diff --git a/fred2/eventeditor.cpp b/fred2/eventeditor.cpp
index 1423ab058b4..63857d3c5b4 100644
--- a/fred2/eventeditor.cpp
+++ b/fred2/eventeditor.cpp
@@ -100,6 +100,10 @@ event_editor::event_editor(CWnd* pParent /*=NULL*/)
 	m_log_last_trigger = 0;
 	m_log_state_change = 0;
 	m_play_icon = nullptr;
+	m_move_to_top_icon = nullptr;
+	m_move_up_icon = nullptr;
+	m_move_down_icon = nullptr;
+	m_move_to_bottom_icon = nullptr;
 }
 
 void event_editor::DoDataExchange(CDataExchange* pDX)
@@ -171,6 +175,7 @@ BEGIN_MESSAGE_MAP(event_editor, CDialog)
 	ON_BN_CLICKED(IDC_INSERT, OnInsert)
 	ON_LBN_SELCHANGE(IDC_MESSAGE_LIST, OnSelchangeMessageList)
 	ON_BN_CLICKED(IDC_NEW_MSG, OnNewMsg)
+	ON_BN_CLICKED(IDC_INSERT_MSG, OnInsertMsg)
 	ON_BN_CLICKED(IDC_DELETE_MSG, OnDeleteMsg)
 	ON_BN_CLICKED(IDC_NEW_NOTE, OnMsgNote)
 	ON_BN_CLICKED(IDC_BROWSE_AVI, OnBrowseAvi)
@@ -182,6 +187,14 @@ BEGIN_MESSAGE_MAP(event_editor, CDialog)
 	ON_CBN_SELCHANGE(IDC_EVENT_TEAM, OnSelchangeTeam)
 	ON_CBN_SELCHANGE(IDC_MESSAGE_TEAM, OnSelchangeMessageTeam)
 	ON_LBN_DBLCLK(IDC_MESSAGE_LIST, OnDblclkMessageList)
+	ON_BN_CLICKED(IDC_EVENT_MOVE_TO_TOP, OnEventMoveToTop)
+	ON_BN_CLICKED(IDC_EVENT_MOVE_UP, OnEventMoveUp)
+	ON_BN_CLICKED(IDC_EVENT_MOVE_DOWN, OnEventMoveDown)
+	ON_BN_CLICKED(IDC_EVENT_MOVE_TO_BOTTOM, OnEventMoveToBottom)
+	ON_BN_CLICKED(IDC_MESSAGE_MOVE_TO_TOP, OnMessageMoveToTop)
+	ON_BN_CLICKED(IDC_MESSAGE_MOVE_UP, OnMessageMoveUp)
+	ON_BN_CLICKED(IDC_MESSAGE_MOVE_DOWN, OnMessageMoveDown)
+	ON_BN_CLICKED(IDC_MESSAGE_MOVE_TO_BOTTOM, OnMessageMoveToBottom)
 	//}}AFX_MSG_MAP
 END_MESSAGE_MAP()
 
@@ -207,6 +220,22 @@ BOOL event_editor::OnInitDialog()
 	m_play_icon = load_button_icon(IDB_PLAY, RGB(192, 192, 192));
 	((CButton *) GetDlgItem(IDC_PLAY)) -> SetIcon(m_play_icon);
 
+	// reorder arrows; one icon is shared between the event and message buttons.
+	// Icons carry a transparency mask, so they blend with the button face and
+	// gray out correctly when disabled (see load_button_icon).
+	m_move_to_top_icon = load_button_icon(IDB_MOVE_TO_TOP, RGB(255, 0, 255));
+	m_move_up_icon = load_button_icon(IDB_MOVE_UP, RGB(255, 0, 255));
+	m_move_down_icon = load_button_icon(IDB_MOVE_DOWN, RGB(255, 0, 255));
+	m_move_to_bottom_icon = load_button_icon(IDB_MOVE_TO_BOTTOM, RGB(255, 0, 255));
+	((CButton *) GetDlgItem(IDC_EVENT_MOVE_TO_TOP)) -> SetIcon(m_move_to_top_icon);
+	((CButton *) GetDlgItem(IDC_EVENT_MOVE_UP)) -> SetIcon(m_move_up_icon);
+	((CButton *) GetDlgItem(IDC_EVENT_MOVE_DOWN)) -> SetIcon(m_move_down_icon);
+	((CButton *) GetDlgItem(IDC_EVENT_MOVE_TO_BOTTOM)) -> SetIcon(m_move_to_bottom_icon);
+	((CButton *) GetDlgItem(IDC_MESSAGE_MOVE_TO_TOP)) -> SetIcon(m_move_to_top_icon);
+	((CButton *) GetDlgItem(IDC_MESSAGE_MOVE_UP)) -> SetIcon(m_move_up_icon);
+	((CButton *) GetDlgItem(IDC_MESSAGE_MOVE_DOWN)) -> SetIcon(m_move_down_icon);
+	((CButton *) GetDlgItem(IDC_MESSAGE_MOVE_TO_BOTTOM)) -> SetIcon(m_move_to_bottom_icon);
+
 	theApp.init_window(&Events_wnd_data, this, 0);
 	m_event_tree.setup((CEdit *) GetDlgItem(IDC_HELP_BOX));
 	load_tree();
@@ -662,6 +691,7 @@ void event_editor::update_cur_message()
 	GetDlgItem(IDC_DELETE_MSG)->EnableWindow(enable);
 	GetDlgItem(IDC_PERSONA_NAME)->EnableWindow(enable);
 	GetDlgItem(IDC_MESSAGE_TEAM)->EnableWindow(enable);
+	update_move_buttons();
 	UpdateData(FALSE);
 }
 
