diff --git a/code/hud/hudsquadmsg.cpp b/code/hud/hudsquadmsg.cpp
index 7d793d7116f..2a3dc2dbae3 100644
--- a/code/hud/hudsquadmsg.cpp
+++ b/code/hud/hudsquadmsg.cpp
@@ -104,8 +104,7 @@ int Menu_pgdn_coords[GR_NUM_RESOLUTIONS][2] = {
 // following defines/vars are used to build menus that are used in messaging mode
 
 char Squad_msg_title[256] = "";
-mmode_item MsgItems[MAX_MENU_ITEMS];
-int Num_menu_items = -1; // number of items for a message menu
+std::optional<SCP_vector<mmode_item>> MsgItems;
 
 static int First_menu_item = -1;							// index of first item in the menu. This tracks what element of comms options collection is displayed as first option, and displays the next 9 options. Changes only by +/- MAX_MENU_ITEMS (10)
 static int Selected_menu_item = First_menu_item;           //!< index of selected item in the menu. Possible index range: 0 - 9, assuming MAX_MENU_ITEMS == 10, and First_menu_item gets initialized
@@ -218,7 +217,7 @@ void hud_squadmsg_start()
 	Msg_key = -1;
 	Msg_key_set_from_scripting = false;
 
-	Num_menu_items = -1;													// reset the menu items
+	MsgItems.reset();												// reset the menu items
 	First_menu_item = 0;
 	Selected_menu_item = First_menu_item;                            // make first menu item a selected object
 	Display_selector = false;
@@ -376,11 +375,7 @@ int hud_squadmsg_count_ships(int add_to_menu)
 		count++;
 		if (add_to_menu)
 		{
-			Assert ( Num_menu_items < MAX_MENU_ITEMS );
-			MsgItems[Num_menu_items].text = shipp->get_display_name();
-			MsgItems[Num_menu_items].instance = SHIP_INDEX(shipp);
-			MsgItems[Num_menu_items].active = 1;
-			Num_menu_items++;
+			MsgItems.value().emplace_back(SHIP_INDEX(shipp), 1, shipp->get_display_name());
 		}
 	}
 
@@ -431,11 +426,7 @@ int hud_squadmsg_count_wings( int add_to_menu )
 		if ( hud_squadmsg_wing_valid(&Wings[wingnum]) ) {
 			count++;
 			if ( add_to_menu ) {
-				Assert ( Num_menu_items < MAX_MENU_ITEMS );
-				MsgItems[Num_menu_items].text = Wings[wingnum].get_display_name();
-				MsgItems[Num_menu_items].instance = wingnum;
-				MsgItems[Num_menu_items].active = 1;
-				Num_menu_items++;
+				MsgItems.value().emplace_back(wingnum, 1, Wings[wingnum].get_display_name());
 			}
 		}
 	}
@@ -452,11 +443,7 @@ int hud_squadmsg_count_wings( int add_to_menu )
 		if ( hud_squadmsg_wing_valid(&Wings[i]) ) {
 			count++;
 			if ( add_to_menu ) {
-				Assert ( Num_menu_items < MAX_MENU_ITEMS );
-				MsgItems[Num_menu_items].text = Wings[i].get_display_name();
-				MsgItems[Num_menu_items].instance = i;
-				MsgItems[Num_menu_items].active = 1;
-				Num_menu_items++;
+				MsgItems.value().emplace_back(i, 1, Wings[i].get_display_name());
 			}
 		}
 	}
@@ -469,15 +456,15 @@ int hud_squadmsg_count_wings( int add_to_menu )
 void hud_squadmsg_do_mode( int mode )
 {
 	Squad_msg_mode = mode;
-	Num_menu_items = -1;
+	MsgItems.reset();
 	First_menu_item = 0;
 }
 
 void hud_squadmsg_page_down()
 {
-	if ( (First_menu_item + MAX_MENU_DISPLAY) < Num_menu_items ) {
+	if ( (First_menu_item + MAX_MENU_DISPLAY) < (MsgItems ? (int)MsgItems.value().size() : -1) ) {
 		First_menu_item += MAX_MENU_DISPLAY;
-		Assert ( First_menu_item < Num_menu_items );
+		Assert ( First_menu_item < (MsgItems ? (int)MsgItems.value().size() : -1) );
 	}
 }
 
@@ -505,14 +492,14 @@ void hud_squadmsg_selection_move_down() {
 
 		//Move to next page if we went outside of current one
 		if (Selected_menu_item == MAX_MENU_DISPLAY 
-			&& (First_menu_item + MAX_MENU_DISPLAY < Num_menu_items))
+			&& (First_menu_item + MAX_MENU_DISPLAY < (MsgItems ? (int)MsgItems.value().size() : -1)))
 		{
 			hud_squadmsg_page_down();
 			Selected_menu_item = 0;
 		}
 
