diff --git a/airbyte-server/src/main/java/io/airbyte/server/ConnectorDefinitionSpecBackfiller.java b/airbyte-server/src/main/java/io/airbyte/server/ConnectorDefinitionSpecBackfiller.java
index 6ca6be7c9fe1..6877b79bb072 100644
--- a/airbyte-server/src/main/java/io/airbyte/server/ConnectorDefinitionSpecBackfiller.java
+++ b/airbyte-server/src/main/java/io/airbyte/server/ConnectorDefinitionSpecBackfiller.java
@@ -10,6 +10,7 @@
 import io.airbyte.analytics.TrackingClient;
 import io.airbyte.api.model.LogRead;
 import io.airbyte.commons.json.Jsons;
+import io.airbyte.commons.resources.MoreResources;
 import io.airbyte.commons.version.AirbyteVersion;
 import io.airbyte.config.ConfigSchema;
 import io.airbyte.config.Configs;
@@ -188,13 +189,17 @@ static void migrateAllDefinitionsToContainSpec(final ConfigRepository configRepo
     }
 
     if (failedBackfillImages.size() > 0 && !configs.getVersion31ForceUpgrade()) {
-      throw new RuntimeException(String.format(
-          "migrateAllDefinitionsToContainSpec - Specs could not be retrieved for the following connector images: %s. Upgrading to version %s "
+      final String attentionBanner = MoreResources.readResource("banner/attention-banner.txt");
+      LOGGER.error(attentionBanner);
+      final String errorMessage = String.format(
+          "Specs could not be retrieved for the following connector images: %s. Upgrading to version %s "
               + "requires specs to be retrieved for all connector definitions, so you must either fix the images or restart the deployment with "
               + "the VERSION_0_31_0_FORCE_UPGRADE environment variable set to true, which will cause any connector definitions for which specs "
               + "cannot be retrieved to be deleted, as well as their associated connections/syncs.",
           failedBackfillImages.toString(),
-          VERSION_BREAK));
+          VERSION_BREAK);
+      LOGGER.error(errorMessage);
+      throw new RuntimeException(errorMessage);
     }
   }
 
diff --git a/airbyte-server/src/main/java/io/airbyte/server/ServerApp.java b/airbyte-server/src/main/java/io/airbyte/server/ServerApp.java
index c11616e53847..3b148b048a1a 100644
--- a/airbyte-server/src/main/java/io/airbyte/server/ServerApp.java
+++ b/airbyte-server/src/main/java/io/airbyte/server/ServerApp.java
@@ -74,8 +74,9 @@ public class ServerApp implements ServerRunnable {
   private static final AirbyteVersion VERSION_BREAK = new AirbyteVersion("0.31.0-alpha");
 
   /**
-   * We can't support automatic migration for kube before this version because we had a bug in kube which would cause airbyte db to erase state upon
-   * termination, as a result the automatic migration wouldn't run
+   * We can't support automatic migration for kube before this version because we had a bug in kube
+   * which would cause airbyte db to erase state upon termination, as a result the automatic migration
+   * wouldn't run
    */
   private static final AirbyteVersion KUBE_SUPPORT_FOR_AUTOMATIC_MIGRATION = new AirbyteVersion("0.26.5-alpha");
   private final AirbyteVersion airbyteVersion;
@@ -171,7 +172,7 @@ public static ServerRunnable getServer(final ServerFactory apiFactory, final Con
         configs.getConfigDatabaseUser(),
         configs.getConfigDatabasePassword(),
         configs.getConfigDatabaseUrl())
-        .getAndInitialize();
+            .getAndInitialize();
     final DatabaseConfigPersistence configPersistence = new DatabaseConfigPersistence(configDatabase).migrateFileConfigs(configs);
 