@@ -1046,6 +1076,7 @@ void event_editor::update_cur_event()
 		GetDlgItem(IDC_MISSION_LOG_LAST_TRIGGER)->EnableWindow(FALSE);
 		GetDlgItem(IDC_MISSION_LOG_STATE_CHANGE)->EnableWindow(FALSE);
 
+		update_move_buttons();
 		UpdateData(FALSE);
 		return;
 	}
@@ -1112,6 +1143,7 @@ void event_editor::update_cur_event()
 	m_log_last_trigger = (m_events[cur_event].mission_log_flags & MLF_LAST_TRIGGER_ONLY) ? TRUE : FALSE;
 	m_log_state_change = (m_events[cur_event].mission_log_flags & MLF_STATE_CHANGE) ? TRUE : FALSE;
 
+	update_move_buttons();
 	UpdateData(FALSE);
 }
 
@@ -1187,7 +1219,121 @@ void event_editor::move_handler(int node1, int node2, bool insert_before)
 	update_cur_event();
 }
 
-void event_editor::OnChained() 
+// Enable/disable the event and message reorder arrows based on the current
+// selection and its position in the list.
+void event_editor::update_move_buttons()
+{
+	int ecount = (int)m_events.size();
+	BOOL e_up = (cur_event > 0 && cur_event < ecount) ? TRUE : FALSE;
+	BOOL e_down = (cur_event >= 0 && cur_event < ecount - 1) ? TRUE : FALSE;
+	GetDlgItem(IDC_EVENT_MOVE_TO_TOP)->EnableWindow(e_up);
+	GetDlgItem(IDC_EVENT_MOVE_UP)->EnableWindow(e_up);
+	GetDlgItem(IDC_EVENT_MOVE_DOWN)->EnableWindow(e_down);
+	GetDlgItem(IDC_EVENT_MOVE_TO_BOTTOM)->EnableWindow(e_down);
+
+	int mcount = (int)m_messages.size();
+	BOOL m_up = (m_cur_msg > 0 && m_cur_msg < mcount) ? TRUE : FALSE;
+	BOOL m_down = (m_cur_msg >= 0 && m_cur_msg < mcount - 1) ? TRUE : FALSE;
+	GetDlgItem(IDC_MESSAGE_MOVE_TO_TOP)->EnableWindow(m_up);
+	GetDlgItem(IDC_MESSAGE_MOVE_UP)->EnableWindow(m_up);
+	GetDlgItem(IDC_MESSAGE_MOVE_DOWN)->EnableWindow(m_down);
+	GetDlgItem(IDC_MESSAGE_MOVE_TO_BOTTOM)->EnableWindow(m_down);
+}
+
+// Reorder the currently-selected event.  'up'/'all_the_way' are interpreted as:
+// move up one, move to top, move down one, move to bottom.
+void event_editor::move_event(bool up, bool all_the_way)
+{
+	int count = (int)m_events.size();
+	if (cur_event < 0 || cur_event >= count)
+		return;
+
+	int from = cur_event;
+	int to;
+	if (up)
+		to = all_the_way ? 0 : from - 1;
+	else
+		to = all_the_way ? count - 1 : from + 1;
+
+	if (to < 0 || to >= count || to == from)
+		return;
+
+	// Perform the move exactly as a drag-and-drop would: move_root shifts the
+	// tree item in place (the on_node_handle_changed hook keeps annotations
+	// attached, and the expanded state is preserved), and move_handler reorders
+	// m_events/m_sig to match (it also calls save() and update_cur_event()).
+	HTREEITEM source = get_event_handle(from);
+	HTREEITEM dest = get_event_handle(to);
+	int node1 = m_events[from].formula;
+	int node2 = m_events[to].formula;
+	bool insert_before = (to < from);
+
+	m_event_tree.move_root(source, dest, insert_before);
+	move_handler(node1, node2, insert_before);
+
+	update_move_buttons();
+}
+
+// Reorder the currently-selected message.  'up'/'all_the_way' are interpreted
+// as: move up one, move to top, move down one, move to bottom.
+void event_editor::move_message(bool up, bool all_the_way)
+{
+	// commit any pending edits first
+	save();
+
+	int count = (int)m_messages.size();
+	if (m_cur_msg < 0 || m_cur_msg >= count)
+		return;
+
+	int from = m_cur_msg;
+	int to;
+	if (up)
+		to = all_the_way ? 0 : from - 1;
+	else
+		to = all_the_way ? count - 1 : from + 1;
+
+	if (to < 0 || to >= count || to == from)
+		return;
+
+	// Rotate m_messages so the item at 'from' lands at 'to'.  MMessage has move
+	// semantics, so this transfers the media-name pointers without copying.
+	MMessage m = std::move(m_messages[from]);
+	if (from < to)
+	{
+		for (int i = from; i < to; ++i)
+			m_messages[i] = std::move(m_messages[i + 1]);
+	}
+	else
+	{
+		for (int i = from; i > to; --i)
+			m_messages[i] = std::move(m_messages[i - 1]);
+	}
+	m_messages[to] = std::move(m);
+
+	// Rebuild the listbox to match the new order.
+	CListBox *list = (CListBox *) GetDlgItem(IDC_MESSAGE_LIST);
+	list->ResetContent();
+	for (const auto &msg : m_messages)
+		list->AddString(msg.name);
+
+	m_cur_msg = to;
+	list->SetCurSel(to);
+
+	update_cur_message();
+	update_move_buttons();
+	modified = 1;
+}
+
+void event_editor::OnEventMoveToTop()    { move_event(true, true); }
+void event_editor::OnEventMoveUp()       { move_event(true, false); }
+void event_editor::OnEventMoveDown()     { move_event(false, false); }
+void event_editor::OnEventMoveToBottom() { move_event(false, true); }
+void event_editor::OnMessageMoveToTop()    { move_message(true, true); }
+void event_editor::OnMessageMoveUp()       { move_message(true, false); }
+void event_editor::OnMessageMoveDown()     { move_message(false, false); }
+void event_editor::OnMessageMoveToBottom() { move_message(false, true); }
+
+void event_editor::OnChained()
 {
 	int image;
 	HTREEITEM h;
@@ -1332,7 +1478,39 @@ void event_editor::OnNewMsg()
 	update_cur_message();
 }
 
