diff --git a/app/Actions/Billing/StartSubscriptionCheckout.php b/app/Actions/Billing/StartSubscriptionCheckout.php
index 6a6798c7..949defc1 100644
--- a/app/Actions/Billing/StartSubscriptionCheckout.php
+++ b/app/Actions/Billing/StartSubscriptionCheckout.php
@@ -27,7 +27,7 @@ public function redirect(Account $account, string $priceId, string $cancelUrl):
         $subscription = $account->newSubscription(Account::SUBSCRIPTION_NAME, $priceId)
             ->quantity(max(1, $account->workspaces()->count()));
 
-        FirstMonthCheckoutDiscount::apply($subscription);
+        FirstMonthCheckoutDiscount::apply($subscription, $account);
 
         $session = $subscription->checkout([
             'success_url' => route('app.billing.processing').'?session_id={CHECKOUT_SESSION_ID}',
diff --git a/app/Support/Billing/FirstMonthCheckoutDiscount.php b/app/Support/Billing/FirstMonthCheckoutDiscount.php
index 064a27dd..aec286b7 100644
--- a/app/Support/Billing/FirstMonthCheckoutDiscount.php
+++ b/app/Support/Billing/FirstMonthCheckoutDiscount.php
@@ -4,6 +4,7 @@
 
 namespace App\Support\Billing;
 
+use App\Models\Account;
 use Laravel\Cashier\SubscriptionBuilder;
 use RuntimeException;
 
@@ -13,16 +14,16 @@ final class FirstMonthCheckoutDiscount
      * Configure a subscription checkout to charge $1 for the first invoice via
      * a `duration: once` Stripe coupon, so a real charge validates the card
      * instead of a $0 trial authorization. Stripe rejects a Checkout Session
-     * that sets both `discounts` and `allow_promotion_codes`, so accounts that
-     * skip the paid first month keep the promotion-code field instead.
+     * that sets both `discounts` and `allow_promotion_codes`, so checkouts that
+     * don't qualify for the paid first month keep the promotion-code field.
      *
-     * @throws RuntimeException when the paid first month is enabled but no
-     *                          coupon is configured — failing loudly beats
-     *                          silently charging every new customer full price.
+     * @throws RuntimeException when a qualifying checkout has the paid first
+     *                          month enabled but no coupon configured — failing
+     *                          loudly beats silently charging full price.
      */
-    public static function apply(SubscriptionBuilder $subscription): SubscriptionBuilder
+    public static function apply(SubscriptionBuilder $subscription, Account $account): SubscriptionBuilder
     {
-        if (! (bool) config('trypost.billing.require_card_for_trial', true)) {
+        if (! self::qualifiesForPaidFirstMonth($account)) {
             return $subscription->allowPromotionCodes();
         }
 
@@ -37,4 +38,21 @@ public static function apply(SubscriptionBuilder $subscription): SubscriptionBui
 
         return $subscription->withCoupon($couponId);
     }
+
+    /**
+     * The fixed-amount first-month coupon only applies to a genuinely new
+     * customer checking out a single workspace: the fixed `amount_off` is only
+     * correct for a quantity of one, and the $1 offer is for first-time signups
+     * — not a returning account re-subscribing with workspaces it kept from a
+     * lapsed subscription.
+     */
+    private static function qualifiesForPaidFirstMonth(Account $account): bool
+    {
+        if (! (bool) config('trypost.billing.require_card_for_trial', true)) {
+            return false;
+        }
+
+        return $account->workspaces()->count() === 1
+            && ! $account->subscriptions()->exists();
+    }
 }
diff --git a/tests/Unit/Support/Billing/FirstMonthCheckoutDiscountTest.php b/tests/Unit/Support/Billing/FirstMonthCheckoutDiscountTest.php
index 21738c2c..c7f3cd34 100644
--- a/tests/Unit/Support/Billing/FirstMonthCheckoutDiscountTest.php
+++ b/tests/Unit/Support/Billing/FirstMonthCheckoutDiscountTest.php
@@ -3,50 +3,91 @@
 declare(strict_types=1);
 
 use App\Models\Account;
+use App\Models\Workspace;
 use App\Support\Billing\FirstMonthCheckoutDiscount;
 use Illuminate\Foundation\Testing\RefreshDatabase;
+use Laravel\Cashier\SubscriptionBuilder;
 
 uses(RefreshDatabase::class);
 
 beforeEach(function () {
     $this->account = Account::factory()->create();
-});
 
