diff --git a/confidence-core/src/main/java/org/saynotobugs/confidence/quality/iterable/Iterates.java b/confidence-core/src/main/java/org/saynotobugs/confidence/quality/iterable/Iterates.java
index c4af86c4..18e9f4ce 100644
--- a/confidence-core/src/main/java/org/saynotobugs/confidence/quality/iterable/Iterates.java
+++ b/confidence-core/src/main/java/org/saynotobugs/confidence/quality/iterable/Iterates.java
@@ -43,7 +43,7 @@
 
 
 @StaticFactories(value = "Core", packageName = "org.saynotobugs.confidence.quality")
-public final class Iterates<T> implements Quality<Iterable<T>>
+public final class Iterates<T> implements Quality<Iterable<? extends T>>
 {
     private final Iterable<? extends Quality<? super T>> mDelegates;
 
@@ -69,7 +69,7 @@ public Iterates(Iterable<? extends Quality<? super T>> delegates)
 
 
     @Override
-    public Assessment assessmentOf(Iterable<T> candidate)
+    public Assessment assessmentOf(Iterable<? extends T> candidate)
     {
         return new AllPassed(new Text("iterated [ "), COMMA_NEW_LINE, new Text(" ]"),
             new Numbered(
diff --git a/confidence-core/src/main/java/org/saynotobugs/confidence/quality/object/InstanceOf.java b/confidence-core/src/main/java/org/saynotobugs/confidence/quality/object/InstanceOf.java
index 78b6d763..3059ba25 100644
--- a/confidence-core/src/main/java/org/saynotobugs/confidence/quality/object/InstanceOf.java
+++ b/confidence-core/src/main/java/org/saynotobugs/confidence/quality/object/InstanceOf.java
@@ -33,8 +33,8 @@
 public final class InstanceOf<T> extends QualityComposition<T>
 {
     /**
-     * A {@link Quality} that matches when the object under test is an instance of the given class and satisfies the
-     * given {@link Quality}.
+     * A {@link Quality} that is satisfied when the object under test is an instance of the given class and satisfies
+     * the given {@link Quality}.
      * <p>
      * This provides a type-safe way to downcast and apply a {@link Quality} of a subtype.
      *
@@ -43,6 +43,8 @@ public final class InstanceOf<T> extends QualityComposition<T>
      * assertThat(someObject,
      *     is(instanceOf(Number.class, that(has(Number::intValue, equalTo(1))))));
      * }</pre>
+     *
+     * @see UnsafeInstanceOf#UnsafeInstanceOf(Class, Quality) for testing generic classes.
      */
     public <V extends T> InstanceOf(Class<? extends V> expectation, Quality<? super V> delegate)
     {
diff --git a/confidence-core/src/main/java/org/saynotobugs/confidence/quality/object/UnsafeInstanceOf.java b/confidence-core/src/main/java/org/saynotobugs/confidence/quality/object/UnsafeInstanceOf.java
new file mode 100644
index 00000000..74c57dc6
--- /dev/null
+++ b/confidence-core/src/main/java/org/saynotobugs/confidence/quality/object/UnsafeInstanceOf.java
@@ -0,0 +1,75 @@
+/*
+ * Copyright 2022 dmfs GmbH
+ *
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ *  You may obtain a copy of the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ *
+ */
+
+package org.saynotobugs.confidence.quality.object;
+
+import org.dmfs.srcless.annotations.staticfactory.StaticFactories;
+import org.saynotobugs.confidence.Quality;
+import org.saynotobugs.confidence.quality.composite.AllOfFailingFast;
+import org.saynotobugs.confidence.quality.composite.QualityComposition;
+
+import static org.saynotobugs.confidence.description.LiteralDescription.NEW_LINE;
+
+
+@StaticFactories(value = "Core", packageName = "org.saynotobugs.confidence.quality")
+public final class UnsafeInstanceOf<T> extends QualityComposition<T>
+{
+    /**
+     * A {@link Quality} that matches when the object under test is an instance of any subclass of the given class and
+     * satisfies the given {@link Quality}.
