diff --git a/Source/controls/plrctrls.cpp b/Source/controls/plrctrls.cpp
index f54860b91..aaba75f40 100644
--- a/Source/controls/plrctrls.cpp
+++ b/Source/controls/plrctrls.cpp
@@ -1479,7 +1479,7 @@ void PerformSpellAction()
 	}
 
 	UpdateSpellTarget();
-	CheckPlrSpell();
+	CheckPlrSpell(false);
 }
 
 void CtrlUseInvItem()
diff --git a/Source/cursor.cpp b/Source/cursor.cpp
index 8bda033f4..d2ffee241 100644
--- a/Source/cursor.cpp
+++ b/Source/cursor.cpp
@@ -373,6 +373,32 @@ void CheckCursMove()
 		my = MAXDUNY - 1;
 	}
 
+	// While holding down left click we should retain target (but potentially lose it if it dies, goes out of view, etc)
+	if (sgbMouseDown == CLICK_LEFT && pcursinvitem == -1) {
+		if (pcursmonst != -1) {
+			if (Monsters[pcursmonst]._mDelFlag || Monsters[pcursmonst]._mhitpoints >> 6 <= 0
+				|| !(dFlags[Monsters[pcursmonst].position.tile.x][Monsters[pcursmonst].position.tile.y] & BFLAG_VISIBLE))
+				pcursmonst = -1;
+		} else if (pcursobj != -1) {
+			if (Objects[pcursobj]._oSelFlag < 1)
+				pcursobj = -1;
+		} else if (pcursplr != -1) {
+			if (Players[pcursplr]._pmode == PM_DEATH || Players[pcursplr]._pmode == PM_QUIT || !Players[pcursplr].plractive
+				|| currlevel != Players[pcursplr].plrlevel || Players[pcursplr]._pHitPoints >> 6 <= 0
+				|| !(dFlags[Players[pcursplr].position.tile.x][Players[pcursplr].position.tile.y] & BFLAG_VISIBLE))
+				pcursplr = -1;
+		}
+
+		if (pcursmonst == -1 && pcursobj == -1 && pcursitem == -1 && pcursinvitem == -1 && pcursplr == -1) {
+			cursmx = mx;
+			cursmy = my;
+			CheckTrigForce();
+			CheckTown();
+			CheckRportal();
+		}
+		return;
+	}
+
 	bool flipflag = (flipy && flipx) || ((flipy || flipx) && px < TILE_WIDTH / 2);
 
 	pcurstemp = pcursmonst;
diff --git a/Source/diablo.cpp b/Source/diablo.cpp
index c19ef478e..6634d05b0 100644
--- a/Source/diablo.cpp
+++ b/Source/diablo.cpp
@@ -19,6 +19,7 @@
 #endif
 #include "DiabloUI/diabloui.h"
 #include "controls/keymapper.hpp"
+#include "diablo.h"
 #include "doom.h"
 #include "drlg_l1.h"
 #include "drlg_l2.h"
@@ -129,6 +130,11 @@ QuickMessage QuickMessages[QUICK_MESSAGE_OPTIONS] = {
 	{ "QuickMessage4", N_("Now you DIE!") }
 };
 
