diff --git a/src/jdk.internal.vm.compiler/share/classes/org.graalvm.compiler.core/src/org/graalvm/compiler/core/gen/DebugInfoBuilder.java b/src/jdk.internal.vm.compiler/share/classes/org.graalvm.compiler.core/src/org/graalvm/compiler/core/gen/DebugInfoBuilder.java
--- a/src/jdk.internal.vm.compiler/share/classes/org.graalvm.compiler.core/src/org/graalvm/compiler/core/gen/DebugInfoBuilder.java
+++ b/src/jdk.internal.vm.compiler/share/classes/org.graalvm.compiler.core/src/org/graalvm/compiler/core/gen/DebugInfoBuilder.java
@@ -43,7 +43,9 @@
 import org.graalvm.compiler.nodes.spi.NodeValueMap;
 import org.graalvm.compiler.nodes.util.GraphUtil;
 import org.graalvm.compiler.nodes.virtual.EscapeObjectState;
+import org.graalvm.compiler.nodes.virtual.VirtualBoxingNode;
 import org.graalvm.compiler.nodes.virtual.VirtualObjectNode;
+import org.graalvm.compiler.serviceprovider.GraalServices;
 import org.graalvm.compiler.virtual.nodes.MaterializedObjectState;
 import org.graalvm.compiler.virtual.nodes.VirtualObjectState;
 
@@ -154,6 +156,10 @@
                 }
                 assert checkValues(vobjValue.getType(), values, slotKinds);
                 vobjValue.setValues(values, slotKinds);
+
+                if (vobjNode instanceof VirtualBoxingNode) {
+                    GraalServices.markVirtualObjectAsAutoBox(vobjValue);
+                }
             }
 
             virtualObjectsArray = new VirtualObject[virtualObjects.size()];
diff --git a/src/jdk.internal.vm.compiler/share/classes/org.graalvm.compiler.hotspot.test/src/org/graalvm/compiler/hotspot/test/BoxDeoptimizationTest.java b/src/jdk.internal.vm.compiler/share/classes/org.graalvm.compiler.hotspot.test/src/org/graalvm/compiler/hotspot/test/BoxDeoptimizationTest.java
new file mode 100644
--- /dev/null
+++ b/src/jdk.internal.vm.compiler/share/classes/org.graalvm.compiler.hotspot.test/src/org/graalvm/compiler/hotspot/test/BoxDeoptimizationTest.java
@@ -0,0 +1,108 @@
+/*
+ * Copyright (c) 2019, Oracle and/or its affiliates. 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.  Oracle designates this
+ * particular file as subject to the "Classpath" exception as provided
+ * by Oracle in the LICENSE file that accompanied this code.
+ *
+ * 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.
+ */
+package org.graalvm.compiler.hotspot.test;
+
+import org.graalvm.compiler.api.directives.GraalDirectives;
+import org.graalvm.compiler.core.test.GraalCompilerTest;
+import org.graalvm.compiler.serviceprovider.JavaVersionUtil;
+import org.junit.Assert;
+import org.junit.Assume;
+import org.junit.Test;
+
+public class BoxDeoptimizationTest extends GraalCompilerTest {
+    private static boolean isJDK13OrLater = JavaVersionUtil.JAVA_SPECIFICATION_VERSION >= 13;
+
+    public static void testInteger() {
+        Object[] values = {42, new Exception()};
+        GraalDirectives.deoptimize();
+        Assert.assertSame(values[0], Integer.valueOf(42));
+    }
+
+    @Test
+    public void test1() {
+        Assume.assumeTrue(isJDK13OrLater);
+        test("testInteger");
+    }
+
+    public static void testLong() {
+        Object[] values = {42L, new Exception()};
+        GraalDirectives.deoptimize();
+        Assert.assertSame(values[0], Long.valueOf(42));
+    }
+
+    @Test
+    public void test2() {
+        Assume.assumeTrue(isJDK13OrLater);
+        test("testLong");
+    }
+
+    public static void testChar() {
+        Object[] values = {'a', new Exception()};
+        GraalDirectives.deoptimize();
+        Assert.assertSame(values[0], Character.valueOf('a'));
+    }
+
+    @Test
+    public void test3() {
+        Assume.assumeTrue(isJDK13OrLater);
+        test("testChar");
+    }
+
+    public static void testShort() {
+        Object[] values = {(short) 42, new Exception()};
+        GraalDirectives.deoptimize();
+        Assert.assertSame(values[0], Short.valueOf((short) 42));
+    }
+
+    @Test
+    public void test4() {
+        Assume.assumeTrue(isJDK13OrLater);
+        test("testShort");
+    }
+
+    public static void testByte() {
+        Object[] values = {(byte) 42, new Exception()};
+        GraalDirectives.deoptimize();
+        Assert.assertSame(values[0], Byte.valueOf((byte) 42));
+    }
+
+    @Test
+    public void test5() {
+        Assume.assumeTrue(isJDK13OrLater);
+        test("testByte");
+    }
+
+    public static void testBoolean() {
+        Object[] values = {true, new Exception()};
+        GraalDirectives.deoptimize();
+        Assert.assertSame(values[0], Boolean.valueOf(true));
+    }
+
+    @Test
+    public void test6() {
+        Assume.assumeTrue(isJDK13OrLater);
+        test("testBoolean");
+    }
+}
diff --git a/src/jdk.internal.vm.compiler/share/classes/org.graalvm.compiler.serviceprovider/src/org/graalvm/compiler/serviceprovider/GraalServices.java b/src/jdk.internal.vm.compiler/share/classes/org.graalvm.compiler.serviceprovider/src/org/graalvm/compiler/serviceprovider/GraalServices.java
--- a/src/jdk.internal.vm.compiler/share/classes/org.graalvm.compiler.serviceprovider/src/org/graalvm/compiler/serviceprovider/GraalServices.java
+++ b/src/jdk.internal.vm.compiler/share/classes/org.graalvm.compiler.serviceprovider/src/org/graalvm/compiler/serviceprovider/GraalServices.java
@@ -42,6 +42,7 @@
 import org.graalvm.compiler.serviceprovider.SpeculationReasonGroup.SpeculationContextObject;
 
 import jdk.vm.ci.code.BytecodePosition;
+import jdk.vm.ci.code.VirtualObject;
 import jdk.vm.ci.meta.ResolvedJavaField;
 import jdk.vm.ci.meta.ResolvedJavaMethod;
 import jdk.vm.ci.meta.ResolvedJavaType;
@@ -519,4 +520,12 @@
     public static double fma(double a, double b, double c) {
         return Math.fma(a, b, c);
     }
+
+    /**
+     * Set the flag in the {@link VirtualObject} that indicates that it is a boxed primitive that
+     * was produced as a result of a call to a {@code valueOf} method.
+     */
+    public static void markVirtualObjectAsAutoBox(VirtualObject virtualObject) {
+       virtualObject.setIsAutoBox(true);
 }
+}