diff --git a/src/NzbDrone.Core.Test/HealthCheck/Checks/MonoVersionCheckFixture.cs b/src/NzbDrone.Core.Test/HealthCheck/Checks/MonoVersionCheckFixture.cs
index 5b5e881b3..28c8827b2 100644
--- a/src/NzbDrone.Core.Test/HealthCheck/Checks/MonoVersionCheckFixture.cs
+++ b/src/NzbDrone.Core.Test/HealthCheck/Checks/MonoVersionCheckFixture.cs
@@ -1,5 +1,4 @@
-using System;
-using NUnit.Framework;
+using NUnit.Framework;
 using NzbDrone.Common.EnvironmentInfo;
 using NzbDrone.Core.HealthCheck.Checks;
 using NzbDrone.Core.Test.Framework;
@@ -22,76 +21,40 @@ namespace NzbDrone.Core.Test.HealthCheck.Checks
                   .Returns(string.Format("{0} (tarball Wed Sep 25 16:35:44 CDT 2013)", version));
         }
 
-        [Test]
-        public void should_return_warning_when_mono_3_0()
+        [TestCase("3.10")]
+        [TestCase("4.0.0.0")]
+        [TestCase("4.2")]
+        [TestCase("4.6")]
+        public void should_return_ok(string version)
         {
-            GivenOutput("3.0.0.1");
-
-            Subject.Check().ShouldBeWarning();
-        }
-
-        [Test]
-        public void should_return_warning_when_mono_2_10_8()
-        {
-            GivenOutput("2.10.8.1");
-
-            Subject.Check().ShouldBeWarning();
-        }
-
-        [Test]
-        public void should_return_warning_when_mono_2_10_2()
-        {
-            GivenOutput("2.10.2");
-
-            Subject.Check().ShouldBeWarning();
-        }
-
-        [Test]
-        public void should_return_ok_when_mono_3_2()
-        {
-            GivenOutput("3.2.0.1");
-
-            Subject.Check().ShouldBeOk();
-        }
-
-        [Test]
-        public void should_return_ok_when_mono_4_0()
-        {
-            GivenOutput("4.0.0.0");
-
-            Subject.Check().ShouldBeOk();
-        }
-
-        [Test]
-        public void should_return_ok_when_mono_3_2_7()
-        {
-            GivenOutput("3.2.7");
+            GivenOutput(version);
 
             Subject.Check().ShouldBeOk();
         }
 
-        [Test]
-        public void should_return_ok_when_mono_3_2_1()
+        [TestCase("2.10.2")]
+        [TestCase("2.10.8.1")]
+        [TestCase("3.0.0.1")]
+        [TestCase("3.2.0.1")]
+        [TestCase("3.2.1")]
+        [TestCase("3.2.7")]
+        [TestCase("3.6.1")]
+        [TestCase("3.8")]
+        public void should_return_warning(string version)
         {
-            GivenOutput("3.2.1");
+            GivenOutput(version);
 
-            Subject.Check().ShouldBeOk();
+            Subject.Check().ShouldBeWarning();
         }
 
-        [Test]
-        public void should_return_ok_when_mono_3_6_1()
-        {
-            GivenOutput("3.6.1");
-
-            Subject.Check().ShouldBeOk();
-        }
 
-        [Test]
-        public void should_return_ok_when_mono_3_10()
+        [TestCase("4.4.0")]
+        [TestCase("4.4.1")]
+        public void should_return_error(string version)
         {
-            GivenOutput("3.10");
+            GivenOutput(version);
 
-            Subject.Check().ShouldBeOk();
+            Subject.Check().ShouldBeError();
         }
     }
 }
diff --git a/src/NzbDrone.Core/HealthCheck/Checks/MonoVersionCheck.cs b/src/NzbDrone.Core/HealthCheck/Checks/MonoVersionCheck.cs
index a94c5d4c6..eac738189 100644
--- a/src/NzbDrone.Core/HealthCheck/Checks/MonoVersionCheck.cs
+++ b/src/NzbDrone.Core/HealthCheck/Checks/MonoVersionCheck.cs
@@ -39,14 +39,20 @@ namespace NzbDrone.Core.HealthCheck.Checks
                     return new HealthCheck(GetType(), HealthCheckResult.Error, "your mono version 3.4.0 has a critical bug, you should upgrade to a higher version");
                 }
 
-                if (version >= new Version(3, 2))
+                if (version >= new Version(4, 4, 0) && version < new Version(4, 5))
                 {
-                    _logger.Debug("mono version is 3.2 or better: {0}", version.ToString());
+                    _logger.Debug("mono version {0}", version);
+                    return new HealthCheck(GetType(), HealthCheckResult.Error, $"your mono version {version} has a bug that causes issues connecting to indexers/download clients");
+                }
+
+                if (version >= new Version(3, 10))
+                {
+                    _logger.Debug("mono version is 3.10 or better: {0}", version.ToString());
                     return new HealthCheck(GetType());
                 }
             }
 
-            return new HealthCheck(GetType(), HealthCheckResult.Warning, "mono version is less than 3.2, upgrade for improved stability");
+            return new HealthCheck(GetType(), HealthCheckResult.Warning, "mono version is less than 3.10, upgrade for improved stability");
         }
 
         public override bool CheckOnConfigChange