diff --git a/src/Acoustics.Shared/AppConfigHelper.cs b/src/Acoustics.Shared/AppConfigHelper.cs
index a3df47fe3..bc2e94621 100644
--- a/src/Acoustics.Shared/AppConfigHelper.cs
+++ b/src/Acoustics.Shared/AppConfigHelper.cs
@@ -38,7 +38,17 @@ public static class AppConfigHelper
         private static readonly string ExecutingAssemblyPath =
             (Assembly.GetEntryAssembly() ?? Assembly.GetExecutingAssembly()).Location;
 
-        private static readonly IConfigurationSection SharedSettings;
+        private static readonly Lazy<IConfigurationSection> SharedSettings = new Lazy<IConfigurationSection>(() =>
+        {
+            var settings = AppConfiguration.Value.GetSection("appSettings");
+            if (!settings.AsEnumerable().Any())
+            {
+                throw new ConfigurationErrorsException("Could not read AP.Settings.json - no values were found in the config file");
+            }
+
+            return settings;
+        });
+
         private static readonly ILog Log = LogManager.GetLogger(nameof(AppConfigHelper));
         private static readonly bool IsLinuxValue;
         private static readonly bool IsWindowsValue;
@@ -46,21 +56,14 @@ public static class AppConfigHelper
 
         static AppConfigHelper()
         {
-            AppConfiguration = new ConfigurationBuilder()
-                .AddJsonFile("AP.Settings.json")
-                .Build();
-
-            SharedSettings = AppConfiguration.GetSection("appSettings");
-            if (!SharedSettings.AsEnumerable().Any())
-            {
-                throw new ConfigurationErrorsException("Could not read AP.Settings.json - no values were found in the config file");
-            }
-
             IsMono = Type.GetType("Mono.Runtime") != null;
             CheckOs(ref IsWindowsValue, ref IsLinuxValue, ref IsMacOsXValue);
         }
 
-        public static IConfigurationRoot AppConfiguration { get; }
+        public static Lazy<IConfigurationRoot> AppConfiguration { get; } = new Lazy<IConfigurationRoot>(() =>
+            new ConfigurationBuilder()
+                .AddJsonFile("AP.Settings.json")
+                .Build());
 
         public static int DefaultTargetSampleRate => GetInt(DefaultTargetSampleRateKey);
 
@@ -166,7 +169,7 @@ public static DirectoryInfo AssemblyDir
 
         public static string GetString(string key)
         {
-            var value = SharedSettings[key];
+            var value = SharedSettings.Value[key];
 
             if (string.IsNullOrEmpty(value))
             {
@@ -333,7 +336,7 @@ private static string GetExeFile(string appConfigKey, bool required = true)
                 key = appConfigKey;
             }
 
-            var path = SharedSettings[key];
+            var path = SharedSettings.Value[key];
 
             Log.Verbose($"Attempted to get exe path `{appConfigKey}`. Value: '{path}'");
 
diff --git a/src/AnalysisPrograms/CheckEnvironment.cs b/src/AnalysisPrograms/CheckEnvironment.cs
index c3f1e6514..59efa8b58 100644
--- a/src/AnalysisPrograms/CheckEnvironment.cs
+++ b/src/AnalysisPrograms/CheckEnvironment.cs
@@ -1,4 +1,4 @@
-// <copyright file="CheckEnvironment.cs" company="QutEcoacoustics">
+// <copyright file="CheckEnvironment.cs" company="QutEcoacoustics">
 // All code in this file and all associated files are the copyright and property of the QUT Ecoacoustics Research Group (formerly MQUTeR, and formerly QUT Bioacoustics Research Group).
 // </copyright>
 
@@ -9,13 +9,14 @@ namespace AnalysisPrograms
     using System.Linq;
     using System.Reflection;
     using System.Text;
+    using System.Text.RegularExpressions;
     using System.Threading.Tasks;
     using Acoustics.Shared;
     using Acoustics.Tools.Audio;
-    using AnalyseLongRecordings;
+    using AnalysisPrograms.AnalyseLongRecordings;
+    using AnalysisPrograms.Production.Arguments;
     using log4net;
     using McMaster.Extensions.CommandLineUtils;
-    using Production.Arguments;
 
     public class CheckEnvironment
     {
@@ -25,10 +26,18 @@ public class CheckEnvironment
 
         private void Execute(Arguments arguments)
         {
+            List<Exception> errors = new List<Exception>();
             Log.Info("Checking required executables can be found");
 
-            // master audio utlility checks for available executables
-            var utility = new MasterAudioUtility();
+            // master audio utility checks for available executables
+            try
+            {
+                var utility = new MasterAudioUtility();
+            }
+            catch (Exception ex)
+            {
+                errors.Add(ex);
+            }
 
             if (AppConfigHelper.IsMono)
             {
@@ -39,17 +48,33 @@ private void Execute(Arguments arguments)
                     if (displayName != null)
                     {
                         var name = displayName.Invoke(null, null);
-                        Log.Info($"Mono version is {name}, we require at least Mono 5.5");
+                        var version = Regex.Match(name as string, @".*(\d+\.\d+\.\d+\.\d+).*").Groups[1].Value;
+                        Console.WriteLine(version);
+                        if (new Version(version) > new Version(5, 5))
+                        {
+                            Log.Success($"Your mono version {name} is greater than our required Mono version 5.5");
+                        }
+                        else
+                        {
+                            errors.Add(new Exception($"Mono version is {name}, we require at least Mono 5.5"));
+                        }
                     }
                     else
                     {
-                        Log.Warn("Could not check Mono version");
+                        errors.Add(new Exception("Could not check Mono version"));
                     }
                 }
             }
 
             // don't have much more to check at the current time
-            Log.Success("Valid environment");
+            if (errors.Count == 0)
+            {
+                Log.Success("Valid environment");
+            }
+            else
+            {
+                throw new AggregateException(errors.ToArray());
+            }
         }
 
         [Command(