diff --git a/Content.Server/GameObjects/EntitySystems/HandsSystem.cs b/Content.Server/GameObjects/EntitySystems/HandsSystem.cs
index 40730bfe0f..97454023fb 100644
--- a/Content.Server/GameObjects/EntitySystems/HandsSystem.cs
+++ b/Content.Server/GameObjects/EntitySystems/HandsSystem.cs
@@ -18,6 +18,7 @@ using Robust.Shared.IoC;
 using Robust.Shared.Localization;
 using Robust.Shared.Map;
 using Robust.Shared.Players;
+using System;
 
 namespace Content.Server.GameObjects.EntitySystems
 {
@@ -121,22 +122,13 @@ namespace Content.Server.GameObjects.EntitySystems
             if (handsComp.GetActiveHand == null)
                 return false;
 
+            var entCoords = ent.Transform.GridPosition.Position;
+            var entToDesiredDropCoords = coords.Position - entCoords;
+            var targetLength = Math.Min(entToDesiredDropCoords.Length, InteractionSystem.InteractionRange - 0.001f); // InteractionRange is reduced due to InRange not dealing with floating point error
+            var newCoords = new GridCoordinates((entToDesiredDropCoords.Normalized * targetLength) + entCoords, coords.GridID);
+            var rayLength = EntitySystem.Get<SharedInteractionSystem>().UnobstructedRayLength(ent.Transform.MapPosition, newCoords.ToMap(_mapManager), ignoredEnt: ent);
 
-            if(EntitySystem.Get<SharedInteractionSystem>().InRangeUnobstructed(coords.ToMap(_mapManager), ent.Transform.MapPosition, ignoredEnt: ent))
-                if (coords.InRange(_mapManager, ent.Transform.GridPosition, InteractionSystem.InteractionRange))
-                {
-                    handsComp.Drop(handsComp.ActiveIndex, coords);
-                }
-                else
-                {
-                    var entCoords = ent.Transform.GridPosition.Position;
-                    var entToDesiredDropCoords = coords.Position - entCoords;
-                    var clampedDropCoords = ((entToDesiredDropCoords.Normalized * InteractionSystem.InteractionRange) + entCoords);
-
-                    handsComp.Drop(handsComp.ActiveIndex, new GridCoordinates(clampedDropCoords, coords.GridID));
-                }
-            else
-                handsComp.Drop(handsComp.ActiveIndex, ent.Transform.GridPosition);
+            handsComp.Drop(handsComp.ActiveIndex, new GridCoordinates(entCoords + (entToDesiredDropCoords.Normalized * rayLength), coords.GridID));
 
             return true;
         }
diff --git a/Content.Shared/GameObjects/EntitySystems/SharedInteractionSystem.cs b/Content.Shared/GameObjects/EntitySystems/SharedInteractionSystem.cs
index f4a5b7d735..6b0a937ff8 100644
--- a/Content.Shared/GameObjects/EntitySystems/SharedInteractionSystem.cs
+++ b/Content.Shared/GameObjects/EntitySystems/SharedInteractionSystem.cs
@@ -26,6 +26,43 @@ namespace Content.Server.GameObjects.EntitySystems
         public const float InteractionRange = 2;
         public const float InteractionRangeSquared = InteractionRange * InteractionRange;
 
+        /// <summary>
+        ///     Traces a ray from coords to otherCoords and returns the length
+        ///     of the vector between coords and the ray's first hit.
+        /// </summary>
+        /// <param name="coords">Set of coordinates to use.</param>
+        /// <param name="otherCoords">Other set of coordinates to use.</param>
+        /// <param name="collisionMask">the mask to check for collisions</param>
+        /// <param name="predicate">.</param>
+        /// <returns>Length of resulting ray.</returns>
+        public float UnobstructedRayLength(MapCoordinates coords, MapCoordinates otherCoords,
+            int collisionMask = (int) CollisionGroup.Impassable, Func<IEntity, bool> predicate = null)
+        {
+            var dir = otherCoords.Position - coords.Position;
+
+            if (dir.LengthSquared.Equals(0f)) return 0f;
+
+            var ray = new CollisionRay(coords.Position, dir.Normalized, collisionMask);
+            var rayResults = _physicsManager.IntersectRayWithPredicate(coords.MapId, ray, dir.Length, predicate, returnOnFirstHit: false).ToList();
+
+            if (rayResults.Count == 0) return dir.Length;
+            return (rayResults[0].HitPos - coords.Position).Length;
+        }
+
+        /// <summary>
+        ///     Traces a ray from coords to otherCoords and returns the length
+        ///     of the vector between coords and the ray's first hit.
+        /// </summary>
+        /// <param name="coords">Set of coordinates to use.</param>
+        /// <param name="otherCoords">Other set of coordinates to use.</param>
+        /// <param name="collisionMask">the mask to check for collisions</param>
+        /// <param name="ignoredEnt">the entity to be ignored when checking for collisions.</param>
+        /// <returns>Length of resulting ray.</returns>
+        public float UnobstructedRayLength(MapCoordinates coords, MapCoordinates otherCoords,
+            int collisionMask = (int) CollisionGroup.Impassable, IEntity ignoredEnt = null) =>
+            UnobstructedRayLength(coords, otherCoords, collisionMask,
+                ignoredEnt == null ? null : (Func<IEntity, bool>) (entity => ignoredEnt == entity));
+
         /// <summary>
         ///     Checks that these coordinates are within a certain distance without any
         ///     entity that matches the collision mask obstructing them.
@@ -51,7 +88,7 @@ namespace Content.Server.GameObjects.EntitySystems
             if (range > 0f && !(dir.LengthSquared <= range * range)) return false;
 
             var ray = new CollisionRay(coords.Position, dir.Normalized, collisionMask);
-            var rayResults = _physicsManager.IntersectRayWithPredicate(coords.MapId, ray, dir.Length, predicate).ToList();
+            var rayResults = _physicsManager.IntersectRayWithPredicate(coords.MapId, ray, dir.Length, predicate, returnOnFirstHit: false).ToList();
             return rayResults.Count == 0 || (insideBlockerValid && rayResults.Count > 0 && (rayResults[0].HitPos - otherCoords.Position).Length < 1f);
         }