diff --git a/src/library_desugar/jdk11/desugar_jdk_libs.json b/src/library_desugar/jdk11/desugar_jdk_libs.json
index 3d23d9f..0020bab 100644
--- a/src/library_desugar/jdk11/desugar_jdk_libs.json
+++ b/src/library_desugar/jdk11/desugar_jdk_libs.json
@@ -403,12 +403,34 @@
         "java.lang.Object java.util.concurrent.atomic.AtomicReference#getAndAccumulate(java.lang.Object, java.util.function.BinaryOperator)": "java.util.concurrent.atomic.DesugarAtomicReference",
         "java.lang.Object java.util.concurrent.atomic.AtomicReference#getAndUpdate(java.util.function.UnaryOperator)": "java.util.concurrent.atomic.DesugarAtomicReference",
         "java.lang.Object java.util.concurrent.atomic.AtomicReference#updateAndGet(java.util.function.UnaryOperator)": "java.util.concurrent.atomic.DesugarAtomicReference",
+        "java.util.Collection java.util.Collections#checkedCollection(java.util.Collection, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.Set java.util.Collections#checkedSet(java.util.Set, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.SortedSet java.util.Collections#checkedSortedSet(java.util.SortedSet, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.List java.util.Collections#checkedList(java.util.List, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.Map java.util.Collections#checkedMap(java.util.Map, java.lang.Class, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.SortedMap java.util.Collections#checkedSortedMap(java.util.SortedMap, java.lang.Class, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.Collection java.util.Collections#unmodifiableCollection(java.util.Collection)": "java.util.DesugarCollections",
+        "java.util.Set java.util.Collections#unmodifiableSet(java.util.Set)": "java.util.DesugarCollections",
+        "java.util.SortedSet java.util.Collections#unmodifiableSortedSet(java.util.SortedSet)": "java.util.DesugarCollections",
+        "java.util.List java.util.Collections#unmodifiableList(java.util.List)": "java.util.DesugarCollections",
+        "java.util.Map java.util.Collections#unmodifiableMap(java.util.Map)": "java.util.DesugarCollections",
+        "java.util.SortedMap java.util.Collections#unmodifiableSortedMap(java.util.SortedMap)": "java.util.DesugarCollections",
+        "java.util.Collection java.util.Collections#synchronizedCollection(java.util.Collection)": "java.util.DesugarCollections",
+        "java.util.Set java.util.Collections#synchronizedSet(java.util.Set)": "java.util.DesugarCollections",
+        "java.util.SortedSet java.util.Collections#synchronizedSortedSet(java.util.SortedSet)": "java.util.DesugarCollections",
+        "java.util.List java.util.Collections#synchronizedList(java.util.List)": "java.util.DesugarCollections",
         "java.util.Map java.util.Collections#synchronizedMap(java.util.Map)": "java.util.DesugarCollections",
         "java.util.SortedMap java.util.Collections#synchronizedSortedMap(java.util.SortedMap)": "java.util.DesugarCollections",
         "long java.util.concurrent.atomic.AtomicLong#accumulateAndGet(long, java.util.function.LongBinaryOperator)": "java.util.concurrent.atomic.DesugarAtomicLong",
         "long java.util.concurrent.atomic.AtomicLong#getAndAccumulate(long, java.util.function.LongBinaryOperator)": "java.util.concurrent.atomic.DesugarAtomicLong",
         "long java.util.concurrent.atomic.AtomicLong#getAndUpdate(java.util.function.LongUnaryOperator)": "java.util.concurrent.atomic.DesugarAtomicLong",
         "long java.util.concurrent.atomic.AtomicLong#updateAndGet(java.util.function.LongUnaryOperator)": "java.util.concurrent.atomic.DesugarAtomicLong"
+      },
+      "api_generic_types_conversion": {
