diff --git a/securedrop_client/gui/widgets.py b/securedrop_client/gui/widgets.py
index e54accd4e..d7b408a38 100644
--- a/securedrop_client/gui/widgets.py
+++ b/securedrop_client/gui/widgets.py
@@ -31,7 +31,8 @@
     QPushButton, QVBoxLayout, QLineEdit, QScrollArea, QDialog, QAction, QMenu, QMessageBox, \
     QToolButton, QSizePolicy, QPlainTextEdit, QStatusBar, QGraphicsDropShadowEffect
 
-from securedrop_client.db import DraftReply, Source, Message, File, Reply, User
+from securedrop_client.db import (DraftReply, Source, Message, File, Reply, User,
+                                  ReplySendStatusCodes)
 from securedrop_client.storage import source_exists
 from securedrop_client.export import ExportStatus, ExportError
 from securedrop_client.gui import SecureQLabel, SvgLabel, SvgPushButton, SvgToggleButton
@@ -1557,9 +1558,10 @@ class SpeechBubble(QWidget):
     TOP_MARGIN = 28
     BOTTOM_MARGIN = 10
 
-    def __init__(self, message_id: str, text: str, update_signal) -> None:
+    def __init__(self, message_id: str, text: str, update_signal, index: int) -> None:
         super().__init__()
         self.message_id = message_id
+        self.index = index
 
         # Set styles
         self.setObjectName('speech_bubble')
@@ -1620,8 +1622,8 @@ class MessageWidget(SpeechBubble):
     Represents an incoming message from the source.
     """
 
-    def __init__(self, message_id: str, message: str, update_signal) -> None:
-        super().__init__(message_id, message, update_signal)
+    def __init__(self, message_id: str, message: str, update_signal, index: int) -> None:
+        super().__init__(message_id, message, update_signal, index)
 
 
 class ReplyWidget(SpeechBubble):
@@ -1702,8 +1704,9 @@ def __init__(
         update_signal,
         message_succeeded_signal,
         message_failed_signal,
+        index: int,
     ) -> None:
-        super().__init__(message_id, message, update_signal)
+        super().__init__(message_id, message, update_signal, index)
         self.message_id = message_id
 
         error_icon = SvgLabel('error_icon.svg', svg_size=QSize(12, 12))
@@ -1833,6 +1836,7 @@ def __init__(
         file_uuid: str,
         controller: Controller,
         file_ready_signal: pyqtBoundSignal,
+        index: int,
     ) -> None:
         """
         Given some text and a reference to the controller, make something to display a file.
@@ -1841,6 +1845,7 @@ def __init__(
 
         self.controller = controller
         self.file = self.controller.get_file(file_uuid)
+        self.index = index
 
         # Set styles
         self.setObjectName('file_widget')
@@ -2388,6 +2393,9 @@ def __init__(self, source_db_object: Source, controller: Controller):
         self.source = source_db_object
         self.controller = controller
 
+        # To hold currently displayed messages.
+        self.current_messages = {}  # type: Dict[str, QWidget]
+
         # Set styles
         self.setStyleSheet(self.CSS)
 
@@ -2413,6 +2421,9 @@ def __init__(self, source_db_object: Source, controller: Controller):
         self.scroll.setWidget(self.container)
         self.scroll.setWidgetResizable(True)
 
+        # Flag to show if the current user has sent a reply. See issue #61.
+        self.reply_flag = False
+
         # Completely unintuitive way to ensure the view remains scrolled to the bottom.
         sb = self.scroll.verticalScrollBar()
         sb.rangeChanged.connect(self.update_conversation_position)
@@ -2428,44 +2439,86 @@ def clear_conversation(self):
                 child.widget().deleteLater()
 