 		//Select the first menu item if we went outside items range, so we can loop around
-		if (First_menu_item + Selected_menu_item >= Num_menu_items) 
+		if (First_menu_item + Selected_menu_item >= (MsgItems ? (int)MsgItems.value().size() : -1)) 
 		{
 			First_menu_item = 0;
 			Selected_menu_item = First_menu_item;
@@ -546,8 +533,8 @@ void hud_squadmsg_selection_move_up() {
 			//Assuming MAX_MENU_DISPLAY = 10, set First_menu_item to the nearest lower multiple of 10
 			//So if we have 85 items in comms menu, looping back from 1st page to last would set First_menu_item to 80
 			//exactly like pageUp/pageDown does
-			First_menu_item = ((Num_menu_items - 1) / MAX_MENU_DISPLAY) * MAX_MENU_DISPLAY;
-			Selected_menu_item = Num_menu_items - 1 - First_menu_item;
+			First_menu_item = (((MsgItems ? (int)MsgItems.value().size() : -1) - 1) / MAX_MENU_DISPLAY) * MAX_MENU_DISPLAY;
+			Selected_menu_item = (MsgItems ? (int)MsgItems.value().size() : -1) - 1 - First_menu_item;
 		}
 	}
 }
@@ -560,7 +547,7 @@ void hud_squadmsg_selection_select() {
 	if (Player->flags & PLAYER_FLAGS_MSG_MODE)
 	{
 		//Check if selected option is even active
-		if ((MsgItems[Selected_menu_item + First_menu_item].active > 0))
+		if (((MsgItems ? (int)MsgItems.value().size() : -1) > Selected_menu_item + First_menu_item) && (MsgItems.value()[Selected_menu_item + First_menu_item].active > 0))
 		{
 			Msg_key_used = 1;
 			Msg_key = Selected_menu_item + 2;	  //+1 because menu items on actual menu start from 1, not 0
@@ -579,7 +566,7 @@ int hud_squadmsg_get_total_keys()
 	int num_keys_used;
 
 	num_keys_used = MAX_KEYS_NO_SCROLL;
-	if ( Num_menu_items > MAX_MENU_DISPLAY )
+	if ( (MsgItems ? (int)MsgItems.value().size() : -1) > MAX_MENU_DISPLAY )
 		num_keys_used = MAX_KEYS_USED;
 
 	return num_keys_used;
@@ -669,15 +656,16 @@ int hud_squadmsg_get_key()
 			} else if ( k == KEY_ESC ) {
 				hud_squadmsg_toggle();
 				return -1;
-			} else if ( (i < Num_menu_items) && (Squad_msg_mode == SM_MODE_REINFORCEMENTS) )		// return any key if selecting reinforcement
+			} else if ( (i < (MsgItems ? (int)MsgItems.value().size() : -1)) && (Squad_msg_mode == SM_MODE_REINFORCEMENTS) ) {		// return any key if selecting reinforcement
 				return i;
+			}
 
 			// play general fail sound if inactive item hit.
-			else if ((i + First_menu_item < Num_menu_items) && (MsgItems[i + First_menu_item].active == 0)) {
+			else if ((i + First_menu_item < (MsgItems ? (int)MsgItems.value().size() : -1)) && (MsgItems.value()[i + First_menu_item].active == 0)) {
 				gamesnd_play_iface(InterfaceSounds::GENERAL_FAIL);
 			}
 
-			else if ((i + First_menu_item < Num_menu_items) && (MsgItems[i + First_menu_item].active > 0)) {	// only return keys that are associated with menu items
+			else if ((i + First_menu_item < (MsgItems ? (int)MsgItems.value().size() : -1)) && (MsgItems.value()[i + First_menu_item].active > 0)) {	// only return keys that are associated with menu items
 				return i + First_menu_item;
 			}
 
@@ -1779,50 +1767,51 @@ void hud_squadmsg_type_select( )
 
 	num_order_types += (int)lua_cat_list.size();
 
+	MsgItems = SCP_vector<mmode_item>();
+
 	// Add the items
 	for (i = 0; i < num_order_types; i++)
 	{
+
 		if (i < NUM_COMM_ORDER_TYPES) {
-			MsgItems[i].text = Comm_order_types[i];
+			MsgItems.value().emplace_back(0, 1, Comm_order_types[i]); // assume active
 		} else {
-			MsgItems[i].text = lua_cat_list[i - NUM_COMM_ORDER_TYPES];
-		}
-		MsgItems[i].active = 1;						// assume active
+			MsgItems.value().emplace_back(0, 1, lua_cat_list[i - NUM_COMM_ORDER_TYPES]); // assume active
+		}				
 	}
-	Num_menu_items = num_order_types;
 
 
 	// check to see if the player is a traitor.  If so, then he will not
 	// be able to do anything from this menu
 	if ((Player_ship != NULL) && (Player_ship->team == Iff_traitor)) {
-		for (i = 0; i < MAX_MENU_ITEMS; i++ )
-			MsgItems[i].active = 0;
+		for (auto &item : MsgItems.value())
+			item.active = 0;
 		goto do_main_menu;
 	}
 