+        "java.util.Collection java.util.Hashtable#values()": [-1, "java.util.Collection java.util.DesugarCollections#bridge_synchronizedCollection(java.util.Collection, java.lang.Object)"],
+        "java.util.Set java.util.Hashtable#entrySet()": [-1, "java.util.Set java.util.DesugarCollections#bridge_synchronizedSet(java.util.Set, java.lang.Object)"],
+        "java.util.Set java.util.Hashtable#keySet()": [-1, "java.util.Set java.util.DesugarCollections#bridge_synchronizedSet(java.util.Set, java.lang.Object)"],
+        "java.util.List java.util.Vector#subList(int, int)": [-1, "java.util.List java.util.DesugarCollections#bridge_synchronizedList(java.util.List, java.lang.Object)"]
       }
     }
   ],
diff --git a/src/library_desugar/jdk11/desugar_jdk_libs_nio.json b/src/library_desugar/jdk11/desugar_jdk_libs_nio.json
index 0f81af4..aa8b1c0 100644
--- a/src/library_desugar/jdk11/desugar_jdk_libs_nio.json
+++ b/src/library_desugar/jdk11/desugar_jdk_libs_nio.json
@@ -571,12 +571,34 @@
         "java.lang.Object java.util.concurrent.atomic.AtomicReference#getAndAccumulate(java.lang.Object, java.util.function.BinaryOperator)": "java.util.concurrent.atomic.DesugarAtomicReference",
         "java.lang.Object java.util.concurrent.atomic.AtomicReference#getAndUpdate(java.util.function.UnaryOperator)": "java.util.concurrent.atomic.DesugarAtomicReference",
         "java.lang.Object java.util.concurrent.atomic.AtomicReference#updateAndGet(java.util.function.UnaryOperator)": "java.util.concurrent.atomic.DesugarAtomicReference",
+        "java.util.Collection java.util.Collections#checkedCollection(java.util.Collection, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.Set java.util.Collections#checkedSet(java.util.Set, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.SortedSet java.util.Collections#checkedSortedSet(java.util.SortedSet, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.List java.util.Collections#checkedList(java.util.List, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.Map java.util.Collections#checkedMap(java.util.Map, java.lang.Class, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.SortedMap java.util.Collections#checkedSortedMap(java.util.SortedMap, java.lang.Class, java.lang.Class)": "java.util.DesugarCollections",
+        "java.util.Collection java.util.Collections#unmodifiableCollection(java.util.Collection)": "java.util.DesugarCollections",
+        "java.util.Set java.util.Collections#unmodifiableSet(java.util.Set)": "java.util.DesugarCollections",
+        "java.util.SortedSet java.util.Collections#unmodifiableSortedSet(java.util.SortedSet)": "java.util.DesugarCollections",
+        "java.util.List java.util.Collections#unmodifiableList(java.util.List)": "java.util.DesugarCollections",
+        "java.util.Map java.util.Collections#unmodifiableMap(java.util.Map)": "java.util.DesugarCollections",
+        "java.util.SortedMap java.util.Collections#unmodifiableSortedMap(java.util.SortedMap)": "java.util.DesugarCollections",
+        "java.util.Collection java.util.Collections#synchronizedCollection(java.util.Collection)": "java.util.DesugarCollections",
+        "java.util.Set java.util.Collections#synchronizedSet(java.util.Set)": "java.util.DesugarCollections",
+        "java.util.SortedSet java.util.Collections#synchronizedSortedSet(java.util.SortedSet)": "java.util.DesugarCollections",
+        "java.util.List java.util.Collections#synchronizedList(java.util.List)": "java.util.DesugarCollections",
         "java.util.Map java.util.Collections#synchronizedMap(java.util.Map)": "java.util.DesugarCollections",
         "java.util.SortedMap java.util.Collections#synchronizedSortedMap(java.util.SortedMap)": "java.util.DesugarCollections",