     def update_conversation(self, collection: list) -> None:
-        # clear all old items
-        self.clear_conversation()
+        """
+        Given a list of conversation items that reflect the new state of the
+        conversation, this method does two things:
+
+        * Checks if the conversation item already exists in the conversation.
+          If so, it checks that it's still in the same position. If it isn't,
+          the item is removed from its current position and re-added at the
+          new position. Then the index meta-data on the widget is updated to
+          reflect this change.
+        * If the item is a new item, this is created (as before) and inserted
+          into the conversation at the correct index.
+
+        Things to note, speech bubbles and files have an index attribute which
+        defines where they currently are. This is the attribute that's checked
+        when the new conversation state (i.e. the collection argument) is
+        passed into this method in case of a mismatch between where the widget
+        has been and now is in terms of its index in the conversation.
+        """
         self.controller.session.refresh(self.source)
-        # add new items
-        for conversation_item in collection:
-            if isinstance(conversation_item, Message):
-                self.add_message(conversation_item)
-            elif isinstance(conversation_item, (DraftReply, Reply)):
-                self.add_reply(conversation_item)
+        for index, conversation_item in enumerate(collection):
+            item_widget = self.current_messages.get(conversation_item.uuid)
+            if item_widget:
+                # check an already displayed item.
+                if item_widget.index != index:
+                    # The existing widget is out of order, remove / re-add it
+                    # and update index details.
+                    self.conversation_layout.removeWidget(item_widget)
+                    item_widget.index = index
+                    if isinstance(item_widget, ReplyWidget):
+                        self.conversation_layout.insertWidget(index, item_widget,
+                                                              alignment=Qt.AlignRight)
+                    else:
+                        self.conversation_layout.insertWidget(index, item_widget,
+                                                              alignment=Qt.AlignLeft)
+                # Check if text in item has changed, then update the
+                # widget to reflect this change.
+                if not isinstance(item_widget, FileWidget):
+                    if item_widget.message.text() != conversation_item.content:
+                        item_widget.message.setText(conversation_item.content)
+                # Check if this is a draft reply then ensure it's removed.
+                if isinstance(conversation_item, DraftReply):
+                    if conversation_item.send_status.name == ReplySendStatusCodes.PENDING.value:
+                        self.conversation_layout.removeWidget(item_widget)
             else:
-                self.add_file(conversation_item)
+                # add a new item to be displayed.
+                if isinstance(conversation_item, Message):
+                    self.add_message(conversation_item, index)
+                elif isinstance(conversation_item, (DraftReply, Reply)):
+                    self.add_reply(conversation_item, index)
+                else:
+                    self.add_file(conversation_item, index)
 
-    def add_file(self, file: File):
+    def add_file(self, file: File, index):
         """
         Add a file from the source.
         """
-        conversation_item = FileWidget(file.uuid, self.controller, self.controller.file_ready)
-        self.conversation_layout.addWidget(conversation_item, alignment=Qt.AlignLeft)
+        conversation_item = FileWidget(file.uuid, self.controller, self.controller.file_ready,
+                                       index)
+        self.conversation_layout.insertWidget(index, conversation_item, alignment=Qt.AlignLeft)
+        self.current_messages[file.uuid] = conversation_item
 
     def update_conversation_position(self, min_val, max_val):
         """
         Handler called when a new item is added to the conversation. Ensures
         it's scrolled to the bottom and thus visible.
         """
-        current_val = self.scroll.verticalScrollBar().value()
-        viewport_height = self.scroll.viewport().height()
-
-        if current_val + viewport_height > max_val:
+        if self.reply_flag and max_val > 0:
             self.scroll.verticalScrollBar().setValue(max_val)
+            self.reply_flag = False
 
-    def add_message(self, message: Message) -> None:
+    def add_message(self, message: Message, index) -> None:
         """
         Add a message from the source.
         """
-        conversation_item = MessageWidget(message.uuid, str(message), self.controller.message_ready)
-        self.conversation_layout.addWidget(conversation_item, alignment=Qt.AlignLeft)
+        conversation_item = MessageWidget(message.uuid, str(message), self.controller.message_ready,
+                                          index)
+        self.conversation_layout.insertWidget(index, conversation_item, alignment=Qt.AlignLeft)
+        self.current_messages[message.uuid] = conversation_item
 
-    def add_reply(self, reply: Union[DraftReply, Reply]) -> None:
+    def add_reply(self, reply: Union[DraftReply, Reply], index) -> None:
         """
         Add a reply from a journalist to the source.
         """
@@ -2481,26 +2534,32 @@ def add_reply(self, reply: Union[DraftReply, Reply]) -> None:
             send_status,
             self.controller.reply_ready,
             self.controller.reply_succeeded,
-            self.controller.reply_failed)
-        self.conversation_layout.addWidget(conversation_item, alignment=Qt.AlignRight)
+            self.controller.reply_failed,
+            index)
+        self.conversation_layout.insertWidget(index, conversation_item, alignment=Qt.AlignRight)
+        self.current_messages[reply.uuid] = conversation_item
 
     def add_reply_from_reply_box(self, uuid: str, content: str) -> None:
         """
         Add a reply from the reply box.
         """
+        index = len(self.current_messages)
         conversation_item = ReplyWidget(
             uuid,
             content,
             'PENDING',
             self.controller.reply_ready,
             self.controller.reply_succeeded,
-            self.controller.reply_failed)
-        self.conversation_layout.addWidget(conversation_item, alignment=Qt.AlignRight)
+            self.controller.reply_failed,
+            index)
+        self.conversation_layout.insertWidget(index, conversation_item, alignment=Qt.AlignRight)
+        self.current_messages[uuid] = conversation_item
 
     def on_reply_sent(self, source_uuid: str, reply_uuid: str, reply_text: str) -> None:
         """
         Add the reply text sent from ReplyBoxWidget to the conversation.
         """
+        self.reply_flag = True
         if source_uuid == self.source.uuid:
             self.add_reply_from_reply_box(reply_uuid, reply_text)
 
