diff --git a/code/game/objects/items/weapons/handcuffs.dm b/code/game/objects/items/weapons/handcuffs.dm
index 5546a0db02..9508341c04 100644
--- a/code/game/objects/items/weapons/handcuffs.dm
+++ b/code/game/objects/items/weapons/handcuffs.dm
@@ -92,6 +92,28 @@
 			return
 	return
 
+var/last_chew = 0
+/mob/living/carbon/human/RestrainedClickOn(var/atom/A)
+	if (A != src) return ..()
+	if (last_chew + 26 > world.time) return
+
+	var/mob/living/carbon/human/H = A
+	if (H.a_intent != "hurt") return
+	if (H.zone_sel.selecting != "mouth") return
+
+	var/datum/organ/external/O = H.organs_by_name[H.hand?"l_hand":"r_hand"]
+	if (!O) return
+
+	var/s = "\red [H.name] chews on \his [O.display_name]!"
+	H.visible_message(s, "\red You chew on your [O.display_name]!")
+	H.attack_log += text("\[[time_stamp()]\] <font color='red'>[s] ([H.ckey])</font>")
+	log_attack("[s] ([H.ckey])")
+
+	if(O.take_damage(3,0,1,"teeth marks"))
+		H:UpdateDamageIcon()
+
+	last_chew = world.time
+
 /obj/item/weapon/handcuffs/cable
 	name = "cable restraints"
 	desc = "Looks like some cables tied together. Could be used to tie something up."
@@ -123,4 +145,4 @@
 	color = "#FFFFFF"
 
 /obj/item/weapon/handcuffs/cyborg
-	dispenser = 1
\ No newline at end of file
+	dispenser = 1
diff --git a/code/modules/organs/organ_external.dm b/code/modules/organs/organ_external.dm
index 8ba5c0939a..466986b008 100644
--- a/code/modules/organs/organ_external.dm
+++ b/code/modules/organs/organ_external.dm
@@ -570,11 +570,32 @@ This function completely restores a damaged organ to perfect condition.
 
 			owner.update_body(1)
 
+			// OK so maybe your limb just flew off, but if it was attached to a pair of cuffs then hooray! Freedom!
+			release_restraints()
 
 /****************************************************
 			   HELPERS
 ****************************************************/
 
+/datum/organ/external/proc/release_restraints()
+	if (owner.handcuffed && body_part in list(ARM_LEFT, ARM_RIGHT, HAND_LEFT, HAND_RIGHT))
+		owner.visible_message(\
+			"\The [owner.handcuffed.name] falls off of [owner.name].",\
+			"\The [owner.handcuffed.name] falls off you.")
+
+		owner.handcuffed.loc = owner.loc
+		owner.handcuffed = null
+		owner.update_inv_handcuffed()
+
+	if (owner.legcuffed && body_part in list(FOOT_LEFT, FOOT_RIGHT, LEG_LEFT, LEG_RIGHT))
+		owner.visible_message(\
+			"\The [owner.legcuffed.name] falls off of [owner.name].",\
+			"\The [owner.legcuffed.name] falls off you.")
+
+		owner.legcuffed.loc = owner.loc
+		owner.legcuffed = null
+		owner.update_inv_legcuffed()
+
 /datum/organ/external/proc/bandage()
 	var/rval = 0
 	src.status &= ~ORGAN_BLEEDING
@@ -603,7 +624,10 @@ This function completely restores a damaged organ to perfect condition.
 /datum/organ/external/proc/fracture()
 	if(status & ORGAN_BROKEN)
 		return
-	owner.visible_message("\red You hear a loud cracking sound coming from \the [owner].","\red <b>Something feels like it shattered in your [display_name]!</b>","You hear a sickening crack.")
+	owner.visible_message(\
+		"\red You hear a loud cracking sound coming from \the [owner].",\
+		"\red <b>Something feels like it shattered in your [display_name]!</b>",\
+		"You hear a sickening crack.")
 
 	if(owner.species && !(owner.species.flags & NO_PAIN))
 		owner.emote("scream")
@@ -612,6 +636,10 @@ This function completely restores a damaged organ to perfect condition.
 	broken_description = pick("broken","fracture","hairline fracture")
 	perma_injury = brute_dam
 
+	// Fractures have a chance of getting you out of restraints
+	if (prob(25))
+		release_restraints()
+
 /datum/organ/external/proc/robotize()
 	src.status &= ~ORGAN_BROKEN
 	src.status &= ~ORGAN_BLEEDING