diff --git a/transactionoutbox-core/src/main/java/com/gruelbox/transactionoutbox/DefaultMigrationManager.java b/transactionoutbox-core/src/main/java/com/gruelbox/transactionoutbox/DefaultMigrationManager.java
index 82cf58d6..dbdc3a51 100644
--- a/transactionoutbox-core/src/main/java/com/gruelbox/transactionoutbox/DefaultMigrationManager.java
+++ b/transactionoutbox-core/src/main/java/com/gruelbox/transactionoutbox/DefaultMigrationManager.java
@@ -68,7 +68,12 @@ class DefaultMigrationManager {
               "ALTER TABLE TXNO_OUTBOX ADD COLUMN lastAttemptTime TIMESTAMP(6) NULL AFTER invocation",
               Map.of(
                   Dialect.POSTGRESQL_9,
-                  "ALTER TABLE TXNO_OUTBOX ADD COLUMN lastAttemptTime TIMESTAMP(6)")));
+                  "ALTER TABLE TXNO_OUTBOX ADD COLUMN lastAttemptTime TIMESTAMP(6)")),
+          new Migration(
+              8,
+              "Update length of invocation column on outbox for MySQL dialects only.",
+              "ALTER TABLE TXNO_OUTBOX MODIFY COLUMN invocation MEDIUMTEXT",
+              Map.of(Dialect.POSTGRESQL_9, "", Dialect.H2, "")));
 
   static void migrate(TransactionManager transactionManager, @NotNull Dialect dialect) {
     transactionManager.inTransaction(
diff --git a/transactionoutbox-core/src/main/java/com/gruelbox/transactionoutbox/DefaultPersistor.java b/transactionoutbox-core/src/main/java/com/gruelbox/transactionoutbox/DefaultPersistor.java
index fe96df77..4dae3f30 100644
--- a/transactionoutbox-core/src/main/java/com/gruelbox/transactionoutbox/DefaultPersistor.java
+++ b/transactionoutbox-core/src/main/java/com/gruelbox/transactionoutbox/DefaultPersistor.java
@@ -114,6 +114,7 @@ public void save(Transaction tx, TransactionOutboxEntry entry)
           throw new AlreadyScheduledException(
               "Request " + entry.description() + " already exists", e);
         }
+        throw e;
       }
     }
   }
diff --git a/transactionoutbox-core/src/test/java/com/gruelbox/transactionoutbox/AbstractDefaultPersistorTest.java b/transactionoutbox-core/src/test/java/com/gruelbox/transactionoutbox/AbstractDefaultPersistorTest.java
index cf7426e8..84e94772 100644
--- a/transactionoutbox-core/src/test/java/com/gruelbox/transactionoutbox/AbstractDefaultPersistorTest.java
+++ b/transactionoutbox-core/src/test/java/com/gruelbox/transactionoutbox/AbstractDefaultPersistorTest.java
@@ -53,6 +53,17 @@ void testInsertAndSelect() throws Exception {
             tx -> assertThat(persistor().selectBatch(tx, 100, now.plusMillis(1)), contains(entry)));
   }
 
+  @Test
+  void testInsertWithUniqueRequestIdFailureBubblesExceptionUp() {
+    var invalidEntry =
+        createEntry("FOO", now, false).toBuilder()
+            .uniqueRequestId("INTENTIONALLY_TOO_LONG_TO_CAUSE_BLOW_UP".repeat(10))
+            .build();
+    assertThrows(
+        RuntimeException.class,
+        () -> txManager().inTransactionThrows(tx -> persistor().save(tx, invalidEntry)));
+  }
+
   @Test
   void testInsertDuplicate() throws Exception {
     TransactionOutboxEntry entry1 = createEntry("FOO1", now, false, "context-clientkey1");
diff --git a/transactionoutbox-core/src/test/java/com/gruelbox/transactionoutbox/acceptance/AbstractAcceptanceTest.java b/transactionoutbox-core/src/test/java/com/gruelbox/transactionoutbox/acceptance/AbstractAcceptanceTest.java
index 88fba757..3d97fb8c 100644
--- a/transactionoutbox-core/src/test/java/com/gruelbox/transactionoutbox/acceptance/AbstractAcceptanceTest.java
+++ b/transactionoutbox-core/src/test/java/com/gruelbox/transactionoutbox/acceptance/AbstractAcceptanceTest.java
@@ -3,22 +3,9 @@
 import static org.hamcrest.Matchers.containsInAnyOrder;
 import static org.hamcrest.Matchers.empty;
 import static org.junit.Assert.*;
+import static org.junit.jupiter.api.Assertions.assertThrows;
 
