diff --git a/.env.example b/.env.example
index 8104df93..4a631e7e 100644
--- a/.env.example
+++ b/.env.example
@@ -191,8 +191,11 @@ STRIPE_SECRET=
 STRIPE_WEBHOOK_SECRET=
 # Set to false to allow generic signup trial without requiring a card.
 REQUIRE_CARD_FOR_TRIAL=true
-# Free trial length in days (Stripe Checkout shows one day fewer).
+# Free trial length in days, used only for the no-card generic trial above.
 CASHIER_TRIAL_DAYS=8
+# Stripe Coupon ID (amount_off, duration=once) so the first invoice at
+# checkout comes out to $1 instead of the full monthly price.
+STRIPE_FIRST_MONTH_COUPON_ID=
 
 # Stripe Plan Price IDs (one per plan × interval). Used by PlanSeeder.
 STRIPE_WORKSPACE_MONTHLY=
diff --git a/app/Actions/Billing/StartSubscriptionCheckout.php b/app/Actions/Billing/StartSubscriptionCheckout.php
index 1515ce11..949defc1 100644
--- a/app/Actions/Billing/StartSubscriptionCheckout.php
+++ b/app/Actions/Billing/StartSubscriptionCheckout.php
@@ -5,6 +5,7 @@
 namespace App\Actions\Billing;
 
 use App\Models\Account;
+use App\Support\Billing\FirstMonthCheckoutDiscount;
 use Inertia\Inertia;
 use Symfony\Component\HttpFoundation\Response;
 
@@ -12,8 +13,9 @@ class StartSubscriptionCheckout
 {
     /**
      * Create a Stripe Checkout session for the given price and return an Inertia
-     * redirect to it. Quantity tracks the account's workspace count; a trial is
-     * attached when the instance requires a card up front.
+     * redirect to it. Quantity tracks the account's workspace count; the first
+     * month's coupon is applied when the instance requires a card up front, so
+     * the first invoice charges $1 instead of running a $0 trial authorization.
      */
     public function redirect(Account $account, string $priceId, string $cancelUrl): Response
     {
@@ -23,12 +25,9 @@ public function redirect(Account $account, string $priceId, string $cancelUrl):
         ]);
 
         $subscription = $account->newSubscription(Account::SUBSCRIPTION_NAME, $priceId)
-            ->quantity(max(1, $account->workspaces()->count()))
-            ->allowPromotionCodes();
+            ->quantity(max(1, $account->workspaces()->count()));
 
-        if ((bool) config('trypost.billing.require_card_for_trial', true)) {
-            $subscription->trialDays(config('cashier.trial_days'));
-        }
+        FirstMonthCheckoutDiscount::apply($subscription, $account);
 
         $session = $subscription->checkout([
             'success_url' => route('app.billing.processing').'?session_id={CHECKOUT_SESSION_ID}',
diff --git a/app/Http/Controllers/App/WorkspaceController.php b/app/Http/Controllers/App/WorkspaceController.php
index d9d394ff..5b2326f2 100644
--- a/app/Http/Controllers/App/WorkspaceController.php
+++ b/app/Http/Controllers/App/WorkspaceController.php
@@ -15,6 +15,7 @@
 use App\Http\Requests\App\Workspace\StoreWorkspaceRequest;
 use App\Http\Requests\App\Workspace\UpdateWorkspaceRequest;
 use App\Http\Resources\App\WorkspaceMemberResource;
+use App\Models\User;
 use App\Models\Workspace;
 use App\Services\Brand\LogoAttacher;
 use Illuminate\Http\JsonResponse;
@@ -66,13 +67,8 @@ public function index(Request $request): Response
 
     public function create(Request $request): Response|RedirectResponse
     {
-        $user = $request->user();
-
-        if (! config('trypost.self_hosted')
-            && $user->ownedWorkspacesCount() > 0
-            && ! $user->account?->hasActiveSubscription()) {
-            return redirect()->route('app.billing.index')
-                ->with('message', 'Subscribe to create more workspaces.');
+        if ($redirect = $this->denyAdditionalWorkspaceWithoutSubscription($request->user())) {
+            return $redirect;
         }
 
         return Inertia::render('workspaces/Create', [
@@ -83,6 +79,24 @@ public function create(Request $request): Response|RedirectResponse
         ]);
     }
 
