diff --git a/packages/core/src/DiscountTypes/AbstractDiscountType.php b/packages/core/src/DiscountTypes/AbstractDiscountType.php
index 87735a83c1..3683185fe4 100644
--- a/packages/core/src/DiscountTypes/AbstractDiscountType.php
+++ b/packages/core/src/DiscountTypes/AbstractDiscountType.php
@@ -84,8 +84,8 @@ protected function checkDiscountConditions(CartContract $cart): bool
 
         $validMaxUses = $this->discount->max_uses ? $this->discount->uses < $this->discount->max_uses : true;
 
-        if ($validMaxUses && $this->discount->max_uses_per_user) {
-            $validMaxUses = $cart->user && ($this->usesByUser($cart->user) < $this->discount->max_uses_per_user);
+        if ($validMaxUses && $this->discount->max_uses_per_user && $cart->user) {
+            $validMaxUses = $this->usesByUser($cart->user) < $this->discount->max_uses_per_user;
         }
 
         return $validCoupon && $validMinSpend && $validMaxUses;
diff --git a/tests/core/Unit/DiscountTypes/AbstractDiscountTypeTest.php b/tests/core/Unit/DiscountTypes/AbstractDiscountTypeTest.php
index 4f41c2b3ee..36abf7b365 100644
--- a/tests/core/Unit/DiscountTypes/AbstractDiscountTypeTest.php
+++ b/tests/core/Unit/DiscountTypes/AbstractDiscountTypeTest.php
@@ -11,6 +11,7 @@
 use Lunar\Models\Product;
 use Lunar\Models\ProductVariant;
 use Lunar\Tests\Core\Stubs\TestAbstractDiscount;
+use Lunar\Tests\Core\Stubs\User;
 use Lunar\Tests\Core\TestCase;
 
 uses(TestCase::class);
@@ -93,3 +94,151 @@
 
     expect($cart->subTotalDiscounted->value)->toBe(900);
 });
+
+test('applies a discount with max uses per user on a guest cart', function () {
+    $channel = Channel::getDefault();
+    $currency = Currency::getDefault();
+
+    $cart = Cart::factory()->create([
+        'channel_id' => $channel->id,
+        'currency_id' => $currency->id,
+        'coupon_code' => '10OFF',
+    ]);
+
+    Discount::factory()->create([
+        'type' => TestAbstractDiscount::class,
+        'name' => 'Test Coupon',
+        'coupon' => '10OFF',
+        'max_uses_per_user' => 1,
+        'data' => [
+            'fixed_value' => true,
+            'fixed_values' => [
+                'GBP' => 10,
+            ],
+        ],
+    ]);
+
+    $purchasable = ProductVariant::factory()->create([
+        'product_id' => Product::factory(),
+    ]);
+
+    Price::factory()->create([
+        'price' => 1000,
+        'min_quantity' => 1,
+        'currency_id' => $currency->id,
+        'priceable_type' => $purchasable->getMorphClass(),
+        'priceable_id' => $purchasable->id,
+    ]);
+
+    $cart->lines()->create([
+        'purchasable_type' => $purchasable->getMorphClass(),
+        'purchasable_id' => $purchasable->id,
+        'quantity' => 1,
+    ]);
+
+    $cart->calculate();
+
+    expect($cart->subTotalDiscounted->value)->toBe(900);
+});
+
+test('applies a discount when the user is under the per-user limit', function () {
+    setAuthUserConfig();
+
+    $channel = Channel::getDefault();
+    $currency = Currency::getDefault();
+    $user = User::factory()->create();
+
+    $cart = Cart::factory()->create([
+        'channel_id' => $channel->id,
+        'currency_id' => $currency->id,
+        'coupon_code' => '10OFF',
+        'user_id' => $user->id,
+    ]);
+
+    Discount::factory()->create([
+        'type' => TestAbstractDiscount::class,
+        'name' => 'Test Coupon',
+        'coupon' => '10OFF',
+        'max_uses_per_user' => 2,
+        'data' => [
+            'fixed_value' => true,
+            'fixed_values' => [
+                'GBP' => 10,
+            ],
+        ],
+    ]);
+
+    $purchasable = ProductVariant::factory()->create([
+        'product_id' => Product::factory(),
+    ]);
+
+    Price::factory()->create([
+        'price' => 1000,
+        'min_quantity' => 1,
+        'currency_id' => $currency->id,
+        'priceable_type' => $purchasable->getMorphClass(),
+        'priceable_id' => $purchasable->id,
+    ]);
+
+    $cart->lines()->create([
+        'purchasable_type' => $purchasable->getMorphClass(),
+        'purchasable_id' => $purchasable->id,
+        'quantity' => 1,
+    ]);
+
+    $cart->calculate();
+
+    expect($cart->subTotalDiscounted->value)->toBe(900);
+});
+
+test('does not apply a discount when the user is at the per-user limit', function () {
+    setAuthUserConfig();
+
+    $channel = Channel::getDefault();
+    $currency = Currency::getDefault();
+    $user = User::factory()->create();
+
+    $cart = Cart::factory()->create([
+        'channel_id' => $channel->id,
+        'currency_id' => $currency->id,
+        'coupon_code' => '10OFF',
+        'user_id' => $user->id,
+    ]);
+
+    $discountModel = Discount::factory()->create([
+        'type' => TestAbstractDiscount::class,
+        'name' => 'Test Coupon',
+        'coupon' => '10OFF',
+        'max_uses_per_user' => 1,
+        'data' => [
+            'fixed_value' => true,
+            'fixed_values' => [
+                'GBP' => 10,
+            ],
+        ],
+    ]);
+
+    $discountModel->users()->attach($user->id);
+
+    $purchasable = ProductVariant::factory()->create([
+        'product_id' => Product::factory(),
+    ]);
+
+    Price::factory()->create([
+        'price' => 1000,
+        'min_quantity' => 1,
+        'currency_id' => $currency->id,
+        'priceable_type' => $purchasable->getMorphClass(),
+        'priceable_id' => $purchasable->id,
+    ]);
+
+    $cart->lines()->create([
+        'purchasable_type' => $purchasable->getMorphClass(),
+        'purchasable_id' => $purchasable->id,
+        'quantity' => 1,
+    ]);
+
+    $cart->calculate();
+
+    expect($cart->subTotalDiscounted->value)->toBe(1000);
+});