-void event_editor::OnDeleteMsg() 
+void event_editor::OnInsertMsg()
+{
+	// with no current message there's nothing to insert ahead of, so just append
+	if (m_cur_msg < 0 || m_messages.empty()) {
+		OnNewMsg();
+		return;
+	}
+
+	save();
+
+	MMessage msg;
+	strcpy_s(msg.name, "<new message>");
+	strcpy_s(msg.message, "<put description here>");
+	msg.avi_info.name = nullptr;
+	msg.wave_info.name = nullptr;
+	msg.persona_index = -1;
+	msg.multi_team = -1;
+
+	// insert ahead of the current message; the new one takes its slot
+	m_messages.insert(m_messages.begin() + m_cur_msg, std::move(msg));
+
+	// rebuild the listbox to match the new order
+	CListBox *list = (CListBox *) GetDlgItem(IDC_MESSAGE_LIST);
+	list->ResetContent();
+	for (const auto &m : m_messages)
+		list->AddString(m.name);
+	list->SetCurSel(m_cur_msg);
+
+	modified = 1;
+	update_cur_message();
+}
+
+void event_editor::OnDeleteMsg()
 {
 	char buf[256];
 
@@ -1524,6 +1702,10 @@ BOOL event_editor::DestroyWindow()
 	m_wave_id = -1;
 
 	if (m_play_icon) DestroyIcon(m_play_icon);
+	if (m_move_to_top_icon) DestroyIcon(m_move_to_top_icon);
+	if (m_move_up_icon) DestroyIcon(m_move_up_icon);
+	if (m_move_down_icon) DestroyIcon(m_move_down_icon);
+	if (m_move_to_bottom_icon) DestroyIcon(m_move_to_bottom_icon);
 	return CDialog::DestroyWindow();
 }
 
@@ -1674,6 +1856,21 @@ int event_annotation_lookup(HTREEITEM handle)
 	return -1;
 }
 
+// The tree recreated (moved) or deleted the item for a node.  Re-point any
+// annotation on the old handle to the new one so it follows the node; a null
+// new_handle means the node was deleted, which clears the handle.  The path is
+// left intact, so an annotation cleared this way is dropped at save (its path
+// can no longer be rebuilt) but survives a Cancel (the path still resolves).
+void event_sexp_tree::on_node_handle_changed(HTREEITEM old_handle, HTREEITEM new_handle)
+{
+	if (!old_handle)
+		return;
+
+	int i = event_annotation_lookup(old_handle);
+	if (i >= 0)
+		Event_annotations[i].handle = new_handle;
+}
+
 void event_annotation_swap_image(event_sexp_tree *tree, HTREEITEM handle, int annotation_index)
 {
 	event_annotation_swap_image(tree, handle, Event_annotations[annotation_index]);
diff --git a/fred2/eventeditor.h b/fred2/eventeditor.h
index 5cb77319730..0f4e34f0bad 100644
--- a/fred2/eventeditor.h
+++ b/fred2/eventeditor.h
@@ -31,6 +31,10 @@ class event_sexp_tree : public sexp_tree
 	virtual void PreSubclassWindow();
 	virtual void OnCustomDraw(NMHDR* pNMHDR, LRESULT* pResult);
 
