diff --git a/src/lang/english.txt b/src/lang/english.txt
index 80eae3b445..df1a368edc 100644
--- a/src/lang/english.txt
+++ b/src/lang/english.txt
@@ -5550,6 +5550,10 @@ STR_ERROR_NAME_MUST_BE_UNIQUE                                   :{WHITE}Name mus
 STR_ERROR_GENERIC_OBJECT_IN_THE_WAY                             :{WHITE}{1:STRING} in the way
 STR_ERROR_NOT_ALLOWED_WHILE_PAUSED                              :{WHITE}Not allowed while paused
 
+# Clear area query
+STR_QUERY_CLEAR_AREA_CAPTION                                    :{WHITE}Clear area
+STR_CLEAR_AREA_CONFIRMATION_TEXT                                :{YELLOW}You are about to destroy an important structure. Are you sure?
+
 # Local authority errors
 STR_ERROR_LOCAL_AUTHORITY_REFUSES_TO_ALLOW_THIS                 :{WHITE}{TOWN} local authority refuses to allow this
 STR_ERROR_LOCAL_AUTHORITY_REFUSES_AIRPORT                       :{WHITE}{TOWN} local authority refuses to allow another airport to be built in this town
diff --git a/src/misc_gui.cpp b/src/misc_gui.cpp
index 49eb34824b..3cc340d696 100644
--- a/src/misc_gui.cpp
+++ b/src/misc_gui.cpp
@@ -12,6 +12,8 @@
 #include "landscape.h"
 #include "error.h"
 #include "gui.h"
+
+#include <utility>
 #include "command_func.h"
 #include "company_func.h"
 #include "town.h"
@@ -1230,19 +1232,19 @@ void ShowQueryString(StringID str, StringID caption, uint maxsize, Window *paren
  * Window used for asking the user a YES/NO question.
  */
 struct QueryWindow : public Window {
-	QueryCallbackProc *proc; ///< callback function executed on closing of popup. Window* points to parent, bool is true if 'yes' clicked, false otherwise
+	QueryCallbackProc proc;  ///< callback function executed on closing of popup. Window* points to parent, bool is true if 'yes' clicked, false otherwise
 	uint64 params[10];       ///< local copy of #_global_string_params
 	StringID message;        ///< message shown for query window
 	StringID caption;        ///< title of window
 
-	QueryWindow(WindowDesc *desc, StringID caption, StringID message, Window *parent, QueryCallbackProc *callback) : Window(desc)
+	QueryWindow(WindowDesc *desc, StringID caption, StringID message, Window *parent, QueryCallbackProc callback) : Window(desc)
 	{
 		/* Create a backup of the variadic arguments to strings because it will be
 		 * overridden pretty often. We will copy these back for drawing */
 		CopyOutDParam(this->params, 0, lengthof(this->params));
 		this->caption = caption;
 		this->message = message;
-		this->proc    = callback;
+		this->proc    = std::move(callback);
 		this->parent  = parent;
 
 		this->InitNested(WN_CONFIRM_POPUP_QUERY);
@@ -1299,7 +1301,7 @@ struct QueryWindow : public Window {
 			case WID_Q_YES: {
 				/* in the Generate New World window, clicking 'Yes' causes
 				 * DeleteNonVitalWindows() to be called - we shouldn't be in a window then */
-				QueryCallbackProc *proc = this->proc;
+				QueryCallbackProc proc = this->proc;
 				Window *parent = this->parent;
 				/* Prevent the destructor calling the callback function */
 				this->proc = nullptr;
@@ -1364,9 +1366,9 @@ static WindowDesc _query_desc(
  * @param message string that will be shown for the window
  * @param parent pointer to parent window, if this pointer is nullptr the parent becomes
  * the main window WC_MAIN_WINDOW
- * @param callback callback function pointer to set in the window descriptor
+ * @param callback callback function to set in the window descriptor
  */
-void ShowQuery(StringID caption, StringID message, Window *parent, QueryCallbackProc *callback)
+void ShowQuery(StringID caption, StringID message, Window *parent, QueryCallbackProc callback)
 {
 	if (parent == nullptr) parent = FindWindowById(WC_MAIN_WINDOW, 0);
 
@@ -1374,7 +1376,7 @@ void ShowQuery(StringID caption, StringID message, Window *parent, QueryCallback
 		if (w->window_class != WC_CONFIRM_POPUP_QUERY) continue;
 
 		const QueryWindow *qw = (const QueryWindow *)w;
-		if (qw->parent != parent || qw->proc != callback) continue;
+		if (qw->parent != parent) continue;
 
 		delete qw;
 		break;
diff --git a/src/network/network_gui.cpp b/src/network/network_gui.cpp
index 844326775b..e0563c04f0 100644
--- a/src/network/network_gui.cpp
+++ b/src/network/network_gui.cpp
@@ -2141,7 +2141,7 @@ public:
 
 			case WID_CL_MATRIX: {
 				StringID text = STR_NULL;
-				QueryCallbackProc *callback = nullptr;
+				QueryCallbackProc callback = nullptr;
 
 				switch (index) {
 					case DD_CLIENT_ADMIN_KICK:
diff --git a/src/terraform_gui.cpp b/src/terraform_gui.cpp
index 2db07278b4..17061601f9 100644
--- a/src/terraform_gui.cpp
+++ b/src/terraform_gui.cpp
@@ -30,6 +30,7 @@
 #include "hotkeys.h"
 #include "engine_base.h"
 #include "terraform_gui.h"
+#include "cheat_func.h"
 #include "town_gui.h"
 #include "zoom_func.h"
 
