diff --git a/source/Octopus.Tentacle.Tests.Integration/Support/TentacleBuilder.cs b/source/Octopus.Tentacle.Tests.Integration/Support/TentacleBuilder.cs
index ef87f9b9d..2ed544ba2 100644
--- a/source/Octopus.Tentacle.Tests.Integration/Support/TentacleBuilder.cs
+++ b/source/Octopus.Tentacle.Tests.Integration/Support/TentacleBuilder.cs
@@ -30,7 +30,7 @@ public abstract class TentacleBuilder<T> : ITentacleBuilder
         protected string TentacleThumbprint = Certificates.TentaclePublicThumbprint;
         bool installAsService = false;
 
-        readonly Regex listeningPortRegex = new (@"listen:\/\/.+:(\d+)\/");
+        static readonly Regex ListeningPortRegex = new (@"listen:\/\/.+:(\d+)\/");
         readonly Dictionary<string, string> runTentacleEnvironmentVariables = new();
 
         TemporaryDirectory? homeDirectory;
@@ -98,10 +98,12 @@ protected async Task<RunningTentacle> StartTentacle(
             ILogger logger,
             CancellationToken cancellationToken)
         {
+            var log = new SerilogLoggerBuilder().Build();
+
             var runningTentacle = new RunningTentacle(
                 new FileInfo(tentacleExe),
                 tempDirectory,
-                startTentacleFunction: ct => RunTentacle(serviceUri, tentacleExe, instanceName, tempDirectory, ct),
+                startTentacleFunction: ct => RunTentacle(serviceUri, tentacleExe, instanceName, tempDirectory, log, ct),
                 tentacleThumbprint,
                 instanceName,
                 HomeDirectory.DirectoryPath,
@@ -122,7 +124,7 @@ protected async Task<RunningTentacle> StartTentacle(
                 }
                 catch (Exception e)
                 {
-                    new SerilogLoggerBuilder().Build().Information(e, "Error disposing tentacle after tentacle failed to start.");
+                    log.Information(e, "Error disposing tentacle after tentacle failed to start.");
                 }
 
                 throw;
@@ -134,12 +136,12 @@ protected async Task<RunningTentacle> StartTentacle(
             string tentacleExe,
             string instanceName,
             TemporaryDirectory tempDirectory, 
+            ILogger log,
             CancellationToken cancellationToken)
         {
             var hasTentacleStarted = new ManualResetEventSlim();
             hasTentacleStarted.Reset();
             int? listeningPort = null;
-            var lastLogContext = string.Empty;
 
             var runningTentacle = Task.Run(async () =>
             {
@@ -188,29 +190,58 @@ await RunTentacleCommandOutOfProcess(
                             throw new Exception("Failed to start service");
                         }
 
-                        while (listeningPort == null && !cancellationToken.IsCancellationRequested)
-                        {
-                            var logFilePath = Path.Combine(tempDirectory.DirectoryPath, "Logs", "OctopusTentacle.txt");
+                        using var timeoutCancellationTokenSource = new CancellationTokenSource(TimeSpan.FromSeconds(20));
+                        using var linkedCancellationTokenSource = CancellationTokenSource.CreateLinkedTokenSource(cancellationToken, timeoutCancellationTokenSource.Token);
+                        
+                        log.Information("Waiting for the Tentacle Service to start up and assign a Listening Port / no port if Polling");
+                        var tentacleState = await WaitForTentacleToStart(tempDirectory, linkedCancellationTokenSource.Token);
 
-                            await using (var stream = new FileStream(logFilePath, FileMode.Open, FileAccess.Read, FileShare.ReadWrite))
-                            using (var reader = new StreamReader(stream))
-                            {
-                                var logContent = await reader.ReadToEndAsync();
-                                lastLogContext = logContent;
-                            }
+                        tentacleState.Started = false;
 