@@ -2651,10 +2710,11 @@ def send_reply(self) -> None:
         """
         reply_text = self.text_edit.toPlainText().strip()
         if reply_text:
+            self.text_edit.clearFocus()  # Fixes #691
+            self.text_edit.setText('')
             reply_uuid = str(uuid4())
             self.controller.send_reply(self.source.uuid, reply_uuid, reply_text)
             self.reply_sent.emit(self.source.uuid, reply_uuid, reply_text)
-            self.text_edit.setText('')
 
     def _on_authentication_changed(self, authenticated: bool) -> None:
         if authenticated:
diff --git a/tests/factory.py b/tests/factory.py
index 4a66e7f59..2ef97f5b5 100644
--- a/tests/factory.py
+++ b/tests/factory.py
@@ -13,6 +13,7 @@
 FILE_COUNT = 0
 REPLY_COUNT = 0
 DRAFT_REPLY_COUNT = 0
+REPLY_SEND_STATUS_COUNT = 0
 USER_COUNT = 0
 
 
@@ -54,7 +55,7 @@ def Message(**attrs):
     global MESSAGE_COUNT
     MESSAGE_COUNT += 1
     defaults = dict(
-        uuid='source-uuid-{}'.format(MESSAGE_COUNT),
+        uuid='msg-uuid-{}'.format(MESSAGE_COUNT),
         filename='{}-msg.gpg'.format(MESSAGE_COUNT),
         size=123,
         download_url='http://wat.onion/abc',
@@ -72,7 +73,7 @@ def Reply(**attrs):
     global REPLY_COUNT
     REPLY_COUNT += 1
     defaults = dict(
-        uuid='source-uuid-{}'.format(REPLY_COUNT),
+        uuid='reply-uuid-{}'.format(REPLY_COUNT),
         filename='{}-reply.gpg'.format(REPLY_COUNT),
         size=123,
         is_decrypted=True,
@@ -95,6 +96,7 @@ def DraftReply(**attrs):
         file_counter=1,
         uuid='draft-reply-uuid-{}'.format(REPLY_COUNT),
         content='content',
+        send_status_id=1,
     )
 
     defaults.update(attrs)
@@ -102,11 +104,23 @@ def DraftReply(**attrs):
     return db.DraftReply(**defaults)
 
 
+def ReplySendStatus(**attrs):
+    global REPLY_SEND_STATUS_COUNT
+    REPLY_SEND_STATUS_COUNT += 1
+    defaults = dict(
+        name=db.ReplySendStatusCodes.PENDING.value,
+    )
+
+    defaults.update(attrs)
+
+    return db.ReplySendStatus(**defaults)
+
+
 def File(**attrs):
     global FILE_COUNT
     FILE_COUNT += 1
     defaults = dict(
-        uuid='source-uuid-{}'.format(FILE_COUNT),
+        uuid='file-uuid-{}'.format(FILE_COUNT),
         filename='{}-doc.gz.gpg'.format(FILE_COUNT),
         original_filename='{}-doc.txt'.format(FILE_COUNT),
         size=123,
diff --git a/tests/gui/test_widgets.py b/tests/gui/test_widgets.py
index 443590b21..07f2f3dc3 100644
--- a/tests/gui/test_widgets.py
+++ b/tests/gui/test_widgets.py
@@ -1279,7 +1279,7 @@ def test_SpeechBubble_init(mocker):
     mock_connect = mocker.Mock()
     mock_signal.connect = mock_connect
 
-    sb = SpeechBubble('mock id', 'hello', mock_signal)
+    sb = SpeechBubble('mock id', 'hello', mock_signal, 0)
     ss = sb.styleSheet()
 
     sb.message.text() == 'hello'
@@ -1294,7 +1294,7 @@ def test_SpeechBubble_update_text(mocker):
     mock_signal = mocker.MagicMock()
 
     msg_id = 'abc123'
-    sb = SpeechBubble(msg_id, 'hello', mock_signal)
+    sb = SpeechBubble(msg_id, 'hello', mock_signal, 0)
 
     new_msg = 'new message'
     sb._update_text(msg_id, new_msg)
@@ -1312,7 +1312,7 @@ def test_SpeechBubble_html_init(mocker):
     """
     mock_signal = mocker.MagicMock()
 
-    bubble = SpeechBubble('mock id', '<b>hello</b>', mock_signal)
+    bubble = SpeechBubble('mock id', '<b>hello</b>', mock_signal, 0)
     assert bubble.message.text() == '<b>hello</b>'
 
