diff --git a/src/jdk.compiler/share/classes/com/sun/tools/javac/jvm/ClassReader.java b/src/jdk.compiler/share/classes/com/sun/tools/javac/jvm/ClassReader.java
index fcc1efda8dc..bd05cf91e91 100644
--- a/src/jdk.compiler/share/classes/com/sun/tools/javac/jvm/ClassReader.java
+++ b/src/jdk.compiler/share/classes/com/sun/tools/javac/jvm/ClassReader.java
@@ -62,6 +62,7 @@ import com.sun.tools.javac.file.PathFileObject;
 import com.sun.tools.javac.jvm.ClassFile.Version;
 import com.sun.tools.javac.jvm.PoolConstant.NameAndType;
 import com.sun.tools.javac.main.Option;
+import com.sun.tools.javac.resources.CompilerProperties.Errors;
 import com.sun.tools.javac.resources.CompilerProperties.Fragments;
 import com.sun.tools.javac.resources.CompilerProperties.Warnings;
 import com.sun.tools.javac.util.*;
@@ -2311,9 +2312,17 @@ public class ClassReader {
      * 4.7.20-A target_type to locate the correct type to rewrite, and then interpreting the JVMS
      * 4.7.20.2 type_path to associate the annotation with the correct contained type.
      */
-    private static void addTypeAnnotationsToSymbol(
-            Symbol s, List<Attribute.TypeCompound> attributes) {
-        new TypeAnnotationSymbolVisitor(attributes).visit(s, null);
+    private void addTypeAnnotationsToSymbol(Symbol s, List<Attribute.TypeCompound> attributes) {
+        try {
+            new TypeAnnotationSymbolVisitor(attributes).visit(s, null);
+        } catch (CompletionFailure ex) {
+            JavaFileObject prev = log.useSource(currentClassFile);
+            try {
+                log.error(Errors.CantAttachTypeAnnotations(attributes, s.owner, s.name, ex.getDetailValue()));
+            } finally {
+                log.useSource(prev);
+            }
+        }
     }
 
     private static class TypeAnnotationSymbolVisitor
diff --git a/src/jdk.compiler/share/classes/com/sun/tools/javac/resources/compiler.properties b/src/jdk.compiler/share/classes/com/sun/tools/javac/resources/compiler.properties
index 8576106e15f..10f06ad7017 100644
--- a/src/jdk.compiler/share/classes/com/sun/tools/javac/resources/compiler.properties
+++ b/src/jdk.compiler/share/classes/com/sun/tools/javac/resources/compiler.properties
@@ -2345,6 +2345,11 @@ compiler.warn.annotation.method.not.found=\
 compiler.warn.annotation.method.not.found.reason=\
     Cannot find annotation method ''{1}()'' in type ''{0}'': {2}
 
+# 0: list of annotation, 1: symbol, 2: name, 3: message segment
+compiler.err.cant.attach.type.annotations=\
+    Cannot attach type annotations {0} to {1}.{2}:\n\
+    {3}
+
 # 0: file object, 1: symbol, 2: name
 compiler.warn.unknown.enum.constant=\
     unknown enum constant {1}.{2}
diff --git a/test/langtools/tools/javac/annotations/typeAnnotations/CompletionErrorOnEnclosingType.java b/test/langtools/tools/javac/annotations/typeAnnotations/CompletionErrorOnEnclosingType.java
new file mode 100644
index 00000000000..11b4e1ccbd4
--- /dev/null
+++ b/test/langtools/tools/javac/annotations/typeAnnotations/CompletionErrorOnEnclosingType.java
@@ -0,0 +1,98 @@
+/*
+ * Copyright (c) 2024, Alphabet LLC. All rights reserved.
+ * DO NOT ALTER OR REMOVE COPYRIGHT NOTICES OR THIS FILE HEADER.
+ *
+ * This code is free software; you can redistribute it and/or modify it
+ * under the terms of the GNU General Public License version 2 only, as
+ * published by the Free Software Foundation.