+	// keep event annotations attached to their node when the tree recreates or
+	// deletes its handle (new_handle == nullptr means the node was deleted)
+	void on_node_handle_changed(HTREEITEM old_handle, HTREEITEM new_handle) override;
+
 	CStringA m_tooltiptextA;
 	CStringW m_tooltiptextW;
 
@@ -109,6 +113,10 @@ class event_editor : public CDialog
 	//}}AFX_DATA
 
 	HICON m_play_icon;
+	HICON m_move_to_top_icon;
+	HICON m_move_up_icon;
+	HICON m_move_down_icon;
+	HICON m_move_to_bottom_icon;
 
 // Overrides
 	// ClassWizard generated virtual function overrides
@@ -140,6 +148,7 @@ class event_editor : public CDialog
 	afx_msg void OnInsert();
 	afx_msg void OnSelchangeMessageList();
 	afx_msg void OnNewMsg();
+	afx_msg void OnInsertMsg();
 	afx_msg void OnDeleteMsg();
 	afx_msg void OnMsgNote();
 	afx_msg void OnBrowseAvi();
@@ -150,12 +159,23 @@ class event_editor : public CDialog
 	afx_msg void OnSelchangeTeam();
 	afx_msg void OnSelchangeMessageTeam();
 	afx_msg void OnDblclkMessageList();
+	afx_msg void OnEventMoveToTop();
+	afx_msg void OnEventMoveUp();
+	afx_msg void OnEventMoveDown();
+	afx_msg void OnEventMoveToBottom();
+	afx_msg void OnMessageMoveToTop();
+	afx_msg void OnMessageMoveUp();
+	afx_msg void OnMessageMoveDown();
+	afx_msg void OnMessageMoveToBottom();
 	//}}AFX_MSG
 	DECLARE_MESSAGE_MAP()
 
 private:
 	int cur_event;
 	void update_cur_event();
+	void move_event(bool up, bool all_the_way);
+	void move_message(bool up, bool all_the_way);
+	void update_move_buttons();
 	SCP_vector<int> m_sig;
 	SCP_vector<mission_event> m_events;
 	SCP_vector<MMessage> m_messages;
diff --git a/fred2/fred.rc b/fred2/fred.rc
index a668814effe..8f2f009cd6f 100644
--- a/fred2/fred.rc
+++ b/fred2/fred.rc
@@ -158,6 +158,14 @@ IDB_CONTAINER_NAME      BITMAP                  "res\\container_name.bmp"
 
 IDB_CONTAINER_DATA      BITMAP                  "res\\container_data.bmp"
 
+IDB_MOVE_TO_TOP         BITMAP                  "res\\move_top.bmp"
+
+IDB_MOVE_UP             BITMAP                  "res\\move_up.bmp"
+
+IDB_MOVE_DOWN           BITMAP                  "res\\move_down.bmp"
+
+IDB_MOVE_TO_BOTTOM      BITMAP                  "res\\move_bot.bmp"
+
 