+     * <p>
+     * This works like {@link InstanceOf} but provides fewer type-safety guarantees allowing you to pass
+     * {@link Quality} of subtypes of {@code V}. This may be required when testing generic classes, because you'll
+     * essentially be forced to work with raw types in such case.
+     *
+     * <h4>Example</h4>
+     * <pre>{@code
+     * Map actual = ...;
+     *
+     * assertThat(actual, unsafeInstanceOf(Map.class, Core.<Map<String, Object>>allOf(
+     *     containsEntry("k1", unsafeInstanceOf(Map.class, allOf(
+     *         containsEntry("k11", "v11"),
+     *         containsEntry("k12", "v12")))),
+     *     containsEntry("k2", unsafeInstanceOf(Iterable.class, iterates("v21", "v22"))),
+     *     containsEntry("k3", unsafeInstanceOf(String.class, equalTo("v3"))))));
+     * }</pre>
+     * <p>
+     * <p>
+     * Be aware that this also allows you to write nonsensical tests like this:
+     * <pre>{@code
+     *     static class C1 {}
+     *
+     *     static class C2 extends C1 {
+     *         int bar() {return 2;}
+     *     }
+     *
+     *     @Test
+     *     void instanceOfTest() {
+     *         Object o = new C1();
+     *         assertThat(o, unsafeInstanceOf(C1.class, has(C2::bar, equalTo(2))));
+     *     }
+     * }</pre>
+     * <p>
+     * In such case, when the Quality is not compatible with the actual type, the test will fail, reporting a
+     * {@link ClassCastException}.
+     */
+    public <V extends T, Q extends V> UnsafeInstanceOf(Class<V> expectation, Quality<? super Q> delegate)
+    {
+        super((Quality<T>) new AllOfFailingFast<>(NEW_LINE, new InstanceOf<>(expectation), delegate));
+    }
+}
diff --git a/confidence-core/src/test/java/org/saynotobugs/confidence/Examples.java b/confidence-core/src/test/java/org/saynotobugs/confidence/Examples.java
index 4484c95e..12d2276c 100644
--- a/confidence-core/src/test/java/org/saynotobugs/confidence/Examples.java
+++ b/confidence-core/src/test/java/org/saynotobugs/confidence/Examples.java
@@ -8,6 +8,7 @@
 import org.saynotobugs.confidence.description.NumberDescription;
 import org.saynotobugs.confidence.description.Spaced;
 import org.saynotobugs.confidence.description.Text;
+import org.saynotobugs.confidence.quality.Core;
 import org.saynotobugs.confidence.quality.comparable.GreaterThan;
 import org.saynotobugs.confidence.quality.comparable.LessThan;
 import org.saynotobugs.confidence.quality.compat.Hamcrest;
@@ -27,6 +28,9 @@
 import org.saynotobugs.confidence.test.quality.Fails;
 import org.saynotobugs.confidence.test.quality.Passes;
 
+import java.util.HashMap;
+import java.util.List;
+import java.util.Map;
 import java.util.Objects;
 import java.util.concurrent.atomic.AtomicInteger;
 import java.util.function.Function;
@@ -300,4 +304,50 @@ void testDelegatingFunction()
             )
         );
     }
-}
+
+
+    @Test
+    void testHamcrestIssue107()
+    {
+        Map<String, Number> m = new HashMap<String, Number>();
+        Integer foo = new Integer(6);
+        m.put("foo", foo);
+        assertThat(m, containsEntry("foo", foo));
+    }
+
+
+    @Test
+    void testHamcrestIssue388()
+    {
+        Map actual = Map.of(
+            "k1", Map.of(
+                "k11", "v11",
+                "k12", "v12"),
+            "k2", List.of("v21", "v22"),
+            "k3", "v3"
+        );
+
+        assertThat(actual, unsafeInstanceOf(Map.class, Core.<Map<String, Object>>allOf(