 
@@ -1321,7 +1321,7 @@ def test_SpeechBubble_with_apostrophe_in_text(mocker):
     mock_signal = mocker.MagicMock()
 
     message = "I'm sure, you are reading my message."
-    bubble = SpeechBubble('mock id', message, mock_signal)
+    bubble = SpeechBubble('mock id', message, mock_signal, 0)
     assert bubble.message.text() == message
 
 
@@ -1333,7 +1333,7 @@ def test_MessageWidget_init(mocker):
     mock_connected = mocker.Mock()
     mock_signal.connect = mock_connected
 
-    MessageWidget('mock id', 'hello', mock_signal)
+    MessageWidget('mock id', 'hello', mock_signal, 0)
 
     assert mock_connected.called
 
@@ -1361,6 +1361,7 @@ def test_ReplyWidget_init(mocker):
         mock_update_signal,
         mock_success_signal,
         mock_failure_signal,
+        0,
     )
 
     assert mock_update_connected.called
@@ -1379,7 +1380,7 @@ def test_FileWidget_init_file_not_downloaded(mocker, source, session):
     get_file = mocker.MagicMock(return_value=file)
     controller = mocker.MagicMock(get_file=get_file)
 
-    fw = FileWidget('mock', controller, mocker.MagicMock())
+    fw = FileWidget('mock', controller, mocker.MagicMock(), 0)
 
     assert fw.controller == controller
     assert fw.file.is_downloaded is False
@@ -1402,7 +1403,7 @@ def test_FileWidget_init_file_downloaded(mocker, source, session):
     get_file = mocker.MagicMock(return_value=file)
     controller = mocker.MagicMock(get_file=get_file)
 
-    fw = FileWidget('mock', controller, mocker.MagicMock())
+    fw = FileWidget('mock', controller, mocker.MagicMock(), 0)
 
     assert fw.controller == controller
     assert fw.file.is_downloaded is True
@@ -1431,7 +1432,7 @@ def test_FileWidget_event_handler(mocker, session, source):
     test_event = QEvent(QEvent.MouseButtonPress)
     test_event.button = mocker.MagicMock(return_value=Qt.LeftButton)
 
-    fw = FileWidget(file_.uuid, mock_controller, mock_signal)
+    fw = FileWidget(file_.uuid, mock_controller, mock_signal, 0)
     fw._on_left_click = mocker.MagicMock()
 
     fw.eventFilter(fw, test_event)
@@ -1454,7 +1455,7 @@ def test_FileWidget_on_left_click_download(mocker, session, source):
     mock_get_file = mocker.MagicMock(return_value=file_)
     mock_controller = mocker.MagicMock(get_file=mock_get_file)
 
-    fw = FileWidget(file_.uuid, mock_controller, mock_signal)
+    fw = FileWidget(file_.uuid, mock_controller, mock_signal, 0)
     fw.download_button = mocker.MagicMock()
     mock_get_file.assert_called_once_with(file_.uuid)
     mock_get_file.reset_mock()
@@ -1482,7 +1483,7 @@ def test_FileWidget_start_button_animation(mocker, session, source):
     session.commit()
     mock_get_file = mocker.MagicMock(return_value=file_)
     mock_controller = mocker.MagicMock(get_file=mock_get_file)
-    fw = FileWidget(file_.uuid, mock_controller, mock_signal)
+    fw = FileWidget(file_.uuid, mock_controller, mock_signal, 0)
     fw.download_button = mocker.MagicMock()
     fw.start_button_animation()
     # Check indicators of activity have been updated.
@@ -1504,7 +1505,7 @@ def test_FileWidget_on_left_click_open(mocker, session, source):
     mock_get_file = mocker.MagicMock(return_value=file_)
     mock_controller = mocker.MagicMock(get_file=mock_get_file)
 
-    fw = FileWidget(file_.uuid, mock_controller, mock_signal)
+    fw = FileWidget(file_.uuid, mock_controller, mock_signal, 0)
     fw._on_left_click()
     fw.controller.on_file_open.assert_called_once_with(file_.uuid)
 
@@ -1525,7 +1526,7 @@ def test_FileWidget_set_button_animation_frame(mocker, session, source):
     mock_get_file = mocker.MagicMock(return_value=file_)
     mock_controller = mocker.MagicMock(get_file=mock_get_file)
 
-    fw = FileWidget(file_.uuid, mock_controller, mock_signal)
+    fw = FileWidget(file_.uuid, mock_controller, mock_signal, 0)
     fw.download_button = mocker.MagicMock()
     fw.set_button_animation_frame(1)
     assert fw.download_button.setIcon.call_count == 1
@@ -1540,7 +1541,7 @@ def test_FileWidget_update(mocker, session, source):
     session.commit()
     get_file = mocker.MagicMock(return_value=file)
     controller = mocker.MagicMock(get_file=get_file)
-    fw = FileWidget(file.uuid, controller, mocker.MagicMock())
+    fw = FileWidget(file.uuid, controller, mocker.MagicMock(), 0)
 
     fw.update()
 
