diff --git a/typescript-generator-core/src/main/java/cz/habarta/typescript/generator/compiler/ModelCompiler.java b/typescript-generator-core/src/main/java/cz/habarta/typescript/generator/compiler/ModelCompiler.java
index 35517b622..81b25e4dc 100644
--- a/typescript-generator-core/src/main/java/cz/habarta/typescript/generator/compiler/ModelCompiler.java
+++ b/typescript-generator-core/src/main/java/cz/habarta/typescript/generator/compiler/ModelCompiler.java
@@ -55,6 +55,7 @@
 import cz.habarta.typescript.generator.parser.RestMethodModel;
 import cz.habarta.typescript.generator.parser.RestQueryParam;
 import cz.habarta.typescript.generator.type.JTypeWithNullability;
+import cz.habarta.typescript.generator.util.DeprecationUtils;
 import cz.habarta.typescript.generator.util.GenericsResolver;
 import cz.habarta.typescript.generator.util.Pair;
 import cz.habarta.typescript.generator.util.Utils;
@@ -72,6 +73,7 @@
 import java.util.Objects;
 import java.util.Set;
 import java.util.concurrent.atomic.AtomicBoolean;
+import java.util.function.Function;
 import java.util.regex.Matcher;
 import java.util.regex.Pattern;
 import java.util.stream.Collectors;
@@ -1019,11 +1021,9 @@ private static TsEnumModel addEnumValuesToJavadoc(TsEnumModel enumModel) {
                             Stream.of("Values:"),
                             enumModel.getMembers().stream()
                                     .map(enumMember -> "- `" + enumMember.getEnumValue() + "`"
-                                            + (enumMember.getComments() != null
-                                            ? " - " + String.join(" ", enumMember.getComments())
-                                            : ""))
+                                            + getEnumItemCommentAsString(enumMember))
                     )
-                    .flatMap(s -> s)
+                    .flatMap(Function.identity())
                     .collect(Collectors.toList())
             );
         } else {
@@ -1031,6 +1031,15 @@ private static TsEnumModel addEnumValuesToJavadoc(TsEnumModel enumModel) {
         }
     }
 
+    private static String getEnumItemCommentAsString(EnumMemberModel enumMember) {
+        if (enumMember.getComments() == null) {
+            return "";
+        }
+        return " - " + enumMember.getComments().stream()
+                .map(s -> s.startsWith(DeprecationUtils.DEPRECATED) ? s.substring(1) : s)
+                .collect(Collectors.joining(" "));
+    }
+
     private TsModel createAndUseTaggedUnions(final SymbolTable symbolTable, TsModel tsModel) {
         if (settings.disableTaggedUnions) {
             return tsModel;
diff --git a/typescript-generator-core/src/test/java/cz/habarta/typescript/generator/JavadocTest.java b/typescript-generator-core/src/test/java/cz/habarta/typescript/generator/JavadocTest.java
index e7795ecba..4d67f42d9 100644
--- a/typescript-generator-core/src/test/java/cz/habarta/typescript/generator/JavadocTest.java
+++ b/typescript-generator-core/src/test/java/cz/habarta/typescript/generator/JavadocTest.java
@@ -8,18 +8,23 @@
 import cz.habarta.typescript.generator.parser.Model;
 import cz.habarta.typescript.generator.parser.PropertyModel;
 import java.io.File;
-import java.util.Arrays;
+import java.util.Collections;
 import org.junit.jupiter.api.Assertions;
+import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.api.Test;
 
 
 public class JavadocTest {
+    final Settings settings = TestUtils.settings();
+    final TypeProcessor typeProcessor = new DefaultTypeProcessor();
+
+    @BeforeEach
+    void initSettings() {
+        settings.javadocXmlFiles = Collections.singletonList(new File("src/test/javadoc/test-javadoc.xml"));
+    }
 
