diff --git a/development.ini b/development.ini
index 6fa67c3..3da0494 100644
--- a/development.ini
+++ b/development.ini
@@ -89,10 +89,11 @@ app.theme = meta
 # choices enabled or disabled. defaults to disabled.
 #app.stand_alone_mode = disabled
 
-# stripe: credit card storage and processing.
+# stripe: Stripe Checkout payment processing.
 # This syntax will automatically expand an ENV var of the same name.
 app.stripe.secret = ${REMARKBOX_APP_STRIPE_SECRET}
 app.stripe.public = ${REMARKBOX_APP_STRIPE_PUBLIC}
+app.stripe.webhook_secret = ${REMARKBOX_APP_STRIPE_WEBHOOK_SECRET:-}
 
 # slack: bot notifications.
 app.slack.secret = ${REMARKBOX_APP_SLACK_SECRET}
diff --git a/remarkbox/__init__.py b/remarkbox/__init__.py
index 863097f..0927803 100644
--- a/remarkbox/__init__.py
+++ b/remarkbox/__init__.py
@@ -407,36 +407,6 @@ def main(global_config, **settings):
             and request.app_domain == request.namespace.name
         )
 
-    def add_stripe(request):
-        """Attach a stripe object with creds to request."""
-        import stripe
-
-        stripe.api_key = request.app.get("stripe.secret")
-        return stripe
-
-    def add_stripe_customer(request):
-        if request.user:
-            if not request.user.stripe_id:
-                # create a new stripe customer.
-                customer = request.stripe.Customer.create(email=request.user.email)
-                request.user.stripe_id = customer.id
-                request.dbsession.add(request.user)
-                request.dbsession.flush()
-            return request.stripe.Customer.retrieve(request.user.stripe_id)
-        return None
-
-    def add_stripe_saved_cards(request):
-        if request.user and request.user.stripe_id:
-            return request.stripe_customer.sources
-        return []
-
-    def add_stripe_active_card(request):
-        if request.user and request.user.stripe_id:
-            if request.stripe_customer.default_source:
-                return request.stripe_customer.sources.retrieve(
-                    request.stripe_customer.default_source
-                )
-        return None
 
     def add_avatar_size(request):
         """Attach avatar size or default."""
@@ -579,10 +549,6 @@ def main(global_config, **settings):
     config.add_request_method(add_marketing_domain, "marketing_domain", reify=True)
     config.add_request_method(add_faq_home, "faq_home", reify=True)
     config.add_request_method(add_saas_home, "saas_home", reify=True)
-    config.add_request_method(add_stripe, "stripe", reify=True)
-    config.add_request_method(add_stripe_customer, "stripe_customer", reify=True)
-    config.add_request_method(add_stripe_saved_cards, "stripe_saved_cards", reify=True)
-    config.add_request_method(add_stripe_active_card, "stripe_active_card", reify=True)
     config.add_request_method(add_stand_alone_mode, "stand_alone_mode", reify=True)
     config.add_request_method(add_avatar_size, "avatar_size", reify=True)
     config.add_request_method(add_theme, "theme", reify=True)
diff --git a/remarkbox/lib/__init__.py b/remarkbox/lib/__init__.py
index dc3e25e..f20d549 100644
--- a/remarkbox/lib/__init__.py
+++ b/remarkbox/lib/__init__.py
@@ -14,6 +14,11 @@ def timestamp_to_date_string(timestamp):
     return timestamp_to_datetime(timestamp).strftime("%b %d, %Y %I:%M %P")
 
 
+def timestamp_to_date(timestamp):
+    """Accepts a timestamp and returns a short date string (e.g., 'Dec 19, 2024')"""
+    return timestamp_to_datetime(timestamp).strftime("%b %d, %Y")
+
+
 def timestamp_to_ago_string(timestamp):
     """Accepts a timestamp and returns a human readable string"""
     return human(timestamp_to_datetime(timestamp), 2, abbreviate=True)
diff --git a/remarkbox/models/__init__.py b/remarkbox/models/__init__.py
index dfef524..1e9e229 100644
--- a/remarkbox/models/__init__.py
+++ b/remarkbox/models/__init__.py
@@ -18,6 +18,7 @@ from .watcher import *
 from .event import *
 from .notification import *
 from .pay_what_you_can import *
+from .payment import *
 