+MouseActionType lastLeftMouseButtonAction = MouseActionType::None; // This and the following mouse variables are for handling in-game click-and-hold actions
+MouseActionType lastRightMouseButtonAction = MouseActionType::None;
+Uint32 lastLeftMouseButtonTime = 0;
+Uint32 lastRightMouseButtonTime = 0;
+
 // Controller support: Actions to run after updating the cursor state.
 // Defined in SourceX/controls/plctrls.cpp.
 extern void finish_simulated_mouse_clicks(int currentMouseX, int currentMouseY);
@@ -248,14 +254,17 @@ bool LeftMouseCmd(bool bShift)
 			NetSendCmdLocParam1(true, pcurs == CURSOR_DISARM ? CMD_DISARMXY : CMD_OPOBJXY, { cursmx, cursmy }, pcursobj);
 		} else if (myPlayer._pwtype == WT_RANGED) {
 			if (bShift) {
+				lastLeftMouseButtonAction = MouseActionType::Attack;
 				NetSendCmdLoc(MyPlayerId, true, CMD_RATTACKXY, { cursmx, cursmy });
 			} else if (pcursmonst != -1) {
 				if (CanTalkToMonst(Monsters[pcursmonst])) {
 					NetSendCmdParam1(true, CMD_ATTACKID, pcursmonst);
 				} else {
+					lastLeftMouseButtonAction = MouseActionType::Attack_MonsterTarget;
 					NetSendCmdParam1(true, CMD_RATTACKID, pcursmonst);
 				}
 			} else if (pcursplr != -1 && !gbFriendlyMode) {
+				lastLeftMouseButtonAction = MouseActionType::Attack_PlayerTarget;
 				NetSendCmdParam1(true, CMD_RATTACKPID, pcursplr);
 			}
 		} else {
@@ -264,14 +273,18 @@ bool LeftMouseCmd(bool bShift)
 					if (CanTalkToMonst(Monsters[pcursmonst])) {
 						NetSendCmdParam1(true, CMD_ATTACKID, pcursmonst);
 					} else {
+						lastLeftMouseButtonAction = MouseActionType::Attack;
 						NetSendCmdLoc(MyPlayerId, true, CMD_SATTACKXY, { cursmx, cursmy });
 					}
 				} else {
+					lastLeftMouseButtonAction = MouseActionType::Attack;
 					NetSendCmdLoc(MyPlayerId, true, CMD_SATTACKXY, { cursmx, cursmy });
 				}
 			} else if (pcursmonst != -1) {
+				lastLeftMouseButtonAction = MouseActionType::Attack_MonsterTarget;
 				NetSendCmdParam1(true, CMD_ATTACKID, pcursmonst);
 			} else if (pcursplr != -1 && !gbFriendlyMode) {
+				lastLeftMouseButtonAction = MouseActionType::Attack_PlayerTarget;
 				NetSendCmdParam1(true, CMD_ATTACKPID, pcursplr);
 			}
 		}
@@ -284,6 +297,9 @@ bool LeftMouseCmd(bool bShift)
 
 bool LeftMouseDown(int wParam)
 {
+	lastLeftMouseButtonAction = MouseActionType::Other;
+	lastLeftMouseButtonTime = SDL_GetTicks();
+
 	if (gmenu_left_mouse(true))
 		return false;
 
@@ -372,6 +388,9 @@ void LeftMouseUp(int wParam)
 
 void RightMouseDown()
 {
+	lastRightMouseButtonAction = MouseActionType::Other;
+	lastRightMouseButtonTime = SDL_GetTicks();
+
 	if (gmenu_is_active() || sgnTimeoutCurs != CURSOR_NONE || PauseMode == 2 || Players[MyPlayerId]._pInvincible) {
 		return;
 	}
@@ -392,7 +411,7 @@ void RightMouseDown()
 	        && (pcursinvitem == -1 || !UseInvItem(MyPlayerId, pcursinvitem)))) {
 		if (pcurs == CURSOR_HAND) {
 			if (pcursinvitem == -1 || !UseInvItem(MyPlayerId, pcursinvitem))
-				CheckPlrSpell();
+				CheckPlrSpell(true);
 		} else if (pcurs > CURSOR_HAND && pcurs < CURSOR_FIRSTITEM) {
 			NewCursor(CURSOR_HAND);
 		}
@@ -720,6 +739,7 @@ void GameEventHandler(uint32_t uMsg, int32_t wParam, int32_t lParam)
 		return;
 	case DVL_WM_LBUTTONUP:
 		GetMousePos(lParam);
+		lastLeftMouseButtonAction = MouseActionType::None;
 		if (sgbMouseDown == CLICK_LEFT) {
 			sgbMouseDown = CLICK_NONE;
 			LeftMouseUp(wParam);
@@ -735,6 +755,7 @@ void GameEventHandler(uint32_t uMsg, int32_t wParam, int32_t lParam)
 		return;
 	case DVL_WM_RBUTTONUP:
 		GetMousePos(lParam);
+		lastRightMouseButtonAction = MouseActionType::None;
 		if (sgbMouseDown == CLICK_RIGHT) {
 			sgbMouseDown = CLICK_NONE;
 		}
@@ -2118,6 +2139,13 @@ void LoadGameLevel(bool firstflag, lvl_entry lvldir)
 
 	if (!gbIsSpawn && setlevel && setlvlnum == SL_SKELKING && Quests[Q_SKELKING]._qactive == QUEST_ACTIVE)
 		PlaySFX(USFX_SKING1);
+
+	// Reset mouse selection of entities
+	pcursmonst = -1;
+	pcursobj = -1;
+	pcursitem = -1;
+	pcursinvitem = -1;
+	pcursplr = -1;
 }
 
