diff --git a/lldb/include/lldb/Host/HostInfoBase.h b/lldb/include/lldb/Host/HostInfoBase.h
--- a/lldb/include/lldb/Host/HostInfoBase.h
+++ b/lldb/include/lldb/Host/HostInfoBase.h
@@ -37,7 +37,13 @@
   ~HostInfoBase() {}
 
 public:
-  static void Initialize();
+  /// A helper function for determining the liblldb location. It receives a
+  /// FileSpec with the location of file containing _this_ code. It can
+  /// (optionally) replace it with a file spec pointing to a more canonical
+  /// copy.
+  using SharedLibraryDirectoryHelper = void(FileSpec &this_file);
+
+  static void Initialize(SharedLibraryDirectoryHelper *helper = nullptr);
   static void Terminate();
 
   /// Gets the host target triple.
diff --git a/lldb/include/lldb/Host/linux/HostInfoLinux.h b/lldb/include/lldb/Host/linux/HostInfoLinux.h
--- a/lldb/include/lldb/Host/linux/HostInfoLinux.h
+++ b/lldb/include/lldb/Host/linux/HostInfoLinux.h
@@ -27,7 +27,7 @@
   ~HostInfoLinux();
 
 public:
-  static void Initialize();
+  static void Initialize(SharedLibraryDirectoryHelper *helper = nullptr);
 
   static llvm::VersionTuple GetOSVersion();
   static bool GetOSBuildString(std::string &s);
diff --git a/lldb/include/lldb/Host/windows/HostInfoWindows.h b/lldb/include/lldb/Host/windows/HostInfoWindows.h
--- a/lldb/include/lldb/Host/windows/HostInfoWindows.h
+++ b/lldb/include/lldb/Host/windows/HostInfoWindows.h
@@ -25,7 +25,7 @@
   ~HostInfoWindows();
 
 public:
-  static void Initialize();
+  static void Initialize(SharedLibraryDirectoryHelper *helper = nullptr);
   static void Terminate();
 
   static size_t GetPageSize();
diff --git a/lldb/include/lldb/Initialization/SystemInitializerCommon.h b/lldb/include/lldb/Initialization/SystemInitializerCommon.h
--- a/lldb/include/lldb/Initialization/SystemInitializerCommon.h
+++ b/lldb/include/lldb/Initialization/SystemInitializerCommon.h
@@ -10,6 +10,7 @@
 #define LLDB_INITIALIZATION_SYSTEMINITIALIZERCOMMON_H
 
 #include "SystemInitializer.h"
+#include "lldb/Host/HostInfo.h"
 
 namespace lldb_private {
 /// Initializes common lldb functionality.
@@ -22,11 +23,14 @@
 /// the constructor.
 class SystemInitializerCommon : public SystemInitializer {
 public:
-  SystemInitializerCommon();
+  SystemInitializerCommon(HostInfo::SharedLibraryDirectoryHelper *helper);
   ~SystemInitializerCommon() override;
 
   llvm::Error Initialize() override;
   void Terminate() override;
+
+private:
+  HostInfo::SharedLibraryDirectoryHelper *m_shlib_dir_helper;
 };
 
 } // namespace lldb_private
diff --git a/lldb/source/API/SystemInitializerFull.cpp b/lldb/source/API/SystemInitializerFull.cpp
--- a/lldb/source/API/SystemInitializerFull.cpp
+++ b/lldb/source/API/SystemInitializerFull.cpp
@@ -29,9 +29,22 @@
 #define LLDB_PLUGIN(p) LLDB_PLUGIN_DECLARE(p)
 #include "Plugins/Plugins.def"
 
+#if LLDB_ENABLE_PYTHON
+#include "Plugins/ScriptInterpreter/Python/ScriptInterpreterPython.h"
+
+constexpr lldb_private::HostInfo::SharedLibraryDirectoryHelper
+    *g_shlib_dir_helper =
+        lldb_private::ScriptInterpreterPython::SharedLibraryDirectoryHelper;
+
+#else
+constexpr lldb_private::HostInfo::SharedLibraryDirectoryHelper
+    *g_shlib_dir_helper = 0;
+#endif
+
 using namespace lldb_private;
 
-SystemInitializerFull::SystemInitializerFull() = default;
+SystemInitializerFull::SystemInitializerFull()
+    : SystemInitializerCommon(g_shlib_dir_helper) {}
 SystemInitializerFull::~SystemInitializerFull() = default;
 
 llvm::Error SystemInitializerFull::Initialize() {
diff --git a/lldb/source/Host/common/HostInfoBase.cpp b/lldb/source/Host/common/HostInfoBase.cpp
--- a/lldb/source/Host/common/HostInfoBase.cpp
+++ b/lldb/source/Host/common/HostInfoBase.cpp
@@ -71,13 +71,18 @@
   llvm::once_flag m_lldb_global_tmp_dir_once;
   FileSpec m_lldb_global_tmp_dir;
 };
+} // namespace
 
