diff --git a/Libraries/SPTarkov.Server.Core/Generators/LocationLootGenerator.cs b/Libraries/SPTarkov.Server.Core/Generators/LocationLootGenerator.cs
index 4c1b4a45..171baca7 100644
--- a/Libraries/SPTarkov.Server.Core/Generators/LocationLootGenerator.cs
+++ b/Libraries/SPTarkov.Server.Core/Generators/LocationLootGenerator.cs
@@ -420,7 +420,7 @@ public class LocationLootGenerator(
         containerClone.Template.Root = parentId;
         containerClone.Template.Items[0].Id = parentId;
 
-        var containerMap = GetContainerMapping(containerTpl);
+        var containerMap = _itemHelper.GetContainerMapping(containerTpl);
 
         // Choose count of items to add to container
         var itemCountToAdd = GetWeightedCountOfContainerItems(containerTpl, staticLootDist, locationName);
@@ -549,22 +549,6 @@ public class LocationLootGenerator(
         };
     }
 
-    /// <summary>
-    ///     Get a 2D grid of a container's item slots
-    /// </summary>
-    /// <param name="containerTpl">Tpl id of the container</param>
-    protected int[][] GetContainerMapping(string containerTpl)
-    {
-        // Get template from db
-        var containerTemplate = _itemHelper.GetItem(containerTpl).Value;
-
-        // Get height/width
-        var height = containerTemplate.Properties.Grids[0].Props.CellsV;
-        var width = containerTemplate.Properties.Grids[0].Props.CellsH;
-
-        return _inventoryHelper.GetBlankContainerMap(height.Value, width.Value);
-    }
-
     /// <summary>
     ///     Look up a containers itemcountDistribution data and choose an item count based on the found weights
     /// </summary>
diff --git a/Libraries/SPTarkov.Server.Core/Generators/LootGenerator.cs b/Libraries/SPTarkov.Server.Core/Generators/LootGenerator.cs
index fedcfdc8..9276e8f4 100644
--- a/Libraries/SPTarkov.Server.Core/Generators/LootGenerator.cs
+++ b/Libraries/SPTarkov.Server.Core/Generators/LootGenerator.cs
@@ -36,9 +36,9 @@ public class LootGenerator(
     /// </summary>
     /// <param name="options">parameters to adjust how loot is generated</param>
     /// <returns>An array of loot items</returns>
-    public List<Item> CreateRandomLoot(LootRequest options)
+    public List<List<Item>> CreateRandomLoot(LootRequest options)
     {
-        var result = new List<Item>();
+        var result = new List<List<Item>>();
         var itemTypeCounts = InitItemLimitCounter(options.ItemLimits);
 
         // Handle sealed weapon containers
@@ -58,7 +58,7 @@ public class LootGenerator(
             {
                 // Choose one at random + add to results array
                 var chosenSealedContainer = _randomUtil.GetArrayValue(sealedWeaponContainerPool);
-                result.Add(
+                result.Add([
                     new Item
                     {
                         Id = _hashUtil.Generate(),
@@ -69,7 +69,7 @@ public class LootGenerator(
                             SpawnedInSession = true
                         }
                     }
-                );
+                ]);
             }
         }
 
@@ -175,9 +175,9 @@ public class LootGenerator(
     /// </summary>
     /// <param name="forcedLootDict">Dictionary of item tpls with minmax values</param>
     /// <returns>Array of Item</returns>
-    public List<Item> CreateForcedLoot(Dictionary<string, MinMax<int>> forcedLootDict)
+    public List<List<Item>> CreateForcedLoot(Dictionary<string, MinMax<int>> forcedLootDict)
     {
-        var result = new List<Item>();
+        var result = new List<List<Item>>();
 
         var forcedItems = forcedLootDict;
 