@@ -1560,7 +1561,7 @@ def test_FileWidget_on_file_download_updates_items_when_uuid_matches(mocker, sou
     get_file = mocker.MagicMock(return_value=file)
     controller = mocker.MagicMock(get_file=get_file)
 
-    fw = FileWidget(file.uuid, controller, mocker.MagicMock())
+    fw = FileWidget(file.uuid, controller, mocker.MagicMock(), 0)
     fw.update = mocker.MagicMock()
 
     fw._on_file_downloaded(file.uuid)
@@ -1586,7 +1587,7 @@ def test_FileWidget_on_file_download_updates_items_when_uuid_does_not_match(
     get_file = mocker.MagicMock(return_value=file)
     controller = mocker.MagicMock(get_file=get_file)
 
-    fw = FileWidget(file.uuid, controller, mocker.MagicMock())
+    fw = FileWidget(file.uuid, controller, mocker.MagicMock(), 0)
     fw.clear = mocker.MagicMock()
     fw.update = mocker.MagicMock()
 
@@ -1612,7 +1613,7 @@ def test_FileWidget__on_export_clicked(mocker, session, source):
     get_file = mocker.MagicMock(return_value=file)
     controller = mocker.MagicMock(get_file=get_file)
 
-    fw = FileWidget(file.uuid, controller, mocker.MagicMock())
+    fw = FileWidget(file.uuid, controller, mocker.MagicMock(), 0)
     fw.update = mocker.MagicMock()
     mocker.patch('securedrop_client.gui.widgets.QDialog.exec')
     controller.run_export_preflight_checks = mocker.MagicMock()
@@ -1639,7 +1640,7 @@ def test_FileWidget__on_export_clicked_missing_file(mocker, session, source):
     get_file = mocker.MagicMock(return_value=file)
     controller = mocker.MagicMock(get_file=get_file)
 
-    fw = FileWidget(file.uuid, controller, mocker.MagicMock())
+    fw = FileWidget(file.uuid, controller, mocker.MagicMock(), 0)
     fw.update = mocker.MagicMock()
     mocker.patch('securedrop_client.gui.widgets.QDialog.exec')
     controller.run_export_preflight_checks = mocker.MagicMock()
@@ -1663,7 +1664,7 @@ def test_FileWidget__on_print_clicked(mocker, session, source):
     get_file = mocker.MagicMock(return_value=file)
     controller = mocker.MagicMock(get_file=get_file)
 
-    fw = FileWidget(file.uuid, controller, mocker.MagicMock())
+    fw = FileWidget(file.uuid, controller, mocker.MagicMock(), 0)
     fw.update = mocker.MagicMock()
     mocker.patch('securedrop_client.gui.widgets.QDialog.exec')
     controller.print_file = mocker.MagicMock()
@@ -1690,7 +1691,7 @@ def test_FileWidget__on_print_clicked_missing_file(mocker, session, source):
     get_file = mocker.MagicMock(return_value=file)
     controller = mocker.MagicMock(get_file=get_file)
 
-    fw = FileWidget(file.uuid, controller, mocker.MagicMock())
+    fw = FileWidget(file.uuid, controller, mocker.MagicMock(), 0)
     fw.update = mocker.MagicMock()
     mocker.patch('securedrop_client.gui.widgets.QDialog.exec')
     controller.print_file = mocker.MagicMock()
@@ -2054,13 +2055,17 @@ def test_ConversationView_update_conversation_position_follow(mocker, homedir):
     """
     Check the signal handler sets the correct value for the scrollbar to be
     the maximum possible value, when the scrollbar is near the bottom, meaning
-    it is following the conversation.
+    it is following the conversation. This should only work if the user has
+    submitted a reply to a source.
     """
     mocked_source = mocker.MagicMock()
     mocked_controller = mocker.MagicMock()
 
     cv = ConversationView(mocked_source, mocked_controller)
 
+    # Flag to denote a reply was sent by the user.
+    cv.reply_flag = True
+
     cv.scroll.verticalScrollBar().value = mocker.MagicMock(return_value=5900)
     cv.scroll.viewport().height = mocker.MagicMock(return_value=500)
     cv.scroll.verticalScrollBar().setValue = mocker.MagicMock()
@@ -2111,14 +2116,14 @@ def test_ConversationView_add_message(mocker, session, source):
     mock_msg_widget = mocker.patch('securedrop_client.gui.widgets.MessageWidget',
                                    return_value=mock_msg_widget_res)
 
