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
@@ -180,6 +180,19 @@
             self.assertIn("is not a valid command", f.read())
 
 
+    @add_test_categories(['pyapi'])
+    def test_legacy_file_error(self):
+        debugger = self.debugger
+        with open(self.out_filename, 'w') as f:
+            debugger.SetErrorFileHandle(f, False)
+            self.handleCmd('lolwut', check=False, collect_result=False)
+            debugger.GetErrorFileHandle().write('FOOBAR\n')
+        with open(self.out_filename, 'r') as f:
+            errors = f.read()
+            self.assertTrue(re.search(r'error:.*lolwut', errors))
+            self.assertTrue(re.search(r'FOOBAR', errors))
+
+
     @add_test_categories(['pyapi'])
     def test_sbfile_type_errors(self):
         sbf = lldb.SBFile()
@@ -269,6 +282,17 @@
             self.assertTrue(re.search(r'Show a list of all debugger commands', f.read()))
 
 
+    @add_test_categories(['pyapi'])
+    def test_help(self):
+        debugger = self.debugger
+        with open(self.out_filename, 'w') as f:
+            status = debugger.SetOutputFile(lldb.SBFile(f))
+            self.assertTrue(status.Success())
+            self.handleCmd("help help", check=False, collect_result=False)
+        with open(self.out_filename, 'r') as f:
+            self.assertIn('Show a list of all debugger commands', f.read())
+
+
     @add_test_categories(['pyapi'])
     def test_immediate(self):
         with open(self.out_filename, 'w') as f:
@@ -278,15 +302,44 @@
             interpreter.HandleCommand("help help", ret)
             # make sure the file wasn't closed early.
             f.write("\nQUUX\n")
-
         ret = None # call destructor and flush streams
-
         with open(self.out_filename, 'r') as f:
             output = f.read()
             self.assertTrue(re.search(r'Show a list of all debugger commands', output))
             self.assertTrue(re.search(r'QUUX', output))
 
 
+    @add_test_categories(['pyapi'])
+    @skipIf(True) # FIXME need SBFile interfaces on SBCommandReturnObject
+    def test_immediate_string(self):
+        f = io.StringIO()
+        ret = lldb.SBCommandReturnObject()
+        ret.SetImmediateOutputFile(f)
+        interpreter = self.debugger.GetCommandInterpreter()
+        interpreter.HandleCommand("help help", ret)
+        # make sure the file wasn't closed early.
+        f.write("\nQUUX\n")
+        ret = None # call destructor and flush streams
+        output = f.getvalue()
+        self.assertTrue(re.search(r'Show a list of all debugger commands', output))
+        self.assertTrue(re.search(r'QUUX', output))
+
+
+    @add_test_categories(['pyapi'])
+    @skipIf(True) # FIXME need SBFile interfaces on SBCommandReturnObject
+    def test_immediate_sbfile_string(self):
+        f = io.StringIO()
+        ret = lldb.SBCommandReturnObject()
+        ret.SetImmediateOutputFile(lldb.SBFile(f))
+        interpreter = self.debugger.GetCommandInterpreter()
+        interpreter.HandleCommand("help help", ret)
+        output = f.getvalue()
+        ret = None # call destructor and flush streams
+        # sbfile default constructor doesn't borrow the file
+        self.assertTrue(f.closed)
+        self.assertTrue(re.search(r'Show a list of all debugger commands', output))
+
+
     @add_test_categories(['pyapi'])
     def test_fileno_inout(self):
         with open(self.in_filename, 'w') as f:
@@ -310,6 +363,76 @@
             self.assertTrue(re.search(r'Show a list of all debugger commands', f.read()))
 