-test('applies the first month coupon when a card is required for trial', function () {
     config([
         'trypost.billing.require_card_for_trial' => true,
         'cashier.first_month_coupon_id' => 'TRIAL1USD',
     ]);
+});
 
-    $subscription = $this->account->newSubscription(Account::SUBSCRIPTION_NAME, 'price_monthly_test');
+function firstMonthSubscription(Account $account): SubscriptionBuilder
+{
+    return $account->newSubscription(Account::SUBSCRIPTION_NAME, 'price_monthly_test');
+}
 
-    FirstMonthCheckoutDiscount::apply($subscription);
+function givePriorSubscription(Account $account): void
+{
+    $account->subscriptions()->create([
+        'type' => Account::SUBSCRIPTION_NAME,
+        'stripe_id' => 'sub_'.fake()->uuid(),
+        'stripe_status' => 'canceled',
+        'stripe_price' => 'price_monthly_test',
+    ]);
+}
+
+test('applies the first month coupon for a first-time single-workspace checkout', function () {
+    Workspace::factory()->create(['account_id' => $this->account->id]);
+
+    $subscription = firstMonthSubscription($this->account);
+
+    FirstMonthCheckoutDiscount::apply($subscription, $this->account);
 
     expect($subscription->couponId)->toBe('TRIAL1USD')
         ->and($subscription->promotionCodeId)->toBeNull()
         ->and($subscription->allowPromotionCodes)->toBeFalse();
 });
 
-test('allows promotion codes instead of a coupon when a card is not required for trial', function () {
+test('skips the coupon and allows promotion codes when a card is not required', function () {
     config(['trypost.billing.require_card_for_trial' => false]);
+    Workspace::factory()->create(['account_id' => $this->account->id]);
 
-    $subscription = $this->account->newSubscription(Account::SUBSCRIPTION_NAME, 'price_monthly_test');
+    $subscription = firstMonthSubscription($this->account);
 
-    FirstMonthCheckoutDiscount::apply($subscription);
+    FirstMonthCheckoutDiscount::apply($subscription, $this->account);
 
     expect($subscription->allowPromotionCodes)->toBeTrue()
         ->and($subscription->couponId)->toBeNull();
 });
 
-test('throws instead of charging full price when the coupon is missing but a card is required', function () {
-    config([
-        'trypost.billing.require_card_for_trial' => true,
-        'cashier.first_month_coupon_id' => '',
-    ]);
+test('skips the coupon when more than one workspace is billed', function () {
+    Workspace::factory()->count(2)->create(['account_id' => $this->account->id]);
 
-    $subscription = $this->account->newSubscription(Account::SUBSCRIPTION_NAME, 'price_monthly_test');
+    $subscription = firstMonthSubscription($this->account);
 
-    expect(fn () => FirstMonthCheckoutDiscount::apply($subscription))
+    FirstMonthCheckoutDiscount::apply($subscription, $this->account);
+
+    expect($subscription->allowPromotionCodes)->toBeTrue()
+        ->and($subscription->couponId)->toBeNull();
+});
+
+test('skips the coupon when the account has subscribed before', function () {
+    Workspace::factory()->create(['account_id' => $this->account->id]);
+    givePriorSubscription($this->account);
+
+    $subscription = firstMonthSubscription($this->account);
+
+    FirstMonthCheckoutDiscount::apply($subscription, $this->account);
+
+    expect($subscription->allowPromotionCodes)->toBeTrue()
+        ->and($subscription->couponId)->toBeNull();
+});
+
+test('throws instead of charging full price when a qualifying checkout has no coupon', function () {
+    config(['cashier.first_month_coupon_id' => '']);
+    Workspace::factory()->create(['account_id' => $this->account->id]);
+
+    $subscription = firstMonthSubscription($this->account);
+
+    expect(fn () => FirstMonthCheckoutDiscount::apply($subscription, $this->account))
         ->toThrow(RuntimeException::class);
 
     expect($subscription->couponId)->toBeNull();