-    cv.add_message(message)
+    cv.add_message(message, 0)
 
     # check that we built the widget was called with the correct args
-    mock_msg_widget.assert_called_once_with(message.uuid, content, mock_message_ready_signal)
+    mock_msg_widget.assert_called_once_with(message.uuid, content, mock_message_ready_signal, 0)
 
     # check that we added the correct widget to the layout
-    cv.conversation_layout.addWidget.assert_called_once_with(
-        mock_msg_widget_res, alignment=Qt.AlignLeft)
+    cv.conversation_layout.insertWidget.assert_called_once_with(
+        0, mock_msg_widget_res, alignment=Qt.AlignLeft)
 
 
 def test_ConversationView_add_message_no_content(mocker, session, source):
@@ -2144,15 +2149,15 @@ def test_ConversationView_add_message_no_content(mocker, session, source):
     mock_msg_widget = mocker.patch('securedrop_client.gui.widgets.MessageWidget',
                                    return_value=mock_msg_widget_res)
 
-    cv.add_message(message)
+    cv.add_message(message, 0)
 
     # check that we built the widget was called with the correct args
     mock_msg_widget.assert_called_once_with(
-        message.uuid, '<Message not yet available>', mock_message_ready_signal)
+        message.uuid, '<Message not yet available>', mock_message_ready_signal, 0)
 
     # check that we added the correct widget to the layout
-    cv.conversation_layout.addWidget.assert_called_once_with(
-        mock_msg_widget_res, alignment=Qt.AlignLeft)
+    cv.conversation_layout.insertWidget.assert_called_once_with(
+        0, mock_msg_widget_res, alignment=Qt.AlignLeft)
 
 
 def test_ConversationView_on_reply_sent(mocker):
@@ -2164,9 +2169,11 @@ def test_ConversationView_on_reply_sent(mocker):
     cv = ConversationView(source, controller)
     cv.add_reply_from_reply_box = mocker.MagicMock()
 
+    assert cv.reply_flag is False
     cv.on_reply_sent(source.uuid, 'abc123', 'test message')
 
     cv.add_reply_from_reply_box.assert_called_with('abc123', 'test message')
+    assert cv.reply_flag is True
 
 
 def test_ConversationView_on_reply_sent_does_not_add_message_intended_for_different_source(mocker):
@@ -2203,9 +2210,9 @@ def test_ConversationView_add_reply_from_reply_box(mocker):
     cv.add_reply_from_reply_box('abc123', 'test message')
 
     reply_widget.assert_called_once_with(
-        'abc123', 'test message', 'PENDING', reply_ready, reply_succeeded, reply_failed)
-    cv.conversation_layout.addWidget.assert_called_once_with(
-        reply_widget_res, alignment=Qt.AlignRight)
+        'abc123', 'test message', 'PENDING', reply_ready, reply_succeeded, reply_failed, 0)
+    cv.conversation_layout.insertWidget.assert_called_once_with(
+        0, reply_widget_res, alignment=Qt.AlignRight)
 
 
 def test_ConversationView_add_reply(mocker, session, source):
@@ -2235,7 +2242,7 @@ def test_ConversationView_add_reply(mocker, session, source):
     mock_reply_widget = mocker.patch('securedrop_client.gui.widgets.ReplyWidget',
                                      return_value=reply_widget_res)
 
-    cv.add_reply(reply)
+    cv.add_reply(reply, 0)
 
     # check that we built the widget was called with the correct args
     mock_reply_widget.assert_called_once_with(
@@ -2244,11 +2251,12 @@ def test_ConversationView_add_reply(mocker, session, source):
         'SUCCEEDED',
         mock_reply_ready_signal,
         mock_reply_succeeded_signal,
-        mock_reply_failed_signal)
+        mock_reply_failed_signal,
+        0)
 
     # check that we added the correct widget to the layout
-    cv.conversation_layout.addWidget.assert_called_once_with(
-        reply_widget_res, alignment=Qt.AlignRight)
+    cv.conversation_layout.insertWidget.assert_called_once_with(
+        0, reply_widget_res, alignment=Qt.AlignRight)
 
 
 def test_ConversationView_add_reply_no_content(mocker, session, source):
@@ -2279,7 +2287,7 @@ def test_ConversationView_add_reply_no_content(mocker, session, source):
     mock_reply_widget = mocker.patch('securedrop_client.gui.widgets.ReplyWidget',
                                      return_value=reply_widget_res)
 
-    cv.add_reply(reply)
+    cv.add_reply(reply, 0)
 