     final SecretsHydrator secretsHydrator = SecretPersistence.getSecretsHydrator(configs);
@@ -186,7 +187,7 @@ public static ServerRunnable getServer(final ServerFactory apiFactory, final Con
         configs.getDatabaseUser(),
         configs.getDatabasePassword(),
         configs.getDatabaseUrl())
-        .getAndInitialize();
+            .getAndInitialize();
     final JobPersistence jobPersistence = new DefaultJobPersistence(jobDatabase);
 
     createDeploymentIfNoneExists(jobPersistence);
@@ -235,6 +236,8 @@ public static ServerRunnable getServer(final ServerFactory apiFactory, final Con
     final HttpClient httpClient = HttpClient.newBuilder().version(HttpClient.Version.HTTP_1_1).build();
 
     if (!isLegalUpgrade(airbyteDatabaseVersion.orElse(null), airbyteVersion)) {
+      final String attentionBanner = MoreResources.readResource("banner/attention-banner.txt");
+      LOGGER.error(attentionBanner);
       final String message = String.format(
           "Cannot upgrade from version %s to version %s directly. First you must upgrade to version %s. After that upgrade is complete, you may upgrade to version %s",
           airbyteDatabaseVersion.get(),
@@ -299,11 +302,11 @@ static boolean isLegalUpgrade(final AirbyteVersion airbyteDatabaseVersion, final
   }
 
   /**
-   * Check to see if given the current version of the app and the version we are trying to upgrade if it passes through a version break (i.e. a major
-   * version bump).
+   * Check to see if given the current version of the app and the version we are trying to upgrade if
+   * it passes through a version break (i.e. a major version bump).
    *
    * @param airbyteDatabaseVersion - current version of the app
-   * @param airbyteVersion         - version we are trying to upgrade to
+   * @param airbyteVersion - version we are trying to upgrade to
    * @return true if upgrading through a major version, otherwise false.
    */
   private static boolean isUpgradingThroughVersionBreak(final AirbyteVersion airbyteDatabaseVersion, final AirbyteVersion airbyteVersion) {
@@ -344,7 +347,8 @@ public static void main(final String[] args) throws Exception {
   }
 
   /**
-   * Ideally when automatic migration runs, we should make sure that we acquire a lock on database and no other operation is allowed
+   * Ideally when automatic migration runs, we should make sure that we acquire a lock on database and
+   * no other operation is allowed
    */
   private static void runAutomaticMigration(final ConfigRepository configRepository,
                                             final JobPersistence jobPersistence,
diff --git a/airbyte-server/src/main/resources/banner/attention-banner.txt b/airbyte-server/src/main/resources/banner/attention-banner.txt
new file mode 100644
index 000000000000..e35652b219ef
--- /dev/null
+++ b/airbyte-server/src/main/resources/banner/attention-banner.txt
@@ -0,0 +1,13 @@
+                              ___  ___________________   ________________  _   __
+                             /   |/_  __/_  __/ ____/ | / /_  __/  _/ __ \/ | / /
+ ________________________   / /| | / /   / / / __/ /  |/ / / /  / // / / /  |/ /  ________________________
+/_____/_____/_____/_____/  / ___ |/ /   / / / /___/ /|  / / / _/ // /_/ / /|  /  /_____/_____/_____/_____/
+   __  _______ __________ /_/ _|_/_/  _/_/_/_____/_/_|_/_/_/ /___/\____/_/_|_/ __  __________  __________
+  / / / / ___// ____/ __ \   /  _/ | / / __ \/ / / /_  __/  / __ \/ ____/ __ \/ / / /  _/ __ \/ ____/ __ \
+ / / / /\__ \/ __/ / /_/ /   / //  |/ / /_/ / / / / / /    / /_/ / __/ / / / / / / // // /_/ / __/ / / / /
+/ /_/ /___/ / /___/ _, _/  _/ // /|  / ____/ /_/ / / /    / _, _/ /___/ /_/ / /_/ // // _, _/ /___/ /_/ /
+\____//____/_____/_/ |_|  /___/_/ |_/_/    \____/ /_/    /_/ |_/_____/\___\_\____/___/_/ |_/_____/_____/
+
+ -------------------
+  See details below
+ -------------------