diff --git a/modules/swagger-parser/src/test/java/io/swagger/parser/util/DeserializationUtilsTest.java b/modules/swagger-parser/src/test/java/io/swagger/parser/util/DeserializationUtilsTest.java
new file mode 100644
index 0000000000..a83428f5b4
--- /dev/null
+++ b/modules/swagger-parser/src/test/java/io/swagger/parser/util/DeserializationUtilsTest.java
@@ -0,0 +1,60 @@
+package io.swagger.parser.util;
+
+import com.fasterxml.jackson.databind.JsonNode;
+import org.testng.annotations.Test;
+
+import java.io.File;
+import java.io.IOException;
+import java.nio.charset.StandardCharsets;
+import java.nio.file.Files;
+
+import static org.testng.AssertJUnit.assertFalse;
+import static org.testng.AssertJUnit.assertNotSame;
+
+public class DeserializationUtilsTest {
+
+    @Test
+    public void testEnumValuesAreNotConvertedToBooleansOAS2() throws IOException {
+        String yaml = readFile("src/test/resources/EnumYesNoOnOffOAS2.yaml");
+
+        JsonNode jsonNode = DeserializationUtils.readYamlTree(yaml, null);
+
+        jsonNode.findPath("EnumWithQuotes").get("enum").elements()
+                .forEachRemaining(element -> {
+                    assertFalse(element.isBoolean());
+                    assertNotSame(element.textValue(), "true");
+                    assertNotSame(element.textValue(), "false");
+                });
+        jsonNode.findPath("EnumNoQuotes").get("enum").elements()
+                .forEachRemaining(element -> {
+                    assertFalse(element.isBoolean());
+                    assertNotSame(element.textValue(), "true");
+                    assertNotSame(element.textValue(), "false");
+                });
+    }
+
+    @Test
+    public void testEnumValuesAreNotConvertedToBooleansOAS3() throws IOException {
+        String yaml = readFile("src/test/resources/EnumYesNoOnOffOAS3.yaml");
+
+        JsonNode jsonNode = DeserializationUtils.readYamlTree(yaml, null);
+
+        jsonNode.findPath("EnumWithQuotes").get("enum").elements()
+                .forEachRemaining(element -> {
+                    assertFalse(element.isBoolean());
+                    assertNotSame(element.textValue(), "true");
+                    assertNotSame(element.textValue(), "false");
+                });
+        jsonNode.findPath("EnumNoQuotes").get("enum").elements()
+                .forEachRemaining(element -> {
+                    assertFalse(element.isBoolean());
+                    assertNotSame(element.textValue(), "true");
+                    assertNotSame(element.textValue(), "false");
+                });
+    }
+
+
+    private String readFile(String name) throws IOException {
+        return new String(Files.readAllBytes(new File(name).toPath()), StandardCharsets.UTF_8);
+    }
+}
diff --git a/modules/swagger-parser/src/test/resources/EnumYesNoOnOffOAS2.yaml b/modules/swagger-parser/src/test/resources/EnumYesNoOnOffOAS2.yaml
new file mode 100644
index 0000000000..2596d549f8
--- /dev/null
+++ b/modules/swagger-parser/src/test/resources/EnumYesNoOnOffOAS2.yaml
@@ -0,0 +1,46 @@
+swagger: '2.0'
+info:
+  title: Yes No On Off string test
+  version: 1.0.0
+paths: {}
+definitions:
+  EnumNoQuotes:
+    type: string
+    enum:
+      - some_string
+      - y
+      - Y
+      - yes
+      - Yes
+      - YES
+      - n
+      - N
+      - no
+      - No
+      - NO
+      - on
+      - On
+      - ON
+      - off
+      - Off
+      - OFF
+  EnumWithQuotes:
+    type: string
+    enum:
+      - some_string
+      - 'y'
+      - 'Y'
+      - 'yes'
+      - 'Yes'
+      - 'YES'
+      - 'n'
+      - 'N'
+      - 'no'
+      - 'No'
+      - 'NO'
+      - 'on'
+      - 'On'
+      - 'ON'
+      - 'off'
+      - 'Off'
+      - 'OFF'
\ No newline at end of file
diff --git a/modules/swagger-parser/src/test/resources/EnumYesNoOnOffOAS3.yaml b/modules/swagger-parser/src/test/resources/EnumYesNoOnOffOAS3.yaml
new file mode 100644
index 0000000000..ce17825826
--- /dev/null
+++ b/modules/swagger-parser/src/test/resources/EnumYesNoOnOffOAS3.yaml
@@ -0,0 +1,47 @@
+openapi: 3.0.0
+info:
+  title: Yes No On Off string test
+  version: 1.0.0
+paths: {}
+components:
+  schemas:
+    EnumNoQuotes:
+      type: string
+      enum:
+        - some_string
+        - y
+        - Y
+        - yes
+        - Yes
+        - YES
+        - n
+        - N
+        - no
+        - No
+        - NO
+        - on
+        - On
+        - ON
+        - off
+        - Off
+        - OFF
+    EnumWithQuotes:
+      type: string
+      enum:
+        - some_string
+        - 'y'
+        - 'Y'
+        - 'yes'
+        - 'Yes'
+        - 'YES'
+        - 'n'
+        - 'N'
+        - 'no'
+        - 'No'
+        - 'NO'
+        - 'on'
+        - 'On'
+        - 'ON'
+        - 'off'
+        - 'Off'
+        - 'OFF'
\ No newline at end of file