diff --git a/.vscode/settings.json b/.vscode/settings.json
index 4c5aadb3..cbe0a073 100644
--- a/.vscode/settings.json
+++ b/.vscode/settings.json
@@ -28,6 +28,7 @@
     "ptcc",
     "Rebinder",
     "stylesheet",
+    "timespan",
     "upserted",
     "USFM"
   ],
diff --git a/src/Machine/src/Serval.Machine.Shared/Configuration/IMachineBuilderExtensions.cs b/src/Machine/src/Serval.Machine.Shared/Configuration/IMachineBuilderExtensions.cs
index 5a577cb5..19f72185 100644
--- a/src/Machine/src/Serval.Machine.Shared/Configuration/IMachineBuilderExtensions.cs
+++ b/src/Machine/src/Serval.Machine.Shared/Configuration/IMachineBuilderExtensions.cs
@@ -158,9 +158,26 @@ public static IMachineBuilder AddClearMLService(this IMachineBuilder builder, st
         builder
             .Services.AddHttpClient("ClearML")
             .ConfigureHttpClient(httpClient => httpClient.BaseAddress = new Uri(connectionString!))
-            // Add retry policy; fail after approx. 2 + 4 + 8 = 14 seconds
             .AddTransientHttpErrorPolicy(b =>
-                b.WaitAndRetryAsync(3, retryAttempt => TimeSpan.FromSeconds(Math.Pow(2, retryAttempt)))
+                b.WaitAndRetryAsync(
+                    7,
+                    retryAttempt => TimeSpan.FromSeconds(2 * retryAttempt), // total 56, less than the 1 minute limit
+                    onRetryAsync: (outcome, timespan, retryAttempt, context) =>
+                    {
+                        if (retryAttempt < 3)
+                            return Task.CompletedTask;
+                        // Log the retry attempt
+                        var serviceProvider = builder.Services.BuildServiceProvider();
+                        var logger = serviceProvider.GetService<ILogger<ClearMLService>>();
+                        logger?.LogInformation(
+                            "Retry {RetryAttempt} encountered an error. Waiting {Timespan} before next retry. Error: {ErrorMessage}",
+                            retryAttempt,
+                            timespan,
+                            outcome.Exception?.Message
+                        );
+                        return Task.CompletedTask;
+                    }
+                )
             );
 
         builder.Services.AddSingleton<IClearMLService, ClearMLService>();
diff --git a/src/Serval/src/Serval.Webhooks/Configuration/IServalBuilderExtensions.cs b/src/Serval/src/Serval.Webhooks/Configuration/IServalBuilderExtensions.cs
index 129804e3..2c2f8503 100644
--- a/src/Serval/src/Serval.Webhooks/Configuration/IServalBuilderExtensions.cs
+++ b/src/Serval/src/Serval.Webhooks/Configuration/IServalBuilderExtensions.cs
@@ -7,7 +7,10 @@ public static IServalBuilder AddWebhooks(this IServalBuilder builder)
         builder
             .Services.AddHttpClient<WebhookJob>()
             .AddTransientHttpErrorPolicy(b =>
-                b.WaitAndRetryAsync(3, retryAttempt => TimeSpan.FromSeconds(Math.Pow(2, retryAttempt)))
+                b.WaitAndRetryAsync(
+                    7,
+                    retryAttempt => TimeSpan.FromSeconds(2 * retryAttempt) // total 56, less than the 1 minute limit
+                )
             );
         builder.Services.AddScoped<IWebhookService, WebhookService>();
         return builder;