diff --git a/Content.Server/_DV/Grappling/EntitySystems/GrapplingSystem.cs b/Content.Server/_DV/Grappling/EntitySystems/GrapplingSystem.cs
index 22ad27545b..187e856a0b 100644
--- a/Content.Server/_DV/Grappling/EntitySystems/GrapplingSystem.cs
+++ b/Content.Server/_DV/Grappling/EntitySystems/GrapplingSystem.cs
@@ -57,6 +57,7 @@ public sealed partial class GrapplingSystem : SharedGrapplingSystem
         SubscribeLocalEvent<GrapplerComponent, EscapeGrappleAlertEvent>(OnEscapeGrapplerAlert);
         SubscribeLocalEvent<GrapplerComponent, MobStateChangedEvent>(OnGrapplerStateChanged);
 
+        SubscribeLocalEvent<GrappledComponent, MobStateChangedEvent>(OnGrappledStateChanged);
         SubscribeLocalEvent<GrappledComponent, MoveInputEvent>(OnGrappledMove);
         SubscribeLocalEvent<GrappledComponent, GrappledEscapeDoAfter>(OnEscapeDoAfter);
         SubscribeLocalEvent<GrappledComponent, EscapeGrappleAlertEvent>(OnEscapeGrappledAlert);
@@ -429,6 +430,24 @@ public sealed partial class GrapplingSystem : SharedGrapplingSystem
         }
     }
 
+    /// <summary>
+    /// Handles when a grappled entity enters crit or dies while being held by a grappler, releasing the
+    /// grappler for them.
+    /// </summary>
+    /// <param name="grappled">Grappled entity which has entered crit or death.</param>
+    /// <param name="args">Args for the event.</param>
+    private void OnGrappledStateChanged(Entity<GrappledComponent> grappled, ref MobStateChangedEvent args)
+    {
+        if (grappled.Comp.Grappler == EntityUid.Invalid)
+            return;
+
+        if (args.NewMobState == MobState.Critical ||
+            args.NewMobState == MobState.Dead)
+        {
+            ReleaseGrapple(grappled.Comp.Grappler, manualRelease: true);
+        }
+    }
+
     /// <summary>
     /// Handles releasing the effects of a grapple from both entities.
     /// </summary>