 	// based on ship counts, wing counts, shortcut active, grey out possible menu choices
 	if ( !hud_squadmsg_count_ships(0) )
-		MsgItems[TYPE_SHIP_ITEM].active = 0;
+		MsgItems.value()[TYPE_SHIP_ITEM].active = 0;
 
 	if ( !hud_squadmsg_count_wings(0) )
-		MsgItems[TYPE_WING_ITEM].active = 0;
+		MsgItems.value()[TYPE_WING_ITEM].active = 0;
 
 	// check to be sure that we have some fighters/bombers on the players team that we
 	// can message
 	if ( !hud_squadmsg_exist_fighters() ){
-		MsgItems[TYPE_ALL_FIGHTERS_ITEM].active = 0;
+		MsgItems.value()[TYPE_ALL_FIGHTERS_ITEM].active = 0;
 	}
 
 	if ((Player_ship != NULL) && !hud_squadmsg_reinforcements_available(Player_ship->team)) {
-		MsgItems[TYPE_REINFORCEMENT_ITEM].active = 0;
+		MsgItems.value()[TYPE_REINFORCEMENT_ITEM].active = 0;
 	}
 
-	MsgItems[TYPE_REPAIR_REARM_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 1;
-	MsgItems[TYPE_REPAIR_REARM_ABORT_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 0;
+	MsgItems.value()[TYPE_REPAIR_REARM_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 1;
+	MsgItems.value()[TYPE_REPAIR_REARM_ABORT_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 0;
 
 	for(const auto& cat : lua_cat_list){
 		if (ai_lua_get_general_orders(false, false, cat).size() == 0) {
-			MsgItems[NUM_COMM_ORDER_TYPES + lua_order_count].active = 0;
+			MsgItems.value()[NUM_COMM_ORDER_TYPES + lua_order_count].active = 0;
 		}
 		lua_order_count++;
 	}
@@ -1833,51 +1822,51 @@ void hud_squadmsg_type_select( )
 	//
 	// also, only allow support ship if this player is not allowed to messaage. 
 	if ( (hud_communications_state(Player_ship) != COMM_OK) || ((Game_mode & GM_MULTIPLAYER) && !multi_can_message(Net_player)) ) {
-		for ( i = 0; i < MAX_MENU_ITEMS; i++ ){
-			MsgItems[i].active = 0;
+		for (auto &item : MsgItems.value()){
+			item.active = 0;
 		}
 
-		MsgItems[TYPE_REPAIR_REARM_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 1;
+		MsgItems.value()[TYPE_REPAIR_REARM_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 1;
 	}
 
 	// check to see if the player is awaiting repair or being repaired.  Active the abort and inactive the repair items
 	// check to see if the player is scheduled to be repaired by incoming ship
 	if (Ai_info[Ships[Player_obj->instance].ai_index].ai_flags.any_of(AI::AI_Flags::Being_repaired,AI::AI_Flags::Awaiting_repair)) {
-		MsgItems[TYPE_REPAIR_REARM_ITEM].active = 0;
-		MsgItems[TYPE_REPAIR_REARM_ABORT_ITEM].active = 1;
+		MsgItems.value()[TYPE_REPAIR_REARM_ITEM].active = 0;
+		MsgItems.value()[TYPE_REPAIR_REARM_ABORT_ITEM].active = 1;
 	}
 	else if ( mission_is_repair_scheduled(Player_obj) ) {
-		MsgItems[TYPE_REPAIR_REARM_ITEM].active = 0;
-		MsgItems[TYPE_REPAIR_REARM_ABORT_ITEM].active = 1;
+		MsgItems.value()[TYPE_REPAIR_REARM_ITEM].active = 0;
+		MsgItems.value()[TYPE_REPAIR_REARM_ABORT_ITEM].active = 1;
 	}
 	// if no support available, can't call one in
 	else if ( !is_support_allowed(Player_obj) ) {
-		MsgItems[TYPE_REPAIR_REARM_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 0;
-		MsgItems[TYPE_REPAIR_REARM_ABORT_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 0;
+		MsgItems.value()[TYPE_REPAIR_REARM_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 0;
+		MsgItems.value()[TYPE_REPAIR_REARM_ABORT_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 0;
 	}
 
 	// de-activate the rearm/repair item if the player has a full load of missiles and
 	// all subsystems at full strength.  We will only check if this item hasn't been marked
 	// inactive because of some other reason
-	if ( MsgItems[TYPE_REPAIR_REARM_ITEM].active > 0 ) {
+	if ( MsgItems.value()[TYPE_REPAIR_REARM_ITEM].active > 0 ) {
 
 		if ( !hud_squadmsg_can_rearm(Player_ship) ){
-			MsgItems[TYPE_REPAIR_REARM_ITEM].active = 0;
+			MsgItems.value()[TYPE_REPAIR_REARM_ITEM].active = 0;
 		}
 	}
 
