diff --git a/src/Support/EloquentCasts/DataCollectionEloquentCast.php b/src/Support/EloquentCasts/DataCollectionEloquentCast.php
index 92e64a11..c253e45c 100644
--- a/src/Support/EloquentCasts/DataCollectionEloquentCast.php
+++ b/src/Support/EloquentCasts/DataCollectionEloquentCast.php
@@ -122,6 +122,10 @@ public function set($model, string $key, $value, array $attributes): ?string
      */
     public function compare($model, string $key, $firstValue, $secondValue): bool
     {
+        if (in_array('encrypted', $this->arguments) && ! empty(Crypt::getPreviousKeys())) {
+            return false;
+        }
+
         return $this->get($model, $key, $firstValue, [])?->toArray() === $this->get($model, $key, $secondValue, [])?->toArray();
     }
 
diff --git a/src/Support/EloquentCasts/DataEloquentCast.php b/src/Support/EloquentCasts/DataEloquentCast.php
index 17d93625..aa65dbc5 100644
--- a/src/Support/EloquentCasts/DataEloquentCast.php
+++ b/src/Support/EloquentCasts/DataEloquentCast.php
@@ -95,6 +95,10 @@ public function set($model, string $key, $value, array $attributes): ?string
      */
     public function compare($model, string $key, $firstValue, $secondValue): bool
     {
+        if (in_array('encrypted', $this->arguments) && ! empty(Crypt::getPreviousKeys())) {
+            return false;
+        }
+
         return $this->get($model, $key, $firstValue, [])?->toArray() === $this->get($model, $key, $secondValue, [])?->toArray();
     }
 
diff --git a/tests/Support/EloquentCasts/DataCollectionEloquentCastTest.php b/tests/Support/EloquentCasts/DataCollectionEloquentCastTest.php
index 05ee4b66..9b82a2ea 100644
--- a/tests/Support/EloquentCasts/DataCollectionEloquentCastTest.php
+++ b/tests/Support/EloquentCasts/DataCollectionEloquentCastTest.php
@@ -15,6 +15,7 @@
 use Spatie\LaravelData\Tests\Fakes\Models\DummyModelWithCasts;
 use Spatie\LaravelData\Tests\Fakes\Models\DummyModelWithCustomCollectionCasts;
 use Spatie\LaravelData\Tests\Fakes\Models\DummyModelWithDefaultCasts;
+use Spatie\LaravelData\Tests\Fakes\Models\DummyModelWithEncryptedCasts;
 use Spatie\LaravelData\Tests\Fakes\Models\DummyModelWithJson;
 use Spatie\LaravelData\Tests\Fakes\MultiData;
 use Spatie\LaravelData\Tests\Fakes\SimpleData;
@@ -265,6 +266,36 @@ public function __construct(public string $b)
         ->and($model->isDirty('data_collection'))->toBeFalse();
 })->skip(fn () => version_compare(app()->version(), '12.18.0', '<'));
 
+it('flags the attribute as dirty when it is encrypted and there are previous encryption keys', function () {
+    config()->set('app.previous_keys', ['base64:'.base64_encode(random_bytes(32))]);
+
+    $model = new DummyModelWithEncryptedCasts();
+    $model->data_collection = [
+        new SimpleData('First'),
+        new SimpleData('Second'),
+    ];
+    $model->save();
+
+    $model->data_collection = $model->data_collection;
+
+    expect($model->getRawOriginal('data_collection'))->not->toBe($model->getAttributes()['data_collection'])
+        ->and($model->isDirty('data_collection'))->toBeTrue();
+})->skip(fn () => version_compare(app()->version(), '12.18.0', '<'));
+
+it('does not flag the attribute as dirty when it is encrypted and there are no previous encryption keys', function () {
+    $model = new DummyModelWithEncryptedCasts();
+    $model->data_collection = [
+        new SimpleData('First'),
+        new SimpleData('Second'),
+    ];
+    $model->save();
+
+    $model->data_collection = $model->data_collection;
+
+    expect($model->getRawOriginal('data_collection'))->not->toBe($model->getAttributes()['data_collection'])
+        ->and($model->isDirty('data_collection'))->toBeFalse();
+})->skip(fn () => version_compare(app()->version(), '12.18.0', '<'));
+
 it('can update a model where the cast is initially null', function () {
     $model = new DummyModelWithCasts();
     $model->setRawAttributes(['data_collection' => null]);
diff --git a/tests/Support/EloquentCasts/DataEloquentCastTest.php b/tests/Support/EloquentCasts/DataEloquentCastTest.php
index 2f5e17c1..8fdc8ad8 100644
--- a/tests/Support/EloquentCasts/DataEloquentCastTest.php
+++ b/tests/Support/EloquentCasts/DataEloquentCastTest.php
@@ -270,6 +270,30 @@ public function __construct(public string $a)
         ->and($model->isDirty('data'))->toBeTrue();
 })->skip(fn () => version_compare(app()->version(), '12.18.0', '<'));
 
+it('flags the attribute as dirty when it is encrypted and there are previous encryption keys', function () {
+    config()->set('app.previous_keys', ['base64:'.base64_encode(random_bytes(32))]);
+
+    $model = new DummyModelWithEncryptedCasts();
+    $model->data = new SimpleData('First');
+    $model->save();
+
+    $model->data = $model->data;
+
+    expect($model->getRawOriginal('data'))->not->toBe($model->getAttributes()['data'])
+        ->and($model->isDirty('data'))->toBeTrue();
+})->skip(fn () => version_compare(app()->version(), '12.18.0', '<'));
+
+it('does not flag the attribute as dirty when it is encrypted and there are no previous encryption keys', function () {
+    $model = new DummyModelWithEncryptedCasts();
+    $model->data = new SimpleData('First');
+    $model->save();
+
+    $model->data = $model->data;
+
+    expect($model->getRawOriginal('data'))->not->toBe($model->getAttributes()['data'])
+        ->and($model->isDirty('data'))->toBeFalse();
+})->skip(fn () => version_compare(app()->version(), '12.18.0', '<'));
+
 it('can update a model where the cast is initially null', function () {
     $model = DummyModelWithCasts::create([
         'data' => null,