diff --git a/plugin/src/test/java/org/elasticsearch/license/LicenseServiceWithSecurityTests.java b/plugin/src/test/java/org/elasticsearch/license/LicenseServiceWithSecurityTests.java
new file mode 100644
index 00000000000..4b7895cda52
--- /dev/null
+++ b/plugin/src/test/java/org/elasticsearch/license/LicenseServiceWithSecurityTests.java
@@ -0,0 +1,53 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License;
+ * you may not use this file except in compliance with the Elastic License.
+ */
+package org.elasticsearch.license;
+
+import org.elasticsearch.analysis.common.CommonAnalysisPlugin;
+import org.elasticsearch.common.unit.TimeValue;
+import org.elasticsearch.plugins.Plugin;
+import org.elasticsearch.test.SecurityIntegTestCase;
+import org.elasticsearch.transport.Netty4Plugin;
+import org.elasticsearch.xpack.XPackPlugin;
+
+import java.util.Arrays;
+import java.util.Collection;
+
+import static org.hamcrest.CoreMatchers.equalTo;
+
+/**
+ * Basic integration test that checks if license can be upgraded to a production license if TLS is enabled and vice versa.
+ */
+public class LicenseServiceWithSecurityTests extends SecurityIntegTestCase {
+
+    @Override
+    protected Collection<Class<? extends Plugin>> nodePlugins() {
+        return Arrays.asList(XPackPlugin.class, CommonAnalysisPlugin.class, Netty4Plugin.class);
+    }
+
+    @Override
+    protected Collection<Class<? extends Plugin>> transportClientPlugins() {
+        return nodePlugins();
+    }
+
+    public void testLicenseUpgradeFailsWithoutTLS() throws Exception {
+        assumeFalse("transport ssl is enabled", isTransportSSLEnabled());
+        LicensingClient licensingClient = new LicensingClient(client());
+        License license = licensingClient.prepareGetLicense().get().license();
+        License prodLicense = TestUtils.generateSignedLicense("platinum", TimeValue.timeValueHours(24));
+        IllegalStateException ise = expectThrows(IllegalStateException.class, () -> licensingClient.preparePutLicense(prodLicense).get());
+        assertEquals("Can not upgrade to a production license unless TLS is configured or security is disabled", ise.getMessage());
+        assertThat(licensingClient.prepareGetLicense().get().license(), equalTo(license));
+    }
+
+    public void testLicenseUpgradeSucceedsWithTLS() throws Exception {
+        assumeTrue("transport ssl is disabled", isTransportSSLEnabled());
+        LicensingClient licensingClient = new LicensingClient(client());
+        License prodLicense = TestUtils.generateSignedLicense("platinum", TimeValue.timeValueHours(24));
+        PutLicenseResponse putLicenseResponse = licensingClient.preparePutLicense(prodLicense).get();
+        assertEquals(putLicenseResponse.status(), LicensesStatus.VALID);
+        assertThat(licensingClient.prepareGetLicense().get().license(), equalTo(prodLicense));
+    }
+}
diff --git a/plugin/src/test/java/org/elasticsearch/test/SecurityIntegTestCase.java b/plugin/src/test/java/org/elasticsearch/test/SecurityIntegTestCase.java
index 7f9539d78e5..09632c649b1 100644
--- a/plugin/src/test/java/org/elasticsearch/test/SecurityIntegTestCase.java
+++ b/plugin/src/test/java/org/elasticsearch/test/SecurityIntegTestCase.java
@@ -518,4 +518,8 @@ public abstract class SecurityIntegTestCase extends ESIntegTestCase {
         }
         return null;
     }
+
+    protected boolean isTransportSSLEnabled() {
+        return customSecuritySettingsSource.isSslEnabled();
+    }
 }
diff --git a/plugin/src/test/java/org/elasticsearch/test/SecuritySettingsSource.java b/plugin/src/test/java/org/elasticsearch/test/SecuritySettingsSource.java
index 6aeec9c236a..02bf772fa4c 100644
--- a/plugin/src/test/java/org/elasticsearch/test/SecuritySettingsSource.java
+++ b/plugin/src/test/java/org/elasticsearch/test/SecuritySettingsSource.java
@@ -339,4 +339,8 @@ public class SecuritySettingsSource extends ClusterDiscoveryConfiguration.Unicas
             throw new ElasticsearchException("exception while reading the store", e);
         }
     }
+
+    public boolean isSslEnabled() {
+        return sslEnabled;
+    }
 }