diff --git a/Source/controls/plrctrls.cpp b/Source/controls/plrctrls.cpp
index 55edf0035..a6b883796 100644
--- a/Source/controls/plrctrls.cpp
+++ b/Source/controls/plrctrls.cpp
@@ -1809,7 +1809,7 @@ void UpdateSpellTarget(spell_id spell)
  */
 bool TryDropItem()
 {
-	auto &myPlayer = Players[MyPlayerId];
+	auto &myPlayer = *MyPlayer;
 
 	if (myPlayer.HoldItem.isEmpty()) {
 		return false;
@@ -1828,18 +1828,21 @@ bool TryDropItem()
 		}
 	}
 
-	cursPosition = myPlayer.position.future + Direction::SouthEast;
-	if (!DropItemBeforeTrig()) {
-		// Try to drop on the other side
-		cursPosition = myPlayer.position.future + Direction::SouthWest;
-		DropItemBeforeTrig();
-	}
-
-	if (pcurs != CURSOR_HAND) {
-		myPlayer.Say(HeroSpeech::WhereWouldIPutThis);
+	Point position = myPlayer.position.future;
+	Direction direction = myPlayer._pdir;
+	if (!CanPut(position, direction)) {
+		direction = Opposite(direction);
+		// if we can't drop in front of the player, can we drop it behind?
+		if (!CanPut(position, direction)) {
+			myPlayer.Say(HeroSpeech::WhereWouldIPutThis);
+			return false;
+		}
 	}
 
-	return pcurs == CURSOR_HAND;
+	NetSendCmdPItem(true, CMD_PUTITEM, position + direction, myPlayer.HoldItem);
+	myPlayer.HoldItem.Clear();
+	NewCursor(CURSOR_HAND);
+	return true;
 }
 
 void PerformSpellAction()
diff --git a/Source/diablo.cpp b/Source/diablo.cpp
index ed44cd3d1..d77672f06 100644
--- a/Source/diablo.cpp
+++ b/Source/diablo.cpp
@@ -343,7 +343,8 @@ void LeftMouseDown(int wParam)
 			} else if (sbookflag && GetRightPanel().Contains(MousePosition)) {
 				CheckSBook();
 			} else if (!MyPlayer->HoldItem.isEmpty()) {
-				if (TryInvPut()) {
+				Point currentPosition = MyPlayer->position.tile;
+				if (CanPut(currentPosition, GetDirection(currentPosition, cursPosition))) {
 					NetSendCmdPItem(true, CMD_PUTITEM, cursPosition, MyPlayer->HoldItem);
 					NewCursor(CURSOR_HAND);
 				}
diff --git a/Source/inv.cpp b/Source/inv.cpp
index deb379581..71ff7f5ac 100644
--- a/Source/inv.cpp
+++ b/Source/inv.cpp
@@ -1736,27 +1736,24 @@ bool CanPut(Point position)
 	return true;
 }
 
-bool TryInvPut()
+bool CanPut(Point position, Direction dir)
 {
 	if (ActiveItemCount >= MAXITEMS)
 		return false;
 
-	auto &myPlayer = Players[MyPlayerId];
-
-	Direction dir = GetDirection(myPlayer.position.tile, cursPosition);
-	if (CanPut(myPlayer.position.tile + dir)) {
+	if (CanPut(position + dir)) {
 		return true;
 	}
 
-	if (CanPut(myPlayer.position.tile + Left(dir))) {
+	if (CanPut(position + Left(dir))) {
 		return true;
 	}
 
-	if (CanPut(myPlayer.position.tile + Right(dir))) {
+	if (CanPut(position + Right(dir))) {
 		return true;
 	}
 
-	return CanPut(myPlayer.position.tile);
+	return CanPut(position);
 }
 
 int InvPutItem(Player &player, Point position, Item &item)
@@ -2163,17 +2160,6 @@ int CalculateGold(Player &player)
 	return gold;
 }
 
-bool DropItemBeforeTrig()
-{
-	if (!TryInvPut()) {
-		return false;
-	}
-
-	NetSendCmdPItem(true, CMD_PUTITEM, cursPosition, Players[MyPlayerId].HoldItem);
-	NewCursor(CURSOR_HAND);
-	return true;
-}
-
 Size GetInventorySize(const Item &item)
 {
 	int itemSizeIndex = item._iCurs + CURSOR_FIRSTITEM;
diff --git a/Source/inv.h b/Source/inv.h
index fe8a615aa..b5da7d856 100644
--- a/Source/inv.h
+++ b/Source/inv.h
@@ -198,8 +198,23 @@ void AutoGetItem(int pnum, Item *item, int ii);
  */
 int FindGetItem(int32_t iseed, _item_indexes idx, uint16_t ci);
 void SyncGetItem(Point position, int32_t iseed, _item_indexes idx, uint16_t ci);
+
+/**
+ * @brief Checks if the tile has room for an item
+ * @param position tile coordinates
+ * @return True if the space is free of obstructions, false if blocked
+ */
 bool CanPut(Point position);
-bool TryInvPut();
+
+/**
+ * @brief Checks for free spaces in the three "adjacent" tiles in the given direction and also the given position.
+ * @see CanPut
+ * @param position base tile coordinates
+ * @param facing direction to check, tiles "left" and "right" of this direction will also be checked.
+ * @return True if any of the four tiles checked can accept an item, false if all blocked
+ */
+bool CanPut(Point position, Direction facing);
+
 int InvPutItem(Player &player, Point position, Item &item);
 int SyncPutItem(Player &player, Point position, int idx, uint16_t icreateinfo, int iseed, int Id, int dur, int mdur, int ch, int mch, int ivalue, uint32_t ibuff, int toHit, int maxDam, int minStr, int minMag, int minDex, int ac);
 int SyncDropItem(Point position, int idx, uint16_t icreateinfo, int iseed, int id, int dur, int mdur, int ch, int mch, int ivalue, uint32_t ibuff, int toHit, int maxDam, int minStr, int minMag, int minDex, int ac);
@@ -212,7 +227,6 @@ Item &GetInventoryItem(Player &player, int location);
 bool UseInvItem(int pnum, int cii);
 void DoTelekinesis();
 int CalculateGold(Player &player);
-bool DropItemBeforeTrig();
 
 /**
  * @brief Gets the size, in inventory cells, of the given item.