diff --git a/src/perf_tests/Python.PerformanceTests.csproj b/src/perf_tests/Python.PerformanceTests.csproj
index 2ef942f0d..b437fe532 100644
--- a/src/perf_tests/Python.PerformanceTests.csproj
+++ b/src/perf_tests/Python.PerformanceTests.csproj
@@ -13,7 +13,7 @@
       <IncludeAssets>runtime; build; native; contentfiles; analyzers; buildtransitive</IncludeAssets>
     </PackageReference>
     <PackageReference Include="Microsoft.NET.Test.Sdk" Version="16.*" />
-    <PackageReference Include="quantconnect.pythonnet" Version="2.0.38" GeneratePathProperty="true">
+    <PackageReference Include="quantconnect.pythonnet" Version="2.0.39" GeneratePathProperty="true">
       <IncludeAssets>compile</IncludeAssets>
     </PackageReference>
   </ItemGroup>
@@ -25,7 +25,7 @@
   </Target>
 
   <Target Name="CopyBaseline" AfterTargets="Build">
-    <Copy SourceFiles="$(NuGetPackageRoot)quantconnect.pythonnet\2.0.38\lib\net6.0\Python.Runtime.dll" DestinationFolder="$(OutDir)baseline" />
+    <Copy SourceFiles="$(NuGetPackageRoot)quantconnect.pythonnet\2.0.39\lib\net6.0\Python.Runtime.dll" DestinationFolder="$(OutDir)baseline" />
   </Target>
 
   <Target Name="CopyNewBuild" AfterTargets="Build">
diff --git a/src/runtime/Properties/AssemblyInfo.cs b/src/runtime/Properties/AssemblyInfo.cs
index 3b88a6eb5..ffb1308a4 100644
--- a/src/runtime/Properties/AssemblyInfo.cs
+++ b/src/runtime/Properties/AssemblyInfo.cs
@@ -4,5 +4,5 @@
 [assembly: InternalsVisibleTo("Python.EmbeddingTest, PublicKey=00240000048000009400000006020000002400005253413100040000110000005ffd8f49fb44ab0641b3fd8d55e749f716e6dd901032295db641eb98ee46063cbe0d4a1d121ef0bc2af95f8a7438d7a80a3531316e6b75c2dae92fb05a99f03bf7e0c03980e1c3cfb74ba690aca2f3339ef329313bcc5dccced125a4ffdc4531dcef914602cd5878dc5fbb4d4c73ddfbc133f840231343e013762884d6143189")]
 [assembly: InternalsVisibleTo("Python.Test, PublicKey=00240000048000009400000006020000002400005253413100040000110000005ffd8f49fb44ab0641b3fd8d55e749f716e6dd901032295db641eb98ee46063cbe0d4a1d121ef0bc2af95f8a7438d7a80a3531316e6b75c2dae92fb05a99f03bf7e0c03980e1c3cfb74ba690aca2f3339ef329313bcc5dccced125a4ffdc4531dcef914602cd5878dc5fbb4d4c73ddfbc133f840231343e013762884d6143189")]
 