@@ -199,7 +199,7 @@ public class LootGenerator(
             };
 
             var splitResults = _itemHelper.SplitStack(newLootItem);
-            result.AddRange(splitResults);
+            result.Add(splitResults);
         }
 
         return result;
@@ -319,7 +319,7 @@ public class LootGenerator(
     /// <returns>true if item was valid and added to pool</returns>
     protected bool FindAndAddRandomItemToLoot(List<TemplateItem> items, Dictionary<string, ItemLimit> itemTypeCounts,
         LootRequest options,
-        List<Item> result)
+        List<List<Item>> result)
     {
         var randomItem = _randomUtil.GetArrayValue(items);
 
@@ -353,7 +353,7 @@ public class LootGenerator(
         }
 
         newLootItem.Template = randomItem.Id;
-        result.Add(newLootItem);
+        result.Add([newLootItem]);
 
         if (randomItemLimitCount is not null)
             // Increment item count as it's in limit array
@@ -396,7 +396,7 @@ public class LootGenerator(
     protected bool FindAndAddRandomPresetToLoot(List<Preset> presetPool,
         Dictionary<string, ItemLimit> itemTypeCounts,
         HashSet<string> itemBlacklist,
-        List<Item> result)
+        List<List<Item>> result)
     {
         // Choose random preset and get details from item db using encyclopedia value (encyclopedia === tplId)
         var chosenPreset = _randomUtil.GetArrayValue(presetPool);
@@ -457,10 +457,7 @@ public class LootGenerator(
         _itemHelper.SetFoundInRaid(presetAndMods);
 
         // Add chosen preset tpl to result array
-        foreach (var item in presetAndMods)
-        {
-            result.Add(item);
-        }
+        result.Add(presetAndMods);
 
         if (itemLimitCount is not null)
             // Increment item count as item has been chosen and its inside itemLimitCount dictionary
diff --git a/Libraries/SPTarkov.Server.Core/Helpers/InventoryHelper.cs b/Libraries/SPTarkov.Server.Core/Helpers/InventoryHelper.cs
index 64063bc1..d4a45a18 100644
--- a/Libraries/SPTarkov.Server.Core/Helpers/InventoryHelper.cs
+++ b/Libraries/SPTarkov.Server.Core/Helpers/InventoryHelper.cs
@@ -795,27 +795,6 @@ public class InventoryHelper(
         ];
     }
 
-    /// <summary>
-    ///     Get a blank two-dimensional representation of a container
-    /// </summary>
-    /// <param name="containerH">Horizontal size of container</param>
-    /// <param name="containerY">Vertical size of container</param>
-    /// <returns>Two-dimensional representation of container</returns>
-    public int[][] GetBlankContainerMap(int containerH, int containerY)
-    {
-        //var x = new int[containerY][];
-        //for (int i = 0; i < containerY; i++)
-        //{
-        //    x[i] = new int[containerH];
-        //}
-
-        //return x;
-
-        return Enumerable.Range(0, containerY)
-            .Select(i => new int[containerH])
-            .ToArray();
-    }
-
     /// <summary>
     ///     Get a 2d mapping of a container with what grid slots are filled
     /// </summary>
@@ -827,7 +806,7 @@ public class InventoryHelper(
     public int[][] GetContainerMap(int containerH, int containerV, List<Item> itemList, string containerId)
     {
         // Create blank 2d map of container
-        var container2D = GetBlankContainerMap(containerH, containerV);
+        var container2D = _itemHelper.GetBlankContainerMap(containerH, containerV);
 
         // Get all items in players inventory keyed by their parentId and by ItemId
         var inventoryItemHash = GetInventoryItemHash(itemList);
@@ -1026,7 +1005,7 @@ public class InventoryHelper(
         var containerH = firstContainerGrid.Props.CellsH;
         var containerV = firstContainerGrid.Props.CellsV;
 
-        return GetBlankContainerMap(containerH.Value, containerV.Value);
+        return _itemHelper.GetBlankContainerMap(containerH.Value, containerV.Value);
     }
 