 # run configure_mappers after defining all of the models to ensure
 # all relationships can be setup
diff --git a/remarkbox/models/meta.py b/remarkbox/models/meta.py
index 5a067a6..80fc32c 100644
--- a/remarkbox/models/meta.py
+++ b/remarkbox/models/meta.py
@@ -39,6 +39,7 @@ CLASS_TO_TABLE = {
     "NodeEvent": "rb_node_event",
     "NodeEventNotification": "rb_node_event_notification",
     "PayWhatYouCan": "rb_pay_what_you_can",
+    "Payment": "rb_payment",
 }
 
 # node (threads), namespace (forum)
diff --git a/remarkbox/models/payment.py b/remarkbox/models/payment.py
new file mode 100644
index 0000000..674fde8
--- /dev/null
+++ b/remarkbox/models/payment.py
@@ -0,0 +1,109 @@
+"""Payment model for tracking Stripe payments."""
+
+from sqlalchemy import BigInteger, Column, Unicode, Enum
+from sqlalchemy.orm import relationship
+
+from .meta import Base, RBase, UUIDType, now_timestamp, foreign_key
+
+from remarkbox.lib import timestamp_to_date
+
+import uuid
+
+
+class Payment(RBase, Base):
+    """
+    Track payments made through Stripe Checkout.
+
+    Each payment record corresponds to a completed Stripe Checkout session.
+    """
+
+    id = Column(UUIDType, primary_key=True, index=True)
+
+    # Link to user who made the payment
+    user_id = Column(UUIDType, foreign_key("User", "id"), index=True, nullable=False)
+
+    # Stripe session ID for reference
+    stripe_session_id = Column(Unicode(128), unique=True, nullable=False, index=True)
+
+    # Payment type: pay_what_you_want, annual, top_up
+    payment_type = Column(
+        Enum("pay_what_you_want", "annual", "top_up", name="payment_type_enum"),
+        nullable=False,
+    )
+
+    # Amount in cents
+    amount_cents = Column(BigInteger, nullable=False)
+
+    # Duration in months (for annual/top_up payments)
+    duration_months = Column(BigInteger, default=0, nullable=False)
+
+    # Payment status: pending, completed, failed, refunded
+    status = Column(
+        Enum("pending", "completed", "failed", "refunded", name="payment_status_enum"),
+        default="pending",
+        nullable=False,
+    )
+
+    # Timestamps
+    created_timestamp = Column(BigInteger, nullable=False)
+    completed_timestamp = Column(BigInteger, nullable=True)
+
+    # Relationship to user
+    user = relationship(
+        argument="User",
+        uselist=False,
+        lazy="joined",
+        back_populates="payments",
+    )
+
+    def __init__(self, user, stripe_session_id, payment_type, amount_cents, duration_months=0):
+        self.id = uuid.uuid1()
+        self.user_id = user.id
+        self.stripe_session_id = stripe_session_id
+        self.payment_type = payment_type
+        self.amount_cents = amount_cents
+        self.duration_months = duration_months
+        self.status = "pending"
+        self.created_timestamp = now_timestamp()
+
+    def mark_completed(self):
+        """Mark payment as completed."""
+        self.status = "completed"
+        self.completed_timestamp = now_timestamp()
+
+    def mark_failed(self):
+        """Mark payment as failed."""
+        self.status = "failed"
+
+    @property
+    def amount_dollars(self):
+        """Return amount in dollars."""
+        return self.amount_cents / 100.0
+
+    @property
+    def human_created_date(self):
+        """Return human-readable creation date."""
+        return timestamp_to_date(self.created_timestamp)
+
+
+def get_payment_by_session_id(dbsession, session_id):
+    """Get payment by Stripe session ID."""
+    return (
+        dbsession.query(Payment)
+        .filter(Payment.stripe_session_id == session_id)
+        .one_or_none()
+    )
+
+
+def create_payment(dbsession, user, stripe_session_id, payment_type, amount_cents, duration_months=0):
+    """Create a new payment record."""
+    payment = Payment(
+        user=user,
+        stripe_session_id=stripe_session_id,
+        payment_type=payment_type,
+        amount_cents=amount_cents,
+        duration_months=duration_months,
+    )
+    dbsession.add(payment)
+    dbsession.flush()
+    return payment
diff --git a/remarkbox/models/user.py b/remarkbox/models/user.py
index 1e194d3..a1fa808 100644
--- a/remarkbox/models/user.py
+++ b/remarkbox/models/user.py
@@ -157,6 +157,14 @@ class User(RBase, Base):
     # 1-to-1 relationships.
     pay_what_you_can = relationship(argument="PayWhatYouCan", uselist=False, lazy="joined")
 