 	// if using keyboard shortcut, these items are always inactive or hidden
 	if ( Msg_shortcut_command != -1 ) {
-		MsgItems[TYPE_REINFORCEMENT_ITEM].active = 0;
-		MsgItems[TYPE_REPAIR_REARM_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 0;
-		MsgItems[TYPE_REPAIR_REARM_ABORT_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 0;
+		MsgItems.value()[TYPE_REINFORCEMENT_ITEM].active = 0;
+		MsgItems.value()[TYPE_REPAIR_REARM_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 0;
+		MsgItems.value()[TYPE_REPAIR_REARM_ABORT_ITEM].active = Hide_main_rearm_items_in_comms_gauge ? -1 : 0;
 	}
 
 do_main_menu:
 	strcpy_s(Squad_msg_title, XSTR( "Message What", 316));
 	k = hud_squadmsg_get_key();
 	if ( k != -1 ) {							// when k != -1, we have a key that associates with menu item
-		Assert ( k < Num_menu_items );
+		Assert ( k < (MsgItems ? (int)MsgItems.value().size() : -1) );
 		if ( k == TYPE_SHIP_ITEM ){
 			hud_squadmsg_do_mode( SM_MODE_SHIP_SELECT );
 		} else if ( k == TYPE_WING_ITEM ) {
@@ -1907,8 +1896,8 @@ void hud_squadmsg_ship_select()
 {
 	int k;
 
-	if ( Num_menu_items == -1 ) {
-		Num_menu_items = 0;
+	if ( !MsgItems ) {
+		MsgItems = SCP_vector<mmode_item>();
 		hud_squadmsg_count_ships( 1 );
 	}
 
@@ -1916,13 +1905,13 @@ void hud_squadmsg_ship_select()
 	k = hud_squadmsg_get_key();
 	if ( k != -1 ) {						// if true, we have selected a ship.
 		if ( Msg_shortcut_command == -1 ) {
-			Msg_instance = MsgItems[k].instance;		// store the instance id in a global
+			Msg_instance = MsgItems.value()[k].instance;		// store the instance id in a global
 			hud_squadmsg_do_mode( SM_MODE_SHIP_COMMAND );				// and move to a new mode
 		} else {
 			// we must convert the Msg_shortcut_command value to a value that the message
 			// system normally uses to select a command.  Since the menu 
 			//Assert( Msg_shortcut_command != IGNORE_TARGET_ITEM );
-			hud_squadmsg_send_ship_command( MsgItems[k].instance, Msg_shortcut_command, 1, SQUADMSG_HISTORY_ADD_ENTRY);
+			hud_squadmsg_send_ship_command( MsgItems.value()[k].instance, Msg_shortcut_command, 1, SQUADMSG_HISTORY_ADD_ENTRY);
 			hud_squadmsg_toggle();
 		}
 	}
@@ -1934,8 +1923,8 @@ void hud_squadmsg_wing_select()
 {
 	int k;
 
-	if ( Num_menu_items == -1 ) {
-		Num_menu_items = 0;
+	if ( !MsgItems ) {
+		MsgItems = SCP_vector<mmode_item>();
 		hud_squadmsg_count_wings( 1 );
 	}
 
@@ -1943,11 +1932,11 @@ void hud_squadmsg_wing_select()
 	k = hud_squadmsg_get_key();
 	if ( k != -1 ) {						// if true, we have selected a ship.
 		if ( Msg_shortcut_command == -1 ) {									// do normal menu stuff when no hoykey active
-			Msg_instance = MsgItems[k].instance;	// store the instance id in a global
+			Msg_instance = MsgItems.value()[k].instance;	// store the instance id in a global
 			hud_squadmsg_do_mode( SM_MODE_WING_COMMAND );				// and move to a new mode
 		} else {
 			//Assert( Msg_shortcut_command != IGNORE_TARGET_ITEM );
-			hud_squadmsg_send_wing_command( MsgItems[k].instance, Msg_shortcut_command, 1, SQUADMSG_HISTORY_ADD_ENTRY );
+			hud_squadmsg_send_wing_command( MsgItems.value()[k].instance, Msg_shortcut_command, 1, SQUADMSG_HISTORY_ADD_ENTRY );
 			hud_squadmsg_toggle();
 		}
 	}
@@ -2045,8 +2034,8 @@ void hud_squadmsg_call_reinforcement(reinforcements &reinforcement, int  /*playe
 // function to display a list of reinforcements available to the player
 void hud_squadmsg_reinforcement_select()
 {
-	if ( Num_menu_items == -1 ) {
-		Num_menu_items = 0;
+	if ( !MsgItems ) {
+		MsgItems = SCP_vector<mmode_item>();
 
 		int i = -1;
 		for (const auto &reinforcement: Reinforcements) {
@@ -2092,16 +2081,7 @@ void hud_squadmsg_reinforcement_select()
 				r_name = p_objp->get_display_name();	// this will handle getting rid of the hash if necessary
 			}
 
-			Assert ( Num_menu_items < MAX_MENU_ITEMS );
-			MsgItems[Num_menu_items].text = r_name;
-			MsgItems[Num_menu_items].instance = i;
-			MsgItems[Num_menu_items].active = 0;
-
-			if ( reinforcement.flags & RF_IS_AVAILABLE ) {
-				MsgItems[Num_menu_items].active = 1;
-			}
-
-			Num_menu_items++;
+			MsgItems.value().emplace_back(i, (reinforcement.flags & RF_IS_AVAILABLE), r_name); // set the item to active if reinforcement is available
 		}
 	}
 