     @Test
-    public void testJavadoc() {
-        final Settings settings = TestUtils.settings();
-        settings.javadocXmlFiles = Arrays.asList(new File("src/test/javadoc/test-javadoc.xml"));
-        final TypeProcessor typeProcessor = new DefaultTypeProcessor();
+    void javadocXml() {
         {
             final Model model = new Jackson2Parser(settings, typeProcessor).parseModel(ClassWithJavadoc.class);
             final BeanModel bean = model.getBeans().get(0);
@@ -32,6 +37,10 @@ public void testJavadoc() {
             final EnumModel enumModel = model.getEnums().get(0);
             Assertions.assertEquals("Documentation for DummyEnum.", enumModel.getComments().get(0));
         }
+    }
+
+    @Test
+    void classWithoutJavadoc() {
         {
             final Model model = new Jackson2Parser(settings, typeProcessor).parseModel(ClassWithoutJavadoc.class);
             final BeanModel bean = model.getBeans().get(0);
@@ -39,6 +48,10 @@ public void testJavadoc() {
             final PropertyModel property = bean.getProperties().get(0);
             Assertions.assertNull(property.getComments());
         }
+    }
+
+    @Test
+    void classWithEmbeddedExample() {
         {
             final String generated = new TypeScriptGenerator(settings).generateTypeScript(
                     Input.from(ClassWithJavadoc.class, InterfaceWithJavadoc.class, ClassWithEmbeddedExample.class));
@@ -61,6 +74,10 @@ public void testJavadoc() {
             Assertions.assertTrue(generated.contains("00ff00"));
             Assertions.assertTrue(generated.contains("0000ff"));
         }
+    }
+
+    @Test
+    void deprecatedClassWithoutJavadoc() {
         {
             final String generated = new TypeScriptGenerator(settings).generateTypeScript(Input.from(DeprecatedClassWithoutJavadoc.class));
             final String expected = ""
@@ -75,6 +92,10 @@ public void testJavadoc() {
                     + "}";
             Assertions.assertEquals(expected.trim(), generated.trim());
         }
+    }
+
+    @Test
+    void deprecatedEnumWithoutJavadoc() {
         {
             final String generated = new TypeScriptGenerator(settings).generateTypeScript(Input.from(DeprecatedEnumWithoutJavadoc.class));
             final String expected = ""
@@ -83,7 +104,7 @@ public void testJavadoc() {
                     + " * \n"
                     + " * Values:\n"
                     + " * - `North`\n"
-                    + " * - `East` - @deprecated\n"
+                    + " * - `East` - deprecated\n"
                     + " * - `South`\n"
                     + " * - `West`\n"
                     + " */\n"
@@ -91,6 +112,33 @@ public void testJavadoc() {
                     + "";
             Assertions.assertEquals(expected.trim(), generated.trim());
         }
+    }
+
+    @Test
+    void deprecatedEnumWItem() {
+        settings.mapEnum = EnumMapping.asEnum;
+        final String generated = new TypeScriptGenerator(settings).generateTypeScript(Input.from(DeprecatedEnumItem.class));
+        final String expected = ""
+                + "/**\n"
+                + " * Values:\n"
+                + " * - `First`\n"
+                + " * - `Second` - deprecated\n"
+                + " * - `Third`\n"
+                + " */\n"
+                + "declare const enum DeprecatedEnumItem {\n" +
+                "    First = \"First\",\n" +
+                "    /**\n" +
+                "     * @deprecated\n" +
+                "     */\n" +
+                "    Second = \"Second\",\n" +
+                "    Third = \"Third\",\n" +
+                "}"
+                + "";
+        Assertions.assertEquals(expected.trim(), generated.trim());
+    }
+
+    @Test
+    void classWithBrInJavadoc() {
         {
             final String generated = new TypeScriptGenerator(settings).generateTypeScript(Input.from(ClassWithBrElements.class));
             Assertions.assertTrue(!generated.contains("<br>"));
@@ -99,6 +147,10 @@ public void testJavadoc() {
             Assertions.assertTrue(generated.contains("Class documentation\n * \n"));
             Assertions.assertTrue(generated.contains("Some documentation\n * \n * for this class."));
         }
+    }
+
+    @Test
+    void classWithPInJavadoc() {
         {
             final String generated = new TypeScriptGenerator(settings).generateTypeScript(Input.from(ClassWithPElements.class));
             Assertions.assertTrue(!generated.contains("<p>"));
@@ -177,6 +229,12 @@ public static enum DeprecatedEnumWithoutJavadoc {
 
     }
 
+    public enum DeprecatedEnumItem {
+        First,
+        @Deprecated Second,
+        Third;
+    }
+
     /**
      * This class comes with an embedded example!
      *