+ *
+ * This code is distributed in the hope that it will be useful, but WITHOUT
+ * ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or
+ * FITNESS FOR A PARTICULAR PURPOSE.  See the GNU General Public License
+ * version 2 for more details (a copy is included in the LICENSE file that
+ * accompanied this code).
+ *
+ * You should have received a copy of the GNU General Public License version
+ * 2 along with this work; if not, write to the Free Software Foundation,
+ * Inc., 51 Franklin St, Fifth Floor, Boston, MA 02110-1301 USA.
+ *
+ * Please contact Oracle, 500 Oracle Parkway, Redwood Shores, CA 94065 USA
+ * or visit www.oracle.com if you need additional information or have any
+ * questions.
+ */
+
+/*
+ * @test
+ * @bug 8337998
+ * @summary CompletionFailure in getEnclosingType attaching type annotations
+ * @library /tools/javac/lib /tools/lib
+ * @modules jdk.compiler/com.sun.tools.javac.api
+ *          jdk.compiler/com.sun.tools.javac.main
+ */
+
+import toolbox.*;
+import toolbox.Task.*;
+
+import java.nio.file.Path;
+import java.nio.file.Paths;
+import java.util.List;
+
+public class CompletionErrorOnEnclosingType {
+    ToolBox tb = new ToolBox();
+
+    public static void main(String... args) throws Exception {
+        CompletionErrorOnEnclosingType t = new CompletionErrorOnEnclosingType();
+        t.testMissingEnclosingType();
+    }
+
+    void testMissingEnclosingType() throws Exception {
+        String annoSrc =
+                """
+                import static java.lang.annotation.ElementType.TYPE_USE;
+                import java.lang.annotation.Target;
+                @Target(TYPE_USE)
+                @interface Anno {}
+
+                class A<E> {}
+
+                class B {
+                  private @Anno A<String> a;
+                }
+                """;
+        String cSrc =
+                """
+                class C {
+                  B b;
+                }
+                """;
+
+        Path base = Paths.get(".");
+        Path src = base.resolve("src");
+        tb.createDirectories(src);
+        tb.writeJavaFiles(src, annoSrc, cSrc);
+        Path out = base.resolve("out");
+        tb.createDirectories(out);
+        new JavacTask(tb).outdir(out).files(tb.findJavaFiles(src)).run();
+
+        // now if we remove A.class there will be an error but javac should not crash
+        tb.deleteFiles(out.resolve("A.class"));
+        List<String> log =
+                new JavacTask(tb)
+                        .outdir(out)
+                        .classpath(out)
+                        .options("-XDrawDiagnostics")
+                        .files(src.resolve("C.java"))
+                        .run(Expect.FAIL)
+                        .writeAll()
+                        .getOutputLines(Task.OutputKind.DIRECT);
+
+        var expectedOutput =
+                List.of(
+                        "B.class:-:-: compiler.err.cant.attach.type.annotations: @Anno, B, a,"
+                            + " (compiler.misc.class.file.not.found: A)",
+                        "1 error");
+        if (!expectedOutput.equals(log)) {
+            throw new Exception("expected output not found: " + log);
+        }
+    }
+}
diff --git a/test/langtools/tools/javac/diags/examples.not-yet.txt b/test/langtools/tools/javac/diags/examples.not-yet.txt
index 9a447927761..b2603338509 100644
--- a/test/langtools/tools/javac/diags/examples.not-yet.txt
+++ b/test/langtools/tools/javac/diags/examples.not-yet.txt
@@ -41,6 +41,7 @@ compiler.err.signature.doesnt.match.intf                # UNUSED
 compiler.err.signature.doesnt.match.supertype           # UNUSED
 compiler.err.source.cant.overwrite.input.file
 compiler.err.stack.sim.error
+compiler.err.cant.attach.type.annotations               # bad class file
 compiler.err.type.var.more.than.once                    # UNUSED
 compiler.err.type.var.more.than.once.in.result          # UNUSED
 compiler.err.unexpected.type