         "long java.util.concurrent.atomic.AtomicLong#accumulateAndGet(long, java.util.function.LongBinaryOperator)": "java.util.concurrent.atomic.DesugarAtomicLong",
         "long java.util.concurrent.atomic.AtomicLong#getAndAccumulate(long, java.util.function.LongBinaryOperator)": "java.util.concurrent.atomic.DesugarAtomicLong",
         "long java.util.concurrent.atomic.AtomicLong#getAndUpdate(java.util.function.LongUnaryOperator)": "java.util.concurrent.atomic.DesugarAtomicLong",
         "long java.util.concurrent.atomic.AtomicLong#updateAndGet(java.util.function.LongUnaryOperator)": "java.util.concurrent.atomic.DesugarAtomicLong"
+      },
+      "api_generic_types_conversion": {
+        "java.util.Collection java.util.Hashtable#values()": [-1, "java.util.Collection java.util.DesugarCollections#bridge_synchronizedCollection(java.util.Collection, java.lang.Object)"],
+        "java.util.Set java.util.Hashtable#entrySet()": [-1, "java.util.Set java.util.DesugarCollections#bridge_synchronizedSet(java.util.Set, java.lang.Object)"],
+        "java.util.Set java.util.Hashtable#keySet()": [-1, "java.util.Set java.util.DesugarCollections#bridge_synchronizedSet(java.util.Set, java.lang.Object)"],
+        "java.util.List java.util.Vector#subList(int, int)": [-1, "java.util.List java.util.DesugarCollections#bridge_synchronizedList(java.util.List, java.lang.Object)"]
       }
     },
     {
diff --git a/src/test/java/com/android/tools/r8/desugar/desugaredlibrary/DesugarCollectionsTest.java b/src/test/java/com/android/tools/r8/desugar/desugaredlibrary/DesugarCollectionsTest.java
new file mode 100644
index 0000000..a740261
--- /dev/null
+++ b/src/test/java/com/android/tools/r8/desugar/desugaredlibrary/DesugarCollectionsTest.java
@@ -0,0 +1,283 @@
+// Copyright (c) 2023, the R8 project authors. Please see the AUTHORS file
+// for details. All rights reserved. Use of this source code is governed by a
+// BSD-style license that can be found in the LICENSE file.
+
+package com.android.tools.r8.desugar.desugaredlibrary;
+
+import static com.android.tools.r8.desugar.desugaredlibrary.test.CompilationSpecification.DEFAULT_SPECIFICATIONS;
+import static com.android.tools.r8.desugar.desugaredlibrary.test.LibraryDesugaringSpecification.JDK11;
+import static com.android.tools.r8.desugar.desugaredlibrary.test.LibraryDesugaringSpecification.JDK11_PATH;
+
+import com.android.tools.r8.TestParameters;
+import com.android.tools.r8.desugar.desugaredlibrary.test.CompilationSpecification;
+import com.android.tools.r8.desugar.desugaredlibrary.test.LibraryDesugaringSpecification;
+import com.android.tools.r8.utils.StringUtils;
+import com.google.common.collect.ImmutableList;
+import java.util.ArrayList;
+import java.util.Collection;
+import java.util.Collections;
+import java.util.Hashtable;
+import java.util.Iterator;
+import java.util.List;
+import java.util.ListIterator;
+import java.util.SortedMap;
+import java.util.SortedSet;
+import java.util.Spliterator;
+import java.util.TreeMap;
+import java.util.TreeSet;
+import java.util.Vector;
+import org.junit.Test;
+import org.junit.runner.RunWith;
+import org.junit.runners.Parameterized;
+import org.junit.runners.Parameterized.Parameters;
+
+@RunWith(Parameterized.class)
+public class DesugarCollectionsTest extends DesugaredLibraryTestBase {
+
+  private final TestParameters parameters;
+  private final CompilationSpecification compilationSpecification;
+  private final LibraryDesugaringSpecification libraryDesugaringSpecification;
+
+  @Parameters(name = "{0}, spec: {1}, {2}")
+  public static List<Object[]> data() {
+    return buildParameters(
+        getTestParameters().withDexRuntimesAndAllApiLevels().build(),
+        ImmutableList.of(JDK11, JDK11_PATH),
+        DEFAULT_SPECIFICATIONS);