-HostInfoBaseFields *g_fields = nullptr;
-}
+static HostInfoBaseFields *g_fields = nullptr;
+static HostInfoBase::SharedLibraryDirectoryHelper *g_shlib_dir_helper = nullptr;
 
-void HostInfoBase::Initialize() { g_fields = new HostInfoBaseFields(); }
+void HostInfoBase::Initialize(SharedLibraryDirectoryHelper *helper) {
+  g_shlib_dir_helper = helper;
+  g_fields = new HostInfoBaseFields();
+}
 
 void HostInfoBase::Terminate() {
+  g_shlib_dir_helper = nullptr;
   delete g_fields;
   g_fields = nullptr;
 }
@@ -249,9 +254,8 @@
       reinterpret_cast<void *>(
           HostInfoBase::ComputeSharedLibraryDirectory)));
 
-  // This is necessary because when running the testsuite the shlib might be a
-  // symbolic link inside the Python resource dir.
-  FileSystem::Instance().ResolveSymbolicLink(lldb_file_spec, lldb_file_spec);
+  if (g_shlib_dir_helper)
+    g_shlib_dir_helper(lldb_file_spec);
 
   // Remove the filename so that this FileSpec only represents the directory.
   file_spec.GetDirectory() = lldb_file_spec.GetDirectory();
diff --git a/lldb/source/Host/linux/HostInfoLinux.cpp b/lldb/source/Host/linux/HostInfoLinux.cpp
--- a/lldb/source/Host/linux/HostInfoLinux.cpp
+++ b/lldb/source/Host/linux/HostInfoLinux.cpp
@@ -33,8 +33,8 @@
 HostInfoLinuxFields *g_fields = nullptr;
 }
 
-void HostInfoLinux::Initialize() {
-  HostInfoPosix::Initialize();
+void HostInfoLinux::Initialize(SharedLibraryDirectoryHelper *helper) {
+  HostInfoPosix::Initialize(helper);
 
   g_fields = new HostInfoLinuxFields();
 }
diff --git a/lldb/source/Host/windows/HostInfoWindows.cpp b/lldb/source/Host/windows/HostInfoWindows.cpp
--- a/lldb/source/Host/windows/HostInfoWindows.cpp
+++ b/lldb/source/Host/windows/HostInfoWindows.cpp
@@ -39,9 +39,9 @@
 
 FileSpec HostInfoWindows::m_program_filespec;
 
-void HostInfoWindows::Initialize() {
+void HostInfoWindows::Initialize(SharedLibraryDirectoryHelper *helper) {
   ::CoInitializeEx(nullptr, COINIT_MULTITHREADED);
-  HostInfoBase::Initialize();
+  HostInfoBase::Initialize(helper);
 }
 
 void HostInfoWindows::Terminate() {
diff --git a/lldb/source/Initialization/SystemInitializerCommon.cpp b/lldb/source/Initialization/SystemInitializerCommon.cpp
--- a/lldb/source/Initialization/SystemInitializerCommon.cpp
+++ b/lldb/source/Initialization/SystemInitializerCommon.cpp
@@ -11,7 +11,6 @@
 #include "Plugins/Process/gdb-remote/ProcessGDBRemoteLog.h"
 #include "lldb/Host/FileSystem.h"
 #include "lldb/Host/Host.h"
-#include "lldb/Host/HostInfo.h"
 #include "lldb/Host/Socket.h"
 #include "lldb/Utility/Log.h"
 #include "lldb/Utility/ReproducerProvider.h"
@@ -35,7 +34,9 @@
 using namespace lldb_private;
 using namespace lldb_private::repro;
 
-SystemInitializerCommon::SystemInitializerCommon() {}
+SystemInitializerCommon::SystemInitializerCommon(
+    HostInfo::SharedLibraryDirectoryHelper *helper)
+    : m_shlib_dir_helper(helper) {}
 
 SystemInitializerCommon::~SystemInitializerCommon() {}
 
@@ -125,7 +126,7 @@
     return e;
 
   Log::Initialize();
-  HostInfo::Initialize();
+  HostInfo::Initialize(m_shlib_dir_helper);
 
   llvm::Error error = Socket::Initialize();
   if (error)
diff --git a/lldb/source/Plugins/ScriptInterpreter/Python/ScriptInterpreterPython.h b/lldb/source/Plugins/ScriptInterpreter/Python/ScriptInterpreterPython.h
--- a/lldb/source/Plugins/ScriptInterpreter/Python/ScriptInterpreterPython.h
+++ b/lldb/source/Plugins/ScriptInterpreter/Python/ScriptInterpreterPython.h
@@ -51,6 +51,7 @@
   static lldb_private::ConstString GetPluginNameStatic();
   static const char *GetPluginDescriptionStatic();
   static FileSpec GetPythonDir();
+  static void SharedLibraryDirectoryHelper(FileSpec &this_file);
 
 protected:
   static void ComputePythonDirForApple(llvm::SmallVectorImpl<char> &path);
diff --git a/lldb/source/Plugins/ScriptInterpreter/Python/ScriptInterpreterPython.cpp b/lldb/source/Plugins/ScriptInterpreter/Python/ScriptInterpreterPython.cpp
--- a/lldb/source/Plugins/ScriptInterpreter/Python/ScriptInterpreterPython.cpp
+++ b/lldb/source/Plugins/ScriptInterpreter/Python/ScriptInterpreterPython.cpp
@@ -410,6 +410,31 @@
   return g_spec;
 }
 