 /////////////////////////////////////////////////////////////////////////////
 //
@@ -1455,9 +1463,9 @@ CAPTION "Mission Event Edit"
 FONT 8, "MS Sans Serif", 0, 0, 0x1
 BEGIN
     CONTROL         "Tree1",IDC_EVENT_TREE,"SysTreeView32",TVS_HASBUTTONS | TVS_HASLINES | TVS_LINESATROOT | TVS_EDITLABELS | TVS_SHOWSELALWAYS | WS_BORDER | WS_HSCROLL | WS_TABSTOP,7,7,196,343,WS_EX_CLIENTEDGE
-    PUSHBUTTON      "New Event",IDC_BUTTON_NEW_EVENT,207,7,50,14,0,WS_EX_STATICEDGE,HIDC_BUTTON_NEW_EVENT
-    PUSHBUTTON      "Insert Event",IDC_INSERT,207,24,50,14,0,WS_EX_STATICEDGE
-    PUSHBUTTON      "Delete Event",IDC_DELETE,207,41,50,14,0,WS_EX_STATICEDGE
+    PUSHBUTTON      "New Event",IDC_BUTTON_NEW_EVENT,227,7,48,14,0,WS_EX_STATICEDGE,HIDC_BUTTON_NEW_EVENT
+    PUSHBUTTON      "Insert Event",IDC_INSERT,227,23,48,14,0,WS_EX_STATICEDGE
+    PUSHBUTTON      "Delete Event",IDC_DELETE,227,39,48,14,0,WS_EX_STATICEDGE
     EDITTEXT        IDC_REPEAT_COUNT,208,108,45,14,ES_AUTOHSCROLL
     EDITTEXT        IDC_INTERVAL_TIME,208,165,45,14,ES_AUTOHSCROLL | ES_NUMBER
     EDITTEXT        IDC_EVENT_SCORE,208,239,45,14,ES_AUTOHSCROLL
@@ -1468,9 +1476,10 @@ BEGIN
     EDITTEXT        IDC_OBJ_TEXT,86,354,117,14,ES_AUTOHSCROLL
     EDITTEXT        IDC_OBJ_KEY_TEXT,86,370,117,14,ES_AUTOHSCROLL
     EDITTEXT        IDC_HELP_BOX,208,313,222,111,ES_MULTILINE | ES_AUTOVSCROLL | ES_READONLY | WS_VSCROLL,WS_EX_TRANSPARENT
-    PUSHBUTTON      "New Msg",IDC_NEW_MSG,229,59,50,14,0,WS_EX_STATICEDGE
-    PUSHBUTTON      "Delete Msg",IDC_DELETE_MSG,229,77,50,14,0,WS_EX_STATICEDGE
-    LISTBOX         IDC_MESSAGE_LIST,285,17,145,74,LBS_NOINTEGRALHEIGHT | WS_VSCROLL | WS_TABSTOP
+    PUSHBUTTON      "New Msg",IDC_NEW_MSG,387,7,43,14,0,WS_EX_STATICEDGE
+    PUSHBUTTON      "Insert Msg",IDC_INSERT_MSG,387,23,43,14,0,WS_EX_STATICEDGE
+    PUSHBUTTON      "Delete Msg",IDC_DELETE_MSG,387,39,43,14,0,WS_EX_STATICEDGE
+    LISTBOX         IDC_MESSAGE_LIST,285,7,78,84,LBS_NOINTEGRALHEIGHT | WS_VSCROLL | WS_TABSTOP
     EDITTEXT        IDC_MESSAGE_NAME,285,95,145,14,ES_AUTOHSCROLL
     EDITTEXT        IDC_MESSAGE_TEXT,261,125,169,54,ES_MULTILINE | ES_AUTOVSCROLL | ES_WANTRETURN
     COMBOBOX        IDC_AVI_FILENAME,303,194,67,111,CBS_DROPDOWN | CBS_AUTOHSCROLL | CBS_SORT | WS_VSCROLL | WS_TABSTOP
@@ -1490,7 +1499,6 @@ BEGIN
     LTEXT           "Directive keypress text",IDC_STATIC,7,372,74,8
     LTEXT           "Message Text",IDC_STATIC,261,114,48,8
     LTEXT           "Name",IDC_STATIC,261,97,20,8
-    LTEXT           "Messages",IDC_STATIC,335,7,35,8
     LTEXT           "ANI file",IDC_STATIC,275,197,23,8
     LTEXT           "Wave file",IDC_STATIC,267,212,31,8
     LTEXT           "Persona",IDC_STATIC,271,227,27,8
@@ -1511,6 +1519,14 @@ BEGIN
     LTEXT           "Log These States To The Event.log",IDC_STATIC,37,386,114,8
     CONTROL         "Interval && Chain in Milliseconds",IDC_USE_MSECS,"Button",BS_AUTOCHECKBOX | BS_MULTILINE | WS_TABSTOP,208,275,65,19
     PUSHBUTTON      "Add Note",IDC_NEW_NOTE,380,111,50,12,0,WS_EX_STATICEDGE
+    PUSHBUTTON      "Top",IDC_EVENT_MOVE_TO_TOP,207,7,16,16,BS_ICON,WS_EX_STATICEDGE
+    PUSHBUTTON      "Up",IDC_EVENT_MOVE_UP,207,23,16,16,BS_ICON,WS_EX_STATICEDGE
+    PUSHBUTTON      "Down",IDC_EVENT_MOVE_DOWN,207,39,16,16,BS_ICON,WS_EX_STATICEDGE
+    PUSHBUTTON      "Bottom",IDC_EVENT_MOVE_TO_BOTTOM,207,55,16,16,BS_ICON,WS_EX_STATICEDGE
+    PUSHBUTTON      "Top",IDC_MESSAGE_MOVE_TO_TOP,367,7,16,16,BS_ICON,WS_EX_STATICEDGE
+    PUSHBUTTON      "Up",IDC_MESSAGE_MOVE_UP,367,23,16,16,BS_ICON,WS_EX_STATICEDGE
+    PUSHBUTTON      "Down",IDC_MESSAGE_MOVE_DOWN,367,39,16,16,BS_ICON,WS_EX_STATICEDGE
+    PUSHBUTTON      "Bottom",IDC_MESSAGE_MOVE_TO_BOTTOM,367,55,16,16,BS_ICON,WS_EX_STATICEDGE
 END
 