@@ -2113,11 +2093,11 @@ void hud_squadmsg_reinforcement_select()
 
 		hud_squadmsg_toggle();						// take us out of message mode
 
-		rnum = MsgItems[k].instance;
+		rnum = MsgItems.value()[k].instance;
 
 		// check to see if trying to call a reinforcement not yet available.  If so, maybe play message, but
 		// definately bail
-		if ( MsgItems[k].active == 0 ) {						
+		if ( MsgItems.value()[k].active == 0 ) {						
 			return;
 		}
 
@@ -2158,25 +2138,22 @@ void hud_squadmsg_ship_command()
 		default_orders.insert(default_messages.cbegin(), default_messages.cend());
 	}
 
-	Num_menu_items = 0;
+	MsgItems = SCP_vector<mmode_item>();
 	for(size_t order_id : default_orders) {
-		Assert (Num_menu_items < MAX_MENU_ITEMS);
-		MsgItems[Num_menu_items].text = Player_orders[order_id].localized_name;
-		MsgItems[Num_menu_items].instance = (int)order_id;
-		MsgItems[Num_menu_items].active = 0;
+		MsgItems.value().emplace_back((int)order_id, 0, Player_orders[order_id].localized_name);
 
 		// check the bit to see if the command is active
 		if (orders.find(order_id) != orders.end())
-			MsgItems[Num_menu_items].active = 1;
+			MsgItems.value().back().active = 1;
 
 		// if the order cannot be carried out by the ship, then item should be inactive
 		if ((Msg_instance != MESSAGE_ALL_FIGHTERS) && !hud_squadmsg_ship_order_valid(Msg_instance, (int)order_id))
-			MsgItems[Num_menu_items].active = 0;
+			MsgItems.value().back().active = 0;
 
 		// do some other checks to possibly gray out other items.
 		// if no target, remove any items which are associated with the players target
 		if (!hud_squadmsg_is_target_order_valid(order_id, nullptr))
-			MsgItems[Num_menu_items].active = 0;
+			MsgItems.value().back().active = 0;
 
 		// if messaging all fighters, see if we should gray out the order if no one will accept it,
 		// or modify the text if only some of the ships will accept it
@@ -2208,14 +2185,13 @@ void hud_squadmsg_ship_command()
 			if (!all_accept) {
 				// either modify the text if a partial accept, or grey it out if no one accepts
 				if (partial_accept) {
-					MsgItems[Num_menu_items].text += XSTR("(*)", 320);
+					MsgItems.value().back().text += XSTR("(*)", 320);
 				} else {
-					MsgItems[Num_menu_items].active = 0;
+					MsgItems.value().back().active = 0;
 				}
 			}
 		}
 
-		Num_menu_items++;
 	
 	}
 
@@ -2225,13 +2201,13 @@ void hud_squadmsg_ship_command()
 	// when we get a valid goal, we must add the goal to the ai ship's goal list
 
 	if ( k != -1 ) {
-		Assert ( k < Num_menu_items );
+		Assert ( k < (MsgItems ? (int)MsgItems.value().size() : -1) );
 		// when messaging all fighters or ignoring target, call the send_to_all_fighters routine
 		// Goober5000 - ignore no longer sends to all fighters
 		if (Msg_instance == MESSAGE_ALL_FIGHTERS)
-			hud_squadmsg_send_to_all_fighters(MsgItems[k].instance);
+			hud_squadmsg_send_to_all_fighters(MsgItems.value()[k].instance);
 		else
-			hud_squadmsg_send_ship_command(Msg_instance, MsgItems[k].instance, 1, SQUADMSG_HISTORY_ADD_ENTRY);
+			hud_squadmsg_send_ship_command(Msg_instance, MsgItems.value()[k].instance, 1, SQUADMSG_HISTORY_ADD_ENTRY);
 
 		hud_squadmsg_toggle();
 	}
@@ -2241,9 +2217,8 @@ void hud_squadmsg_msg_general()
 {
 	int k;
 
-	Num_menu_items = 0;
+	MsgItems = SCP_vector<mmode_item>();
 	for (size_t order_id = 0; order_id < Player_orders.size(); order_id++) {
-		Assert(Num_menu_items < MAX_MENU_ITEMS);
 
 		if (Player_orders[order_id].lua_id <= 0) {
 			continue;
@@ -2263,17 +2238,12 @@ void hud_squadmsg_msg_general()
 
 		//Only add it if it is enabled for the mission
 		if (lua_porder->cur_enabled) {
-
-			MsgItems[Num_menu_items].text = Player_orders[order_id].localized_name;
-			MsgItems[Num_menu_items].instance = Player_orders[order_id].lua_id;
-			MsgItems[Num_menu_items].active = (int)lua_porder->cur_valid;
+			MsgItems.value().emplace_back(Player_orders[order_id].lua_id, (int)lua_porder->cur_valid, Player_orders[order_id].localized_name);
 