-[assembly: AssemblyVersion("2.0.38")]
-[assembly: AssemblyFileVersion("2.0.38")]
+[assembly: AssemblyVersion("2.0.39")]
+[assembly: AssemblyFileVersion("2.0.39")]
diff --git a/src/runtime/Python.Runtime.csproj b/src/runtime/Python.Runtime.csproj
index 7c25c9219..c579abaa5 100644
--- a/src/runtime/Python.Runtime.csproj
+++ b/src/runtime/Python.Runtime.csproj
@@ -5,7 +5,7 @@
     <RootNamespace>Python.Runtime</RootNamespace>
     <AssemblyName>Python.Runtime</AssemblyName>
     <PackageId>QuantConnect.pythonnet</PackageId>
-    <Version>2.0.38</Version>
+    <Version>2.0.39</Version>
     <GenerateAssemblyInfo>false</GenerateAssemblyInfo>
     <PackageLicenseFile>LICENSE</PackageLicenseFile>
     <RepositoryUrl>https://github.com/pythonnet/pythonnet</RepositoryUrl>
diff --git a/src/runtime/Types/ClassBase.cs b/src/runtime/Types/ClassBase.cs
index d71897605..ded315952 100644
--- a/src/runtime/Types/ClassBase.cs
+++ b/src/runtime/Types/ClassBase.cs
@@ -94,7 +94,7 @@ public virtual NewReference type_subscript(BorrowedReference idx)
         public static NewReference tp_richcompare(BorrowedReference ob, BorrowedReference other, int op)
         {
             CLRObject co1;
-            CLRObject? co2;
+            object co2Inst;
             BorrowedReference tp = Runtime.PyObject_TYPE(ob);
             var cls = (ClassBase)GetManagedObject(tp)!;
             // C# operator methods take precedence over IComparable.
@@ -127,17 +127,12 @@ public static NewReference tp_richcompare(BorrowedReference ob, BorrowedReferenc
                         return new NewReference(pytrue);
                     }
 
-                    co1 = (CLRObject)GetManagedObject(ob)!;
-                    co2 = GetManagedObject(other) as CLRObject;
-                    if (null == co2)
+                    if (!TryGetSecondCompareOperandInstance(ob, other, out co1, out co2Inst))
                     {
                         return new NewReference(pyfalse);
                     }
 
-                    object o1 = co1.inst;
-                    object o2 = co2.inst;
-
-                    if (Equals(o1, o2))
+                    if (Equals(co1.inst, co2Inst))
                     {
                         return new NewReference(pytrue);
                     }
@@ -147,12 +142,11 @@ public static NewReference tp_richcompare(BorrowedReference ob, BorrowedReferenc
                 case Runtime.Py_LE:
                 case Runtime.Py_GT:
                 case Runtime.Py_GE:
-                    co1 = (CLRObject)GetManagedObject(ob)!;
-                    co2 = GetManagedObject(other) as CLRObject;
-                    if (co1 == null || co2 == null)
+                    if (!TryGetSecondCompareOperandInstance(ob, other, out co1, out co2Inst))
                     {
                         return Exceptions.RaiseTypeError("Cannot get managed object");
                     }
+
                     var co1Comp = co1.inst as IComparable;
                     if (co1Comp == null)
                     {
@@ -161,7 +155,7 @@ public static NewReference tp_richcompare(BorrowedReference ob, BorrowedReferenc
                     }
                     try
                     {
-                        int cmp = co1Comp.CompareTo(co2.inst);
+                        int cmp = co1Comp.CompareTo(co2Inst);
 
                         BorrowedReference pyCmp;
                         if (cmp < 0)
@@ -208,6 +202,38 @@ public static NewReference tp_richcompare(BorrowedReference ob, BorrowedReferenc
             }
         }
 
+        private static bool TryGetSecondCompareOperandInstance(BorrowedReference left, BorrowedReference right, out CLRObject co1, out object co2Inst)
+        {
+            co2Inst = null;
+
+            co1 = (CLRObject)GetManagedObject(left)!;
+            if (co1 == null)
+            {
+                return false;
+            }
+
+            var co2 = GetManagedObject(right) as CLRObject;
+
+            // The object comparing against is not a managed object. It could still be a Python object
+            // that can be compared against (e.g. comparing against a Python string)
+            if (co2 == null)
+            {
+                if (right != null)
+                {
+                    using var pyCo2 = new PyObject(right);
+                    if (Converter.ToManagedValue(pyCo2, typeof(object), out var result, false))
+                    {
+                        co2Inst = result;
+                        return true;
+                    }
+                }
+                return false;
+            }
+
+            co2Inst = co2.inst;
+            return true;
+        }
+
         /// <summary>
         /// Standard iteration support for instances of reflected types. This
         /// allows natural iteration over objects that either are IEnumerable