     # check that we built the widget was called with the correct args
     mock_reply_widget.assert_called_once_with(
@@ -2288,11 +2296,12 @@ def test_ConversationView_add_reply_no_content(mocker, session, source):
         'SUCCEEDED',
         mock_reply_ready_signal,
         mock_reply_succeeded_signal,
-        mock_reply_failed_signal)
+        mock_reply_failed_signal,
+        0)
 
     # check that we added the correct widget to the layout
-    cv.conversation_layout.addWidget.assert_called_once_with(
-        reply_widget_res, alignment=Qt.AlignRight)
+    cv.conversation_layout.insertWidget.assert_called_once_with(
+        0, reply_widget_res, alignment=Qt.AlignRight)
 
 
 def test_ConversationView_add_downloaded_file(mocker, homedir, source, session):
@@ -2315,13 +2324,13 @@ def test_ConversationView_add_downloaded_file(mocker, homedir, source, session):
     mocker.patch('securedrop_client.gui.widgets.QHBoxLayout.addWidget')
     mocker.patch('securedrop_client.gui.widgets.FileWidget.setLayout')
 
-    cv.add_file(file)
+    cv.add_file(file, 0)
 
     mock_label.assert_called_with('123B')  # default factory filesize
-    assert cv.conversation_layout.addWidget.call_count == 1
+    assert cv.conversation_layout.insertWidget.call_count == 1
 
-    cal = cv.conversation_layout.addWidget.call_args_list
-    assert isinstance(cal[0][0][0], FileWidget)
+    cal = cv.conversation_layout.insertWidget.call_args_list
+    assert isinstance(cal[0][0][1], FileWidget)
 
 
 def test_ConversationView_add_not_downloaded_file(mocker, homedir, source, session):
@@ -2342,11 +2351,11 @@ def test_ConversationView_add_not_downloaded_file(mocker, homedir, source, sessi
     mocker.patch('securedrop_client.gui.widgets.QHBoxLayout.addWidget')
     mocker.patch('securedrop_client.gui.widgets.FileWidget.setLayout')
 
-    cv.add_file(file)
-    assert cv.conversation_layout.addWidget.call_count == 1
+    cv.add_file(file, 0)
+    assert cv.conversation_layout.insertWidget.call_count == 1
 
-    cal = cv.conversation_layout.addWidget.call_args_list
-    assert isinstance(cal[0][0][0], FileWidget)
+    cal = cv.conversation_layout.insertWidget.call_args_list
+    assert isinstance(cal[0][0][1], FileWidget)
 
 
 def test_DeleteSourceMessageBox_init(mocker, source):
@@ -2638,7 +2647,8 @@ def test_ReplyWidget_success_failure_slots(mocker):
                          'PENDING',
                          mock_update_signal,
                          mock_success_signal,
-                         mock_failure_signal)
+                         mock_failure_signal,
+                         0)
 
     # ensure we have connected the slots
     mock_success_signal.connect.assert_called_once_with(widget._on_reply_success)
@@ -2845,11 +2855,12 @@ def test_ReplyTextEdit_set_logged_in(mocker):
 
 def test_update_conversation_maintains_old_items(mocker, session):
     """
-    Calling update_conversation deletes and adds old items back to layout
+    Calling update_conversation maintains old item state / position if there's
+    no change to the conversation collection.
     """
     source = factory.Source()
     session.add(source)
-    session.flush()
+    session.commit()
 
     file_ = factory.File(filename='1-source-doc.gpg', source=source)
     session.add(file_)
@@ -2870,13 +2881,82 @@ def test_update_conversation_maintains_old_items(mocker, session):
     assert cv.conversation_layout.count() == 3
 
