diff --git a/container/openejb-core/src/main/java/org/apache/openejb/assembler/classic/Assembler.java b/container/openejb-core/src/main/java/org/apache/openejb/assembler/classic/Assembler.java
index 50be16d782f..6967f23b15a 100644
--- a/container/openejb-core/src/main/java/org/apache/openejb/assembler/classic/Assembler.java
+++ b/container/openejb-core/src/main/java/org/apache/openejb/assembler/classic/Assembler.java
@@ -1100,6 +1100,14 @@ private AppContext createApplication(final AppInfo appInfo, ClassLoader classLoa
 
                 return appContext;
             } catch (final ValidationException | DeploymentException ve) {
+                // these are not wrapped, but the partially deployed application still has to be
+                // rolled back or its deployment ids stay registered and make the next app reusing
+                // one of them fail with a DuplicateDeploymentIdException (TOMEE-4655)
+                try {
+                    destroyApplication(appInfo);
+                } catch (final Exception e1) {
+                    logger.debug("createApplication.undeployFailed", e1, appInfo.path);
+                }
                 throw ve;
             } catch (final Throwable t) {
                 try {
diff --git a/container/openejb-core/src/test/java/org/apache/openejb/assembler/classic/FailedDeploymentIdCleanupTest.java b/container/openejb-core/src/test/java/org/apache/openejb/assembler/classic/FailedDeploymentIdCleanupTest.java
new file mode 100644
index 00000000000..5906b6f988e
--- /dev/null
+++ b/container/openejb-core/src/test/java/org/apache/openejb/assembler/classic/FailedDeploymentIdCleanupTest.java
@@ -0,0 +1,120 @@
+/**
+ * Licensed to the Apache Software Foundation (ASF) under one or more
+ * contributor license agreements.  See the NOTICE file distributed with
+ * this work for additional information regarding copyright ownership.
+ * The ASF licenses this file to You under the Apache License, Version 2.0
+ * (the "License"); you may not use this file except in compliance with
+ * the License.  You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ *  Unless required by applicable law or agreed to in writing, software
+ *  distributed under the License is distributed on an "AS IS" BASIS,
+ *  WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ *  See the License for the specific language governing permissions and
+ *  limitations under the License.
+ */
+package org.apache.openejb.assembler.classic;
+
+import jakarta.ejb.Singleton;
+import jakarta.inject.Inject;
+import org.apache.openejb.OpenEJB;
+import org.apache.openejb.config.ConfigurationFactory;
+import org.apache.openejb.config.EjbModule;
+import org.apache.openejb.jee.Beans;
+import org.apache.openejb.jee.EjbJar;
+import org.apache.openejb.jee.SingletonBean;
+import org.apache.openejb.jee.oejb3.EjbDeployment;
+import org.apache.openejb.jee.oejb3.OpenejbJar;
+import org.apache.openejb.loader.SystemInstance;
+import org.apache.openejb.spi.ContainerSystem;
+import org.junit.After;
+import org.junit.Test;
+
+import static org.junit.Assert.assertNotNull;
+import static org.junit.Assert.assertNull;
+import static org.junit.Assert.fail;
+
+/**
+ * TOMEE-4655: when a deployment fails, the deployment ids it already registered must be
+ * released again. Otherwise the next application reusing one of those ids fails with a
+ * DuplicateDeploymentIdException before any of its own checks get a chance to run.
+ */
+public class FailedDeploymentIdCleanupTest {
+
+    private static final String DEPLOYMENT_ID = "TheSharedDeploymentId";
+
+    @After
+    public void tearDown() {
+        OpenEJB.destroy();
+    }
+
+    @Test
+    public void deploymentIdIsReusableAfterAFailedCdiDeployment() throws Exception {
+        final ConfigurationFactory config = new ConfigurationFactory();
+        final Assembler assembler = new Assembler();
+
+        assembler.createTransactionManager(config.configureService(TransactionServiceInfo.class));
+        assembler.createSecurityService(config.configureService(SecurityServiceInfo.class));
+
+        // this app fails while CDI is starting, i.e. after initEjbs already registered the id
+        try {
+            assembler.createApplication(config.configureApplication(failingModule()));
+            fail("the deployment was expected to fail while starting CDI");
+        } catch (final Exception expected) {
+            // that is the point of the test
+        }
+
+        final ContainerSystem containerSystem = SystemInstance.get().getComponent(ContainerSystem.class);
+        assertNull("the failed deployment leaked its deployment id",
+                containerSystem.getBeanContext(DEPLOYMENT_ID));
+
+        // a later, perfectly valid app reusing the same id must deploy just fine
+        assembler.createApplication(config.configureApplication(workingModule()));
+
+        assertNotNull("the deployment id could not be reused after a failed deployment",
+                containerSystem.getBeanContext(DEPLOYMENT_ID));
+    }
+
+    private EjbModule failingModule() {
+        // the unsatisfied injection point makes OWB fail the application start
+        return module("failing-app", BrokenSingleton.class);
+    }
+
+    private EjbModule workingModule() {
+        return module("working-app", WorkingSingleton.class);
+    }
+
+    private EjbModule module(final String moduleId, final Class<?> beanClass) {
+        final EjbJar ejbJar = new EjbJar(moduleId);
+        ejbJar.addEnterpriseBean(new SingletonBean(beanClass));
+
+        final OpenejbJar openejbJar = new OpenejbJar();
+        final EjbDeployment deployment = new EjbDeployment();
+        deployment.setEjbName(beanClass.getSimpleName());
+        deployment.setDeploymentId(DEPLOYMENT_ID);
+        openejbJar.addEjbDeployment(deployment);
+
+        final EjbModule module = new EjbModule(ejbJar, openejbJar);
+        module.setModuleId(moduleId);
+        module.setBeans(new Beans());
+        return module;
+    }
+
+    public interface NoImplementationAnywhere {
+        void doSomething();
+    }
+
+    @Singleton
+    public static class BrokenSingleton {
+        @Inject
+        private NoImplementationAnywhere unsatisfied;
+    }
+
+    @Singleton
+    public static class WorkingSingleton {
+        public String hello() {
+            return "hello";
+        }
+    }
+}