+    /**
+     * Block creating a paid additional workspace without an active subscription.
+     * Guards both the form (`create`) and the write (`store`) so a direct POST
+     * can't bootstrap a second billable workspace — which would also inflate the
+     * checkout quantity past the fixed first-month coupon.
+     */
+    private function denyAdditionalWorkspaceWithoutSubscription(User $user): ?RedirectResponse
+    {
+        if (! config('trypost.self_hosted')
+            && $user->ownedWorkspacesCount() > 0
+            && ! $user->account?->hasActiveSubscription()) {
+            return redirect()->route('app.billing.index')
+                ->with('message', 'Subscribe to create more workspaces.');
+        }
+
+        return null;
+    }
+
     public function autofillBrand(AutofillBrandRequest $request, AutofillBrand $autofill): JsonResponse
     {
         try {
@@ -98,6 +112,10 @@ public function store(StoreWorkspaceRequest $request, LogoAttacher $logoAttacher
     {
         $user = $request->user();
 
+        if ($redirect = $this->denyAdditionalWorkspaceWithoutSubscription($user)) {
+            return $redirect;
+        }
+
         $validated = $request->validated();
 
         $workspace = CreateWorkspace::execute($user, $validated);
diff --git a/app/Support/Billing/FirstMonthCheckoutDiscount.php b/app/Support/Billing/FirstMonthCheckoutDiscount.php
new file mode 100644
index 00000000..2fba2131
--- /dev/null
+++ b/app/Support/Billing/FirstMonthCheckoutDiscount.php
@@ -0,0 +1,66 @@
+<?php
+
+declare(strict_types=1);
+
+namespace App\Support\Billing;
+
+use App\Models\Account;
+use Laravel\Cashier\SubscriptionBuilder;
+use RuntimeException;
+use Stripe\Subscription as StripeSubscription;
+
+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 checkouts that
+     * don't qualify for the paid first month keep the promotion-code field.
+     *
+     * @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, Account $account): SubscriptionBuilder
+    {
+        if (! self::qualifiesForPaidFirstMonth($account)) {
+            return $subscription->allowPromotionCodes();
+        }
+
+        $couponId = config('cashier.first_month_coupon_id');
+
+        if (! is_string($couponId) || $couponId === '') {
+            throw new RuntimeException(
+                'STRIPE_FIRST_MONTH_COUPON_ID must be set when REQUIRE_CARD_FOR_TRIAL is enabled, '
+                .'otherwise checkout would charge the full price instead of the $1 first month.'
+            );
+        }
+
+        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. A subscription that never left `incomplete` never
+     * became real, so a new customer retrying after a failed first attempt
+     * still qualifies; any started subscription (even canceled) does not.
+     */
+    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()
+                ->whereNotIn('stripe_status', [
+                    StripeSubscription::STATUS_INCOMPLETE,
+                    StripeSubscription::STATUS_INCOMPLETE_EXPIRED,
+                ])
+                ->exists();
+    }
+}
diff --git a/config/cashier.php b/config/cashier.php
index 44c30230..523c76b0 100644
--- a/config/cashier.php
+++ b/config/cashier.php
@@ -137,4 +137,19 @@
 