 /**
diff --git a/Source/diablo.h b/Source/diablo.h
index 538051d80..f14a2d94c 100644
--- a/Source/diablo.h
+++ b/Source/diablo.h
@@ -43,6 +43,16 @@ enum class GameLogicStep {
 	ProcessMissilesTown,
 };
 
+enum class MouseActionType : int {
+	None,
+	Spell,
+	Spell_ComplainedAboutMana,
+	Attack,
+	Attack_MonsterTarget,
+	Attack_PlayerTarget,
+	Other,
+};
+
 extern SDL_Window *ghMainWnd;
 extern DWORD glSeedTbl[NUMLEVELS];
 extern dungeon_type gnLevelTypeTbl[NUMLEVELS];
@@ -69,6 +79,11 @@ extern clicktype sgbMouseDown;
 extern uint16_t gnTickDelay;
 extern char gszProductName[64];
 
+extern MouseActionType lastLeftMouseButtonAction;
+extern MouseActionType lastRightMouseButtonAction;
+extern Uint32 lastLeftMouseButtonTime;
+extern Uint32 lastRightMouseButtonTime;
+
 void FreeGameMem();
 bool StartGame(bool bNewGame, bool bSinglePlayer);
 [[noreturn]] void diablo_quit(int exitStatus);
diff --git a/Source/items.cpp b/Source/items.cpp
index 4ab1e4f53..5e7f99935 100644
--- a/Source/items.cpp
+++ b/Source/items.cpp
@@ -3710,6 +3710,8 @@ void DeleteItem(int ii, int i)
 	ActiveItemCount--;
 	if (ActiveItemCount > 0 && i != ActiveItemCount)
 		ActiveItems[i] = ActiveItems[ActiveItemCount];
+	if (pcursitem == ii) // Unselect item if player has it highlighted
+		pcursitem = -1;
 }
 
 void ProcessItems()
diff --git a/Source/monster.cpp b/Source/monster.cpp
index 3527f94cd..1dda0d277 100644
--- a/Source/monster.cpp
+++ b/Source/monster.cpp
@@ -4446,6 +4446,8 @@ void DeleteMonsterList()
 
 	for (int i = MAX_PLRS; i < ActiveMonsterCount;) {
 		if (Monsters[ActiveMonsters[i]]._mDelFlag) {
+			if (pcursmonst == ActiveMonsters[i]) // Unselect monster if player highlighted it
+				pcursmonst = -1;
 			DeleteMonster(i);
 		} else {
 			i++;
diff --git a/Source/objects.cpp b/Source/objects.cpp
index a572a945c..32add173c 100644
--- a/Source/objects.cpp
+++ b/Source/objects.cpp
@@ -1212,6 +1212,8 @@ void DeleteObject(int oi, int i)
 	dObject[ox][oy] = 0;
 	AvailableObjects[-ActiveObjectCount + MAXOBJECTS] = oi;
 	ActiveObjectCount--;
+	if (pcursobj == oi) // Unselect object if this was highlighted by player
+		pcursobj = -1;
 	if (ActiveObjectCount > 0 && i != ActiveObjectCount)
 		ActiveObjects[i] = ActiveObjects[ActiveObjectCount];
 }
diff --git a/Source/player.cpp b/Source/player.cpp
index c3b4dbae3..55f0c8bb5 100644
--- a/Source/player.cpp
+++ b/Source/player.cpp
@@ -3572,7 +3572,7 @@ void CalcPlrStaff(PlayerStruct &player)
 	}
 }
 