 IDD_BG_BITMAP DIALOGEX 0, 0, 431, 470
@@ -3412,8 +3428,9 @@ BEGIN
     0, 100, 50, 0,
     0, 100, 50, 0,
     50, 50, 50, 50,
-    50, 50, 0, 0,
-    50, 50, 0, 0,
+    100, 0, 0, 0,
+    100, 0, 0, 0,
+    100, 0, 0, 0,
     50, 0, 50, 50,
     50, 50, 50, 0,
     50, 50, 50, 0,
@@ -3434,7 +3451,6 @@ BEGIN
     0, 100, 0, 0,
     50, 50, 0, 0,
     50, 50, 0, 0,
-    75, 0, 0, 0,
     50, 50, 0, 0,
     50, 50, 0, 0,
     50, 50, 0, 0,
@@ -3454,7 +3470,15 @@ BEGIN
     25, 100, 0, 0,
     25, 100, 0, 0,
     50, 50, 0, 0,
-    50, 50, 0, 0
+    100, 50, 0, 0,
+    50, 0, 0, 0,
+    50, 0, 0, 0,
+    50, 0, 0, 0,
+    50, 0, 0, 0,
+    100, 0, 0, 0,
+    100, 0, 0, 0,
+    100, 0, 0, 0,
+    100, 0, 0, 0
 END
 
 IDD_ASTEROID_EDITOR AFX_DIALOG_LAYOUT
diff --git a/fred2/res/move_bot.bmp b/fred2/res/move_bot.bmp
new file mode 100644
index 00000000000..b2224d50d8c
Binary files /dev/null and b/fred2/res/move_bot.bmp differ
diff --git a/fred2/res/move_bot2.bmp b/fred2/res/move_bot2.bmp
new file mode 100644
index 00000000000..7d6777b7e5c
Binary files /dev/null and b/fred2/res/move_bot2.bmp differ
diff --git a/fred2/res/move_down.bmp b/fred2/res/move_down.bmp
new file mode 100644
index 00000000000..6ff650c2605
Binary files /dev/null and b/fred2/res/move_down.bmp differ
diff --git a/fred2/res/move_down2.bmp b/fred2/res/move_down2.bmp
new file mode 100644
index 00000000000..cadaa2d8d7b
Binary files /dev/null and b/fred2/res/move_down2.bmp differ
diff --git a/fred2/res/move_top.bmp b/fred2/res/move_top.bmp
new file mode 100644
index 00000000000..9993a4490bd
Binary files /dev/null and b/fred2/res/move_top.bmp differ
diff --git a/fred2/res/move_top2.bmp b/fred2/res/move_top2.bmp
new file mode 100644
index 00000000000..293f3de6931
Binary files /dev/null and b/fred2/res/move_top2.bmp differ
diff --git a/fred2/res/move_up.bmp b/fred2/res/move_up.bmp
new file mode 100644
index 00000000000..3dba22e08e4
Binary files /dev/null and b/fred2/res/move_up.bmp differ
diff --git a/fred2/res/move_up2.bmp b/fred2/res/move_up2.bmp
new file mode 100644
index 00000000000..7c8ab57b925
Binary files /dev/null and b/fred2/res/move_up2.bmp differ
diff --git a/fred2/resource.h b/fred2/resource.h
index 35e6ed4f750..f05d12a8885 100644
--- a/fred2/resource.h
+++ b/fred2/resource.h
@@ -138,6 +138,11 @@
 #define IDD_VOLUMETRICS                 332
 #define IDD_EDIT_CUSTOM_STRINGS         333
 #define IDD_SUPPORT_REARM_OPTIONS       334
+#define IDD_REORDER                     335
+#define IDB_MOVE_TO_TOP                 336
+#define IDB_MOVE_UP                     337
+#define IDB_MOVE_DOWN                   338
+#define IDB_MOVE_TO_BOTTOM              339
 #define IDC_SHIP_CLASS                  1003
 #define IDC_SHIP_WING                   1004
 #define IDC_SOUND_CLIP_NAME             1007
@@ -1290,6 +1295,21 @@
 #define IDC_SUPPORT_REARM_SET_ALL_UNLIMITED 1729
 #define IDC_SUPPORT_REARM_SET_ALL_ZERO   1730
 #define IDC_SUPPORT_REARM_POOL_TEAM      1731
+#define IDC_REORDER_TYPE                1732
+#define IDC_REORDER_LIST                1733
+#define IDC_REORDER_MOVE_TO_TOP         1734
+#define IDC_REORDER_MOVE_UP             1735
+#define IDC_REORDER_MOVE_DOWN           1736
+#define IDC_REORDER_MOVE_TO_BOTTOM      1737
+#define IDC_EVENT_MOVE_TO_TOP           1738
+#define IDC_EVENT_MOVE_UP               1739
+#define IDC_EVENT_MOVE_DOWN             1740
+#define IDC_EVENT_MOVE_TO_BOTTOM        1741
+#define IDC_MESSAGE_MOVE_TO_TOP         1742
+#define IDC_MESSAGE_MOVE_UP             1743
+#define IDC_MESSAGE_MOVE_DOWN           1744
+#define IDC_MESSAGE_MOVE_TO_BOTTOM      1745
+#define IDC_INSERT_MSG                  1746
 #define IDC_SEXP_POPUP_LIST             32770
 #define ID_FILE_MISSIONNOTES            32771
 #define ID_DUPLICATE                    32774
@@ -1604,9 +1624,9 @@
 #ifdef APSTUDIO_INVOKED
 #ifndef APSTUDIO_READONLY_SYMBOLS
 #define _APS_3D_CONTROLS                     1
-#define _APS_NEXT_RESOURCE_VALUE        335
+#define _APS_NEXT_RESOURCE_VALUE        340
+#define _APS_NEXT_CONTROL_VALUE         1747
 #define _APS_NEXT_COMMAND_VALUE         33112
-#define _APS_NEXT_CONTROL_VALUE         1732
 #define _APS_NEXT_SYMED_VALUE           105
 #endif
 #endif
diff --git a/fred2/sexp_tree.cpp b/fred2/sexp_tree.cpp
index a37a1d03cdf..8d6372cee39 100644
--- a/fred2/sexp_tree.cpp
+++ b/fred2/sexp_tree.cpp
@@ -479,6 +479,11 @@ void sexp_tree::free_node2(int node)
 	Assert(tree_nodes[node].type != SEXPT_UNUSED);
 	Assert(total_nodes > 0);
 	*modified = 1;
+
+	// the node is being deleted; let subclasses drop anything attached to its handle
+	if (tree_nodes[node].handle)
+		on_node_handle_changed(tree_nodes[node].handle, nullptr);
+
 	tree_nodes[node].type = SEXPT_UNUSED;
 	total_nodes--;
 	if (tree_nodes[node].child != -1)
@@ -2640,6 +2645,9 @@ void sexp_tree::NodeDelete()
 
