diff --git a/substratevm/src/com.oracle.svm.core/src/com/oracle/svm/core/layeredimagesingleton/LayeredImageSingleton.java b/substratevm/src/com.oracle.svm.core/src/com/oracle/svm/core/layeredimagesingleton/LayeredImageSingleton.java
index 7a4961a61d50..e1c196b21477 100644
--- a/substratevm/src/com.oracle.svm.core/src/com/oracle/svm/core/layeredimagesingleton/LayeredImageSingleton.java
+++ b/substratevm/src/com.oracle.svm.core/src/com/oracle/svm/core/layeredimagesingleton/LayeredImageSingleton.java
@@ -30,6 +30,8 @@
 import org.graalvm.nativeimage.Platform;
 import org.graalvm.nativeimage.Platforms;
 
+import com.oracle.svm.core.imagelayer.ImageLayerBuildingSupport;
+
 /**
  * In additional to the traditional singleton model, i.e. a key-value map whose lookups are constant
  * folded within generated code, we provide two additional options:
@@ -42,12 +44,13 @@
  * <li>{@link MultiLayeredImageSingleton}: {@link ImageSingletons#lookup} calls continue to refer to
  * the appropriate per layer image singleton, but there is also an additional method
  * {@link MultiLayeredImageSingleton#getAllLayers} which returns an array with the image singletons
- * corresponding to this key in all layers they were created. The length of this array will vary
- * from [0, total #layers], based on the number of layers singletons were installed in (i.e., it is
- * not required for the singleton to be installed in all layers). Within the array, the singletons
- * will be arranged so that index [0] corresponds to the singleton originating from the oldest layer
- * in which the singleton was installed and index [length - 1] holds the singleton from the newest
- * layer.</li>
+ * corresponding to this key for all layers. The length of this array will always be the total
+ * number of layers. If a singleton corresponding to this key was not installed in a given layer
+ * (and this is allowed), then the array will contain null for the given index. See
+ * {@link MultiLayeredAllowNullEntries} for more details. Within the array, the singletons will be
+ * arranged so that index [0] corresponds to the singleton originating from the initial layer and
+ * index [length - 1] holds the singleton from the application layer. See
+ * {@link ImageLayerBuildingSupport} for a description of the different layer names.</li>
  * </ul>
  *
  * Note the unique behavior of {@link ApplicationLayerOnlyImageSingleton} applies only when building
diff --git a/substratevm/src/com.oracle.svm.core/src/com/oracle/svm/core/layeredimagesingleton/MultiLayeredAllowNullEntries.java b/substratevm/src/com.oracle.svm.core/src/com/oracle/svm/core/layeredimagesingleton/MultiLayeredAllowNullEntries.java
new file mode 100644
index 000000000000..d48e9aa1f72f
--- /dev/null
+++ b/substratevm/src/com.oracle.svm.core/src/com/oracle/svm/core/layeredimagesingleton/MultiLayeredAllowNullEntries.java
@@ -0,0 +1,43 @@
+/*
+ * Copyright (c) 2025, 2025, 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 com.oracle.svm.core.layeredimagesingleton;
+
+import java.lang.annotation.ElementType;
+import java.lang.annotation.Retention;
+import java.lang.annotation.RetentionPolicy;
+import java.lang.annotation.Target;
+
+/**
+ * By default, it is expected a given {@link MultiLayeredImageSingleton} has a singleton installed
+ * in each layer. If instead you want to make installation optional, you must add this annotation to
+ * your class.
+ *
+ * Note this annotation is only meaningful when applied to {@link MultiLayeredImageSingleton}. In
+ * all other scenarios it is ignored.
+ */
+@Retention(RetentionPolicy.RUNTIME)
+@Target(ElementType.TYPE)
+public @interface MultiLayeredAllowNullEntries {
+}
diff --git a/substratevm/src/com.oracle.svm.core/src/com/oracle/svm/core/layeredimagesingleton/MultiLayeredImageSingleton.java b/substratevm/src/com.oracle.svm.core/src/com/oracle/svm/core/layeredimagesingleton/MultiLayeredImageSingleton.java
index b27605f8b3f2..f70f14d06ca1 100644
--- a/substratevm/src/com.oracle.svm.core/src/com/oracle/svm/core/layeredimagesingleton/MultiLayeredImageSingleton.java
+++ b/substratevm/src/com.oracle.svm.core/src/com/oracle/svm/core/layeredimagesingleton/MultiLayeredImageSingleton.java
@@ -41,9 +41,9 @@ static <T extends MultiLayeredImageSingleton> T[] getAllLayers(Class<T> key) {
     }
 
