diff --git a/sources/Data/Collections/AssociativeArray.uc b/sources/Data/Collections/AssociativeArray.uc
index be9ecbd..72a82cf 100644
--- a/sources/Data/Collections/AssociativeArray.uc
+++ b/sources/Data/Collections/AssociativeArray.uc
@@ -474,10 +474,13 @@ public final function AssociativeArray CreateItem(
  *  Removed values are deallocated if they are managed. If you wish to avoid
  *  that, use `TakeItem()` or `TakeEntry()` methods.
  *
- *  @param  key Key for which to remove value.
+ *  @param  key             Key for which to remove value.
+ *  @param  deallocateKey   Should key be also deallocated?
  *  @return Caller `AssociativeArray` to allow for method chaining.
  */
-public final function AssociativeArray RemoveItem(AcediaObject key)
+public final function AssociativeArray RemoveItem(
+    AcediaObject    key,
+    optional bool   deallocateKey)
 {
     local Entry entryToRemove;
     local int   bucketIndex, entryIndex;
@@ -493,23 +496,16 @@ public final function AssociativeArray RemoveItem(AcediaObject key)
     if (entryToRemove.managed && entryToRemove.value != none) {
         entryToRemove.value.FreeSelf(entryToRemove.valueLifeVersion);
     }
+    if (deallocateKey && entryToRemove.key != none) {
+        entryToRemove.key.FreeSelf(entryToRemove.keyLifeVersion);
+    }
     return self;
 }
 
-/**
- *  Completely clears caller `AssociativeArray` of all stored entries,
- *  deallocating any stored managed values.
- *
- *  @param  deallocateKeys  Setting this to `true` will force this method to
- *      also deallocate all keys from the caller `AssociativeArray`.
- *      Since we do not record whether `AssociativeArray` manages keys like it
- *      does values - all keys will be deallocated, so use this parameter with
- *      caution.
- *  @return Caller `AssociativeArray` to allow for method chaining.
- */
 public function Empty(optional bool deallocateKeys)
 {
     local int           i, j;
+    local Collection    subCollection;
     local array<Entry>  nextEntries;
     for (i = 0; i < hashTable.length; i += 1)
     {
@@ -518,6 +514,17 @@ public function Empty(optional bool deallocateKeys)
         {
             if (!nextEntries[j].managed)      continue;
             if (nextEntries[j].value == none) continue;
+            if (    nextEntries[j].value.GetLifeVersion()
+                !=  nextEntries[j].valueLifeVersion) {
+                continue;
+            }
+            if (deallocateKeys)
+            {
+                subCollection = Collection(nextEntries[j].value);
+                if (subCollection != none) {
+                    subCollection.Empty(true);
+                }
+            }
             nextEntries[j].value.FreeSelf(nextEntries[j].valueLifeVersion);
         }
         if (deallocateKeys)
diff --git a/sources/Data/Collections/Collection.uc b/sources/Data/Collections/Collection.uc
index 16d03a4..f882f9b 100644
--- a/sources/Data/Collections/Collection.uc
+++ b/sources/Data/Collections/Collection.uc
@@ -60,6 +60,22 @@ public final function Iter Iterate()
     return newIterator;
 }
 
+/**
+ *  Completely clears caller `Collections` of all stored entries,
+ *  deallocating any stored managed values.
+ *
+ *  @param  deallocateKeys  Setting this to `true` will force this method to
+ *      also deallocate all keys from the caller `Collection`, if it uses them.
+ *      If this parameter is set to `true`, then `Empty()` call will also be
+ *      made recursively for all stored `Collection`, also causing them to
+ *      deallocate their keys.
+ *      For Acedia keys are only used by `AssociativeArray`.
+ *      Since we do not record whether `Collection` manages keys like it
+ *      does values - all keys will be deallocated, so use this parameter with
+ *      caution.
+ */
+public function Empty(optional bool deallocateKeys) {}
+
 /**
  *  Returns stored `AcediaObject` from the caller storage
  *  (or from it's sub-storages) via given `JSONPointer` path.
diff --git a/sources/Data/Collections/DynamicArray.uc b/sources/Data/Collections/DynamicArray.uc
index 34cb7d5..c4e985f 100644
--- a/sources/Data/Collections/DynamicArray.uc
+++ b/sources/Data/Collections/DynamicArray.uc
@@ -114,16 +114,21 @@ protected final function DynamicArray FreeManagedItem(int index)
     return self;
 }
 
-/**
- *  Empties caller `DynamicArray`, erasing it's contents.
- *  All managed objects will be deallocated.
- *
- *  @return Reference to the caller `DynamicArray` to allow for method chaining.
- */
-public final function DynamicArray Empty()
+public function Empty(optional bool deallocateKeys)
 {
+    local int           i;
+    local Collection    subCollection;
+    if (deallocateKeys)
+    {
+        for (i = 0; i < storedObjects.length; i += 1)
+        {
+            subCollection = Collection(GetItem(i));
+            if (subCollection != none) {
+                subCollection.Empty(true);
+            }
+        }
+    }
     SetLength(0);
-    return self;
 }
 
 /**
diff --git a/sources/Data/Collections/Tests/TEST_CollectionsMixed.uc b/sources/Data/Collections/Tests/TEST_CollectionsMixed.uc
index c8bd615..ec58a9b 100644
--- a/sources/Data/Collections/Tests/TEST_CollectionsMixed.uc
+++ b/sources/Data/Collections/Tests/TEST_CollectionsMixed.uc
@@ -27,6 +27,8 @@ protected static function TESTS()
     Context("Testing accessing collections by JSON pointers.");
     Test_GetBy();
     Test_GetTypeBy();
+    Context("Testing erasing collections with keys via `Empty()` method.");
+    Test_EmptyWithKeys();
 }
 
 protected static function Test_GetBy()
@@ -96,6 +98,33 @@ protected static function Test_GetTypeBy()
     TEST_ExpectNone(obj.GetTextBy(P("")));
 }
 
+protected static function Test_EmptyWithKeys()
+{
+    local Text              outerKey, innerKey1, innerKey2, innerKey3;
+    local DynamicArray      middleArray;
+    local AssociativeArray  outerObject, innerObject1, innerObject2;
+    outerKey = __().text.FromString("first");
+    innerKey1 = __().text.FromString("third?");
+    innerKey2 = __().text.FromString("Or not?");
+    innerKey3 = __().text.FromString("Like hell if I know!!!1111");
+    outerObject = __().collections.EmptyAssociativeArray();
+    innerObject1 = __().collections.EmptyAssociativeArray();
+    innerObject2 = __().collections.EmptyAssociativeArray();
+    middleArray = __().collections.EmptyDynamicArray();
+    innerObject1.SetItem(innerKey1, __().box.int(4));
+    innerObject1.SetItem(innerKey2, __().box.float(-4.6));
+    innerObject2.SetItem(innerKey2, __().ref.bool(true));
+    innerObject2.SetItem(innerKey3, none);
+    middleArray.AddItem(innerObject1).AddItem(innerObject2);
+    outerObject.SetItem(outerKey, middleArray);
+    outerObject.Empty(true);
+    Issue("Collection keys are not deallocated by `Empty(true)` method");
+    TEST_ExpectFalse(outerKey.IsAllocated());
+    TEST_ExpectFalse(innerKey1.IsAllocated());
+    TEST_ExpectFalse(innerKey2.IsAllocated());
+    TEST_ExpectFalse(innerKey3.IsAllocated());
+}
+
 defaultproperties
 {
     caseGroup = "Collections"