diff --git a/core/trino-main/src/main/java/io/trino/server/testing/TestingTrinoServer.java b/core/trino-main/src/main/java/io/trino/server/testing/TestingTrinoServer.java
index ce3a6fddb579..4e51a76de52b 100644
--- a/core/trino-main/src/main/java/io/trino/server/testing/TestingTrinoServer.java
+++ b/core/trino-main/src/main/java/io/trino/server/testing/TestingTrinoServer.java
@@ -36,6 +36,7 @@
 import io.airlift.jaxrs.JaxrsModule;
 import io.airlift.jmx.testing.TestingJmxModule;
 import io.airlift.json.JsonModule;
+import io.airlift.log.Logger;
 import io.airlift.node.testing.TestingNodeModule;
 import io.airlift.tracetoken.TraceTokenModule;
 import io.trino.connector.CatalogName;
@@ -96,6 +97,8 @@
 import io.trino.testing.TestingWarningCollectorModule;
 import io.trino.transaction.TransactionManager;
 import io.trino.transaction.TransactionManagerModule;
+import net.jodah.failsafe.Failsafe;
+import net.jodah.failsafe.RetryPolicy;
 import org.weakref.jmx.guice.MBeanModule;
 
 import javax.annotation.concurrent.GuardedBy;
@@ -120,6 +123,7 @@
 
 import static com.google.common.base.Preconditions.checkState;
 import static com.google.common.base.Strings.nullToEmpty;
+import static com.google.common.base.Throwables.getStackTraceAsString;
 import static com.google.common.io.MoreFiles.deleteRecursively;
 import static com.google.common.io.RecursiveDeleteOption.ALLOW_INSECURE;
 import static com.google.inject.util.Modules.EMPTY_MODULE;
@@ -133,6 +137,8 @@
 public class TestingTrinoServer
         implements Closeable
 {
+    private static final Logger log = Logger.get(TestingTrinoServer.class);
+
     public static TestingTrinoServer create()
     {
         return builder().build();
@@ -286,17 +292,17 @@ private TestingTrinoServer(
 
         modules.add(additionalModule);
 
-        Bootstrap app = new Bootstrap(modules.build());
-
         Map<String, String> optionalProperties = new HashMap<>();
         environment.ifPresent(env -> optionalProperties.put("node.environment", env));
 
-        injector = app
-                .doNotInitializeLogging()
-                .setRequiredConfigurationProperties(serverProperties.buildOrThrow())
-                .setOptionalConfigurationProperties(optionalProperties)
-                .quiet()
-                .initialize();
+        injector = Failsafe.with(new RetryPolicy<>()
+                        .withMaxRetries(5)
+                        .handleIf(throwable -> getStackTraceAsString(throwable).contains("BindException: Address already in use"))
+                .onRetry(event -> log.debug(
+                        "Initialization failed on attempt %s, will retry. Exception: %s",
+                        event.getAttemptCount(),
+                        event.getLastFailure().getMessage())))
+                .get(() -> initialize(serverProperties.buildOrThrow(), modules.build(), optionalProperties));
 
         injector.getInstance(Announcer.class).start();
 
@@ -363,6 +369,16 @@ private TestingTrinoServer(
         refreshNodes();
     }
 
+    private static Injector initialize(Map<String, String> serverProperties, List<Module> modules, Map<String, String> optionalProperties)
+    {
+        return new Bootstrap(modules)
+                .doNotInitializeLogging()
+                .setRequiredConfigurationProperties(serverProperties)
+                .setOptionalConfigurationProperties(optionalProperties)
+                .quiet()
+                .initialize();
+    }
+
     @Override
     public void close()
             throws IOException