     'trial_days' => env('CASHIER_TRIAL_DAYS', 8),
 
+    /*
+    |--------------------------------------------------------------------------
+    | Paid First Month Coupon
+    |--------------------------------------------------------------------------
+    |
+    | Stripe Coupon ID applied at checkout so the first invoice comes out to
+    | $1 instead of the full monthly price — a real charge validates the
+    | card up front instead of a $0 trial authorization. Must be an
+    | `amount_off` coupon with `duration: once`, so it discounts only the
+    | first invoice and the full price bills automatically afterward.
+    |
+    */
+
+    'first_month_coupon_id' => env('STRIPE_FIRST_MONTH_COUPON_ID'),
+
 ];
diff --git a/tests/Feature/WorkspaceControllerTest.php b/tests/Feature/WorkspaceControllerTest.php
index 796bef21..e1354dc5 100644
--- a/tests/Feature/WorkspaceControllerTest.php
+++ b/tests/Feature/WorkspaceControllerTest.php
@@ -677,6 +677,26 @@
     expect(Workspace::where('account_id', $account->id)->count())->toBe(2);
 });
 
+test('store blocks a second workspace without an active subscription', function () {
+    config(['trypost.self_hosted' => false]);
+
+    $account = Account::factory()->create();
+    $user = User::factory()->create(['account_id' => $account->id]);
+    $account->update(['owner_id' => $user->id]);
+
+    // The account already owns one workspace and has no subscription, so a
+    // direct POST must not bootstrap a second (billable) workspace.
+    $existing = Workspace::factory()->create(['account_id' => $account->id, 'user_id' => $user->id]);
+    $existing->members()->attach($user->id, ['role' => Role::Member->value]);
+
+    $response = $this->actingAs($user)->post(route('app.workspaces.store'), [
+        'name' => 'Second Workspace',
+    ]);
+
+    $response->assertRedirect(route('app.billing.index'));
+    expect(Workspace::where('account_id', $account->id)->count())->toBe(1);
+});
+
 test('store attaches logo when logo_url is provided', function () {
     $account = Account::factory()->create();
     $user = User::factory()->create(['account_id' => $account->id]);
diff --git a/tests/Unit/Support/Billing/FirstMonthCheckoutDiscountTest.php b/tests/Unit/Support/Billing/FirstMonthCheckoutDiscountTest.php
new file mode 100644
index 00000000..86d048ce
--- /dev/null
+++ b/tests/Unit/Support/Billing/FirstMonthCheckoutDiscountTest.php
@@ -0,0 +1,106 @@
+<?php
+
+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();
+
+    config([
+        'trypost.billing.require_card_for_trial' => true,
+        'cashier.first_month_coupon_id' => 'TRIAL1USD',
+    ]);
+});
+
+function firstMonthSubscription(Account $account): SubscriptionBuilder
+{
+    return $account->newSubscription(Account::SUBSCRIPTION_NAME, 'price_monthly_test');
+}
+
+function givePriorSubscription(Account $account, string $status = 'canceled'): void
+{
+    $account->subscriptions()->create([
+        'type' => Account::SUBSCRIPTION_NAME,
+        'stripe_id' => 'sub_'.fake()->uuid(),
+        'stripe_status' => $status,
+        '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('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]);
+
+    $subscription = firstMonthSubscription($this->account);
+
+    FirstMonthCheckoutDiscount::apply($subscription, $this->account);
+
+    expect($subscription->allowPromotionCodes)->toBeTrue()
+        ->and($subscription->couponId)->toBeNull();
+});
+
+test('skips the coupon when more than one workspace is billed', function () {
+    Workspace::factory()->count(2)->create(['account_id' => $this->account->id]);
+
+    $subscription = firstMonthSubscription($this->account);
+
+    FirstMonthCheckoutDiscount::apply($subscription, $this->account);
+
+    expect($subscription->allowPromotionCodes)->toBeTrue()
+        ->and($subscription->couponId)->toBeNull();
+});
+
+test('skips the coupon when the account has a prior canceled subscription', 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('still applies the coupon when the only prior subscription never left incomplete', function () {
+    Workspace::factory()->create(['account_id' => $this->account->id]);
+    givePriorSubscription($this->account, 'incomplete_expired');
+
+    $subscription = firstMonthSubscription($this->account);
+
+    FirstMonthCheckoutDiscount::apply($subscription, $this->account);
+
+    expect($subscription->couponId)->toBe('TRIAL1USD')
+        ->and($subscription->allowPromotionCodes)->toBeFalse();
+});
+
+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();
+});