     /**
-     * Retrieve a specific layer from a MultiLayeredImageSingleton. Note if a
-     * MultiLayeredImageSingleton is not installed in all layers, then the singletons index will not
-     * match the layer number it was installed in.
+     * Retrieve a specific layer's singleton from a MultiLayeredImageSingleton. The index represents
+     * which layer number's singleton to retrieve. If a singleton was not installed in that layer
+     * (and this is allowed), then null is returned.
      */
     @SuppressWarnings("unused")
     static <T extends MultiLayeredImageSingleton> T getForLayer(Class<T> key, int index) {
diff --git a/substratevm/src/com.oracle.svm.hosted/src/com/oracle/svm/hosted/imagelayer/LoadImageSingletonFeature.java b/substratevm/src/com.oracle.svm.hosted/src/com/oracle/svm/hosted/imagelayer/LoadImageSingletonFeature.java
index 853fa32e6cdc..5e960747628e 100644
--- a/substratevm/src/com.oracle.svm.hosted/src/com/oracle/svm/hosted/imagelayer/LoadImageSingletonFeature.java
+++ b/substratevm/src/com.oracle.svm.hosted/src/com/oracle/svm/hosted/imagelayer/LoadImageSingletonFeature.java
@@ -35,10 +35,11 @@
 import java.util.Map;
 import java.util.Objects;
 import java.util.concurrent.ConcurrentHashMap;
+import java.util.function.BiConsumer;
 import java.util.function.BiFunction;
 import java.util.function.Consumer;
-import java.util.stream.Stream;
 
+import org.graalvm.nativeimage.AnnotationAccess;
 import org.graalvm.nativeimage.ImageSingletons;
 import org.graalvm.word.Pointer;
 
@@ -54,6 +55,7 @@
 import com.oracle.svm.core.feature.AutomaticallyRegisteredFeature;
 import com.oracle.svm.core.feature.InternalFeature;
 import com.oracle.svm.core.graal.code.CGlobalDataInfo;
+import com.oracle.svm.core.imagelayer.DynamicImageLayerInfo;
 import com.oracle.svm.core.imagelayer.ImageLayerBuildingSupport;
 import com.oracle.svm.core.imagelayer.LoadImageSingletonFactory;
 import com.oracle.svm.core.layeredimagesingleton.ApplicationLayerOnlyImageSingleton;
@@ -63,8 +65,10 @@
 import com.oracle.svm.core.layeredimagesingleton.LayeredImageSingleton;
 import com.oracle.svm.core.layeredimagesingleton.LayeredImageSingletonBuilderFlags;
 import com.oracle.svm.core.layeredimagesingleton.LayeredImageSingletonSupport;
+import com.oracle.svm.core.layeredimagesingleton.MultiLayeredAllowNullEntries;
 import com.oracle.svm.core.layeredimagesingleton.MultiLayeredImageSingleton;
 import com.oracle.svm.core.layeredimagesingleton.UnsavedSingleton;
+import com.oracle.svm.core.util.UserError;
 import com.oracle.svm.core.util.VMError;
 import com.oracle.svm.hosted.FeatureImpl;
 import com.oracle.svm.hosted.c.CGlobalDataFeature;
@@ -74,6 +78,7 @@
 import com.oracle.svm.util.ReflectionUtil;
 
 import jdk.graal.compiler.api.replacements.SnippetReflectionProvider;
+import jdk.graal.compiler.debug.GraalError;
 import jdk.graal.compiler.nodes.ConstantNode;
 import jdk.graal.compiler.nodes.ValueNode;
 import jdk.graal.compiler.nodes.graphbuilderconf.GraphBuilderConfiguration;
@@ -166,6 +171,12 @@ public void duringSetup(DuringSetupAccess access) {
         LayeredImageHeapObjectAdder.singleton().registerObjectAdder(this::addInitialObjects);
     }
 
