diff --git a/airbyte-db/db-lib/src/main/java/io/airbyte/db/jdbc/DefaultJdbcDatabase.java b/airbyte-db/db-lib/src/main/java/io/airbyte/db/jdbc/DefaultJdbcDatabase.java
index faf328623007b1..01d39635692190 100644
--- a/airbyte-db/db-lib/src/main/java/io/airbyte/db/jdbc/DefaultJdbcDatabase.java
+++ b/airbyte-db/db-lib/src/main/java/io/airbyte/db/jdbc/DefaultJdbcDatabase.java
@@ -5,6 +5,7 @@
 package io.airbyte.db.jdbc;
 
 import com.google.errorprone.annotations.MustBeClosed;
+import io.airbyte.commons.exceptions.ConfigErrorException;
 import io.airbyte.commons.exceptions.ConnectionErrorException;
 import io.airbyte.commons.functional.CheckedConsumer;
 import io.airbyte.commons.functional.CheckedFunction;
@@ -14,6 +15,7 @@
 import java.sql.PreparedStatement;
 import java.sql.ResultSet;
 import java.sql.SQLException;
+import java.sql.SQLTransientException;
 import java.util.List;
 import java.util.Objects;
 import java.util.stream.Collectors;
@@ -76,8 +78,12 @@ public <T> Stream<T> unsafeResultSetQuery(final CheckedFunction<Connection, Resu
   @Override
   public DatabaseMetaData getMetaData() throws SQLException {
     try (final Connection connection = dataSource.getConnection()) {
-      final DatabaseMetaData metaData = connection.getMetaData();
-      return metaData;
+      return connection.getMetaData();
+    } catch (final SQLTransientException e) {
+      final String message = e.getMessage();
+      if (message.contains("request timed out")) {
+        throw new ConfigErrorException("Connection timed out. Unable to contact server. Please check your server settings or try again later", e);
+      }
     } catch (final SQLException e) {
       // Some databases like Redshift will have null cause
       if (Objects.isNull(e.getCause()) || !(e.getCause() instanceof SQLException)) {
@@ -87,6 +93,7 @@ public DatabaseMetaData getMetaData() throws SQLException {
         throw new ConnectionErrorException(e.getSQLState(), cause.getErrorCode(), cause.getMessage(), e);
       }
     }
+    throw new RuntimeException("Failed to get metadata fron Datasource");
   }
 
   /**