diff --git a/code/game/objects/items/weapons/glass.dm b/code/game/objects/items/weapons/glass.dm
index 68f877f12af..38ce5ea77c6 100644
--- a/code/game/objects/items/weapons/glass.dm
+++ b/code/game/objects/items/weapons/glass.dm
@@ -89,19 +89,31 @@ SHARDS
 		return
 	switch(alert("Sheet-Glass", "Would you like full tile glass or one direction?", "one direct", "full (2 sheets)", "cancel", null))
 		if("one direct")
-			var/obj/window/W = new /obj/window( usr.loc )
-			W.anchored = 0
-			if (src.amount < 1)
-				return
-			src.amount--
+			var/go = 1
+			for (var/obj/window/win in usr.loc)
+				if(win.ini_dir == NORTHWEST || win.ini_dir == NORTHEAST || win.ini_dir == SOUTHWEST || win.ini_dir == SOUTHEAST)
+					go = 0
+			if(go)
+				var/obj/window/W = new /obj/window( usr.loc )
+				W.anchored = 0
+				if (src.amount < 1)
+					return
+				src.amount--
+			else usr << "Can't let you do that."
 		if("full (2 sheets)")
-			if (src.amount < 2)
-				return
-			src.amount -= 2
-			var/obj/window/W = new /obj/window( usr.loc )
-			W.dir = SOUTHWEST
-			W.ini_dir = SOUTHWEST
-			W.anchored = 0
+			var/go = 1
+			for (var/obj/window/win in usr.loc)
+				if(win)
+					go = 0
+			if (go)
+				if (src.amount < 2)
+					return
+				src.amount -= 2
+				var/obj/window/W = new /obj/window( usr.loc )
+				W.dir = SOUTHWEST
+				W.ini_dir = SOUTHWEST
+				W.anchored = 0
+			else usr << "Can't let you do that."
 		else
 	if (src.amount <= 0)
 		user.u_equip(src)
@@ -166,21 +178,33 @@ SHARDS
 		return
 	switch(alert("Sheet Reinf. Glass", "Would you like full tile glass or one direction?", "one direct", "full (2 sheets)", "cancel", null))
 		if("one direct")
-			var/obj/window/W = new /obj/window( usr.loc, 1 )
-			W.anchored = 0
-			W.state = 0
-			if (src.amount < 1)
-				return
-			src.amount--
+			var/go = 1
+			for (var/obj/window/win in usr.loc)
+				if(win.ini_dir == NORTHWEST || win.ini_dir == NORTHEAST || win.ini_dir == SOUTHWEST || win.ini_dir == SOUTHEAST)
+					go = 0
+			if(go)
+				var/obj/window/W = new /obj/window( usr.loc, 1 )
+				W.anchored = 0
+				W.state = 0
+				if (src.amount < 1)
+					return
+				src.amount--
+			else usr << "Can't let you do that."
 		if("full (2 sheets)")
-			if (src.amount < 2)
-				return
-			src.amount -= 2
-			var/obj/window/W = new /obj/window( usr.loc, 1 )
-			W.dir = SOUTHWEST
-			W.ini_dir = SOUTHWEST
-			W.anchored = 0
-			W.state = 0
+			var/go = 1
+			for (var/obj/window/win in usr.loc)
+				if(win)
+					go = 0
+			if(go)
+				if (src.amount < 2)
+					return
+				src.amount -= 2
+				var/obj/window/W = new /obj/window( usr.loc, 1 )
+				W.dir = SOUTHWEST
+				W.ini_dir = SOUTHWEST
+				W.anchored = 0
+				W.state = 0
+			else usr << "Can't let you do that."
 		else
 	if (src.amount <= 0)
 		user.u_equip(src)
diff --git a/code/modules/mob/living/carbon/alien/humanoid/humanoid.dm b/code/modules/mob/living/carbon/alien/humanoid/humanoid.dm
index 94bc7cac566..84ff7b6660e 100644
--- a/code/modules/mob/living/carbon/alien/humanoid/humanoid.dm
+++ b/code/modules/mob/living/carbon/alien/humanoid/humanoid.dm
@@ -94,6 +94,10 @@ to clean it up, or just beat the shit out of it (which takes ages).
 			src.now_pushing = 1
 			if (!AM.anchored)
 				var/t = get_dir(src, AM)
+				if (istype(AM, /obj/window))
+					if(AM:ini_dir == NORTHWEST || AM:ini_dir == NORTHEAST || AM:ini_dir == SOUTHWEST || AM:ini_dir == SOUTHEAST)
+						for(var/obj/window/win in get_step(AM,t))
+							return
 				step(AM, t)
 			src.now_pushing = null
 		return
@@ -422,6 +426,11 @@ to clean it up, or just beat the shit out of it (which takes ages).