 
+    @add_test_categories(['pyapi'])
+    def test_inout(self):
+        with open(self.in_filename, 'w') as f:
+            f.write("help help\n")
+        with  open(self.out_filename, 'w') as outf, \
+              open(self.in_filename, 'r') as inf:
+            status = self.debugger.SetOutputFile(lldb.SBFile(outf))
+            self.assertTrue(status.Success())
+            status = self.debugger.SetInputFile(lldb.SBFile(inf))
+            self.assertTrue(status.Success())
+            opts = lldb.SBCommandInterpreterRunOptions()
+            self.debugger.RunCommandInterpreter(True, False, opts, 0, False, False)
+            self.debugger.GetOutputFile().Flush()
+        with open(self.out_filename, 'r') as f:
+            output = f.read()
+            self.assertIn('Show a list of all debugger commands', output)
+
+
+    @add_test_categories(['pyapi'])
+    def test_binary_inout(self):
+        debugger = self.debugger
+        with open(self.in_filename, 'w') as f:
+            f.write("help help\n")
+        with  open(self.out_filename, 'wb') as outf, \
+              open(self.in_filename, 'rb') as inf:
+            status = debugger.SetOutputFile(lldb.SBFile(outf))
+            self.assertTrue(status.Success())
+            status = debugger.SetInputFile(lldb.SBFile(inf))
+            self.assertTrue(status.Success())
+            opts = lldb.SBCommandInterpreterRunOptions()
+            debugger.RunCommandInterpreter(True, False, opts, 0, False, False)
+            debugger.GetOutputFile().Flush()
+        with open(self.out_filename, 'r') as f:
+            output = f.read()
+            self.assertIn('Show a list of all debugger commands', output)
+
+
+    @add_test_categories(['pyapi'])
+    @skipIf(True) # FIXME IOHandler still using FILE*
+    def test_string_inout(self):
+        inf = io.StringIO("help help\n")
+        outf = io.StringIO()
+        status = self.debugger.SetOutputFile(lldb.SBFile(outf))
+        self.assertTrue(status.Success())
+        status = self.debugger.SetInputFile(lldb.SBFile(inf))
+        self.assertTrue(status.Success())
+        opts = lldb.SBCommandInterpreterRunOptions()
+        self.debugger.RunCommandInterpreter(True, False, opts, 0, False, False)
+        self.debugger.GetOutputFile().Flush()
+        output = outf.getvalue()
+        self.assertIn('Show a list of all debugger commands', output)
+
+
+    @add_test_categories(['pyapi'])
+    @skipIf(True) # FIXME IOHandler still using FILE*
+    def test_bytes_inout(self):
+        inf = io.BytesIO(b"help help\nhelp b\n")
+        outf = io.BytesIO()
+        status = self.debugger.SetOutputFile(lldb.SBFile(outf))
+        self.assertTrue(status.Success())
+        status = self.debugger.SetInputFile(lldb.SBFile(inf))
+        self.assertTrue(status.Success())
+        opts = lldb.SBCommandInterpreterRunOptions()
+        self.debugger.RunCommandInterpreter(True, False, opts, 0, False, False)
+        self.debugger.GetOutputFile().Flush()
+        output = outf.getvalue()
+        self.assertIn(b'Show a list of all debugger commands', output)
+        self.assertIn(b'Set a breakpoint', output)
+
+
     @add_test_categories(['pyapi'])
     def test_fileno_error(self):
         with open(self.out_filename, 'w') as f:
@@ -339,6 +462,23 @@
             self.assertEqual(sys.stdout, f)
 
 
+    @add_test_categories(['pyapi'])
+    @skipIf(True) #FIXME bug in ScriptInterpreterPython
+    def test_replace_stdout_with_nonfile(self):
+        debugger = self.debugger
+        f = io.StringIO()
+        with replace_stdout(f):
+            class Nothing():
+                pass
+            with replace_stdout(Nothing):
+                self.assertEqual(sys.stdout, Nothing)
+                self.handleCmd('script sys.stdout.write("lol")',
+                    check=False, collect_result=False)
+                self.assertEqual(sys.stdout, Nothing)
+            sys.stdout.write(u"FOO")
+        self.assertEqual(f.getvalue(), "FOO")
+
+
     @add_test_categories(['pyapi'])
     def test_sbfile_write_borrowed(self):
         with open(self.out_filename, 'w') as f:
@@ -408,6 +548,31 @@
         sbf.Close()
         self.assertTrue(f.closed)
 
