diff --git a/src/hotspot/share/jvmci/jvmciCodeInstaller.cpp b/src/hotspot/share/jvmci/jvmciCodeInstaller.cpp
index 6bca2aa644e55..dc3eecd57917e 100644
--- a/src/hotspot/share/jvmci/jvmciCodeInstaller.cpp
+++ b/src/hotspot/share/jvmci/jvmciCodeInstaller.cpp
@@ -343,6 +343,7 @@ narrowKlass CodeInstaller::record_narrow_metadata_reference(CodeSection* section
   int index = _oop_recorder->find_index(klass);
   section->relocate(dest, metadata_Relocation::spec(index));
   JVMCI_event_3("narrowKlass[%d of %d] = %s", index, _oop_recorder->metadata_count(), klass->name()->as_C_string());
+  guarantee(CompressedKlassPointers::is_encodable(klass), "klass cannot be compressed: %s", klass->external_name());
   return CompressedKlassPointers::encode(klass);
 }
 #endif
diff --git a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/DirectHotSpotObjectConstantImpl.java b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/DirectHotSpotObjectConstantImpl.java
index cc553a39f89ba..8385aaa6560e1 100644
--- a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/DirectHotSpotObjectConstantImpl.java
+++ b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/DirectHotSpotObjectConstantImpl.java
@@ -51,13 +51,17 @@ private DirectHotSpotObjectConstantImpl(Object object, boolean compressed) {
 
     @Override
     public JavaConstant compress() {
-        assert !compressed;
+        if (compressed) {
+            throw new IllegalArgumentException("already compressed: " + this);
+        }
         return new DirectHotSpotObjectConstantImpl(object, true);
     }
 
     @Override
     public JavaConstant uncompress() {
-        assert compressed;
+        if (!compressed) {
+            throw new IllegalArgumentException("not compressed: " + this);
+        }
         return new DirectHotSpotObjectConstantImpl(object, false);
     }
 
diff --git a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotCompressedNullConstant.java b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotCompressedNullConstant.java
index 7c6d94bba999a..0becdf299765d 100644
--- a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotCompressedNullConstant.java
+++ b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotCompressedNullConstant.java
@@ -51,9 +51,14 @@ public boolean isCompressed() {
         return true;
     }
 
+    @Override
+    public boolean isCompressible() {
+        return false;
+    }
+
     @Override
     public Constant compress() {
-        throw new IllegalArgumentException();
+        throw new IllegalArgumentException("not compressible");
     }
 
     @Override
diff --git a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotConstant.java b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotConstant.java
index ee4cb7bb397d0..e0ae6b4c881f3 100644
--- a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotConstant.java
+++ b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotConstant.java
@@ -25,13 +25,34 @@
 import jdk.vm.ci.meta.Constant;
 
 /**
- * Marker interface for hotspot specific constants.
+ * A value in a space managed by Hotspot (e.g. heap or metaspace).
+ * Some of these values can be referenced with a compressed pointer
+ * instead of a full word-sized pointer.
  */
 public interface HotSpotConstant extends Constant {
 
+    /**
+     * Determines if this constant is compressed.
+     */
     boolean isCompressed();
 
+    /**
+     * Determines if this constant is compressible.
+     */
+    boolean isCompressible();
+
+    /**
+     * Gets a compressed version of this uncompressed constant.
+     *
+     * @throws IllegalArgumentException if this constant is not compressible
+     */
     Constant compress();
 
+    /**
+     * Gets an uncompressed version of this compressed constant.
+     *
+     * @throws IllegalArgumentException if this is an uncompressed constant
+     *         or this constant is not compressible
+     */
     Constant uncompress();
 }
diff --git a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotMetaspaceConstantImpl.java b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotMetaspaceConstantImpl.java
index b819eaf748448..358441d0b2282 100644
--- a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotMetaspaceConstantImpl.java
+++ b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotMetaspaceConstantImpl.java
@@ -43,6 +43,9 @@ static MetaspaceObject getMetaspaceObject(Constant constant) {
     private HotSpotMetaspaceConstantImpl(MetaspaceObject metaspaceObject, boolean compressed) {
         this.metaspaceObject = metaspaceObject;
         this.compressed = compressed;
+        if (compressed && !canBeStoredInCompressibleMetaSpace()) {
+            throw new IllegalArgumentException("constant cannot be compressed: " + metaspaceObject);
+        }
     }
 
     @Override
@@ -83,9 +86,28 @@ public boolean isCompressed() {
         return compressed;
     }
 
+    @Override
+    public boolean isCompressible() {
+        if (compressed) {
+            return false;
+        }
+        return canBeStoredInCompressibleMetaSpace();
+    }
+
+    private boolean canBeStoredInCompressibleMetaSpace() {
+        if (metaspaceObject instanceof HotSpotResolvedJavaType t && !t.isArray()) {
+            // As of JDK-8338526, interface and abstract types are not stored
+            // in compressible metaspace.
+            return !t.isInterface() && !t.isAbstract();
+        }
+        return true;
+    }
+
     @Override
     public Constant compress() {
-        assert !isCompressed();
+        if (compressed) {
+            throw new IllegalArgumentException("already compressed: " + this);
+        }
         HotSpotMetaspaceConstantImpl res = HotSpotMetaspaceConstantImpl.forMetaspaceObject(metaspaceObject, true);
         assert res.isCompressed();
         return res;
@@ -93,7 +115,9 @@ public Constant compress() {
 
     @Override
     public Constant uncompress() {
-        assert isCompressed();
+        if (!compressed) {
+            throw new IllegalArgumentException("not compressed: " + this);
+        }
         HotSpotMetaspaceConstantImpl res = HotSpotMetaspaceConstantImpl.forMetaspaceObject(metaspaceObject, false);
         assert !res.isCompressed();
         return res;
diff --git a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotObjectConstantImpl.java b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotObjectConstantImpl.java
index 443673a8783bc..e4a77daf0d448 100644
--- a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotObjectConstantImpl.java
+++ b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/HotSpotObjectConstantImpl.java
@@ -52,6 +52,11 @@ public boolean isCompressed() {
         return compressed;
     }
 
+    @Override
+    public boolean isCompressible() {
+        return !compressed;
+    }
+
     @Override
     public abstract JavaConstant compress();
 
diff --git a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/IndirectHotSpotObjectConstantImpl.java b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/IndirectHotSpotObjectConstantImpl.java
index 33c6fde3b1880..fe268e9047662 100644
--- a/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/IndirectHotSpotObjectConstantImpl.java
+++ b/src/jdk.internal.vm.ci/share/classes/jdk/vm/ci/hotspot/IndirectHotSpotObjectConstantImpl.java
@@ -164,13 +164,17 @@ static void clearHandle(long handle) {
 
     @Override
     public JavaConstant compress() {
-        assert !compressed;
+        if (compressed) {
+            throw new IllegalArgumentException("already compressed: " + this);
+        }
         return new IndirectHotSpotObjectConstantImpl(this, true);
     }
 
     @Override
     public JavaConstant uncompress() {
-        assert compressed;
+        if (!compressed) {
+            throw new IllegalArgumentException("not compressed: " + this);
+        }
         return new IndirectHotSpotObjectConstantImpl(this, false);
     }