diff --git a/rewrite-java/src/main/java/org/openrewrite/java/tree/TypeUtils.java b/rewrite-java/src/main/java/org/openrewrite/java/tree/TypeUtils.java
index 89034bd0985..a0a29a1a338 100644
--- a/rewrite-java/src/main/java/org/openrewrite/java/tree/TypeUtils.java
+++ b/rewrite-java/src/main/java/org/openrewrite/java/tree/TypeUtils.java
@@ -209,6 +209,8 @@ public static boolean isAssignableTo(@Nullable JavaType to, @Nullable JavaType f
                     JavaType.Primitive toPrimitive = JavaType.Primitive.fromClassName(toFq.getFullyQualifiedName());
                     if (toPrimitive != null) {
                         return isAssignableTo(toPrimitive, from);
+                    } else if (toFq.getFullyQualifiedName().equals("java.lang.Object")) {
+                        return true;
                     }
                 }
                 return isAssignableTo(toFq.getFullyQualifiedName(), from);
@@ -224,6 +226,13 @@ public static boolean isAssignableTo(@Nullable JavaType to, @Nullable JavaType f
                         }
                     }
                     return true;
+                } else if (toGeneric.getVariance() == JavaType.GenericTypeVariable.Variance.CONTRAVARIANT) {
+                    for (JavaType toBound : toBounds) {
+                        if (!isAssignableTo(from, toBound)) {
+                            return false;
+                        }
+                    }
+                    return true;
                 }
                 return false;
             } else if (to instanceof JavaType.Variable) {