+
+    @add_test_categories(['pyapi'])
+    @skipIf(py_version=['<', (3,)])
+    @skipIf(True) # fixme multiple problems with this
+    def test_string_out(self):
+        f = io.StringIO()
+        status = self.debugger.SetOutputFile(f)
+        self.assertTrue(status.Success())
+        self.handleCmd("script 'foobar'")
+        self.assertEqual(f.getvalue().strip(), "'foobar'")
+
+
+    @add_test_categories(['pyapi'])
+    @skipIf(True) # FIXME need FileSP version of SBDebugger::SetErrorFile
+    @skipIf(py_version=['<', (3,)])
+    def test_string_error(self):
+        f = io.StringIO()
+        debugger = self.debugger
+        status = debugger.SetErrorFile(f)
+        self.assertTrue(status.Success())
+        self.handleCmd('lolwut', check=False, collect_result=False)
+        errors = f.getvalue()
+        self.assertTrue(re.search(r'error:.*lolwut', errors))
+
+
     @add_test_categories(['pyapi'])
     @skipIf(py_version=['<', (3,)])
     def test_sbfile_write_bytes(self):
@@ -466,6 +631,18 @@
             self.assertEqual(f.read().strip(), '4')
 
 
+    @add_test_categories(['pyapi'])
+    @skipIf(True) # FIXME need FileSP version of SBDebugger::SetErrorFile
+    @skipIf(py_version=['<', (3,)])
+    def test_file_out(self):
+        with open(self.out_filename, 'w') as f:
+            status = self.debugger.SetOutputFile(f)
+            self.assertTrue(status.Success())
+            self.handleCmd('script 2+2')
+        with open(self.out_filename, 'r') as f:
+            self.assertEqual(f.read().strip(), '4')
+
+
     @add_test_categories(['pyapi'])
     def test_sbfile_error(self):
         with open(self.out_filename, 'w') as f:
@@ -478,6 +655,18 @@
             self.assertTrue(re.search(r'error:.*lolwut', errors))
 
