diff --git a/src/NzbDrone.Core.Test/HealthCheck/Checks/MonoDebugCheckFixture.cs b/src/NzbDrone.Core.Test/HealthCheck/Checks/MonoDebugCheckFixture.cs
new file mode 100644
index 000000000..d56ff463d
--- /dev/null
+++ b/src/NzbDrone.Core.Test/HealthCheck/Checks/MonoDebugCheckFixture.cs
@@ -0,0 +1,59 @@
+using NUnit.Framework;
+using NzbDrone.Core.HealthCheck.Checks;
+using NzbDrone.Core.Test.Framework;
+using NzbDrone.Test.Common;
+using static NzbDrone.Core.HealthCheck.Checks.MonoDebugCheck;
+
+namespace NzbDrone.Core.Test.HealthCheck.Checks
+{
+    [TestFixture]
+    public class MonoDebugCheckFixture : CoreTest<MonoDebugCheck>
+    {
+        private void GivenHasStackFrame(bool hasStackFrame)
+        {
+            Mocker.GetMock<StackFrameHelper>()
+                .Setup(f => f.HasStackFrameInfo())
+                .Returns(hasStackFrame);
+        }
+
+        [Test]
+        public void should_return_ok_if_windows()
+        {
+            WindowsOnly();
+
+            Subject.Check().ShouldBeOk();
+        }
+
+        [Test]
+        public void should_return_ok_if_not_debug()
+        {
+            MonoOnly();
+
+            GivenHasStackFrame(false);
+
+            Subject.Check().ShouldBeOk();
+        }
+
+        [Test]
+        public void should_log_warning_if_not_debug()
+        {
+            MonoOnly();
+
+            GivenHasStackFrame(false);
+
+            Subject.Check();
+
+            ExceptionVerification.ExpectedWarns(1);
+        }
+
+        [Test]
+        public void should_return_ok_if_debug()
+        {
+            MonoOnly();
+
+            GivenHasStackFrame(true);
+
+            Subject.Check().ShouldBeOk();
+        }
+    }
+}
diff --git a/src/NzbDrone.Core.Test/NzbDrone.Core.Test.csproj b/src/NzbDrone.Core.Test/NzbDrone.Core.Test.csproj
index e01f3dc9c..19145520d 100644
--- a/src/NzbDrone.Core.Test/NzbDrone.Core.Test.csproj
+++ b/src/NzbDrone.Core.Test/NzbDrone.Core.Test.csproj
@@ -210,6 +210,7 @@
     <Compile Include="HealthCheck\Checks\IndexerSearchCheckFixture.cs" />
     <Compile Include="HealthCheck\Checks\IndexerRssCheckFixture.cs" />
     <Compile Include="HealthCheck\Checks\ImportListStatusCheckFixture.cs" />
+    <Compile Include="HealthCheck\Checks\MonoDebugCheckFixture.cs" />
     <Compile Include="HealthCheck\Checks\MonoVersionCheckFixture.cs" />
     <Compile Include="HealthCheck\Checks\IndexerStatusCheckFixture.cs" />
     <Compile Include="HealthCheck\Checks\RootFolderCheckFixture.cs" />
diff --git a/src/NzbDrone.Core/HealthCheck/Checks/MonoDebugCheck.cs b/src/NzbDrone.Core/HealthCheck/Checks/MonoDebugCheck.cs
new file mode 100644
index 000000000..30cdb4085
--- /dev/null
+++ b/src/NzbDrone.Core/HealthCheck/Checks/MonoDebugCheck.cs
@@ -0,0 +1,46 @@
+using System.Diagnostics;
+using NLog;
+using NzbDrone.Common.EnvironmentInfo;
+
+namespace NzbDrone.Core.HealthCheck.Checks
+{
+    public class MonoDebugCheck : HealthCheckBase
+    {
+        private readonly Logger _logger;
+        private readonly StackFrameHelper _stackFrameHelper;
+
+        public override bool CheckOnSchedule => false;
+
+        public MonoDebugCheck(Logger logger, StackFrameHelper stackFrameHelper)
+        {
+            _logger = logger;
+            _stackFrameHelper = stackFrameHelper;
+        }
+
+        public class StackFrameHelper
+        {
+            public virtual bool HasStackFrameInfo()
+            {
+                var stackTrace = new StackTrace();
+
+                return stackTrace.FrameCount > 0 && stackTrace.GetFrame(0).GetFileColumnNumber() > 0;
+            }
+        }
+
+        public override HealthCheck Check()
+        {
+            if (!PlatformInfo.IsMono)
+            {
+                return new HealthCheck(GetType());
+            }
+
+            if (!_stackFrameHelper.HasStackFrameInfo())
+            {
+                _logger.Warn("Mono is not running with --debug switch");
+                return new HealthCheck(GetType());
+            }
+
+            return new HealthCheck(GetType());
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/NzbDrone.Core.csproj b/src/NzbDrone.Core/NzbDrone.Core.csproj
index ac9306487..6bc7201a1 100644
--- a/src/NzbDrone.Core/NzbDrone.Core.csproj
+++ b/src/NzbDrone.Core/NzbDrone.Core.csproj
@@ -466,6 +466,7 @@
     <Compile Include="HealthCheck\Checks\DownloadClientCheck.cs" />
     <Compile Include="HealthCheck\Checks\DownloadClientStatusCheck.cs" />
     <Compile Include="HealthCheck\Checks\ImportListStatusCheck.cs" />
+    <Compile Include="HealthCheck\Checks\MonoDebugCheck.cs" />
     <Compile Include="HealthCheck\Checks\MonoTlsCheck.cs" />
     <Compile Include="HealthCheck\Checks\MountCheck.cs" />
     <Compile Include="HealthCheck\Checks\ImportMechanismCheck.cs" />