 			// do some other checks to possibly gray out other items.
 			// if no target, remove any items which are associated with the players target
 			if (!hud_squadmsg_is_target_order_valid(order_id, nullptr))
-				MsgItems[Num_menu_items].active = 0;
-
-			Num_menu_items++;
+				MsgItems.value().back().active = 0;
 		}
 	}
 
@@ -2283,9 +2253,9 @@ void hud_squadmsg_msg_general()
 	// when we get a valid goal, we must add the goal to the ai ship's goal list
 
 	if (k != -1) {
-		Assert(k < Num_menu_items);
+		Assert(k < (MsgItems ? (int)MsgItems.value().size() : -1));
 		
-		ai_lua_start_general(MsgItems[k].instance, Player_ai->target_objnum);
+		ai_lua_start_general(MsgItems.value()[k].instance, Player_ai->target_objnum);
 
 		hud_squadmsg_toggle();
 	}
@@ -2314,7 +2284,7 @@ void hud_squadmsg_wing_command()
 	
 	default_orders.erase(CAPTURE_TARGET_ITEM); // we cannot capture any target with a wing.
 
-	Num_menu_items = 0;
+	MsgItems = SCP_vector<mmode_item>();
 	shipnum = wingp->ship_index[wingp->special_ship];
 	Assertion(shipnum >= 0, "Special ship (%d) for wing '%s' has a negative ship_index (%d). This should not happen; get a coder!\n", wingp->special_ship, wingp->name, shipnum);
 	orders = Ships[shipnum].orders_accepted;		// get the orders that the wing leader will accept
@@ -2322,24 +2292,21 @@ void hud_squadmsg_wing_command()
 	for ( size_t order_id : default_orders ) {
 		// add the set of default orders to the comm menu.  We will currently allow all messages
 		// to be available in the wing.
-		Assert ( Num_menu_items < MAX_MENU_ITEMS );
-		MsgItems[Num_menu_items].text = Player_orders[order_id].localized_name;
-		MsgItems[Num_menu_items].instance = (int)order_id;
-		MsgItems[Num_menu_items].active = 0;
+		MsgItems.value().emplace_back((int)order_id, 0, Player_orders[order_id].localized_name);
 
 		// possibly grey out the menu item depending on whether or not the "wing" will accept this order
 		// the "wing" won't accept the order if the first ship in the wing doesn't accept it.
 		if ( orders.find(order_id) != orders.end() )
-			MsgItems[Num_menu_items].active = 1;
+			MsgItems.value().back().active = 1;
 
 		// do some other checks to possibly gray out other items.
 		// if no target, remove any items which are associated with the players target
 		if ( !hud_squadmsg_is_target_order_valid((int)order_id, 0, true) )
-			MsgItems[Num_menu_items].active = 0;
+			MsgItems.value().back().active = 0;
 
 		// if no ship in the wing can depart then gray out the departure order
 		if (order_id == DEPART_ITEM) {
-			if (MsgItems[Num_menu_items].active > 0) {
+			if (MsgItems.value().back().active > 0) {
 				int active = 0;
 				for (int i = 0; i < wingp->current_count; i++) {
 					if (hud_squadmsg_ship_order_valid(wingp->ship_index[i], (int)order_id)) {
@@ -2347,12 +2314,9 @@ void hud_squadmsg_wing_command()
 						break;
 					}
 				}
-				MsgItems[Num_menu_items].active = active;
+				MsgItems.value().back().active = active;
 			}
-		}
-
-		Num_menu_items++;
-	
+		}	
 	}
 
 	
@@ -2365,7 +2329,7 @@ void hud_squadmsg_wing_command()
 		if (MsgItems[k].instance == IGNORE_TARGET_ITEM)
 			hud_squadmsg_send_to_all_fighters(MsgItems[k].instance);
 		else */
-			hud_squadmsg_send_wing_command(Msg_instance, MsgItems[k].instance, 1);
+			hud_squadmsg_send_wing_command(Msg_instance, MsgItems.value()[k].instance, 1);
 
 		hud_squadmsg_toggle();
 	}
@@ -2906,13 +2870,13 @@ void HudGaugeSquadMessage::render(float  /*frametime*/, bool config)
 
 	int nitems;
 	if (!config) {
-		if (Num_menu_items < MAX_MENU_DISPLAY)
-			nitems = Num_menu_items;
+		if ((MsgItems ? (int)MsgItems.value().size() : -1) < MAX_MENU_DISPLAY)
+			nitems = (MsgItems ? (int)MsgItems.value().size() : -1);
 		else {
 			if (First_menu_item == 0) // First_menu_item == 0 means first page of items
 				nitems = MAX_MENU_DISPLAY;
-			else if ((Num_menu_items - First_menu_item) <= MAX_MENU_DISPLAY) // check if remaining items fit on one page
-				nitems = Num_menu_items - First_menu_item;
+			else if (((MsgItems ? (int)MsgItems.value().size() : -1) - First_menu_item) <= MAX_MENU_DISPLAY) // check if remaining items fit on one page
+				nitems = (MsgItems ? (int)MsgItems.value().size() : -1) - First_menu_item;
 			else {
 				nitems = MAX_MENU_DISPLAY;
 			}
@@ -2941,7 +2905,7 @@ void HudGaugeSquadMessage::render(float  /*frametime*/, bool config)
 		char text[256];
 