+    static void checkAllowNullEntries(Class<?> key) {
+        boolean nullEntriesAllowed = AnnotationAccess.isAnnotationPresent(key, MultiLayeredAllowNullEntries.class);
+        UserError.guarantee(nullEntriesAllowed,
+                        "This MultiLayeredSingleton requires an entry to be installed in every layer. Please see the javadoc within MultiLayeredAllowNullEntries for more details.");
+    }
+
     /**
      * This method needs to be called after all image singletons are registered. Currently, some
      * singletons are registered in
@@ -229,6 +240,8 @@ public void processRegisteredSingletons(AnalysisUniverse universe) {
                         Class<?> key = slotInfo.keyClass();
                         if (ImageSingletons.contains(key)) {
                             multiLayerEmbeddedRoots.add(layeredImageSingletonSupport.runtimeLookup(key));
+                        } else {
+                            checkAllowNullEntries(key);
                         }
                         /*
                          * Within the application layer there will be an array created to hold all
@@ -262,6 +275,9 @@ public void processRegisteredSingletons(AnalysisUniverse universe) {
             if (!multiLayerEmbeddedRoots.isEmpty()) {
                 multiLayerEmbeddedRootsRegistration.accept(multiLayerEmbeddedRoots.toArray());
             }
+        } else {
+            // GR-58631
+            throw GraalError.unimplemented("More work needed for 3+ layer support");
         }
     }
 
@@ -273,15 +289,46 @@ public void beforeCompilation(BeforeCompilationAccess access) {
 
     ImageHeapObjectArray createMultiLayerArray(Class<?> key, AnalysisType arrayType, SnippetReflectionProvider snippetReflectionProvider) {
         List<Integer> priorIds = getCrossLayerSingletonMappingInfo().getPriorLayerObjectIDs(key);
-        Stream<JavaConstant> values = priorIds.stream().map(priorId -> loader.getOrCreateConstant(priorId));
+        var layerInfo = DynamicImageLayerInfo.singleton();
+
+        final JavaConstant[] elements = new JavaConstant[layerInfo.numLayers];
+        BiConsumer<JavaConstant, Integer> installElement = (priorConstant, index) -> {
+            assert elements[index] == null : elements[index];
+            elements[index] = priorConstant;
+        };
 
+        // first install prior singletons
+        priorIds.forEach(priorId -> {
+            var priorConstant = loader.getOrCreateConstant(priorId);
+            int index = 0;
+            assert layerInfo.numLayers == 2 : "incompatible with 3+ layers";
+            installElement.accept(priorConstant, index);
+        });
+
+        // next install current singleton
         if (ImageSingletons.contains(key)) {
             var singleton = LayeredImageSingletonSupport.singleton().runtimeLookup(key);
             JavaConstant singletonConstant = snippetReflectionProvider.forObject(singleton);
-            values = Stream.concat(values, Stream.of(singletonConstant));
+            installElement.accept(singletonConstant, layerInfo.layerNumber);
+        }
+
+        // finally fill any missing holes
+        boolean holesPresent = false;
+        for (int i = 0; i < layerInfo.numLayers; i++) {
+            if (elements[i] == null) {
+                holesPresent = true;
+                installElement.accept(JavaConstant.NULL_POINTER, i);
+            }
+        }
+
+        if (holesPresent) {
+            /*
+             * Once more validate that null entries are allowed. However, any issues are expected to
+             * be caught before this point.
+             */
+            checkAllowNullEntries(key);
         }
 
-        Object[] elements = values.toArray();
         return ImageHeapObjectArray.createUnbackedImageHeapArray(arrayType, elements);
     }
 
@@ -477,6 +524,15 @@ private LoadImageSingletonData getImageSingletonInfo(Class<?> keyClass, SlotReco
             return result;
         }
 
+        if (result.kind == SlotRecordKind.MULTI_LAYERED_SINGLETON) {
+            if (!ImageSingletons.contains(keyClass)) {
+                /*
+                 * If the singleton doesn't exist, ensure this is allowed.
+                 */
+                LoadImageSingletonFeature.checkAllowNullEntries(keyClass);
+            }
+        }
+
         SlotInfo priorSlotInfo = priorKeyToSlotInfoMap.get(keyClass);
         if (priorSlotInfo != null && priorSlotInfo.recordKind() != kind) {
             VMError.shouldNotReachHere("A singleton cannot implement both %s and %s", priorSlotInfo.recordKind(), kind);