@@ -95,6 +96,30 @@ static void GenerateRockyArea(TileIndex end, TileIndex start)
 	if (success && _settings_client.sound.confirm) SndPlayTileFx(SND_1F_CONSTRUCTION_OTHER, end);
 }
 
+/** Checks if the area contains any structures that are important enough to query about first */
+static bool IsIndustryOrRailStationInArea(TileIndex start_tile, TileIndex end_tile, bool diagonal)
+{
+	std::unique_ptr<TileIterator> tile_iterator;
+
+	if (diagonal) {
+		tile_iterator = std::make_unique<DiagonalTileIterator>(end_tile, start_tile);
+	} else {
+		tile_iterator = std::make_unique<OrthogonalTileIterator>(end_tile, start_tile);
+	}
+
+	bool destroying_industry_or_station = false;
+
+	for (; *tile_iterator != INVALID_TILE; ++(*tile_iterator)) {
+		if ((_cheats.magic_bulldozer.value && IsTileType(*tile_iterator, MP_INDUSTRY)) ||
+		    IsRailStationTile(*tile_iterator)) {
+			destroying_industry_or_station = true;
+			break;
+		}
+	}
+
+	return destroying_industry_or_station;
+}
+
 /**
  * A central place to handle all X_AND_Y dragged GUI functions.
  * @param proc       Procedure related to the dragging
@@ -114,9 +139,23 @@ bool GUIPlaceProcDragXY(ViewportDragDropSelectionProcess proc, TileIndex start_t
 	}
 
 	switch (proc) {
-		case DDSP_DEMOLISH_AREA:
-			DoCommandP(end_tile, start_tile, _ctrl_pressed ? 1 : 0, CMD_CLEAR_AREA | CMD_MSG(STR_ERROR_CAN_T_CLEAR_THIS_AREA), CcPlaySound_EXPLOSION);
+		case DDSP_DEMOLISH_AREA: {
+			const bool should_query_first = IsIndustryOrRailStationInArea(start_tile, end_tile, _ctrl_pressed);
+
+			const auto cmd_clear_area = [=](Window*, bool confirmed) {
+				if (confirmed) {
+					DoCommandP(end_tile, start_tile, _ctrl_pressed ? 1 : 0, CMD_CLEAR_AREA | CMD_MSG(STR_ERROR_CAN_T_CLEAR_THIS_AREA), CcPlaySound_EXPLOSION);
+				}
+			};
+
+			if (should_query_first) {
+				ShowQuery(STR_QUERY_CLEAR_AREA_CAPTION, STR_CLEAR_AREA_CONFIRMATION_TEXT, nullptr, cmd_clear_area);
+			} else {
+				cmd_clear_area(nullptr, true);
+			}
+
 			break;
+		}
 		case DDSP_RAISE_AND_LEVEL_AREA:
 			DoCommandP(end_tile, start_tile, LM_RAISE << 1 | (_ctrl_pressed ? 1 : 0), CMD_LEVEL_LAND | CMD_MSG(STR_ERROR_CAN_T_RAISE_LAND_HERE), CcTerraform);
 			break;
diff --git a/src/textbuf_gui.h b/src/textbuf_gui.h
index c96f4e2e06..a7a225eb49 100644
--- a/src/textbuf_gui.h
+++ b/src/textbuf_gui.h
@@ -10,10 +10,13 @@
 #ifndef TEXTBUF_GUI_H
 #define TEXTBUF_GUI_H
 
-#include "window_type.h"
 #include "string_type.h"
 #include "strings_type.h"
 
+#include <functional>
+
+struct Window;
+
 /** Flags used in ShowQueryString() call */
 enum QueryStringFlags {
 	QSF_NONE             =    0,
@@ -26,10 +29,10 @@ enum QueryStringFlags {
 DECLARE_ENUM_AS_BIT_SET(QueryStringFlags)
 
 /** Callback procedure for the ShowQuery method. */
-typedef void QueryCallbackProc(Window*, bool);
+typedef std::function<void(Window*, bool)> QueryCallbackProc;
 
 void ShowQueryString(StringID str, StringID caption, uint max_len, Window *parent, CharSetFilter afilter, QueryStringFlags flags);
-void ShowQuery(StringID caption, StringID message, Window *w, QueryCallbackProc *callback);
+void ShowQuery(StringID caption, StringID message, Window *w, QueryCallbackProc callback);
 
 /** The number of 'characters' on the on-screen keyboard. */
 static const uint OSK_KEYBOARD_ENTRIES = 50;