diff --git a/README.rst b/README.rst
index 996bfab27..c0e4229d3 100644
--- a/README.rst
+++ b/README.rst
@@ -45,10 +45,11 @@ module:
 Embedding Python in .NET
 ------------------------
 
--  You must set `Runtime.PythonDLL` property or `PYTHONNET_PYDLL` environment variable
-   starting with version 3.0, otherwise you will receive `TypeInitializationException`.
-   Typical values are `python38.dll` (Windows), `libpython3.8.dylib` (Mac),
-   `libpython3.8.so` (most other *nix).
+-  You must set ``Runtime.PythonDLL`` property or ``PYTHONNET_PYDLL`` environment variable
+   starting with version 3.0, otherwise you will receive ``BadPythonDllException``
+   (internal, derived from ``MissingMethodException``) upon calling ``Initialize``.
+   Typical values are ``python38.dll`` (Windows), ``libpython3.8.dylib`` (Mac),
+   ``libpython3.8.so`` (most other *nix).
 -  All calls to python should be inside a
    ``using (Py.GIL()) {/* Your code here */}`` block.
 -  Import python modules using ``dynamic mod = Py.Import("mod")``, then
diff --git a/src/embed_tests/TestPythonEngineProperties.cs b/src/embed_tests/TestPythonEngineProperties.cs
index 626e3c77f..ca9164a1d 100644
--- a/src/embed_tests/TestPythonEngineProperties.cs
+++ b/src/embed_tests/TestPythonEngineProperties.cs
@@ -81,7 +81,7 @@ public static void GetPythonPathDefault()
         public static void GetProgramNameDefault()
         {
             PythonEngine.Initialize();
-            string s = PythonEngine.PythonHome;
+            string s = PythonEngine.ProgramName;
 
             Assert.NotNull(s);
             PythonEngine.Shutdown();
diff --git a/src/runtime/platform/LibraryLoader.cs b/src/runtime/platform/LibraryLoader.cs
index e361f87e4..78bf48112 100644
--- a/src/runtime/platform/LibraryLoader.cs
+++ b/src/runtime/platform/LibraryLoader.cs
@@ -111,7 +111,7 @@ public IntPtr Load(string dllToLoad)
         {
             var res = WindowsLoader.LoadLibrary(dllToLoad);
             if (res == IntPtr.Zero)
-                throw new DllNotFoundException($"Could not load {dllToLoad}", new Win32Exception());
+                throw new DllNotFoundException($"Could not load {dllToLoad}.", new Win32Exception());
             return res;
         }
 
@@ -128,7 +128,7 @@ public IntPtr GetFunction(IntPtr hModule, string procedureName)
 
             var res = WindowsLoader.GetProcAddress(hModule, procedureName);
             if (res == IntPtr.Zero)
-                throw new MissingMethodException($"Failed to load symbol {procedureName}", new Win32Exception());
+                throw new MissingMethodException($"Failed to load symbol {procedureName}.", new Win32Exception());
             return res;
         }
 