+    # Payment history
+    payments = relationship(
+        argument="Payment",
+        lazy="dynamic",
+        back_populates="user",
+        order_by="desc(Payment.created_timestamp)",
+    )
+
     @property
     def node_watchers(self):
         return self.watchers.filter(Watcher.type == "node")
diff --git a/remarkbox/routes.py b/remarkbox/routes.py
index 7fd724b..725032b 100644
--- a/remarkbox/routes.py
+++ b/remarkbox/routes.py
@@ -7,14 +7,12 @@ def includeme(config):
     config.add_route("embed-iframe", "/embed-iframe.txt")
     config.add_route("embed-iframe-min", "/embed-iframe-min.txt")
 
-    # stripe: credit card storage and processing.
+    # stripe: payment processing via Stripe Checkout
     config.add_route("billing", "/billing")
-    config.add_route("add-card", "/billing/add-card")
-    config.add_route(
-        "confirm-update-card", "/billing/confirm-update-card/{action}/{card_id}"
-    )
-    config.add_route("update-card", "/billing/update-card")
     config.add_route("pay-what-you-can", "/pay-what-you-can")
+    config.add_route("create-checkout", "/billing/checkout")
+    config.add_route("billing-success", "/billing/success")
+    config.add_route("stripe-webhook", "/webhook/stripe")
 
