diff --git a/make_post_sell/templates/offer.j2 b/make_post_sell/templates/offer.j2
index 5ffa80e..cdd9cc1 100644
--- a/make_post_sell/templates/offer.j2
+++ b/make_post_sell/templates/offer.j2
@@ -110,7 +110,8 @@
     {% elif request.user %}
       <section class="well offer-await-pay">
         <h3 class="type-title">Awaiting payment</h3>
-        <p>You accepted <a href="/profile/{{ buyer_handle }}?shop={{ shop_id }}">{{ buyer_name }}</a>&rsquo;s offer at <strong>${{ "%.2f"|format(current_amount) }}</strong>. They need to sign in and pay from this same page &mdash; send them the link:</p>
+        <p>You accepted <a href="/profile/{{ buyer_handle }}?shop={{ shop_id }}">{{ buyer_name }}</a>&rsquo;s offer at <strong>${{ "%.2f"|format(current_amount) }}</strong>. We emailed them a one-time checkout link &mdash; this offer can be redeemed only once.</p>
+        <p class="offer-await-share-note">If they need it again, share this same page:</p>
         <div class="offer-pay-link-row">
           <input type="text" readonly class="offer-pay-link" value="{{ request.scheme }}://{{ request.host }}/o/{{ id }}" onclick="this.select();" />
           <button type="button" class="mps-button-small js-only"
diff --git a/make_post_sell/tests/test_functional.py b/make_post_sell/tests/test_functional.py
index 171bfa2..24dda7a 100644
--- a/make_post_sell/tests/test_functional.py
+++ b/make_post_sell/tests/test_functional.py
@@ -6844,9 +6844,42 @@ class TestOfferCheckout(_AuthenticatedBase):
         self.assertIn("Awaiting payment", body)
         self.assertIn("offer-pay-link", body)
         self.assertIn("waiting on the buyer to pay $75.00", body)
+        # Auto-email language: seller is told the buyer was emailed a
+        # one-time link, not that they need to courier it themselves.
+        self.assertIn("emailed", body)
+        self.assertIn("one-time checkout link", body)
         # Seller never sees the buyer's pay-now form (they cannot pay).
         self.assertNotIn(f"/o/{offer_id}/checkout", body)
 
+    def test_offer_checkout_is_single_redemption(self):
+        """Repeated POSTs to /o/{id}/checkout must reuse the same cart
+        — one offer, one cart, one chance to redeem. Otherwise a buyer
+        could spawn N carts on a single accepted offer and pay any one,
+        which leaves N-1 orphaned carts the buyer could also try to pay.
+        """
+        offer_id = self._accepted_offer()
+        self.testapp.get("/log-out")
+        self.log_in_user(self.user2_creds)
+
+        first = self.testapp.post(f"/o/{offer_id}/checkout", status=302)
+        first_cart_url = first.location
+        second = self.testapp.post(f"/o/{offer_id}/checkout", status=302)
+        third = self.testapp.post(f"/o/{offer_id}/checkout", status=302)
+
+        self.assertEqual(first_cart_url, second.location)
+        self.assertEqual(first_cart_url, third.location)
+
+        # Exactly ONE cart_offer row exists for this offer.
+        from ..models.cart_offer import MpsCartOffer
+        from ..models.offer import get_offer_by_id
+        offer = get_offer_by_id(self.dbsession, offer_id)
+        rows = (
+            self.dbsession.query(MpsCartOffer)
+            .filter(MpsCartOffer.offer_id == offer.id)
+            .all()
+        )
+        self.assertEqual(len(rows), 1)
+
     def test_accepted_offer_buyer_sees_pay_now(self):
         offer_id = self._accepted_offer()
         self.testapp.get("/log-out")
diff --git a/make_post_sell/views/offer.py b/make_post_sell/views/offer.py
index 510b67e..9dd7335 100644
--- a/make_post_sell/views/offer.py
+++ b/make_post_sell/views/offer.py
@@ -390,9 +390,15 @@ def offer_withdraw(request):
 @view_config(route_name="offer_checkout", request_method="POST")
 @user_required(flash_msg="Please log in to pay.")
 def offer_checkout(request):
-    """Buyer checkout for an accepted offer: build a fresh cart linked to
-    the offer and redirect into it. Cart total is overridden to the agreed
-    amount via the cart_offer association.
+    """Buyer checkout for an accepted offer: build (or reuse) a cart
+    linked to the offer and redirect into it. Cart total is overridden
+    to the agreed amount via the cart_offer association.
+
+    Single-redemption: an accepted offer maps to at most ONE cart. If
+    the buyer revisits /o/{id}/checkout after a cart was already opened,
+    we redirect them into that same cart instead of spawning a fresh
+    one — otherwise the buyer could create N parallel carts on a single
+    offer and try to pay each.
     """
     from ..models.cart_offer import MpsCartOffer
     from ..models.offer import OFFER_STATE_ACCEPTED
@@ -407,16 +413,24 @@ def offer_checkout(request):
         request.session.flash(("Only the buyer can check out.", "error"))
         return HTTPFound(f"/o/{offer.uuid_str}")
 
-    # create_new_cart_for_user flips every other cart for this user+shop
-    # to inactive and activates the new one — so /cart resolves to it.
-    # (Setting cart.active = True by hand left two active carts and /cart
-    # would land on the old empty one.)
+    # Reuse-or-create. One offer → one cart_offer → one cart, ever.
+    existing = (
+        request.dbsession.query(MpsCartOffer)
+        .filter(MpsCartOffer.offer_id == offer.id)
+        .first()
+    )
+    if existing is not None:
+        cart = existing.cart
+        # Make sure this cart is active (the buyer's most recent
+        # interaction makes it the one /cart resolves to).
+        offer.shop.make_cart_active_for_user(request.user, cart)
+        return HTTPFound(f"/cart/{cart.uuid_str}")
+
+    # First-time checkout for this offer — spawn the cart.
     cart = offer.shop.create_new_cart_for_user(request.user)
     cart.add_product(offer.product)
     request.dbsession.add(MpsCartOffer(cart=cart, offer=offer))
     request.dbsession.flush()
-    # Land directly in the cart by id — works regardless of which shop the
-    # request happens to be scoped to (SaaS domain vs the offer's shop).
     return HTTPFound(f"/cart/{cart.uuid_str}")