-void CheckPlrSpell()
+void CheckPlrSpell(bool mouseClick)
 {
 	bool addflag = false;
 	int sl;
@@ -3643,11 +3643,16 @@ void CheckPlrSpell()
 			sl = GetSpellLevel(MyPlayerId, myPlayer._pRSpell);
 			NetSendCmdLocParam2(true, CMD_SPELLXY, { cursmx, cursmy }, myPlayer._pRSpell, sl);
 		}
+		if (mouseClick)
+			lastRightMouseButtonAction = MouseActionType::Spell;
 		return;
 	}
 
 	if (myPlayer._pRSplType == RSPLTYPE_SPELL) {
-		myPlayer.Say(HeroSpeech::NotEnoughMana);
+		if (!mouseClick || lastRightMouseButtonAction != MouseActionType::Spell_ComplainedAboutMana)
+			myPlayer.Say(HeroSpeech::NotEnoughMana);
+		if (mouseClick)
+			lastRightMouseButtonAction = MouseActionType::Spell_ComplainedAboutMana;
 	}
 }
 
diff --git a/Source/player.h b/Source/player.h
index dc3099b29..7021053ca 100644
--- a/Source/player.h
+++ b/Source/player.h
@@ -490,7 +490,7 @@ void ClrPlrPath(PlayerStruct &player);
 bool PosOkPlayer(int pnum, Point position);
 void MakePlrPath(int pnum, Point targetPosition, bool endspace);
 void CalcPlrStaff(PlayerStruct &player);
-void CheckPlrSpell();
+void CheckPlrSpell(bool mouseClick);
 void SyncPlrAnim(int pnum);
 void SyncInitPlrPos(int pnum);
 void SyncInitPlr(int pnum);
diff --git a/Source/track.cpp b/Source/track.cpp
index a863f3ac0..7c1f9203d 100644
--- a/Source/track.cpp
+++ b/Source/track.cpp
@@ -21,8 +21,60 @@ bool sgbIsWalking;
 
 } // namespace
 
+static bool RepeatMouseAttack(bool leftButton)
+{
+	if (pcurs != CURSOR_HAND)
+		return false;
+
+	Uint32 *timePressed;
+	MouseActionType lastAction;
+	if (leftButton) {
+		if (sgbMouseDown != CLICK_LEFT)
+			return false;
+		timePressed = &lastLeftMouseButtonTime;
+		lastAction = lastLeftMouseButtonAction;
+	} else {
+		if (sgbMouseDown != CLICK_RIGHT)
+			return false;
+		timePressed = &lastRightMouseButtonTime;
+		lastAction = lastRightMouseButtonAction;
+	}
+
+	if (lastAction != MouseActionType::Attack && lastAction != MouseActionType::Attack_MonsterTarget && lastAction != MouseActionType::Attack_PlayerTarget && lastAction != MouseActionType::Spell && lastAction != MouseActionType::Spell_ComplainedAboutMana)
+		return false;
+
+	if (Players[MyPlayerId]._pmode != PM_DEATH && Players[MyPlayerId]._pmode != PM_QUIT &&
+		Players[MyPlayerId].destAction == ACTION_NONE && SDL_GetTicks() - *timePressed >= (Uint32)gnTickDelay * 4) {
+		bool rangedAttack = Players[MyPlayerId]._pwtype == WT_RANGED;
+		*timePressed = SDL_GetTicks();
+		switch (lastAction) {
+		case MouseActionType::Attack:
+			if (cursmx >= 0 && cursmx < MAXDUNX && cursmy >= 0 && cursmy < MAXDUNY)
+				NetSendCmdLoc(MyPlayerId, true, rangedAttack ? CMD_RATTACKXY : CMD_SATTACKXY, { cursmx, cursmy });
+			break;
+		case MouseActionType::Attack_MonsterTarget:
+			if (pcursmonst != -1)
+				NetSendCmdParam1(true, rangedAttack ? CMD_RATTACKID : CMD_ATTACKID, pcursmonst);
+			break;
+		case MouseActionType::Attack_PlayerTarget:
+			if (pcursplr != -1 && !gbFriendlyMode)
+				NetSendCmdParam1(true, rangedAttack ? CMD_RATTACKPID : CMD_ATTACKPID, pcursplr);
+			break;
+		case MouseActionType::Spell:
+		case MouseActionType::Spell_ComplainedAboutMana:
+			CheckPlrSpell(true);
+			break;
+		}
+	}
+
+	return true;
+}
+
 void track_process()
 {
+	if (RepeatMouseAttack(true) || RepeatMouseAttack(false))
+		return;
+
 	if (!sgbIsWalking)
 		return;