     # slack: bot notifications and oauth.
     config.add_route("oauth-slack", "/oauth/slack")
diff --git a/remarkbox/scripts/alembic/versions/a1b2c3d4e5f6_add_payment_table.py b/remarkbox/scripts/alembic/versions/a1b2c3d4e5f6_add_payment_table.py
new file mode 100644
index 0000000..699c5b9
--- /dev/null
+++ b/remarkbox/scripts/alembic/versions/a1b2c3d4e5f6_add_payment_table.py
@@ -0,0 +1,47 @@
+"""Add payment table for Stripe Checkout
+
+Revision ID: a1b2c3d4e5f6
+Revises: fa8402aa1a00
+Create Date: 2024-12-19
+
+"""
+
+# revision identifiers, used by Alembic.
+revision = "a1b2c3d4e5f6"
+down_revision = None
+branch_labels = None
+depends_on = None
+
+from alembic import op
+import sqlalchemy as sa
+from sqlalchemy_utils import UUIDType
+
+
+def upgrade():
+    op.create_table(
+        "rb_payment",
+        sa.Column("id", UUIDType(binary=False), primary_key=True, index=True),
+        sa.Column("user_id", UUIDType(binary=False), sa.ForeignKey("rb_user.id"), index=True, nullable=False),
+        sa.Column("stripe_session_id", sa.Unicode(128), unique=True, nullable=False, index=True),
+        sa.Column(
+            "payment_type",
+            sa.Enum("pay_what_you_want", "annual", "top_up", name="payment_type_enum"),
+            nullable=False,
+        ),
+        sa.Column("amount_cents", sa.BigInteger(), nullable=False),
+        sa.Column("duration_months", sa.BigInteger(), default=0, nullable=False),
+        sa.Column(
+            "status",
+            sa.Enum("pending", "completed", "failed", "refunded", name="payment_status_enum"),
+            default="pending",
+            nullable=False,
+        ),
+        sa.Column("created_timestamp", sa.BigInteger(), nullable=False),
+        sa.Column("completed_timestamp", sa.BigInteger(), nullable=True),
+    )
+
+
+def downgrade():
+    op.drop_table("rb_payment")
+    op.execute("DROP TYPE IF EXISTS payment_type_enum")
+    op.execute("DROP TYPE IF EXISTS payment_status_enum")
diff --git a/remarkbox/stripe/__init__.py b/remarkbox/stripe/__init__.py
new file mode 100644
index 0000000..36d7e0f
--- /dev/null
+++ b/remarkbox/stripe/__init__.py
@@ -0,0 +1 @@
+# Stripe integration module
diff --git a/remarkbox/stripe/checkout.py b/remarkbox/stripe/checkout.py
new file mode 100644
index 0000000..93e709e
--- /dev/null
+++ b/remarkbox/stripe/checkout.py
@@ -0,0 +1,138 @@
+"""
+Stripe Checkout integration for Remarkbox payments.
+
+Supports:
+- Pay What You Want (custom amount, one-time payment)
+- Annual subscription (yearly recurring via one-time payment with duration)
+- Top-up payments (extend subscription)
+"""
+
+import stripe
+import logging
+
+log = logging.getLogger(__name__)
+
+
+def configure_stripe(api_key):
+    """Configure Stripe with API key."""
+    stripe.api_key = api_key
+
+
+def create_checkout_session(
+    amount_cents,
+    payment_type,
+    duration_months=1,
+    email=None,
+    success_url=None,
+    cancel_url=None,
+    metadata=None,
+):
+    """
+    Create a Stripe Checkout session for payment.
+
+    Parameters:
+    - amount_cents: Payment amount in cents (USD)
+    - payment_type: "pay_what_you_want", "annual", or "top_up"
+    - duration_months: For annual/top_up, number of months (default 1)
+    - email: Optional customer email
+    - success_url: URL to redirect on success (must include {CHECKOUT_SESSION_ID})
+    - cancel_url: URL to redirect on cancel
+    - metadata: Additional metadata to store with the session
+
+    Returns:
+        Tuple of (session, error) - session object or None, and error message or None
+    """
+    if amount_cents < 100:  # Minimum $1.00
+        return None, "Minimum payment amount is $1.00"
+
+    # Build product description based on payment type
+    if payment_type == "pay_what_you_want":
+        product_name = "Remarkbox - Pay What You Want"
+        description = "Thank you for supporting Remarkbox!"
+    elif payment_type == "annual":
+        product_name = f"Remarkbox - {duration_months} Month Subscription"
+        description = f"Access to Remarkbox for {duration_months} month(s)"
+    elif payment_type == "top_up":
+        product_name = f"Remarkbox - Top Up ({duration_months} months)"
+        description = f"Extend your subscription by {duration_months} month(s)"
+    else:
+        return None, f"Invalid payment type: {payment_type}"
+
+    # Build session metadata
+    session_metadata = {
+        "payment_type": payment_type,
+        "duration_months": str(duration_months),
+        "amount_cents": str(amount_cents),
+    }
+    if metadata:
+        session_metadata.update(metadata)
+
+    # Build session parameters
+    session_params = {
+        "mode": "payment",
+        "payment_method_types": ["card"],
+        "line_items": [
+            {
+                "price_data": {
+                    "currency": "usd",
+                    "product_data": {
+                        "name": product_name,
+                        "description": description,
+                    },
+                    "unit_amount": amount_cents,
+                },
+                "quantity": 1,
+            }
+        ],
+        "success_url": success_url,
+        "cancel_url": cancel_url,
+        "metadata": session_metadata,
+    }
+
+    # Add customer email if provided
+    if email:
+        session_params["customer_email"] = email
+
+    try:
+        session = stripe.checkout.Session.create(**session_params)
+        log.info(
+            f"Created Stripe checkout session: {session.id}, "
+            f"type={payment_type}, amount=${amount_cents/100:.2f}"
+        )
+        return session, None
+    except stripe.error.StripeError as e:
+        log.error(f"Stripe checkout creation failed: {e}")
+        return None, str(e)
+
+
+def retrieve_checkout_session(session_id):
+    """
+    Retrieve a Stripe Checkout session by ID.
+
+    Returns:
+        Tuple of (session, error)
+    """
+    try:
+        session = stripe.checkout.Session.retrieve(session_id)
+        return session, None
+    except stripe.error.StripeError as e:
+        log.error(f"Failed to retrieve session {session_id}: {e}")
+        return None, str(e)
+
+
+def verify_webhook_signature(payload, sig_header, webhook_secret):
+    """
+    Verify Stripe webhook signature.
+
+    Returns:
+        Tuple of (event, error)
+    """
+    try:
+        event = stripe.Webhook.construct_event(payload, sig_header, webhook_secret)
+        return event, None
+    except ValueError as e:
+        log.error(f"Invalid webhook payload: {e}")
+        return None, "Invalid payload"
+    except stripe.error.SignatureVerificationError as e:
+        log.error(f"Invalid webhook signature: {e}")
+        return None, "Invalid signature"
diff --git a/remarkbox/templates/billing-success.j2 b/remarkbox/templates/billing-success.j2
new file mode 100644
index 0000000..105ec15
--- /dev/null
+++ b/remarkbox/templates/billing-success.j2
@@ -0,0 +1,34 @@
+{% extends request.base_funnel_template -%}
+
+{% block title %}{{ the_title }} | {{ request.domain }}{%- endblock -%}
+{% block content -%}
+
+<center>
+<h4>{{ the_title }}</h4>
+</center>
+
+<br>
+
+<div style="text-align: center; padding: 20px;">
+    <div style="font-size: 48px; color: #4CAF50;">&#10003;</div>
+    <h3>Thank You!</h3>
+
+    {% if payment %}
+    <p>Your payment of <strong>${{ "%.2f" | format(payment.amount_dollars) }}</strong> has been received.</p>
+
+    {% if payment.payment_type == "annual" %}
+    <p>Your annual subscription is now active.</p>
+    {% elif payment.payment_type == "top_up" %}
+    <p>Your subscription has been extended by {{ payment.duration_months }} month(s).</p>
+    {% else %}
+    <p>Your contribution helps keep Remarkbox running. We truly appreciate your support!</p>
+    {% endif %}
+    {% else %}
+    <p>Your payment has been processed successfully.</p>
+    {% endif %}
+
+    <br>
+    <a href="/billing" class="button green-button">Back to Billing</a>
+</div>
+
+{%- endblock -%}
diff --git a/remarkbox/templates/billing.j2 b/remarkbox/templates/billing.j2
index 9d6fa61..d681167 100644
--- a/remarkbox/templates/billing.j2
+++ b/remarkbox/templates/billing.j2
@@ -1,5 +1,4 @@
 {% extends request.base_funnel_template -%}
-{%- import 'snippets/stripe.j2' as stripe with context -%}
 {% import 'snippets/forms.j2' as forms with context %}
 