     /// <summary>
diff --git a/Libraries/SPTarkov.Server.Core/Helpers/ItemHelper.cs b/Libraries/SPTarkov.Server.Core/Helpers/ItemHelper.cs
index 99090494..3125c474 100644
--- a/Libraries/SPTarkov.Server.Core/Helpers/ItemHelper.cs
+++ b/Libraries/SPTarkov.Server.Core/Helpers/ItemHelper.cs
@@ -1203,8 +1203,10 @@ public class ItemHelper(
         {
             if (IsOfBaseclasses(item.Template, [BaseClasses.MONEY, BaseClasses.AMMO]))
             {
-                item.Upd ??= new Upd();
-                item.Upd.SpawnedInSession = null;
+                if (item.Upd is not null)
+                {
+                    item.Upd.SpawnedInSession = null;
+                }
 
                 continue;
             }
@@ -2181,6 +2183,43 @@ public class ItemHelper(
             }
         }
     }
+
+    /// <summary>
+    ///     Get a 2D grid of a container's item slots
+    /// </summary>
+    /// <param name="containerTpl">Tpl id of the container</param>
+    public int[][] GetContainerMapping(string containerTpl)
+    {
+        // Get template from db
+        var containerTemplate = GetItem(containerTpl).Value;
+
+        // Get height/width
+        var height = containerTemplate.Properties.Grids[0].Props.CellsV;
+        var width = containerTemplate.Properties.Grids[0].Props.CellsH;
+
+        return GetBlankContainerMap(height.Value, width.Value);
+    }
+
+    /// <summary>
+    ///     Get a blank two-dimensional representation of a container
+    /// </summary>
+    /// <param name="containerH">Horizontal size of container</param>
+    /// <param name="containerY">Vertical size of container</param>
+    /// <returns>Two-dimensional representation of container</returns>
+    public int[][] GetBlankContainerMap(int containerH, int containerY)
+    {
+        //var x = new int[containerY][];
+        //for (int i = 0; i < containerY; i++)
+        //{
+        //    x[i] = new int[containerH];
+        //}
+
+        //return x;
+
+        return Enumerable.Range(0, containerY)
+            .Select(i => new int[containerH])
+            .ToArray();
+    }
 }
 
 public class ItemSize
diff --git a/Libraries/SPTarkov.Server.Core/Services/AirdropService.cs b/Libraries/SPTarkov.Server.Core/Services/AirdropService.cs
index 5d85185c..8d71c2c6 100644
--- a/Libraries/SPTarkov.Server.Core/Services/AirdropService.cs
+++ b/Libraries/SPTarkov.Server.Core/Services/AirdropService.cs
@@ -3,6 +3,7 @@ using SPTarkov.Server.Core.Generators;
 using SPTarkov.Server.Core.Helpers;
 using SPTarkov.Server.Core.Models.Eft.Common.Tables;
 using SPTarkov.Server.Core.Models.Eft.Location;
+using SPTarkov.Server.Core.Models.Eft.Player;
 using SPTarkov.Server.Core.Models.Enums;
 using SPTarkov.Server.Core.Models.Spt.Config;
 using SPTarkov.Server.Core.Models.Spt.Services;
@@ -20,6 +21,7 @@ public class AirdropService(
     LootGenerator _lootGenerator,
     HashUtil _hashUtil,
     WeightedRandomHelper _weightedRandomHelper,
+    ContainerHelper _containerHelper,
     LocalisationService _localisationService,
     ItemFilterService _itemFilterService,
     ItemHelper _itemHelper)
@@ -59,18 +61,24 @@ public class AirdropService(
         var airdropConfig = GetAirdropLootConfigByType(airdropType);
 
         // generate loot to put into airdrop crate
-        var crateLoot = airdropConfig.UseForcedLoot.GetValueOrDefault(false)
+        var crateLootPool = airdropConfig.UseForcedLoot.GetValueOrDefault(false)
             ? _lootGenerator.CreateForcedLoot(airdropConfig.ForcedLoot)
             : _lootGenerator.CreateRandomLoot(airdropConfig);
 