 						step(src.pulling, get_dir(src.pulling.loc, T))
 						M.pulling = t
 				else
+					if (src.pulling)
+						if (istype(src.pulling, /obj/window))
+							if(src.pulling:ini_dir == NORTHWEST || src.pulling:ini_dir == NORTHEAST || src.pulling:ini_dir == SOUTHWEST || src.pulling:ini_dir == SOUTHEAST)
+								for(var/obj/window/win in get_step(src.pulling,get_dir(src.pulling.loc, T)))
+									src.pulling = null
 					if (src.pulling)
 						step(src.pulling, get_dir(src.pulling.loc, T))
 	else
diff --git a/code/modules/mob/living/carbon/human/human.dm b/code/modules/mob/living/carbon/human/human.dm
index aa3b571df2f..bcf68283189 100644
--- a/code/modules/mob/living/carbon/human/human.dm
+++ b/code/modules/mob/living/carbon/human/human.dm
@@ -107,6 +107,10 @@
 			src.now_pushing = 1
 			if (!AM.anchored)
 				var/t = get_dir(src, AM)
+				if (istype(AM, /obj/window))
+					if(AM:ini_dir == NORTHWEST || AM:ini_dir == NORTHEAST || AM:ini_dir == SOUTHWEST || AM:ini_dir == SOUTHEAST)
+						for(var/obj/window/win in get_step(AM,t))
+							return
 				step(AM, t)
 			src.now_pushing = null
 		return
@@ -917,6 +921,11 @@
 						step(src.pulling, get_dir(src.pulling.loc, T))
 						M.pulling = t
 				else
+					if (src.pulling)
+						if (istype(src.pulling, /obj/window))
+							if(src.pulling:ini_dir == NORTHWEST || src.pulling:ini_dir == NORTHEAST || src.pulling:ini_dir == SOUTHWEST || src.pulling:ini_dir == SOUTHEAST)
+								for(var/obj/window/win in get_step(src.pulling,get_dir(src.pulling.loc, T)))
+									src.pulling = null
 					if (src.pulling)
 						step(src.pulling, get_dir(src.pulling.loc, T))
 	else
diff --git a/code/modules/mob/living/carbon/monkey/monkey.dm b/code/modules/mob/living/carbon/monkey/monkey.dm
index c0e3f964772..1aa07746ec4 100644
--- a/code/modules/mob/living/carbon/monkey/monkey.dm
+++ b/code/modules/mob/living/carbon/monkey/monkey.dm
@@ -62,6 +62,10 @@
 			src.now_pushing = 1
 			if (!( AM.anchored ))
 				var/t = get_dir(src, AM)
+				if (istype(AM, /obj/window))
+					if(AM:ini_dir == NORTHWEST || AM:ini_dir == NORTHEAST || AM:ini_dir == SOUTHWEST || AM:ini_dir == SOUTHEAST)
+						for(var/obj/window/win in get_step(AM,t))
+							return
 				step(AM, t)
 			src.now_pushing = null
 		return
@@ -367,7 +371,13 @@
 					step(src.pulling, get_dir(src.pulling.loc, T))
 					M.pulling = t
 			else
-				step(src.pulling, get_dir(src.pulling.loc, T))
+				if (src.pulling)
+					if (istype(src.pulling, /obj/window))
+						if(src.pulling:ini_dir == NORTHWEST || src.pulling:ini_dir == NORTHEAST || src.pulling:ini_dir == SOUTHWEST || src.pulling:ini_dir == SOUTHEAST)
+							for(var/obj/window/win in get_step(src.pulling,get_dir(src.pulling.loc, T)))
+								src.pulling = null
+				if (src.pulling)
+					step(src.pulling, get_dir(src.pulling.loc, T))
 	else
 		src.pulling = null
 		. = ..()
diff --git a/code/modules/mob/living/silicon/robot/robot.dm b/code/modules/mob/living/silicon/robot/robot.dm
index e81e95d4136..79da5b3d8a2 100644
--- a/code/modules/mob/living/silicon/robot/robot.dm
+++ b/code/modules/mob/living/silicon/robot/robot.dm
@@ -277,6 +277,10 @@
 			src.now_pushing = 1
 			if (!AM.anchored)
 				var/t = get_dir(src, AM)
+				if (istype(AM, /obj/window))
+					if(AM:ini_dir == NORTHWEST || AM:ini_dir == NORTHEAST || AM:ini_dir == SOUTHWEST || AM:ini_dir == SOUTHEAST)
+						for(var/obj/window/win in get_step(AM,t))
+							return
 				step(AM, t)
 			src.now_pushing = null
 		return
@@ -790,6 +794,11 @@ Frequency:
 						step(src.pulling, get_dir(src.pulling.loc, T))
 						M.pulling = t
 				else
+					if (src.pulling)
+						if (istype(src.pulling, /obj/window))
+							if(src.pulling:ini_dir == NORTHWEST || src.pulling:ini_dir == NORTHEAST || src.pulling:ini_dir == SOUTHWEST || src.pulling:ini_dir == SOUTHEAST)
+								for(var/obj/window/win in get_step(src.pulling,get_dir(src.pulling.loc, T)))
+									src.pulling = null
 					if (src.pulling)
 						step(src.pulling, get_dir(src.pulling.loc, T))
 	else