diff --git a/src/runtime/pythonengine.cs b/src/runtime/pythonengine.cs
index d7322dcc2..ece70c485 100644
--- a/src/runtime/pythonengine.cs
+++ b/src/runtime/pythonengine.cs
@@ -86,13 +86,15 @@ public static string ProgramName
         {
             get
             {
-                IntPtr p = Runtime.Py_GetProgramName();
+                IntPtr p = Runtime.TryUsingDll(() => Runtime.Py_GetProgramName());
                 return UcsMarshaler.PtrToPy3UnicodePy2String(p) ?? "";
             }
             set
             {
                 Marshal.FreeHGlobal(_programName);
-                _programName = UcsMarshaler.Py3UnicodePy2StringtoPtr(value);
+                _programName = Runtime.TryUsingDll(
+                    () => UcsMarshaler.Py3UnicodePy2StringtoPtr(value)
+                );
                 Runtime.Py_SetProgramName(_programName);
             }
         }
@@ -101,14 +103,16 @@ public static string PythonHome
         {
             get
             {
-                IntPtr p = Runtime.Py_GetPythonHome();
+                IntPtr p = Runtime.TryUsingDll(() => Runtime.Py_GetPythonHome());
                 return UcsMarshaler.PtrToPy3UnicodePy2String(p) ?? "";
             }
             set
             {
                 // this value is null in the beginning
                 Marshal.FreeHGlobal(_pythonHome);
-                _pythonHome = UcsMarshaler.Py3UnicodePy2StringtoPtr(value);
+                _pythonHome = Runtime.TryUsingDll(
+                    () => UcsMarshaler.Py3UnicodePy2StringtoPtr(value)
+                );
                 Runtime.Py_SetPythonHome(_pythonHome);
             }
         }
@@ -117,13 +121,15 @@ public static string PythonPath
         {
             get
             {
-                IntPtr p = Runtime.Py_GetPath();
+                IntPtr p = Runtime.TryUsingDll(() => Runtime.Py_GetPath());
                 return UcsMarshaler.PtrToPy3UnicodePy2String(p) ?? "";
             }
             set
             {
                 Marshal.FreeHGlobal(_pythonPath);
-                _pythonPath = UcsMarshaler.Py3UnicodePy2StringtoPtr(value);
+                _pythonPath = Runtime.TryUsingDll(
+                    () => UcsMarshaler.Py3UnicodePy2StringtoPtr(value)
+                );
                 Runtime.Py_SetPath(_pythonPath);
             }
         }
diff --git a/src/runtime/runtime.cs b/src/runtime/runtime.cs
index 318c7b794..a7420f946 100644
--- a/src/runtime/runtime.cs
+++ b/src/runtime/runtime.cs
@@ -93,7 +93,6 @@ internal static Version PyVersion
             }
         }
 
-
         /// <summary>
         /// Initialize the runtime...
         /// </summary>
@@ -113,7 +112,10 @@ internal static void Initialize(bool initSigs = false, ShutdownMode mode = Shutd
             }
             ShutdownMode = mode;
 
-            if (Py_IsInitialized() == 0)
+            bool interpreterAlreadyInitialized = TryUsingDll(
+                () => Py_IsInitialized() != 0
+            );
+            if (!interpreterAlreadyInitialized)
             {
                 Py_InitializeEx(initSigs ? 1 : 0);
                 if (PyEval_ThreadsInitialized() == 0)
@@ -787,6 +789,34 @@ internal static unsafe long Refcount(IntPtr op)
             return *p;
         }
 
+        /// <summary>
+        /// Call specified function, and handle PythonDLL-related failures.
+        /// </summary>
+        internal static T TryUsingDll<T>(Func<T> op)
+        {
+            try
+            {
+                return op();
+            }
+            catch (TypeInitializationException loadFailure)
+            {
+                var delegatesLoadFailure = loadFailure;
+                // failure to load Delegates type might have been the cause
+                // of failure to load some higher-level type
+                while (delegatesLoadFailure.InnerException is TypeInitializationException nested)
+                {
+                    delegatesLoadFailure = nested;
+                }
+
+                if (delegatesLoadFailure.InnerException is BadPythonDllException badDll)
+                {
+                    throw badDll;
+                }
+
+                throw;
+            }
+        }
+
         /// <summary>
         /// Export of Macro Py_XIncRef. Use XIncref instead.
         /// Limit this function usage for Testing and Py_Debug builds
@@ -2270,10 +2300,6 @@ internal static void SetNoSiteFlag()
             if (_PythonDll != "__Internal")
             {
                 dllLocal = loader.Load(_PythonDll);
-                if (dllLocal == IntPtr.Zero)
-                {
-                    throw new Exception($"Cannot load {_PythonDll}");
-                }
             }
             try
             {
@@ -2617,8 +2643,8 @@ static Delegates()
                 }
                 catch (MissingMethodException e) when (libraryHandle == IntPtr.Zero)
                 {
-                    throw new MissingMethodException(
-                        "Did you forget to set Runtime.PythonDLL?" +
+                    throw new BadPythonDllException(
+                        "Runtime.PythonDLL was not set or does not point to a supported Python runtime DLL." +
                         " See https://github.com/pythonnet/pythonnet#embedding-python-in-net",
                         e);
                 }
@@ -2889,6 +2915,12 @@ static Delegates()
         }
     }
 
+    internal class BadPythonDllException : MissingMethodException
+    {
+        public BadPythonDllException(string message, Exception innerException)
+            : base(message, innerException) { }
+    }
+
 
     public enum ShutdownMode
     {