diff --git a/lldb/source/Plugins/ScriptInterpreter/Python/PythonDataObjects.h b/lldb/source/Plugins/ScriptInterpreter/Python/PythonDataObjects.h
--- a/lldb/source/Plugins/ScriptInterpreter/Python/PythonDataObjects.h
+++ b/lldb/source/Plugins/ScriptInterpreter/Python/PythonDataObjects.h
@@ -88,12 +88,21 @@
   StructuredPythonObject() : StructuredData::Generic() {}
 
   StructuredPythonObject(void *obj) : StructuredData::Generic(obj) {
+    assert(PyGILState_Check());
     Py_XINCREF(GetValue());
   }
 
   ~StructuredPythonObject() override {
-    if (Py_IsInitialized())
-      Py_XDECREF(GetValue());
+    if (Py_IsInitialized()) {
+      if (_Py_IsFinalizing()) {
+        // Leak GetValue() rather than crashing the process.
+        // https://docs.python.org/3/c-api/init.html#c.PyGILState_Ensure
+      } else {
+        auto gstate = PyGILState_Ensure();
+        Py_XDECREF(GetValue());
+        PyGILState_Release(gstate);
+      }
+    }
     SetValue(nullptr);
   }
 
@@ -264,8 +273,16 @@
   ~PythonObject() { Reset(); }
 
   void Reset() {
-    if (m_py_obj && Py_IsInitialized())
-      Py_DECREF(m_py_obj);
+    if (m_py_obj && Py_IsInitialized()) {
+      if (_Py_IsFinalizing()) {
+        // Leak m_py_obj rather than crashing the process.
+        // https://docs.python.org/3/c-api/init.html#c.PyGILState_Ensure
+      } else {
+        auto gstate = PyGILState_Ensure();
+        Py_DECREF(m_py_obj);
+        PyGILState_Release(gstate);
+      }
+    }
     m_py_obj = nullptr;
   }
 
diff --git a/lldb/source/Plugins/ScriptInterpreter/Python/PythonDataObjects.cpp b/lldb/source/Plugins/ScriptInterpreter/Python/PythonDataObjects.cpp
--- a/lldb/source/Plugins/ScriptInterpreter/Python/PythonDataObjects.cpp
+++ b/lldb/source/Plugins/ScriptInterpreter/Python/PythonDataObjects.cpp
@@ -257,6 +257,7 @@
 }
 
 StructuredData::ObjectSP PythonObject::CreateStructuredObject() const {
+  assert(PyGILState_Check());
   switch (GetObjectType()) {
   case PyObjectType::Dictionary:
     return PythonDictionary(PyRefType::Borrowed, m_py_obj)
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
@@ -1568,9 +1568,9 @@
                    Locker::FreeLock);
     ret_val = LLDBSWIGPython_CreateFrameRecognizer(class_name,
                                                    m_dictionary_name.c_str());
-  }
 
-  return StructuredData::GenericSP(new StructuredPythonObject(ret_val));
+    return StructuredData::GenericSP(new StructuredPythonObject(ret_val));
+  }
 }
 
 lldb::ValueObjectListSP ScriptInterpreterPythonImpl::GetRecognizedArguments(
@@ -1632,9 +1632,9 @@
                    Locker::FreeLock);
     ret_val = LLDBSWIGPythonCreateOSPlugin(
         class_name, m_dictionary_name.c_str(), process_sp);
-  }
 
-  return StructuredData::GenericSP(new StructuredPythonObject(ret_val));
+    return StructuredData::GenericSP(new StructuredPythonObject(ret_val));
+  }
 }
 
 StructuredData::DictionarySP ScriptInterpreterPythonImpl::OSPlugin_RegisterInfo(
@@ -1890,9 +1890,9 @@
         args_data, error_str, thread_plan_sp);
     if (!ret_val)
       return {};
-  }
 
-  return StructuredData::ObjectSP(new StructuredPythonObject(ret_val));
+    return StructuredData::ObjectSP(new StructuredPythonObject(ret_val));
+  }
 }
 
 bool ScriptInterpreterPythonImpl::ScriptedThreadPlanExplainsStop(
@@ -1992,9 +1992,9 @@
     ret_val = LLDBSwigPythonCreateScriptedBreakpointResolver(
         class_name, python_interpreter->m_dictionary_name.c_str(), args_data,
         bkpt_sp);
-  }
 
-  return StructuredData::GenericSP(new StructuredPythonObject(ret_val));
+    return StructuredData::GenericSP(new StructuredPythonObject(ret_val));
+  }
 }
 
 bool ScriptInterpreterPythonImpl::ScriptedBreakpointResolverSearchCallback(
@@ -2067,9 +2067,9 @@
     ret_val = LLDBSwigPythonCreateScriptedStopHook(
         target_sp, class_name, python_interpreter->m_dictionary_name.c_str(),
         args_data, error);
-  }
 
-  return StructuredData::GenericSP(new StructuredPythonObject(ret_val));
+    return StructuredData::GenericSP(new StructuredPythonObject(ret_val));
+  }
 }
 
 bool ScriptInterpreterPythonImpl::ScriptedStopHookHandleStop(
@@ -2165,9 +2165,9 @@
                    Locker::AcquireLock | Locker::InitSession | Locker::NoSTDIN);
     ret_val = LLDBSwigPythonCreateSyntheticProvider(
         class_name, python_interpreter->m_dictionary_name.c_str(), valobj);
-  }
 
-  return StructuredData::ObjectSP(new StructuredPythonObject(ret_val));
+    return StructuredData::ObjectSP(new StructuredPythonObject(ret_val));
+  }
 }
 
 StructuredData::GenericSP
@@ -2187,9 +2187,9 @@
                    Locker::AcquireLock | Locker::InitSession | Locker::NoSTDIN);
     ret_val = LLDBSwigPythonCreateCommandObject(
         class_name, m_dictionary_name.c_str(), debugger_sp);
-  }
 
-  return StructuredData::GenericSP(new StructuredPythonObject(ret_val));
+    return StructuredData::GenericSP(new StructuredPythonObject(ret_val));
+  }
 }
 
 bool ScriptInterpreterPythonImpl::GenerateTypeScriptFunction(
@@ -2299,8 +2299,11 @@
     return false;
   }
 
-  if (new_callee && old_callee != new_callee)
+  if (new_callee && old_callee != new_callee) {
+    Locker py_lock(this,
+                   Locker::AcquireLock | Locker::InitSession | Locker::NoSTDIN);
     callee_wrapper_sp = std::make_shared<StructuredPythonObject>(new_callee);
+  }
 
   return ret_val;
 }