diff --git a/Source/inv.cpp b/Source/inv.cpp
index d6a05e951..83a3b8d2c 100644
--- a/Source/inv.cpp
+++ b/Source/inv.cpp
@@ -1769,29 +1769,30 @@ void SyncGetItem(Point position, int32_t iseed, _item_indexes idx, uint16_t ci)
 
 bool CanPut(Point position)
 {
-	if (dItem[position.x][position.y] != 0)
+	if (!InDungeonBounds(position)) {
 		return false;
-	if (nSolidTable[dPiece[position.x][position.y]])
+	}
+
+	if (IsTileSolid(position)) {
 		return false;
-	if (dObject[position.x][position.y] != 0 && Objects[abs(dObject[position.x][position.y]) - 1]._oSolidFlag)
+	}
+
+	if (dItem[position.x][position.y] != 0) {
 		return false;
+	}
 
-	if (dObject[position.x + 1][position.y + 1] != 0) {
-		int8_t oi = abs(dObject[position.x + 1][position.y + 1]) - 1;
-		if (Objects[oi]._oSelFlag != 0) {
+	if (currlevel == 0) {
+		if (dMonster[position.x][position.y] != 0) {
 			return false;
 		}
-	}
-
-	if (dObject[position.x + 1][position.y] > 0 && dObject[position.x][position.y + 1] > 0) {
-		if (Objects[dObject[position.x + 1][position.y] - 1]._oSelFlag != 0 && Objects[dObject[position.x][position.y + 1] - 1]._oSelFlag != 0)
+		if (dMonster[position.x + 1][position.y + 1] != 0) {
 			return false;
+		}
 	}
 
-	if (currlevel == 0 && dMonster[position.x][position.y] != 0)
-		return false;
-	if (currlevel == 0 && dMonster[position.x + 1][position.y + 1] != 0)
+	if (IsItemBlockingObjectAtPosition(position)) {
 		return false;
+	}
 
 	return true;
 }
diff --git a/Source/items.cpp b/Source/items.cpp
index ad1a5e736..f27b3a722 100644
--- a/Source/items.cpp
+++ b/Source/items.cpp
@@ -396,11 +396,11 @@ bool ItemPlace(Point position)
 		return false;
 	if (dItem[position.x][position.y] != 0)
 		return false;
-	if (dObject[position.x][position.y] != 0)
+	if (IsObjectAtPosition(position))
 		return false;
 	if (TileContainsSetPiece(position))
 		return false;
-	if (nSolidTable[dPiece[position.x][position.y]])
+	if (IsTileSolid(position))
 		return false;
 
 	return true;
@@ -3106,44 +3106,31 @@ void CreatePlrItems(int playerId)
 
 bool ItemSpaceOk(Point position)
 {
-	if (!InDungeonBounds(position))
+	if (!InDungeonBounds(position)) {
 		return false;
+	}
 
-	if (dMonster[position.x][position.y] != 0)
+	if (IsTileSolid(position)) {
 		return false;
+	}
 
-	if (dPlayer[position.x][position.y] != 0)
+	if (dItem[position.x][position.y] != 0) {
 		return false;
+	}
 
-	if (dItem[position.x][position.y] != 0)
+	if (dMonster[position.x][position.y] != 0) {
 		return false;
-
-	if (dObject[position.x][position.y] != 0) {
-		int oi = abs(dObject[position.x][position.y]) - 1;
-		if (Objects[oi]._oSolidFlag)
-			return false;
 	}
 
-	Point south = position + Direction::South;
-	if (InDungeonBounds(south)) {
-		int objectId = dObject[south.x][south.y];
-		if (objectId != 0 && Objects[abs(objectId) - 1]._oSelFlag != 0)
-			return false;
+	if (dPlayer[position.x][position.y] != 0) {
+		return false;
 	}
 