 		Assert(theNode >= 0);
 		free_node2(theNode);
+		// the event-root item is not a tree_nodes entry, so free_node2 above does
+		// not cover an annotation attached to the event root itself
+		on_node_handle_changed(item_handle, nullptr);
 		DeleteItem(item_handle);
 		*modified = 1;
 		return;
@@ -4668,6 +4676,10 @@ HTREEITEM sexp_tree::move_branch(HTREEITEM source, HTREEITEM parent, HTREEITEM a
   			h = insert(GetItemText(source), image1, image2, parent, after);
 		}
 
+		// the item was recreated with a new handle; let subclasses follow it
+		// (covers both tree_nodes entries and the event-root item, which is not one)
+		on_node_handle_changed(source, h);
+
 		SetItemData(h, GetItemData(source));
 		child = GetChildItem(source);
 		while (child) {
diff --git a/fred2/sexp_tree.h b/fred2/sexp_tree.h
index fd712f4009d..3dffb01afc6 100644
--- a/fred2/sexp_tree.h
+++ b/fred2/sexp_tree.h
@@ -367,6 +367,11 @@ class sexp_tree : public CTreeCtrl
 	virtual void NodeReplacePaste();
 	virtual void NodeAddPaste();
 
+	// Notifies that the tree item for a node changed handle (moved/recreated), or
+	// was deleted (new_handle == nullptr).  The event tree overrides this to keep
+	// event annotations attached to their node.  Default: no-op.
+	virtual void on_node_handle_changed(HTREEITEM /*old_handle*/, HTREEITEM /*new_handle*/) {}
+
 	void update_item(HTREEITEM handle);
 
 	int load_branch(int index, int parent);
diff --git a/qtfred/src/mission/dialogs/MissionEventsDialogModel.cpp b/qtfred/src/mission/dialogs/MissionEventsDialogModel.cpp
index 386b59b7dc3..7d9a4c2bb82 100644
--- a/qtfred/src/mission/dialogs/MissionEventsDialogModel.cpp
+++ b/qtfred/src/mission/dialogs/MissionEventsDialogModel.cpp
@@ -609,8 +609,12 @@ void MissionEventsDialogModel::reorderByRootFormulaOrder(const SCP_vector<int>&
 	// Keep selection reasonable (select the first event after reorder)
 	setCurrentlySelectedEvent(m_events.empty() ? -1 : 0);
 
-	// Rebuild applied annotations against new handles/order if needed
-	initializeEventAnnotations();
+	// A root reorder moves top-level items via take/insert, which preserves their
+	// handles (see sexp_tree::move_root), so the cached annotation handles are still
+	// valid and still point at the correct nodes.  Do NOT re-resolve handles from the
+	// stored paths here: the paths carry the pre-reorder event index, so re-resolving
+	// would re-point annotations at the wrong event.  applyAnnotations() rebuilds each
+	// path from its live handle at save time.
 
 	set_modified();
 }
@@ -1138,6 +1142,20 @@ void MissionEventsDialogModel::setNodeBgColor(IEventTreeOps::Handle h, int r, in
 	set_modified();
 }
 
