diff --git a/lldb/include/lldb/Host/File.h b/lldb/include/lldb/Host/File.h
--- a/lldb/include/lldb/Host/File.h
+++ b/lldb/include/lldb/Host/File.h
@@ -411,6 +411,8 @@
   size_t PrintfVarArg(const char *format, va_list args) override;
   llvm::Expected<OpenOptions> GetOptions() const override;
 
+  static FILE *ReleaseFILE(NativeFile &&file);
+
   static char ID;
   virtual bool isA(const void *classID) const override {
     return classID == &ID || File::isA(classID);
diff --git a/lldb/packages/Python/lldbsuite/test/python_api/file_handle/TestFileHandle.py b/lldb/packages/Python/lldbsuite/test/python_api/file_handle/TestFileHandle.py
--- a/lldb/packages/Python/lldbsuite/test/python_api/file_handle/TestFileHandle.py
+++ b/lldb/packages/Python/lldbsuite/test/python_api/file_handle/TestFileHandle.py
@@ -845,6 +845,7 @@
             def i(sbf):
                 for i in range(10):
                     f = sbf.GetFile()
+                    self.assertEqual(f.mode, "w")
                     yield f
                     sbf = lldb.SBFile.Create(f, borrow=True)
                     yield sbf
diff --git a/lldb/source/Host/common/File.cpp b/lldb/source/Host/common/File.cpp
--- a/lldb/source/Host/common/File.cpp
+++ b/lldb/source/Host/common/File.cpp
@@ -304,13 +304,25 @@
   return m_stream;
 }
 
+FILE *NativeFile::ReleaseFILE(NativeFile &&file) {
+  FILE *stream = nullptr;
+  file.GetStream();
+  if (file.m_own_stream) {
+    stream = file.m_stream;
+    file.m_own_stream = false;
+    file.m_stream = nullptr;
+  }
+  file.Close();
+  return stream;
+}
+
 Status NativeFile::Close() {
   Status error;
   if (StreamIsValid()) {
     if (m_own_stream) {
       if (::fclose(m_stream) == EOF)
         error.SetErrorToErrno();
-    } else {
+    } else if (m_options & eOpenOptionWrite) {
       if (::fflush(m_stream) == EOF)
         error.SetErrorToErrno();
     }
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
@@ -189,6 +189,14 @@
                                  "key not in dict");
 }
 
+#if PY_MAJOR_VERSION < 3
+// The python 2 API declares some arguments as char* that should
+// be const char *, but it doesn't actually modify them.
+inline char *py2_const_cast(const char *s) { return const_cast<char *>(s); }
+#else
+inline const char *py2_const_cast(const char *s) { return s; }
+#endif
+
 enum class PyInitialValue { Invalid, Empty };
 
 template <typename T, typename Enable = void> struct PythonFormat;
@@ -309,16 +317,6 @@
 
   StructuredData::ObjectSP CreateStructuredObject() const;
 
-protected:
-
-#if PY_MAJOR_VERSION < 3
-  // The python 2 API declares some arguments as char* that should
-  // be const char *, but it doesn't actually modify them.
-  static char *py2_const_cast(const char *s) { return const_cast<char *>(s); }
-#else
-  static const char *py2_const_cast(const char *s) { return s; }
-#endif
-
 public:
   template <typename... T>
   llvm::Expected<PythonObject> CallMethod(const char *name,
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
@@ -1502,12 +1502,28 @@
   file_obj = PyFile_FromFd(file.GetDescriptor(), nullptr, mode, -1, nullptr,
                            "ignore", nullptr, 0);
 #else
-  // Read through the Python source, doesn't seem to modify these strings
-  char *cmode = const_cast<char *>(mode);
-  // We pass ::flush instead of ::fclose here so we borrow the FILE* --
-  // the lldb_private::File still owns it.
-  file_obj =
-      PyFile_FromFile(file.GetStream(), const_cast<char *>(""), cmode, ::fflush);
+  // It's more or less safe to let a python program borrow a file descriptor.
+  // If they let it dangle and then use it, they'll probably get an exception.
+  // The worst that can happen is they'll wind up doing IO on the wrong
+  // descriptor.   But it would be very unsafe to let a python program borrow
+  // a FILE*.   They could actually crash the program just by keeping a
+  // reference to it around.    Since in python 2 we must have a FILE* and
+  // not a descriptor, we dup the descriptor and fdopen a new FILE* to it
+  // so python can have something it can own safely.
+  auto opts = File::GetOptionsFromMode(mode);
+  if (!opts)
+    return opts.takeError();
+  int fd = file.GetDescriptor();
+  if (!File::DescriptorIsValid(fd))
+    return llvm::createStringError(llvm::inconvertibleErrorCode(),
+                                   "File has no file descriptor");
+  NativeFile dupfile(fd, opts.get(), false);
+  FILE *stream = NativeFile::ReleaseFILE(std::move(dupfile));
+  if (!stream)
+    return llvm::createStringError(llvm::inconvertibleErrorCode(),
+                                   "could not create FILE* stream");
+  file_obj = PyFile_FromFile(stream, py2_const_cast(""), py2_const_cast(mode),
+                             ::fclose);
 #endif
 
   if (!file_obj)