+  }
+
+  public DesugarCollectionsTest(
+      TestParameters parameters,
+      LibraryDesugaringSpecification libraryDesugaringSpecification,
+      CompilationSpecification compilationSpecification) {
+    this.parameters = parameters;
+    this.compilationSpecification = compilationSpecification;
+    this.libraryDesugaringSpecification = libraryDesugaringSpecification;
+  }
+
+  @Test
+  public void testDesugarCollectionsTest() throws Throwable {
+    testForDesugaredLibrary(parameters, libraryDesugaringSpecification, compilationSpecification)
+        .addInnerClasses(getClass())
+        .addKeepMainRule(Main.class)
+        .run(parameters.getRuntime(), Main.class)
+        .assertSuccessWithOutput(getExpectedResult());
+  }
+
+  private String getExpectedResult() {
+    List<String> result = new ArrayList<>();
+    for (int i = 0; i < 9; i++) {
+      result.add("item");
+    }
+    for (int i = 0; i < 6; i++) {
+      result.add("k v");
+    }
+    for (int i = 0; i < 6; i++) {
+      result.add("exception");
+    }
+    result.addAll(ImmutableList.of("one", "v", "k", "k=v"));
+    return StringUtils.lines(result);
+  }
+
+  public static class Main {
+
+    public static void main(String[] args) {
+      successTest();
+      exceptionTest();
+      apiTest();
+    }
+
+    private static void apiTest() {
+      Vector<String> strings = new Vector<>();
+      strings.add("one");
+      strings.subList(0, 1).forEach(System.out::println);
+      Hashtable<String, String> table = new Hashtable<>();
+      table.put("k", "v");
+      table.values().forEach(System.out::println);
+      table.keySet().forEach(System.out::println);
+      table.entrySet().forEach(System.out::println);
+    }
+
+    private static void successTest() {
+      SortedSet<String> set = new TreeSet<>();
+      set.add("item");
+      Collections.unmodifiableCollection(set).forEach(System.out::println);
+      Collections.unmodifiableSet(set).forEach(System.out::println);
+      Collections.unmodifiableSortedSet(set).forEach(System.out::println);
+      Collections.synchronizedCollection(set).forEach(System.out::println);
+      Collections.synchronizedSet(set).forEach(System.out::println);
+      Collections.synchronizedSortedSet(set).forEach(System.out::println);
+      Collections.checkedCollection(set, String.class).forEach(System.out::println);
+      Collections.checkedSet(set, String.class).forEach(System.out::println);
+      Collections.checkedSortedSet(set, String.class).forEach(System.out::println);
+      SortedMap<String, String> map = new TreeMap<>();
+      map.put("k", "v");
+      Collections.unmodifiableMap(map).forEach((k, v) -> System.out.println(k + " " + v));
+      Collections.unmodifiableSortedMap(map).forEach((k, v) -> System.out.println(k + " " + v));
+      Collections.synchronizedMap(map).forEach((k, v) -> System.out.println(k + " " + v));
+      Collections.synchronizedSortedMap(map).forEach((k, v) -> System.out.println(k + " " + v));
+      Collections.checkedMap(map, String.class, String.class)
+          .forEach((k, v) -> System.out.println(k + " " + v));
+      Collections.checkedSortedMap(map, String.class, String.class)
+          .forEach((k, v) -> System.out.println(k + " " + v));
+    }
+
+    private static void exceptionTest() {
+      try {
+        Collections.unmodifiableCollection(new ImmutableList<>()).spliterator();
+        System.out.println("working");
+      } catch (UnsupportedOperationException e) {
+        System.out.println("exception");
+      }
+      try {
+        Collections.unmodifiableList(new ImmutableList<>()).spliterator();
+        System.out.println("working");
+      } catch (UnsupportedOperationException e) {