+// The tree recreated (moved) or deleted the item for a node.  Re-point any
+// annotation on the old handle to the new one so it follows the node; a null
+// new_handle means the node was deleted, which clears the cached handle so
+// applyAnnotations() resolves it from the path (and drops it if the node is gone).
+void MissionEventsDialogModel::onNodeHandleChanged(IEventTreeOps::Handle old_handle, IEventTreeOps::Handle new_handle)
+{
+	if (!old_handle)
+		return;
+
+	for (auto& ea : m_event_annotations)
+		if (ea.handle == old_handle)
+			ea.handle = new_handle;
+}
+
 void MissionEventsDialogModel::createMessage()
 {
 	MMessage msg;
diff --git a/qtfred/src/mission/dialogs/MissionEventsDialogModel.h b/qtfred/src/mission/dialogs/MissionEventsDialogModel.h
index 99699ad80a3..fdfb00397b2 100644
--- a/qtfred/src/mission/dialogs/MissionEventsDialogModel.h
+++ b/qtfred/src/mission/dialogs/MissionEventsDialogModel.h
@@ -142,6 +142,10 @@ class MissionEventsDialogModel : public AbstractDialogModel {
 	void setNodeAnnotation(IEventTreeOps::Handle h, const SCP_string& note);
 	void setNodeBgColor(IEventTreeOps::Handle h, int r, int g, int b, bool has_color);
 
+	// Keep annotations attached to their node when the tree recreates (move) or
+	// deletes (new_handle == nullptr) the item's handle.
+	void onNodeHandleChanged(IEventTreeOps::Handle old_handle, IEventTreeOps::Handle new_handle);
+
 	// Message Management
 	void createMessage();
 	void insertMessage();
diff --git a/qtfred/src/ui/dialogs/MissionEventsDialog.cpp b/qtfred/src/ui/dialogs/MissionEventsDialog.cpp
index d8a033df3a5..7c7cc94c795 100644
--- a/qtfred/src/ui/dialogs/MissionEventsDialog.cpp
+++ b/qtfred/src/ui/dialogs/MissionEventsDialog.cpp
@@ -245,6 +245,10 @@ void MissionEventsDialog::initEventWidgets() {
 		_model->setNodeBgColor(h, c.red(), c.green(), c.blue(), c.isValid());
 	});
 
+	connect(ui->eventTree, &sexp_tree::nodeHandleChanged, this, [this](void* old_h, void* new_h) {
+		_model->onNodeHandleChanged(old_h, new_h);
+	});
+
 	connect(ui->eventTree, &sexp_tree::rootOrderChanged, this, [this] {
 		SCP_vector<int> order;
 		order.reserve(ui->eventTree->topLevelItemCount());
diff --git a/qtfred/src/ui/widgets/sexp_tree.cpp b/qtfred/src/ui/widgets/sexp_tree.cpp
index c4e0d23e7f8..6b1e6f72e79 100644
--- a/qtfred/src/ui/widgets/sexp_tree.cpp
+++ b/qtfred/src/ui/widgets/sexp_tree.cpp
@@ -673,6 +673,11 @@ void sexp_tree::free_node2(int node) {
 	Assert(tree_nodes[node].type != SEXPT_UNUSED);
 	Assert(total_nodes > 0);
 	modified();
+
+	// the node is being deleted; let the model drop anything attached to its handle
+	if (tree_nodes[node].handle)
+		nodeHandleChanged(tree_nodes[node].handle, nullptr);
+
 	tree_nodes[node].type = SEXPT_UNUSED;
 	total_nodes--;
 	if (tree_nodes[node].child != -1) {
@@ -2739,6 +2744,9 @@ QTreeWidgetItem* sexp_tree::move_branch(QTreeWidgetItem* source, QTreeWidgetItem
 	h->setData(0, BgColorRole, source->data(0, BgColorRole));
 	applyVisuals(h);
 
+	// the item was recreated with a new handle; let the model follow it
+	nodeHandleChanged(source, h);
+
 	// Move children safely
 	while (source->childCount() > 0) {
 		auto* child = source->child(0);
@@ -7297,6 +7305,10 @@ void sexp_tree::deleteActionHandler()
 			free_node2(formulaNode);
 		}
 
+		// the event-root item is not a tree_nodes entry, so free_node2 above does
+		// not cover an annotation attached to the event root itself
+		nodeHandleChanged(item, nullptr);
+
 		// Remove the UI item and reset selection/index
 		delete item;
 		setCurrentItemIndex(-1);
diff --git a/qtfred/src/ui/widgets/sexp_tree.h b/qtfred/src/ui/widgets/sexp_tree.h
index 6385b08aa16..6b939c7405f 100644
--- a/qtfred/src/ui/widgets/sexp_tree.h
+++ b/qtfred/src/ui/widgets/sexp_tree.h
@@ -410,6 +410,11 @@ class sexp_tree: public QTreeWidget {
 	void nodeAnnotationChanged(void* handle, const QString& note);
 	void nodeBgColorChanged(void* handle, const QColor& color);
 
+	// Emitted when a node's tree item changed handle (moved/recreated), or was
+	// deleted (new_handle == nullptr).  Lets the model keep event annotations
+	// attached to their node across tree mutations.
+	void nodeHandleChanged(void* old_handle, void* new_handle);
+
 	// Generated message map functions
  protected:
 	void keyPressEvent(QKeyEvent* e) override;