diff --git a/plugin/core/src/main/java/org/elasticsearch/license/LicenseService.java b/plugin/core/src/main/java/org/elasticsearch/license/LicenseService.java
index adbe0c6df10..d0d882b7bda 100644
--- a/plugin/core/src/main/java/org/elasticsearch/license/LicenseService.java
+++ b/plugin/core/src/main/java/org/elasticsearch/license/LicenseService.java
@@ -216,8 +216,8 @@ public class LicenseService extends AbstractLifecycleComponent implements Cluste
                     && XPackSettings.TRANSPORT_SSL_ENABLED.get(settings) == false
                     && "single-node".equals(DiscoveryModule.DISCOVERY_TYPE_SETTING.get(settings)) == false) {
                 // security is on but TLS is not configured we gonna fail the entire request and throw an exception
-                throw new IllegalStateException("Can not upgrade to a production license unless TLS is configured or " +
-                        "security is disabled");
+                throw new IllegalStateException("Cannot install a [" + newLicense.operationMode() +
+                        "] license unless TLS is configured or security is disabled");
                 // TODO we should really validate that all nodes have xpack installed and are consistently configured but this
                 // should happen on a different level and not in this code
             } else {
diff --git a/plugin/core/src/test/java/org/elasticsearch/license/LicensesAcknowledgementTests.java b/plugin/core/src/test/java/org/elasticsearch/license/LicensesAcknowledgementTests.java
index eed19785b1b..211215da21c 100644
--- a/plugin/core/src/test/java/org/elasticsearch/license/LicensesAcknowledgementTests.java
+++ b/plugin/core/src/test/java/org/elasticsearch/license/LicensesAcknowledgementTests.java
@@ -48,7 +48,7 @@ public class LicensesAcknowledgementTests extends AbstractLicenseServiceTestCase
         // ensure acknowledgement message was part of the response
         IllegalStateException ise = expectThrows(IllegalStateException.class, () ->
                 licenseService.registerLicense(putLicenseRequest, new AssertingLicensesUpdateResponse(false, LicensesStatus.VALID, true)));
-        assertEquals("Can not upgrade to a production license unless TLS is configured or security is disabled", ise.getMessage());
+        assertEquals("Cannot install a [PLATINUM] license unless TLS is configured or security is disabled", ise.getMessage());
     }
 
     public void testUpgradeToProductionWithoutTLSAndSecurityDisabled() throws Exception {
diff --git a/plugin/security/src/test/java/org/elasticsearch/license/LicenseServiceWithSecurityTests.java b/plugin/security/src/test/java/org/elasticsearch/license/LicenseServiceWithSecurityTests.java
index 230e29c6b80..42bfd2df1d5 100644
--- a/plugin/security/src/test/java/org/elasticsearch/license/LicenseServiceWithSecurityTests.java
+++ b/plugin/security/src/test/java/org/elasticsearch/license/LicenseServiceWithSecurityTests.java
@@ -11,7 +11,6 @@ import org.elasticsearch.plugins.Plugin;
 import org.elasticsearch.test.SecurityIntegTestCase;
 import org.elasticsearch.transport.Netty4Plugin;
 import org.elasticsearch.xpack.security.LocalStateSecurity;
-import org.elasticsearch.xpack.security.Security;
 
 import java.util.Arrays;
 import java.util.Collection;
@@ -39,7 +38,7 @@ public class LicenseServiceWithSecurityTests extends SecurityIntegTestCase {
         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());
+        assertEquals("Cannot install a [PLATINUM] license unless TLS is configured or security is disabled", ise.getMessage());
         assertThat(licensingClient.prepareGetLicense().get().license(), equalTo(license));
     }