+        System.out.println("exception");
+      }
+      try {
+        Collections.synchronizedList(new ImmutableList<>()).spliterator();
+        System.out.println("working");
+      } catch (UnsupportedOperationException e) {
+        System.out.println("exception");
+      }
+      try {
+        Collections.synchronizedList(new ImmutableList<>()).spliterator();
+        System.out.println("working");
+      } catch (UnsupportedOperationException e) {
+        System.out.println("exception");
+      }
+      try {
+        Collections.checkedList(new ImmutableList<>(), Vector.class).spliterator();
+        System.out.println("working");
+      } catch (UnsupportedOperationException e) {
+        System.out.println("exception");
+      }
+      try {
+        Collections.checkedList(new ImmutableList<>(), Vector.class).spliterator();
+        System.out.println("working");
+      } catch (UnsupportedOperationException e) {
+        System.out.println("exception");
+      }
+    }
+
+    static class ImmutableList<T> implements List<T> {
+
+      @Override
+      public int size() {
+        return 0;
+      }
+
+      @Override
+      public boolean isEmpty() {
+        return false;
+      }
+
+      @Override
+      public boolean contains(Object o) {
+        return false;
+      }
+
+      @Override
+      public Iterator<T> iterator() {
+        return null;
+      }
+
+      @Override
+      public Object[] toArray() {
+        return new Object[0];
+      }
+
+      @Override
+      public <T1> T1[] toArray(T1[] a) {
+        return null;
+      }
+
+      @Override
+      public boolean add(T t) {
+        return false;
+      }
+
+      @Override
+      public boolean remove(Object o) {
+        return false;
+      }
+
+      @Override
+      public boolean containsAll(Collection<?> c) {
+        return false;
+      }
+
+      @Override
+      public boolean addAll(Collection<? extends T> c) {
+        return false;
+      }
+
+      @Override
+      public boolean addAll(int index, Collection<? extends T> c) {
+        return false;
+      }
+
+      @Override
+      public boolean removeAll(Collection<?> c) {
+        return false;
+      }
+
+      @Override
+      public boolean retainAll(Collection<?> c) {
+        return false;
+      }
+
+      @Override
+      public void clear() {}
+
+      @Override
+      public T get(int index) {
+        return null;
+      }
+
+      @Override
+      public T set(int index, T element) {
+        return null;
+      }
+
+      @Override
+      public void add(int index, T element) {}
+
+      @Override
+      public T remove(int index) {
+        return null;
+      }
+
+      @Override
+      public int indexOf(Object o) {
+        return 0;
+      }
+
+      @Override
+      public int lastIndexOf(Object o) {
+        return 0;
+      }
+
+      @Override
+      public ListIterator<T> listIterator() {
+        return null;
+      }
+
+      @Override
+      public ListIterator<T> listIterator(int index) {
+        return null;
+      }
+
+      @Override
+      public List<T> subList(int fromIndex, int toIndex) {
+        return null;
+      }
+
+      @Override
+      public Spliterator<T> spliterator() {
+        throw new UnsupportedOperationException();
+      }
+    }
+  }
+}
diff --git a/third_party/openjdk/desugar_jdk_libs_11.tar.gz.sha1 b/third_party/openjdk/desugar_jdk_libs_11.tar.gz.sha1
index 758e8f0..c5ef954 100644
--- a/third_party/openjdk/desugar_jdk_libs_11.tar.gz.sha1
+++ b/third_party/openjdk/desugar_jdk_libs_11.tar.gz.sha1
@@ -1 +1 @@
-47cfa6d72be316cdaff6e5042111a18215ac4405
\ No newline at end of file
+d50abf6c508c1332eb80f35f5631e99e2e8329b5
\ No newline at end of file