+void ScriptInterpreterPython::SharedLibraryDirectoryHelper(
+    FileSpec &this_file) {
+  // When we're loaded from python, this_file will point to the file inside the
+  // python package directory. Replace it with the one in the lib directory.
+#ifdef _WIN32
+  // On windows, we need to manually back out of the python tree, and go into
+  // the bin directory. This is pretty much the inverse of what ComputePythonDir
+  // does.
+  if (this_file.GetFileNameExtension() == ConstString(".pyd")) {
+    this_file.RemoveLastPathComponent(); // _lldb.pyd or _lldb_d.pyd
+    this_file.RemoveLastPathComponent(); // lldb
+    for (auto it = llvm::sys::path::begin(LLDB_PYTHON_RELATIVE_LIBDIR),
+              end = llvm::sys::path::end(LLDB_PYTHON_RELATIVE_LIBDIR);
+         it != end; ++it)
+      this_file.RemoveLastPathComponent();
+    this_file.AppendPathComponent("bin");
+    this_file.AppendPathComponent("liblldb.dll");
+  }
+#else
+  // The python file is a symlink, so we can find the real library by resolving
+  // it. We can do this unconditionally.
+  FileSystem::Instance().ResolveSymbolicLink(this_file, this_file);
+#endif
+}
+
 lldb_private::ConstString ScriptInterpreterPython::GetPluginNameStatic() {
   static ConstString g_name("script-python");
   return g_name;
diff --git a/lldb/test/API/functionalities/paths/TestPaths.py b/lldb/test/API/functionalities/paths/TestPaths.py
--- a/lldb/test/API/functionalities/paths/TestPaths.py
+++ b/lldb/test/API/functionalities/paths/TestPaths.py
@@ -8,6 +8,7 @@
 from lldbsuite.test.decorators import *
 from lldbsuite.test.lldbtest import *
 from lldbsuite.test import lldbutil
+from lldbsuite.test import lldbplatformutil
 
 
 class TestPaths(TestBase):
@@ -29,7 +30,18 @@
         for path_type in dir_path_types:
             f = lldb.SBHostOS.GetLLDBPath(path_type)
             # No directory path types should have the filename set
-            self.assertTrue(f.GetFilename() is None)
+            self.assertIsNone(f.GetFilename())
+
+        shlib_dir = lldb.SBHostOS.GetLLDBPath(lldb.ePathTypeLLDBShlibDir).GetDirectory()
+        if lldbplatformutil.getHostPlatform() == 'windows':
+            filenames = ['liblldb.dll']
+        elif lldbplatformutil.getHostPlatform() == 'darwin':
+            filenames = ['LLDB', 'liblldb.dylib']
+        else:
+            filenames = ['liblldb.so']
+        self.assertTrue(any([os.path.exists(os.path.join(shlib_dir, f)) for f in
+            filenames]), "shlib_dir = " + shlib_dir)
+
 
     @no_debug_info_test
     def test_directory_doesnt_end_with_slash(self):
diff --git a/lldb/tools/lldb-server/SystemInitializerLLGS.h b/lldb/tools/lldb-server/SystemInitializerLLGS.h
--- a/lldb/tools/lldb-server/SystemInitializerLLGS.h
+++ b/lldb/tools/lldb-server/SystemInitializerLLGS.h
@@ -14,6 +14,8 @@
 
 class SystemInitializerLLGS : public lldb_private::SystemInitializerCommon {
 public:
+  SystemInitializerLLGS() : SystemInitializerCommon(nullptr) {}
+
   llvm::Error Initialize() override;
   void Terminate() override;
 };
diff --git a/lldb/tools/lldb-test/SystemInitializerTest.cpp b/lldb/tools/lldb-test/SystemInitializerTest.cpp
--- a/lldb/tools/lldb-test/SystemInitializerTest.cpp
+++ b/lldb/tools/lldb-test/SystemInitializerTest.cpp
@@ -22,7 +22,8 @@
 
 using namespace lldb_private;
 
-SystemInitializerTest::SystemInitializerTest() = default;
+SystemInitializerTest::SystemInitializerTest()
+    : SystemInitializerCommon(nullptr) {}
 SystemInitializerTest::~SystemInitializerTest() = default;
 
 llvm::Error SystemInitializerTest::Initialize() {