 		if (!config) {
-			strcpy_s(text, MsgItems[First_menu_item + i].text.c_str());
+			strcpy_s(text, MsgItems.value()[First_menu_item + i].text.c_str());
 		} else {
 			// in config mode, so create just the first page of the Comms Menu
 			// as other functions, such as hud_squadmsg_type_select() will not be run in config mode
@@ -2954,7 +2918,7 @@ void HudGaugeSquadMessage::render(float  /*frametime*/, bool config)
 			};
 			strcpy_s(text, temp_comm_order_types[i]);
 			if (Hide_main_rearm_items_in_comms_gauge && (i == TYPE_REPAIR_REARM_ITEM || i == TYPE_REPAIR_REARM_ABORT_ITEM)) {
-				MsgItems[First_menu_item + i].active = -1;
+				MsgItems.value()[First_menu_item + i].active = -1;
 			}
 		}
 
@@ -2966,7 +2930,7 @@ void HudGaugeSquadMessage::render(float  /*frametime*/, bool config)
 		by += fl2i(Item_h * scale);
 
 		// set the text color
-		if (!config && (MsgItems[First_menu_item + i].active > 0)) {
+		if (!config && (MsgItems.value()[First_menu_item + i].active > 0)) {
 			setGaugeColor(HUD_C_BRIGHT, config);
 		}
 		else if (isSelectedItem) {
@@ -2976,7 +2940,7 @@ void HudGaugeSquadMessage::render(float  /*frametime*/, bool config)
 			setGaugeColor(HUD_C_DIM, config);
 		}
 
-		if (MsgItems[First_menu_item + i].active >= 0) {
+		if (MsgItems.value()[First_menu_item + i].active >= 0) {
 			// first print an icon to indicate selected item
 			item_num = (i + 1) % MAX_MENU_DISPLAY;
 			if (isSelectedItem && Display_selector) {
@@ -2995,13 +2959,13 @@ void HudGaugeSquadMessage::render(float  /*frametime*/, bool config)
 
 		// if we have at least one item active, then set the variable so we don't display any
 		// message about no active items
-		if (config || (MsgItems[First_menu_item+i].active > 0) )
+		if (config || (MsgItems.value()[First_menu_item+i].active > 0) )
 			none_valid = false;
 	}
 
 	// maybe draw an extra line in to make room for [pgdn], or for the 'no active items'
 	// display
-	if (!config && (!messaging_allowed || none_valid || ((First_menu_item + nitems) < Num_menu_items) || (Msg_shortcut_command != -1))) {
+	if (!config && (!messaging_allowed || none_valid || ((First_menu_item + nitems) < (MsgItems ? (int)MsgItems.value().size() : -1)) || (Msg_shortcut_command != -1))) {
 		// blit the background
 		setGaugeColor(HUD_C_NONE, config);
 		if ( Mbox_gauge[1].first_frame >= 0 ) {		
@@ -3026,7 +2990,7 @@ void HudGaugeSquadMessage::render(float  /*frametime*/, bool config)
 		renderPrintf(x + fl2i(Pgup_offsets[0] * scale), y + fl2i(Pgup_offsets[1] * scale), scale, config, "%s", XSTR( "[pgup]", 312) );
 	}
 
-	if ( (First_menu_item + nitems) < Num_menu_items ) {
+	if ( (First_menu_item + nitems) < (MsgItems ? (int)MsgItems.value().size() : -1) ) {
 		renderPrintf(x + fl2i(Pgdn_offsets[0] * scale), y + fl2i(Pgdn_offsets[1] * scale), scale, config, "%s", XSTR( "[pgdn]", 313));
 	}
 
diff --git a/code/hud/hudsquadmsg.h b/code/hud/hudsquadmsg.h
index 7cf6eb016c2..5db8031ef9f 100644
--- a/code/hud/hudsquadmsg.h
+++ b/code/hud/hudsquadmsg.h
@@ -62,7 +62,6 @@ struct reinforcements;
 // used for Message box gauge
 #define NUM_MBOX_FRAMES		3
 
-#define MAX_MENU_ITEMS 50   // max number of items in the menu
 #define MAX_MENU_DISPLAY 10 // max number that can be displayed
 