-                            if (lastLogContext.Contains("Listener started"))
+                        if (tentacleState.Started)
+                        {
+                            listeningPort = tentacleState.ListeningPort;
+                            hasTentacleStarted.Set();
+                        }
+                        else
+                        {
+                            log.Warning("The Tentacle failed to start correctly. Trying Again. Last Log File Content");
+                            log.Warning(tentacleState.LogContent);
+
+                            File.Delete(Path.Combine(tempDirectory.DirectoryPath, "Logs", "OctopusTentacle.txt"));
+
+                            await RunTentacleCommandOutOfProcess(
+                                tentacleExe,
+                                new[] { "service", "--stop", $"--instance={instanceName}" },
+                                tempDirectory,
+                                s =>
+                                { },
+                                runTentacleEnvironmentVariables,
+                                cancellationToken);
+
+                            File.Delete(Path.Combine(tempDirectory.DirectoryPath, "Logs", "OctopusTentacle.txt"));
+
+                            await RunTentacleCommandOutOfProcess(
+                                tentacleExe,
+                                new[] { "service", "--start", $"--instance={instanceName}" },
+                                tempDirectory,
+                                s =>
+                                { },
+                                runTentacleEnvironmentVariables,
+                                cancellationToken);
+
+                            tentacleState = await WaitForTentacleToStart(tempDirectory, cancellationToken);
+
+                            if (tentacleState.Started)
                             {
-                                listeningPort = Convert.ToInt32(listeningPortRegex.Match(lastLogContext).Groups[1].Value);
+                                listeningPort = tentacleState.ListeningPort;
+                                hasTentacleStarted.Set();
                             }
-                            
-                            if (lastLogContext.Contains("Agent will not listen") || lastLogContext.Contains("Agent listening on"))
+                            else
                             {
-                                hasTentacleStarted.Set();
-                                break;
+                                log.Error("The Tentacle failed to start correctly. Last Log File Content");
+                                log.Error(tentacleState.LogContent);
                             }
-
-                            await Task.Delay(TimeSpan.FromSeconds(2), cancellationToken);
                         }
                     }
                     else
@@ -223,7 +254,7 @@ await RunTentacleCommandOutOfProcess(
                             {
                                 if (s.Contains("Listener started"))
                                 {
-                                    listeningPort = Convert.ToInt32(listeningPortRegex.Match(s).Groups[1].Value);
+                                    listeningPort = Convert.ToInt32(ListeningPortRegex.Match(s).Groups[1].Value);
                                 }
                                 else if (s.Contains("Agent will not listen") || s.Contains("Agent listening on"))
                                 {
@@ -241,7 +272,9 @@ await RunTentacleCommandOutOfProcess(
                 }
             }, cancellationToken);
 
-            await Task.WhenAny(runningTentacle, WaitHandleAsyncFactory.FromWaitHandle(hasTentacleStarted.WaitHandle, TimeSpan.FromMinutes(1)));
+            using var cleanupCancellationTokenSource = new CancellationTokenSource();
+            await Task.WhenAny(runningTentacle, Task.Delay(TimeSpan.FromMinutes(1), cleanupCancellationTokenSource.Token));
+            cleanupCancellationTokenSource.Cancel();
 
             // Will throw.
             if (runningTentacle.IsCompleted)
@@ -251,8 +284,6 @@ await RunTentacleCommandOutOfProcess(
 
             if (!hasTentacleStarted.IsSet)
             {
-                new SerilogLoggerBuilder().Build().Information(lastLogContext);
-
                 throw new Exception("Tentacle did not appear to start correctly");
             }
 
@@ -264,6 +295,38 @@ await RunTentacleCommandOutOfProcess(
             return (runningTentacle, serviceUri);
         }
 
+        static async Task<(bool Started, int? ListeningPort, string LogContent)> WaitForTentacleToStart(TemporaryDirectory tempDirectory, CancellationToken localCancellationToken)
+        {
+            var lastLogFileContents = string.Empty;
+            int? listeningPort = null;
+
+            while (listeningPort == null && !localCancellationToken.IsCancellationRequested)
+            {
+                var logFilePath = Path.Combine(tempDirectory.DirectoryPath, "Logs", "OctopusTentacle.txt");
+
+                await using (var stream = new FileStream(logFilePath, FileMode.Open, FileAccess.Read, FileShare.ReadWrite))
+                using (var reader = new StreamReader(stream))
+                {
+                    var logContent = await reader.ReadToEndAsync();
+                    lastLogFileContents = logContent;
+                }
+
+                if (lastLogFileContents.Contains("Listener started"))
+                {
+                    listeningPort = Convert.ToInt32(ListeningPortRegex.Match(lastLogFileContents).Groups[1].Value);
+                }
+
+                if (lastLogFileContents.Contains("Agent will not listen") || lastLogFileContents.Contains("Agent listening on"))
+                {
+                    return (true, listeningPort, lastLogFileContents);
+                }
+
+                await Task.Delay(TimeSpan.FromSeconds(1), CancellationToken.None);
+            }
+
+            return (false, listeningPort, lastLogFileContents);
+        }
+
         protected async Task AddCertificateToTentacle(string tentacleExe, string instanceName, string tentaclePfxPath, TemporaryDirectory tmp, CancellationToken cancellationToken)
         {
             await RunTentacleCommand(tentacleExe, new[] {"import-certificate", $"--from-file={tentaclePfxPath}", $"--instance={instanceName}"}, tmp, cancellationToken);
diff --git a/source/Octopus.Tentacle/Tentacle.exe.nlog b/source/Octopus.Tentacle/Tentacle.exe.nlog
index 83e4454ff..e9230dcef 100644
--- a/source/Octopus.Tentacle/Tentacle.exe.nlog
+++ b/source/Octopus.Tentacle/Tentacle.exe.nlog
@@ -34,7 +34,7 @@
     <logger name="LogFileOnlyLogger" writeTo="octopus-log-file" final="true" />
     <logger name="*" minlevel="Info" maxLevel="Warn" writeTo="stdout" />
     <logger name="*" minlevel="Error" writeTo="stderr" />
-    <logger name="*" minlevel="Info" writeTo="octopus-log-file" />
+    <logger name="*" minlevel="Trace" writeTo="octopus-log-file" />
     <logger name="*" minlevel="Fatal" writeTo="eventlog" />
 </rules>
 </nlog>