-	Point southEast = position + Direction::SouthEast;
-	Point southWest = position + Direction::SouthWest;
-	if (InDungeonBounds(southEast) && InDungeonBounds(southWest)) {
-		int objectIdSE = dObject[southEast.x][southEast.y];
-		int objectIdSW = dObject[southWest.x][southWest.y];
-		if (objectIdSE > 0 && objectIdSW > 0) {
-			if (Objects[objectIdSE - 1]._oSelFlag != 0 && Objects[objectIdSW - 1]._oSelFlag != 0) {
-				return false;
-			}
-		}
+	if (IsItemBlockingObjectAtPosition(position)) {
+		return false;
 	}
 
-	return IsTileNotSolid(position);
+	return true;
 }
 
 int AllocateItem()
diff --git a/Source/objects.cpp b/Source/objects.cpp
index 9acb08757..c07028c1b 100644
--- a/Source/objects.cpp
+++ b/Source/objects.cpp
@@ -4347,19 +4347,46 @@ bool Object::IsDisabled() const
 	return IsAnyOf(static_cast<shrine_type>(_oVar1), shrine_type::ShrineFascinating, shrine_type::ShrineOrnate, shrine_type::ShrineSacred);
 }
 
-Object *ObjectAtPosition(Point position)
+Object *ObjectAtPosition(Point position, bool considerLargeObjects)
 {
-	if (InDungeonBounds(position) && dObject[position.x][position.y] != 0) {
-		return &Objects[abs(dObject[position.x][position.y]) - 1];
+	if (!InDungeonBounds(position)) {
+		return nullptr;
+	}
+
+	auto objectId = dObject[position.x][position.y];
+
+	if (objectId > 0 || (considerLargeObjects && objectId != 0)) {
+		return &Objects[abs(objectId) - 1];
 	}
 
 	// nothing at this position, return a nullptr
 	return nullptr;
 }
 
-bool IsObjectAtPosition(Point position)
+bool IsItemBlockingObjectAtPosition(Point position)
 {
-	return ObjectAtPosition(position) != nullptr;
+	Object *object = ObjectAtPosition(position);
+	if (object != nullptr && object->_oSolidFlag) {
+		// solid object
+		return true;
+	}
+
+	object = ObjectAtPosition(position + Direction::South);
+	if (object != nullptr && object->_oSelFlag != 0) {
+		// An unopened container or breakable object exists which potentially overlaps this tile, the player might not be able to pick up an item dropped here.
+		return true;
+	}
+
+	object = ObjectAtPosition(position + Direction::SouthEast, false);
+	if (object != nullptr) {
+		Object *otherDoor = ObjectAtPosition(position + Direction::SouthWest, false);
+		if (otherDoor != nullptr && object->_oSelFlag != 0 && otherDoor->_oSelFlag != 0) {
+			// Two interactive objects potentially overlap both sides of this tile, as above the player might not be able to pick up an item which is dropped here.
+			return true;
+		}
+	}
+
+	return false;
 }
 
 void InitObjectGFX()
diff --git a/Source/objects.h b/Source/objects.h
index 1c6192886..5b9e23b70 100644
--- a/Source/objects.h
+++ b/Source/objects.h
@@ -242,16 +242,28 @@ extern bool LoadingMapObjects;
  * @brief Find an object given a point in map coordinates
  *
  * @param position The map coordinate to test
+ * @param considerLargeObjects Default behaviour will return a pointer to a large object that covers this tile, set
+ *                             this param to false if you only want the object whose base position matches this tile
  * @return A pointer to the object or nullptr if no object exists at this location
  */
-Object *ObjectAtPosition(Point position);
+Object *ObjectAtPosition(Point position, bool considerLargeObjects = true);
 
 /**
  * @brief Check whether an item occupies this tile position
  * @param position The map coordinate to test
  * @return true if the tile is occupied
  */
-bool IsObjectAtPosition(Point position);
+inline bool IsObjectAtPosition(Point position)
+{
+	return ObjectAtPosition(position) != nullptr;
+}
+
+/**
+ * @brief Check whether an item blocking object (solid object or open door) is located at this tile position
+ * @param position The map coordinate to test
+ * @return true if the tile is blocked
+ */
+bool IsItemBlockingObjectAtPosition(Point position);
 
 void InitObjectGFX();
 void FreeObjectGFX();