 
+def test_update_conversation_removes_draft_items(mocker, session):
+    """
+    Calling update_conversation removes items that were added as drafts.
+    """
+    source = factory.Source()
+    session.add(source)
+    send_status = factory.ReplySendStatus()
+    session.add(send_status)
+    session.commit()
+
+    file_ = factory.File(filename='1-source-doc.gpg', source=source)
+    session.add(file_)
+    message = factory.Message(filename='2-source-msg.gpg', source=source)
+    session.add(message)
+    draft_reply = factory.DraftReply(source=source, send_status=send_status)
+    session.add(draft_reply)
+    session.commit()
+
+    mock_get_file = mocker.MagicMock(return_value=file_)
+    mock_controller = mocker.MagicMock(get_file=mock_get_file)
+
+    cv = ConversationView(source, mock_controller)
+    assert cv.conversation_layout.count() == 3  # precondition with draft
+
+    # add the new message and persist
+    new_message = factory.Message(filename='4-source-msg.gpg', source=source)
+    session.add(new_message)
+    session.commit()
+
+    # New message added, draft message removed.
+    cv.update_conversation(cv.source.collection)
+    assert cv.conversation_layout.count() == 3
+
+
+def test_update_conversation_keeps_failed_draft_items(mocker, session):
+    """
+    Calling update_conversation keeps items that were added as drafts but which
+    have failed.
+    """
+    source = factory.Source()
+    session.add(source)
+    send_status = factory.ReplySendStatus(name="FAILED")
+    session.add(send_status)
+    session.commit()
+
+    file_ = factory.File(filename='1-source-doc.gpg', source=source)
+    session.add(file_)
+    message = factory.Message(filename='2-source-msg.gpg', source=source)
+    session.add(message)
+    draft_reply = factory.DraftReply(source=source, send_status=send_status)
+    session.add(draft_reply)
+    session.commit()
+
+    mock_get_file = mocker.MagicMock(return_value=file_)
+    mock_controller = mocker.MagicMock(get_file=mock_get_file)
+
+    cv = ConversationView(source, mock_controller)
+    assert cv.conversation_layout.count() == 3  # precondition with draft
+
+    # add the new message and persist
+    new_message = factory.Message(filename='4-source-msg.gpg', source=source)
+    session.add(new_message)
+    session.commit()
+
+    # New message added, draft message retained.
+    cv.update_conversation(cv.source.collection)
+    assert cv.conversation_layout.count() == 4
+
+
 def test_update_conversation_adds_new_items(mocker, session):
     """
     Calling update_conversation adds new items to layout
     """
     source = factory.Source()
     session.add(source)
-    session.flush()
+    session.commit()
 
     file_ = factory.File(filename='1-source-doc.gpg', source=source)
     session.add(file_)
@@ -2901,6 +2981,42 @@ def test_update_conversation_adds_new_items(mocker, session):
     assert cv.conversation_layout.count() == 4
 
 
+def test_update_conversation_position_updates(mocker, session):
+    """
+    Calling update_conversation adds new items to layout
+    """
+    source = factory.Source()
+    session.add(source)
+    session.commit()
+
+    file_ = factory.File(filename='1-source-doc.gpg', source=source)
+    session.add(file_)
+    message = factory.Message(filename='2-source-msg.gpg', source=source)
+    session.add(message)
+    reply = factory.Reply(filename='3-source-reply.gpg', source=source)
+    session.add(reply)
+    session.commit()
+
+    mock_get_file = mocker.MagicMock(return_value=file_)
+    mock_controller = mocker.MagicMock(get_file=mock_get_file)
+
+    cv = ConversationView(source, mock_controller)
+    assert cv.conversation_layout.count() == 3  # precondition
+
+    # Change the position of the Reply.
+    reply_widget = cv.current_messages[reply.uuid]
+    reply_widget.index = 1
+
+    # add the new message and persist
+    new_message = factory.Message(filename='4-source-msg.gpg', source=source)
+    session.add(new_message)
+    session.commit()
+
+    cv.update_conversation(cv.source.collection)
+    assert cv.conversation_layout.count() == 4
+    assert reply_widget.index == 2  # re-ordered.
+
+
 def test_update_conversation_content_updates(mocker, session):
     """
     Subsequent calls to update_conversation update the content of the conversation_item
@@ -2911,15 +3027,17 @@ def test_update_conversation_content_updates(mocker, session):
     mock_controller.session = session
     source = factory.Source()
     session.add(source)
-    session.flush()
+    session.commit()
 
     message = factory.Message(filename='2-source-msg.gpg', source=source, content=None)
     session.add(message)
     session.commit()
 
     cv = ConversationView(source, mock_controller)
+    cv.current_messages = {}  # Reset!
 
-    cv.conversation_layout.addWidget = mocker.MagicMock()
+    cv.conversation_layout.insertWidget = mocker.MagicMock()
+    cv.conversation_layout.removeWidget = mocker.MagicMock()
     # this is the MessageWidget that __init__() would return
     mock_msg_widget_res = mocker.MagicMock()
     # mock MessageWidget so we can inspect the __init__ call to see what content
@@ -2947,7 +3065,7 @@ def test_update_conversation_content_updates(mocker, session):
     cv.update_conversation(cv.source.collection)
 
     # Check that the widget was updated with the expected content.
-    assert mock_msg_widget.call_args[0][1] == expected_content
+    assert mock_msg_widget_res.message.setText.call_args[0][0] == expected_content
 
 
 def test_clear_conversation_deletes_items(mocker, homedir):
@@ -2958,7 +3076,7 @@ def test_clear_conversation_deletes_items(mocker, homedir):
     mock_source = mocker.MagicMock()
     message = db.Message(uuid='uuid', content='message', filename='1-foo')
     cv = ConversationView(mock_source, mock_controller)
-    cv.add_message(message)
+    cv.add_message(message, 0)
     assert cv.conversation_layout.count() == 1
 
     cv.clear_conversation()