitespace(String yaml) {
-        return yaml.replaceAll("\\s+", " ").trim();
+        JsonAssert.assertJsonEquals(Yaml31.mapper(), serializedYaml, yamlAgain, "YAML round-trip failed");
     }
     
     /**
diff --git a/modules/swagger-core/src/test/java/io/swagger/v3/core/serialization/properties/PropertySerializationTest.java b/modules/swagger-core/src/test/java/io/swagger/v3/core/serialization/properties/PropertySerializationTest.java
index 3025b23a4a..3cd5ea4022 100644
--- a/modules/swagger-core/src/test/java/io/swagger/v3/core/serialization/properties/PropertySerializationTest.java
+++ b/modules/swagger-core/src/test/java/io/swagger/v3/core/serialization/properties/PropertySerializationTest.java
@@ -317,6 +317,6 @@ public void deserializeObjectPropertyWithRequiredProperties() throws IOException
                 .addProperties("stringProperty", new StringSchema());
         p.required(Arrays.asList("stringProperty"));
         final String json = "{\"type\":\"object\",\"properties\":{\"stringProperty\":{\"type\":\"string\"}},\"required\":[\"stringProperty\"]}";
-        assertEquals(p, m.readValue(json, Schema.class));
+        JsonAssert.assertJsonEquals(m, m.writeValueAsString(p), json);
     }
 }
diff --git a/modules/swagger-core/src/test/java/io/swagger/v3/core/util/JsonAssert.java b/modules/swagger-core/src/test/java/io/swagger/v3/core/util/JsonAssert.java
index 72a1870ced..f9ff7c2047 100644
--- a/modules/swagger-core/src/test/java/io/swagger/v3/core/util/JsonAssert.java
+++ b/modules/swagger-core/src/test/java/io/swagger/v3/core/util/JsonAssert.java
@@ -8,11 +8,31 @@ public final class JsonAssert {
     private JsonAssert() {
     }
 
+    /**
+     * Asserts that two JSON strings are semantically equal, ignoring key order.
+     * This version uses a default failure message.
+     *
+     * @param mapper       The ObjectMapper to use for parsing.
+     * @param expectedJson The expected JSON/YAML string.
+     * @param actualJson   The actual JSON/YAML string.
+    */
     public static void assertJsonEquals(ObjectMapper mapper, String expectedJson, String actualJson) {
+        assertJsonEquals(mapper, expectedJson, actualJson, "The JSON structures are not equal.");
+    }
+
+    /**
+     * This version allows for a custom failure message.
+     *
+     * @param mapper       The ObjectMapper to use for parsing.
+     * @param expectedJson The expected JSON/YAML string.
+     * @param actualJson   The actual JSON/YAML string.
+     * @param message      The custom message to display if the assertion fails.
+    */
+    public static void assertJsonEquals(ObjectMapper mapper, String expectedJson, String actualJson, String message) {
         try {
             JsonNode expectedNode = mapper.readTree(expectedJson);
             JsonNode actualNode = mapper.readTree(actualJson);
-            assertTrue(expectedNode.equals(actualNode));
+            assertTrue(expectedNode.equals(actualNode), message);
         } catch (Exception e) {
             throw new RuntimeException(e);
         }