diff --git a/code/game/objects/items/weapons/material/ashtray.dm b/code/game/objects/items/weapons/material/ashtray.dm
index efa3911323c..00630002558 100644
--- a/code/game/objects/items/weapons/material/ashtray.dm
+++ b/code/game/objects/items/weapons/material/ashtray.dm
@@ -18,15 +18,17 @@
 	return
 
 /obj/item/material/ashtray/shatter()
+	..()
 	if(emptyout(get_turf(src)))
 		visible_message(SPAN_DANGER("The contents of [src] spill everywhere!"))
 
 /obj/item/material/ashtray/proc/emptyout(atom/dest)
-	var/count = 0
-	for (var/obj/item/clothing/mask/smokable/cigarette/O in contents)
-		count++
+	if(!contents.len)
+		return FALSE
+	for (var/obj/O in contents)
 		O.forceMove(dest)
-	return count > 0
+	update_icon()
+	return TRUE
 
 /obj/item/material/ashtray/attack_self(mob/user)
 	var/turf/dest = get_turf(src)
@@ -68,7 +70,7 @@
 		if (istype(W,/obj/item/clothing/mask/smokable/cigarette))
 			var/obj/item/clothing/mask/smokable/cigarette/cig = W
 			if (cig.lit == TRUE)
-				user.visible_message("<b>[user]</b> crushes [cig] in \the [src], putting it out.", SPAN_NOTICE(""))
+				user.visible_message("<b>[user]</b> crushes [cig] in [src], putting it out.", SPAN_NOTICE("You crush [cig] in [src], putting it out."))
 				playsound(src.loc, 'sound/items/cigs_lighters/cig_snuff.ogg', 50, 1)
 				STOP_PROCESSING(SSprocessing, cig)
 				var/obj/item/butt = new cig.type_butt(src)
@@ -82,8 +84,9 @@
 					"<b>[user]</b> places [cig] in [src] without even smoking it.",
 					SPAN_NOTICE("You place [cig] in [src] without even smoking it. Why would you do that?")
 				)
+		else
+			user.visible_message("<b>[user]</b> places [W] in [src].", SPAN_NOTICE("You place [W] in [src]."))
 
-		src.visible_message("[user] places [W] in [src].")
 		user.update_inv_l_hand()
 		user.update_inv_r_hand()
 		add_fingerprint(user)
diff --git a/code/game/objects/structures/watercloset.dm b/code/game/objects/structures/watercloset.dm
index 0a66c80d5ff..6d1d7d64a4f 100644
--- a/code/game/objects/structures/watercloset.dm
+++ b/code/game/objects/structures/watercloset.dm
@@ -459,8 +459,6 @@
 
 	// Filling/emptying open reagent containers
 	var/obj/item/reagent_containers/RG = O
-	if (istype(RG, /obj/item/reagent_containers/glass/rag))
-		return
 
 	if (istype(RG) && RG.is_open_container())
 		var/atype = alert(usr, "Do you want to fill or empty \the [RG] at \the [src]?", "Fill or Empty", "Fill", "Empty", "Cancel")
@@ -534,7 +532,7 @@
 	// Short of a rewrite, this is necessary to stop monkeycubes being washed.
 	else if(istype(O, /obj/item/reagent_containers/food/snacks/monkeycube))
 		return
-	else if(istype(O, /obj/item/mop) || istype(O, /obj/item/reagent_containers/glass/rag))
+	else if(istype(O, /obj/item/mop))
 		O.reagents.add_reagent(/decl/reagent/water, 5)
 		to_chat(user, SPAN_NOTICE("You wet \the [O] in \the [src]."))
 		playsound(loc, 'sound/effects/slosh.ogg', 25, 1)
diff --git a/code/modules/detectivework/tools/rag.dm b/code/modules/detectivework/tools/rag.dm
index e62977e2686..07a7deca815 100644
--- a/code/modules/detectivework/tools/rag.dm
+++ b/code/modules/detectivework/tools/rag.dm
@@ -182,7 +182,10 @@
 	if(!proximity)
 		return
 
-	if(istype(A, /obj/structure/reagent_dispensers) || istype(A, /obj/structure/mopbucket) || istype(A, /obj/item/reagent_containers/glass) || istype(A, /obj/structure/sink))
+	if(istype(A, /obj/structure/sink))
+		return
+
+	else if(istype(A, /obj/structure/reagent_dispensers) || istype(A, /obj/structure/mopbucket) || istype(A, /obj/item/reagent_containers/glass))
 		if(!REAGENTS_FREE_SPACE(reagents))
 			to_chat(user, SPAN_WARNING("\The [src] is already soaked."))
 			return
@@ -194,7 +197,7 @@
 			update_icon()
 		return
 
-	if(!on_fire && istype(A) && (src in user))
+	else if(!on_fire && istype(A) && (src in user))
 		if(A.is_open_container() && !(A in user))
 			remove_contents(user, A)
 		else if(!ismob(A)) //mobs are handled in attack() - this prevents us from wiping down people while smothering them.
diff --git a/html/changelogs/johnwildkins-ashtray.yml b/html/changelogs/johnwildkins-ashtray.yml
new file mode 100644
index 00000000000..b8bd27a811a
--- /dev/null
+++ b/html/changelogs/johnwildkins-ashtray.yml
@@ -0,0 +1,5 @@
+author: JohnWildkins
+delete-after: True
+changes:
+  - bugfix: "Rags can now be filled at sinks once again."
+  - bugfix: "Ashtrays can now be emptied properly, and ashtray icons now update properly when emptied and filled. Ashtrays made of a brittle material will now also shatter if destroyed."