diff --git a/src/Jackett.Server/Initialisation.cs b/src/Jackett.Server/Initialisation.cs
index a6d43263f..34b1942dd 100644
--- a/src/Jackett.Server/Initialisation.cs
+++ b/src/Jackett.Server/Initialisation.cs
@@ -153,5 +153,32 @@ namespace Jackett.Server
                 }
             }
         }
+
+        public static void CheckEnvironmentalVariables(Logger logger)
+        {
+            //Check the users environmental variables to ensure they aren't using Mono legacy TLS
+
+            var enumerator = Environment.GetEnvironmentVariables().GetEnumerator();
+            while (enumerator.MoveNext())
+            {
+                if (enumerator.Key.ToString().Equals("MONO_TLS_PROVIDER", StringComparison.OrdinalIgnoreCase))
+                {
+                    logger.Info("MONO_TLS_PROVIDER is present with a value of: " + enumerator.Value.ToString());
+
+                    if (enumerator.Value.ToString().IndexOf("legacy", StringComparison.OrdinalIgnoreCase) >= 0)
+                    {
+                        logger.Error("The MONO_TLS_PROVIDER=legacy environment variable is not supported, please remove it.");
+                        Environment.Exit(1);
+                    }
+                }
+                else
+                {
+                    if (enumerator.Key.ToString().IndexOf("MONO_", StringComparison.OrdinalIgnoreCase) >= 0)
+                    {
+                        logger.Info($"Environment variable {enumerator.Key} is present");
+                    }
+                }
+            }
+        }
     }
 }
diff --git a/src/Jackett.Server/Program.cs b/src/Jackett.Server/Program.cs
index 02295361d..543c584e8 100644
--- a/src/Jackett.Server/Program.cs
+++ b/src/Jackett.Server/Program.cs
@@ -82,6 +82,7 @@ namespace Jackett.Server
                 }
             }
 
+            Initialisation.CheckEnvironmentalVariables(logger);
             Initialisation.ProcessSettings(Settings, logger);
 
             ISerializeService serializeService = new SerializeService();