diff --git a/src/NzbDrone.Core.Test/HealthCheck/Checks/MonoVersionCheckFixture.cs b/src/NzbDrone.Core.Test/HealthCheck/Checks/MonoVersionCheckFixture.cs
index 28c8827b2..420e0268a 100644
--- a/src/NzbDrone.Core.Test/HealthCheck/Checks/MonoVersionCheckFixture.cs
+++ b/src/NzbDrone.Core.Test/HealthCheck/Checks/MonoVersionCheckFixture.cs
@@ -25,6 +25,7 @@ private void GivenOutput(string version)
         [TestCase("4.0.0.0")]
         [TestCase("4.2")]
         [TestCase("4.6")]
+        [TestCase("4.4.2")]
         public void should_return_ok(string version)
         {
             GivenOutput(version);
diff --git a/src/NzbDrone.Core/HealthCheck/Checks/MonoVersionCheck.cs b/src/NzbDrone.Core/HealthCheck/Checks/MonoVersionCheck.cs
index eac738189..113af9b37 100644
--- a/src/NzbDrone.Core/HealthCheck/Checks/MonoVersionCheck.cs
+++ b/src/NzbDrone.Core/HealthCheck/Checks/MonoVersionCheck.cs
@@ -39,7 +39,7 @@ public override HealthCheck Check()
                     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(4, 4, 0) && version < new Version(4, 5))
+                if (version == new Version(4, 4, 0) || version == new Version(4, 4, 1))
                 {
                     _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");