 
+    @add_test_categories(['pyapi'])
+    @skipIf(True) # FIXME need FileSP version of SBDebugger::SetErrorFile
+    def test_file_error(self):
+        with open(self.out_filename, 'w') as f:
+            status = self.debugger.SetErrorFile(f)
+            self.assertTrue(status.Success())
+            self.handleCmd('lolwut', check=False, collect_result=False)
+        with open(self.out_filename, 'r') as f:
+            errors = f.read()
+            self.assertTrue(re.search(r'error:.*lolwut', errors))
+
+
     @add_test_categories(['pyapi'])
     def test_exceptions(self):
         self.assertRaises(TypeError, lldb.SBFile, None)
@@ -556,3 +745,91 @@
             self.assertFalse(f.closed)
             f.seek(0)
             self.assertEqual(f.read(), 'foobar')
+
+
+    @add_test_categories(['pyapi'])
+    @skipIf(True) # FIXME need FileSP version of SBDebugger::SetOutputFile
+    def test_close(self):
+        debugger = self.debugger
+        with open(self.out_filename, 'w') as f:
+            status = debugger.SetOutputFile(f)
+            self.assertTrue(status.Success())
+            self.handleCmd("help help", check=False, collect_result=False)
+            # make sure the file wasn't closed early.
+            f.write("\nZAP\n")
+            lldb.SBDebugger.Destroy(debugger)
+            # check that output file was closed when debugger was destroyed.
+            with self.assertRaises(ValueError):
+                f.write("\nQUUX\n")
+        with open(self.out_filename, 'r') as f:
+            output = f.read()
+            self.assertTrue(re.search(r'Show a list of all debugger commands', output))
+            self.assertTrue(re.search(r'ZAP', output))
+
+
+    @add_test_categories(['pyapi'])
+    @skipIf(py_version=['<', (3,)])
+    @skipIf(True) # FIXME need FileSP version of SBDebugger::SetOutputFile
+    def test_stdout(self):
+        f = io.StringIO()
+        status = self.debugger.SetOutputFile(f)
+        self.assertTrue(status.Success())
+        self.handleCmd(r"script sys.stdout.write('foobar\n')")
+        self.assertEqual(f.getvalue().strip().split(), ["foobar", "7"])
+
+
+    @add_test_categories(['pyapi'])
+    @skipIf(True) # FIXME implement SBFile::GetFile
+    @skipIf(py_version=['<', (3,)])
+    def test_identity(self):
+
+        f = io.StringIO()
+        sbf = lldb.SBFile(f)
+        self.assertTrue(f is sbf.GetFile())
+        sbf.Close()
+        self.assertTrue(f.closed)
+
+        f = io.StringIO()
+        sbf = lldb.SBFile.Create(f, borrow=True)
+        self.assertTrue(f is sbf.GetFile())
+        sbf.Close()
+        self.assertFalse(f.closed)
+
+        with open(self.out_filename, 'w') as f:
+            sbf = lldb.SBFile(f)
+            self.assertTrue(f is sbf.GetFile())
+            sbf.Close()
+            self.assertTrue(f.closed)
+
+        with open(self.out_filename, 'w') as f:
+            sbf = lldb.SBFile.Create(f, borrow=True)
+            self.assertFalse(f is sbf.GetFile())
+            sbf.Write(b"foobar\n")
+            self.assertEqual(f.fileno(), sbf.GetFile().fileno())
+            sbf.Close()
+            self.assertFalse(f.closed)
+
+        with open(self.out_filename, 'r') as f:
+            self.assertEqual("foobar", f.read().strip())
+
+        with open(self.out_filename, 'wb') as f:
+            sbf = lldb.SBFile.Create(f, borrow=True, force_io_methods=True)
+            self.assertTrue(f is sbf.GetFile())
+            sbf.Write(b"foobar\n")
+            self.assertEqual(f.fileno(), sbf.GetFile().fileno())
+            sbf.Close()
+            self.assertFalse(f.closed)
+
+        with open(self.out_filename, 'r') as f:
+            self.assertEqual("foobar", f.read().strip())
+
+        with open(self.out_filename, 'wb') as f:
+            sbf = lldb.SBFile.Create(f, force_io_methods=True)
+            self.assertTrue(f is sbf.GetFile())
+            sbf.Write(b"foobar\n")
+            self.assertEqual(f.fileno(), sbf.GetFile().fileno())
+            sbf.Close()
+            self.assertTrue(f.closed)
+
+        with open(self.out_filename, 'r') as f:
+            self.assertEqual("foobar", f.read().strip())
diff --git a/lldb/scripts/Python/python-typemaps.swig b/lldb/scripts/Python/python-typemaps.swig
--- a/lldb/scripts/Python/python-typemaps.swig
+++ b/lldb/scripts/Python/python-typemaps.swig
@@ -440,19 +440,19 @@
       $1 = nullptr;
    else if (!lldb_private::PythonFile::Check($input)) {
       int fd = PyObject_AsFileDescriptor($input);
+      if (fd < 0 || PyErr_Occurred())
+        return nullptr;
       PythonObject py_input(PyRefType::Borrowed, $input);
       PythonString py_mode = py_input.GetAttributeValue("mode").AsType<PythonString>();
-
-      if (-1 != fd && py_mode.IsValid()) {
-         FILE *f;
-         if ((f = fdopen(fd, py_mode.GetString().str().c_str())))
-            $1 = f;
-         else
-            PyErr_SetString(PyExc_TypeError, strerror(errno));
-      } else {
-         PyErr_SetString(PyExc_TypeError,"not a file-like object");
-         return nullptr;
-      }
+      if (!py_mode.IsValid() || PyErr_Occurred())
+        return nullptr;
+        FILE *f;
+        if ((f = fdopen(fd, py_mode.GetString().str().c_str())))
+          $1 = f;
+        else {
+          PyErr_SetString(PyExc_TypeError, strerror(errno));
+          return nullptr;
+        }
    }
    else
    {