diff --git a/nullaway/src/main/java/com/uber/nullaway/ErrorMessage.java b/nullaway/src/main/java/com/uber/nullaway/ErrorMessage.java
index 5ff89d51d1..a7f0899ba6 100644
--- a/nullaway/src/main/java/com/uber/nullaway/ErrorMessage.java
+++ b/nullaway/src/main/java/com/uber/nullaway/ErrorMessage.java
@@ -60,7 +60,8 @@ public enum MessageTypes {
     WRONG_OVERRIDE_PARAM_GENERIC,
     ASSIGN_NULLABLE_TO_NONNULL_ARRAY,
     GENERIC_INFERENCE_FAILURE,
-    NULLABLE_ON_WRONG_NESTED_CLASS_LEVEL
+    NULLABLE_ON_WRONG_NESTED_CLASS_LEVEL,
+    UNRECOGNIZED_NULLNESS_ANNOTATION_LOCATION
   }
 
   public String getMessage() {
diff --git a/nullaway/src/main/java/com/uber/nullaway/NullAway.java b/nullaway/src/main/java/com/uber/nullaway/NullAway.java
index 6773c68808..ca8296810e 100644
--- a/nullaway/src/main/java/com/uber/nullaway/NullAway.java
+++ b/nullaway/src/main/java/com/uber/nullaway/NullAway.java
@@ -186,6 +186,7 @@ public class NullAway extends BugChecker
         BugChecker.SwitchExpressionTreeMatcher,
         BugChecker.TypeCastTreeMatcher,
         BugChecker.ParameterizedTypeTreeMatcher,
+        BugChecker.AnnotatedTypeTreeMatcher,
         BugChecker.SynchronizedTreeMatcher {
 
   static final String INITIALIZATION_CHECK_NAME = "NullAway.Init";
@@ -778,6 +779,14 @@ public Description matchParameterizedType(ParameterizedTypeTree tree, VisitorSta
     return Description.NO_MATCH;
   }
 
+  @Override
+  public Description matchAnnotatedType(AnnotatedTypeTree tree, VisitorState state) {
+    if (withinAnnotatedCode(state) && config.isJSpecifyMode() && config.handleWildcardGenerics()) {
+      genericsChecks.checkForNullnessAnnotationsOnWildcards(tree, state);
+    }
+    return Description.NO_MATCH;
+  }
+
   /**
    * checks that an overriding method does not override a {@code @Nullable} parameter with a
    * {@code @NonNull} parameter
diff --git a/nullaway/src/main/java/com/uber/nullaway/generics/GenericsChecks.java b/nullaway/src/main/java/com/uber/nullaway/generics/GenericsChecks.java
index de818c77f7..400f32431a 100644
--- a/nullaway/src/main/java/com/uber/nullaway/generics/GenericsChecks.java
+++ b/nullaway/src/main/java/com/uber/nullaway/generics/GenericsChecks.java
@@ -28,6 +28,7 @@
 import com.sun.source.tree.ReturnTree;
 import com.sun.source.tree.Tree;
 import com.sun.source.tree.VariableTree;
+import com.sun.source.tree.WildcardTree;
 import com.sun.source.util.TreePath;
 import com.sun.source.util.TreePathScanner;
 import com.sun.tools.javac.code.Attribute;
@@ -163,6 +164,11 @@ public void checkInstantiationForParameterizedTypedTree(
     for (int i = 0; i < typeArguments.size(); i++) {
       Tree curTypeArg = typeArguments.get(i);
       if (curTypeArg instanceof AnnotatedTypeTree annotatedType) {
+        // Annotations directly on wildcards are illegal in JSpecify mode and are diagnosed in
+        // checkForNullnessAnnotationsOnWildcards().
+        if (annotatedType.getUnderlyingType() instanceof WildcardTree) {
+          continue;
+        }
         for (AnnotationTree annotation : annotatedType.getAnnotations()) {
           Type annotationType = ASTHelpers.getType(annotation);
           if (annotationType != null
@@ -190,6 +196,36 @@ public void checkInstantiationForParameterizedTypedTree(
     }
   }
 
+  /**
+   * Reports nullness annotations written directly on a wildcard, which is not a legal annotation
+   * location under JSpecify.
+   */
+  public void checkForNullnessAnnotationsOnWildcards(
+      AnnotatedTypeTree annotatedType, VisitorState state) {
+    if (!(annotatedType.getUnderlyingType() instanceof WildcardTree)) {
+      return;
+    }
+    for (AnnotationTree annotation : annotatedType.getAnnotations()) {
+      Type annotationType = ASTHelpers.getType(annotation);
+      if (annotationType == null) {
+        continue;
+      }
+      String annotationName = annotationType.toString();
+      if (!Nullness.isNullableAnnotation(annotationName, config)
+          && !Nullness.isNonNullAnnotation(annotationName, config)) {
+        continue;
+      }
+      ErrorBuilder errorBuilder = analysis.getErrorBuilder();
+      ErrorMessage errorMessage =
+          new ErrorMessage(
+              ErrorMessage.MessageTypes.UNRECOGNIZED_NULLNESS_ANNOTATION_LOCATION,
+              "illegal location for annotation: nullness annotations cannot be written directly on a wildcard; annotate the wildcard bound instead");
+      state.reportMatch(
+          errorBuilder.createErrorDescription(
+              errorMessage, analysis.buildDescription(annotation), state, null));
+    }
+  }
+
   private boolean[] getTypeParamsWithNullableUpperBound(Type type) {
     Symbol.TypeSymbol tsym = type.tsym;
     com.sun.tools.javac.util.List<Type> baseTypeArgs = tsym.type.getTypeArguments();
diff --git a/nullaway/src/test/java/com/uber/nullaway/jspecify/WildcardTests.java b/nullaway/src/test/java/com/uber/nullaway/jspecify/WildcardTests.java
index deccdba575..81293edb32 100644
--- a/nullaway/src/test/java/com/uber/nullaway/jspecify/WildcardTests.java
+++ b/nullaway/src/test/java/com/uber/nullaway/jspecify/WildcardTests.java
@@ -903,6 +903,36 @@ Foo<?> test(Foo<@Nullable Void> foo) {
         .doTest();
   }
 
+  @Test
+  public void nullableOnWildcard() {
+    makeHelperWithInferenceFailureWarning()
+        .addSourceLines(
+            "Test.java",
+            """
+            import org.jspecify.annotations.NullMarked;
+            import org.jspecify.annotations.NonNull;
+            import org.jspecify.annotations.Nullable;
+            import java.util.function.Function;
+            @NullMarked
+            class Test<K,V> {
+              @Nullable V testPositive(@Nullable K k,
+                Function<
+                  // BUG: Diagnostic contains: illegal location for annotation
+                  @Nullable ? super K,
+                  // BUG: Diagnostic contains: illegal location for annotation
+                  @NonNull ? extends V> function) {
+                // BUG: Diagnostic contains: passing @Nullable parameter 'k' where @NonNull is required
+                return function.apply(k);
+              }
+
+              @Nullable V testNegative(@Nullable K k, Function<? super @Nullable K, ? extends @Nullable V> function) {
+                return function.apply(k);
+              }
+            }
+            """)
+        .doTest();
+  }
+
   private CompilationTestHelper makeHelper() {
     return makeTestHelperWithArgs(
         JSpecifyJavacConfig.withJSpecifyModeArgs(