         // Create airdrop crate and add to result in first spot
         var airdropCrateItem = GetAirdropCrateItem(airdropType);
 
-        // Add crate to front of list
-        crateLoot.Insert(0, airdropCrateItem);
+        // Filter loot pool to just items that fit crate
+        var crateLoot = GetLootThatFitsContainer(airdropCrateItem, crateLootPool);
 
-        // Re-parent loot items to crate we added above
-        foreach (var item in crateLoot)
+        // Flatten loot into single array ready to be returned
+        var flattenedCrateLoot = crateLoot.SelectMany(x => x).ToList();
+
+        // Add crate to front of loot rewards
+        flattenedCrateLoot.Insert(0, airdropCrateItem);
+
+        // Re-parent loot items to crate we just added
+        foreach (var item in flattenedCrateLoot)
         {
             if (item.Id == airdropCrateItem.Id)
                 // Crate itself, don't alter
@@ -79,7 +87,7 @@ public class AirdropService(
             }
 
             // no parentId = root item, make item have crate as parent
-            if (item.ParentId is null)
+            if (string.IsNullOrEmpty(item.ParentId))
             {
                 item.ParentId = airdropCrateItem.Id;
                 item.SlotId = "main";
@@ -89,10 +97,49 @@ public class AirdropService(
         return new GetAirdropLootResponse
         {
             Icon = airdropConfig.Icon,
-            Container = crateLoot
+            Container = flattenedCrateLoot
         };
     }
 
+    /// <summary>
+    /// Check if the items provided fit into the passed in container
+    /// </summary>
+    /// <param name="container">Crate item to fit items into</param>
+    /// <param name="crateLootPool">Item pool to try and fit into container</param>
+    /// <returns>Items that will fit container</returns>
+    protected List<List<Item>> GetLootThatFitsContainer(Item container, List<List<Item>> crateLootPool)
+    {
+        var lootResult = new List<List<Item>>();
+        var containerMap = _itemHelper.GetContainerMapping(container.Template);
+
+        var failedToFitAttemptCount = 0;
+        foreach (var itemAndChildren in crateLootPool)
+        {
+            var itemSize = _itemHelper.GetItemSize(itemAndChildren, itemAndChildren[0].Id);
+
+            // look for open slot to put chosen item into
+            var result = _containerHelper.FindSlotForItem(containerMap, itemSize.Width, itemSize.Height);
+            if (result.Success.GetValueOrDefault(false))
+            {
+                // It Fits!
+                lootResult.AddRange(itemAndChildren);
+
+                continue;
+            }
+
+            if (failedToFitAttemptCount > 3)
+                // x attempts to fit an item, container is probably full, stop trying to add more
+            {
+                break;
+            }
+
+            // Can't fit item, skip
+            failedToFitAttemptCount++;
+        }
+
+        return lootResult;
+    }
+
     /// <summary>
     ///     Create a container create item based on passed in airdrop type
     /// </summary>
diff --git a/Libraries/SPTarkov.Server.Core/Services/LocationLifecycleService.cs b/Libraries/SPTarkov.Server.Core/Services/LocationLifecycleService.cs
index bdf850db..ec5a7db7 100644
--- a/Libraries/SPTarkov.Server.Core/Services/LocationLifecycleService.cs
+++ b/Libraries/SPTarkov.Server.Core/Services/LocationLifecycleService.cs
@@ -503,12 +503,15 @@ public class LocationLifecycleService
         var mailableLoot = new List<Item>();
 
         var parentId = _hashUtil.Generate();
-        foreach (var item in loot)
+        foreach (var itemAndChildren in loot)
         {
-            item.ParentId = parentId;
-            mailableLoot.Add(item);
+            // Set all root items parent to new id
+            itemAndChildren[0].ParentId = parentId;
         }
 
+        // Flatten
+        mailableLoot.AddRange(loot.SelectMany(x => x));
+
         // Send message from fence giving player reward generated above
         _mailSendService.SendLocalisedNpcMessageToPlayer(
             sessionId,