diff --git a/src/DaemonTests/Internals/HighWaterAgentTests.cs b/src/DaemonTests/Internals/HighWaterAgentTests.cs
index c15ec96dc3..c76ee53ed8 100644
--- a/src/DaemonTests/Internals/HighWaterAgentTests.cs
+++ b/src/DaemonTests/Internals/HighWaterAgentTests.cs
@@ -107,6 +107,32 @@ public async Task will_not_go_in_loop_when_sequence_is_advanced_but_gaps_from_hi
         await agent2.Tracker.WaitForHighWaterMark(NumberOfEvents + 5);
     }
 
+    [Fact]
+    public async Task skips_multiple_gaps_and_keeps_advancing()
+    {
+        NumberOfStreams = 10;
+        await PublishSingleThreaded();
+
+        // Create multiple gaps in the event sequence
+        var gaps = new[] { NumberOfEvents - 9, NumberOfEvents - 6, NumberOfEvents - 5, NumberOfEvents - 3 };
+        await deleteEvents(gaps);
+
+        // Make gap skipping kick in faster
+        theStore.Options.Projections.StaleSequenceThreshold = 1.Seconds();
+
+        using var agent = await StartDaemon();
+
+        // Expect the agent to move beyond each gap by reporting the last contiguous (safe harbor) mark
+        await agent.Tracker.WaitForHighWaterMark(gaps[0], 2.Seconds());
+        await agent.Tracker.WaitForHighWaterMark(gaps[1], 2.Seconds());
+        await agent.Tracker.WaitForHighWaterMark(gaps[2], 2.Seconds());
+        await agent.Tracker.WaitForHighWaterMark(gaps[3], 2.Seconds());
+        // And eventually reach the head
+        await agent.Tracker.WaitForHighWaterMark(NumberOfEvents, 2.Seconds());
+
+        await agent.StopAllAsync();
+    }
+
     private async Task deleteEvents(params long[] ids)
     {
         await using var conn = theStore.CreateConnection();