+                containsEntry("k1", unsafeInstanceOf(Map.class, allOf(
+                    containsEntry("k11", "v11"),
+                    containsEntry("k12", "v12")))),
+                containsEntry("k2", unsafeInstanceOf(Iterable.class, iterates("v21", "v22"))),
+                containsEntry("k3", unsafeInstanceOf(String.class, equalTo("v3")))
+            )
+        ));
+    }
+
+
+    static class C1 {}
+
+    static class C2 extends C1 {
+        int bar() {return 2;}
+    }
+
+    @Test
+    void instanceOfTest()
+    {
+        Object o = new C1();
+        assertThat(o, unsafeInstanceOf(C1.class, has(C2::bar, equalTo(2))));
+    }
+}
\ No newline at end of file
diff --git a/confidence-core/src/test/java/org/saynotobugs/confidence/quality/object/UnsafeInstanceOfTest.java b/confidence-core/src/test/java/org/saynotobugs/confidence/quality/object/UnsafeInstanceOfTest.java
new file mode 100644
index 00000000..48f7c826
--- /dev/null
+++ b/confidence-core/src/test/java/org/saynotobugs/confidence/quality/object/UnsafeInstanceOfTest.java
@@ -0,0 +1,63 @@
+/*
+ * Copyright 2023 dmfs GmbH
+ *
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ *  You may obtain a copy of the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ *
+ */
+
+package org.saynotobugs.confidence.quality.object;
+
+import org.dmfs.jems2.iterable.Seq;
+import org.junit.jupiter.api.Test;
+import org.saynotobugs.confidence.quality.composite.AllOf;
+import org.saynotobugs.confidence.quality.composite.Has;
+import org.saynotobugs.confidence.quality.grammar.That;
+import org.saynotobugs.confidence.quality.iterable.Iterates;
+import org.saynotobugs.confidence.test.quality.Fails;
+import org.saynotobugs.confidence.test.quality.HasDescription;
+import org.saynotobugs.confidence.test.quality.Passes;
+
+import static org.saynotobugs.confidence.Assertion.assertThat;
+
+class UnsafeInstanceOfTest
+{
+
+    @Test
+    void testDelegate()
+    {
+        assertThat(new UnsafeInstanceOf<>(Number.class, new That<>(new Has<>("intValue", Number::intValue, new EqualTo<>(1)))),
+            new AllOf<>(
+                new Passes<>(1, 1.001, 1L, 1f),
+                new Fails<>(0.999, "(1) that had intValue <0>"),
+                new Fails<>(2, "(1) that had intValue <2>"),
+                new Fails<>("string", "(0) instance of <class java.lang.String>"),
+                new Fails<>(new Object(), "(0) instance of <class java.lang.Object>"),
+                new HasDescription("(0) instance of <class java.lang.Number>\n  (1) that has intValue <1>")
+            ));
+    }
+
+    @Test
+    void testSubClassDelegate()
+    {
+        assertThat(new UnsafeInstanceOf<>(Iterable.class, new That<>(new Iterates<>(1, "abc", true))),
+            new AllOf<>(
+                new Passes<>(new Seq<Object>(1, "abc", true), new Seq(1, "abc", true)),
+                new Fails<>(new Seq<Object>(1.1, "abc", true), "(1) that iterated [ 0: <1.1>\n  ... ]"),
+                new Fails<>(2, "(0) instance of <class java.lang.Integer>"),
+                new Fails<>("string", "(0) instance of <class java.lang.String>"),
+                new Fails<>(new Object(), "(0) instance of <class java.lang.Object>"),
+                new HasDescription("(0) instance of <interface java.lang.Iterable>\n  (1) that iterates [ 0: <1>,\n    1: \"abc\",\n    2: <true> ]")
+            ));
+    }
+}
\ No newline at end of file