 // following are defines and character strings that are used as part of messaging mode
@@ -80,11 +79,15 @@ typedef struct mmode_item {
 	int instance;    // instance in Ships/Wings array of this menu item
 	int active;      // active items are in bold text (1) -- inactive items greyed out (0) -- hidden objects not rendered (-1)
 	SCP_string text; // text to display on the menu
+	mmode_item(int param_instance, int param_active, SCP_string param_text) {
+		instance = param_instance;
+		active = param_active;
+		text = std::move(param_text);
+	};
 } mmode_item;
 
 extern char Squad_msg_title[256];
-extern mmode_item MsgItems[MAX_MENU_ITEMS];
-extern int Num_menu_items; // number of items for a message menu
+extern std::optional<SCP_vector<mmode_item>> MsgItems;
 
 typedef struct player_order {
 private:
diff --git a/code/parse/sexp/LuaAISEXP.cpp b/code/parse/sexp/LuaAISEXP.cpp
index 0e9bc995672..045a66877bf 100644
--- a/code/parse/sexp/LuaAISEXP.cpp
+++ b/code/parse/sexp/LuaAISEXP.cpp
@@ -154,13 +154,6 @@ void LuaAISEXP::parseTable() {
 				// Now get a list of all lua categories to add. Meow.
 				SCP_vector<SCP_string> lua_cat_list = ai_lua_get_general_order_categories();
 
-				// If we have too many categories then we have an oopsie!
-				if ((int)lua_cat_list.size() > (MAX_MENU_ITEMS - NUM_COMM_ORDER_TYPES)) {
-					Warning(LOCATION, "Too many defined Lua General Order Categories! Setting order to first available: %s", lua_cat_list[0].c_str());
-
-					order.category = lua_cat_list[0];
-				}
-
 				// General orders explicitely do not show up in FRED as sexps because they
 				// they are only meant for the comms board
 				_return_type = OPR_NONE;
diff --git a/code/scripting/api/libs/mission.cpp b/code/scripting/api/libs/mission.cpp
index 14df3af0562..ad1a69454d7 100644
--- a/code/scripting/api/libs/mission.cpp
+++ b/code/scripting/api/libs/mission.cpp
@@ -343,7 +343,7 @@ ADE_INDEXER(l_Mission_Comm_Items,
 	// convert from lua index
 	idx--;
 
-	if ((idx < 0) || idx >= MAX_MENU_ITEMS)
+	if ((idx < 0))
 		return ade_set_args(L, "o", l_Comm_Item.Set(-1));
 
 	return ade_set_args(L, "o", l_Comm_Item.Set(idx));
@@ -356,7 +356,7 @@ ADE_FUNC(__len,
 	"number",
 	"Number of comm orders in the mission. 0 if comm menu is closed")
 {
-	return ade_set_args(L, "i", Num_menu_items);
+	return ade_set_args(L, "i", (MsgItems ? (int)MsgItems.value().size() : -1));
 }
 
 //****SUBLIBRARY: Mission/Debris
diff --git a/code/scripting/api/objs/comm_order.cpp b/code/scripting/api/objs/comm_order.cpp
index fe18f0da567..f75913f5004 100644
--- a/code/scripting/api/objs/comm_order.cpp
+++ b/code/scripting/api/objs/comm_order.cpp
@@ -17,8 +17,11 @@ ADE_VIRTVAR(Name, l_Comm_Item, nullptr, "The name of the comm item", "string", "
 	if (ADE_SETTING_VAR) {
 		LuaError(L, "This property is read only.");
 	}
-
-	return ade_set_args(L, "s", MsgItems[current].text.c_str());
+	SCP_string message = "Invalid comm item!";
+	if ((MsgItems ? (int)MsgItems.value().size() : -1) > current) {
+		message = MsgItems.value()[current].text;
+	};
+	return ade_set_args(L, "s", message.c_str());
 }
 
 ADE_VIRTVAR(Active, l_Comm_Item, nullptr, "Whether or not the item is active", "boolean", "The active status")
@@ -32,7 +35,7 @@ ADE_VIRTVAR(Active, l_Comm_Item, nullptr, "Whether or not the item is active", "
 		LuaError(L, "This property is read only.");
 	}
 
-	if (MsgItems[current].active > 0) {
+	if ((MsgItems ? (int)MsgItems.value().size() : -1) > current && MsgItems.value()[current].active > 0) {
 		return ADE_RETURN_TRUE;
 	}
 
@@ -60,7 +63,7 @@ ADE_FUNC(selectItem, l_Comm_Item, nullptr, "Selects the item and either proceeds
 	if (!ade_get_args(L, "o", l_Comm_Item.Get(&current)))
 		return ADE_RETURN_FALSE;
 
-	if (current < 0 || current >= Num_menu_items) {
+	if (current < 0 || current >= (MsgItems ? (int)MsgItems.value().size() : -1)) {
 		LuaError(L, "Lua tried to select squad message that is not valid!");
 		return ADE_RETURN_FALSE;
 	}
@@ -77,7 +80,7 @@ ADE_FUNC(isValid, l_Comm_Item, nullptr, "Detect if the handle is valid", "boolea
 	if (!ade_get_args(L, "o", l_Comm_Item.Get(&current)))
 		return ADE_RETURN_FALSE;
 
-	return ade_set_args(L, "b", (current >= 0) && (current < Num_menu_items));
+	return ade_set_args(L, "b", (current >= 0) && (current < (MsgItems ? (int)MsgItems.value().size() : -1)));
 }
 
 } // namespace scripting::api