diff --git a/code/modules/mob/living/carbon/human/emote_vr.dm b/code/modules/mob/living/carbon/human/emote_vr.dm
index 48d3c95a737..561a67a0247 100644
--- a/code/modules/mob/living/carbon/human/emote_vr.dm
+++ b/code/modules/mob/living/carbon/human/emote_vr.dm
@@ -8,10 +8,35 @@
 			message = "awoos loudly. AwoooOOOOoooo!"
 			m_type = 2
 		if ("flip")
-			message = "does a flip!"
-			if(!src.sleeping || !src.resting || !src.buckled || !src.restrained())
+			var/danger = 1 //Base 1% chance to break something.
+			var/list/involved_parts = list(BP_L_LEG, BP_R_LEG, BP_L_FOOT, BP_R_FOOT)
+			for(var/organ_name in involved_parts)
+				var/obj/item/organ/external/E = get_organ(organ_name)
+				if(!E || E.is_stump() || E.splinted || (E.status & ORGAN_BROKEN))
+					involved_parts -= organ_name
+					danger += 2
+
+			//Taurs are harder to flip
+			if(istype(tail_style, /datum/sprite_accessory/tail/taur))
+				danger += 1
+
+			//Check if they are physically capable
+			if(src.sleeping || src.resting || src.buckled || src.weakened || src.restrained() || involved_parts.len < 2)
+				src << "<span class='warning'>You can't *flip in your current state!</span>"
+				return 1
+			else
 				src.SpinAnimation(7,1)
-			m_type = 1
+				message = "does a flip!"
+				m_type = 1
+
+				world.log << "[src] *flip with danger [danger]%"
+				if(prob(danger))
+					spawn(10) //Stick the landing.
+						var/breaking = pick(involved_parts)
+						var/obj/item/organ/external/E = get_organ(breaking)
+						src.Weaken(5)
+						E.fracture()
+						log_and_message_admins("broke their [breaking] with *flip, ahahah.", src)
 
 	if (message)
 		log_emote("[name]/[key] : [message]")