-import com.gruelbox.transactionoutbox.AlreadyScheduledException;
-import com.gruelbox.transactionoutbox.DefaultPersistor;
-import com.gruelbox.transactionoutbox.Dialect;
-import com.gruelbox.transactionoutbox.Instantiator;
-import com.gruelbox.transactionoutbox.NoTransactionActiveException;
-import com.gruelbox.transactionoutbox.Persistor;
-import com.gruelbox.transactionoutbox.Submitter;
-import com.gruelbox.transactionoutbox.ThreadLocalContextTransactionManager;
-import com.gruelbox.transactionoutbox.ThrowingRunnable;
-import com.gruelbox.transactionoutbox.ThrowingTransactionalSupplier;
-import com.gruelbox.transactionoutbox.Transaction;
-import com.gruelbox.transactionoutbox.TransactionManager;
-import com.gruelbox.transactionoutbox.TransactionOutbox;
-import com.gruelbox.transactionoutbox.TransactionOutboxEntry;
-import com.gruelbox.transactionoutbox.TransactionOutboxListener;
+import com.gruelbox.transactionoutbox.*;
 import com.zaxxer.hikari.HikariConfig;
 import com.zaxxer.hikari.HikariDataSource;
 import java.sql.Connection;
@@ -45,6 +32,9 @@
 import lombok.Value;
 import lombok.experimental.Accessors;
 import lombok.extern.slf4j.Slf4j;
+import org.hamcrest.Description;
+import org.hamcrest.Matcher;
+import org.junit.Assume;
 import org.junit.jupiter.api.Assertions;
 import org.junit.jupiter.api.Test;
 import org.slf4j.Logger;
@@ -402,6 +392,65 @@ final void retryBehaviour() throws Exception {
         });
   }
 
+  @Test
+  final void onSchedulingFailure_BubbleExceptionsUp() throws Exception {
+    TransactionManager transactionManager = simpleTxnManager();
+    CountDownLatch latch = new CountDownLatch(1);
+    TransactionOutbox outbox =
+        TransactionOutbox.builder()
+            .transactionManager(transactionManager)
+            .instantiator(
+                Instantiator.using(
+                    clazz ->
+                        (InterfaceProcessor)
+                            (foo, bar) ->
+                                LOGGER.info(
+                                    "Entered the method to process successfully. Processing ({}, {})",
+                                    foo,
+                                    bar)))
+            .persistor(Persistor.forDialect(connectionDetails().dialect()))
+            .submitter(Submitter.withExecutor(unreliablePool))
+            .attemptFrequency(Duration.ofMillis(500))
+            .listener(new LatchListener(latch))
+            .build();
+
+    clearOutbox();
+
+    withRunningFlusher(
+        outbox,
+        () -> {
+          // run for mysql only.
+          var dialect = connectionDetails().dialect();
+          Assume.assumeThat(
+              dialect,
+              new Matcher<>() {
+                @Override
+                public void describeTo(Description description) {}
+
+                @Override
+                public boolean matches(Object o) {
+                  return Dialect.MY_SQL_8.equals(o) || Dialect.MY_SQL_5.equals(o);
+                }
+
+                @Override
+                public void describeMismatch(Object o, Description description) {}
+
+                @Override
+                public void _dont_implement_Matcher___instead_extend_BaseMatcher_() {}
+              });
+          assertThrows(
+              Exception.class,
+              () ->
+                  transactionManager.inTransaction(
+                      () ->
+                          outbox
+                              .with()
+                              .uniqueRequestId("some_unique_id")
+                              .schedule(InterfaceProcessor.class)
+                              .process(1, "This invocation is too long".repeat(650000))));
+        });
+  }
+
   @Test
   final void lastAttemptTime_updatesEveryTime() throws Exception {
     TransactionManager transactionManager = simpleTxnManager();