 {% block title %}{{ the_title }} | {{ request.domain }}{%- endblock -%}
@@ -9,36 +8,131 @@
 <h4>{{ the_title }}</h4>
 </center>
 
+<p>Support Remarkbox with a contribution. Set your preferences below, then pay when you're ready.</p>
+
 <br>
 
+{# Pay What You Can Preferences #}
 {{ forms.pay_what_you_can() }}
 
-<br>
 <br>
 
-<label>Active Card</label>
-{{ stripe.active_card() }}
+{# Pay Now Button - uses saved preferences or custom amount #}
+<form method="post" action="/billing/checkout">
+<fieldset>
+    <legend>Pay Now</legend>
+    {% if request.user.pay_what_you_can and request.user.pay_what_you_can.amount %}
+    <p>Pay your configured amount of <strong>${{ request.user.pay_what_you_can.amount }}</strong> now.</p>
+    <input type="hidden" name="payment_type" value="pay_what_you_want">
+    <input type="hidden" name="amount" value="{{ request.user.pay_what_you_can.amount }}">
+    <input type="hidden" name="duration_months" value="{% if request.user.pay_what_you_can.frequency == 'yearly' %}12{% else %}0{% endif %}">
+    {% include 'snippets/csrf.j2' %}
+    <button type="submit" class="green-button">Pay ${{ request.user.pay_what_you_can.amount }} Now</button>
+    {% else %}
+    <p>Set your contribution amount above first, or enter a custom amount:</p>
+    <input type="hidden" name="payment_type" value="pay_what_you_want">
+    <input type="hidden" name="duration_months" value="0">
+    <label for="custom-amount">Amount (USD)</label>
+    <input type="text"
+           id="custom-amount"
+           name="amount"
+           placeholder="$10.00"
+           required
+           style="width: 100%; max-width: 200px;">
+    <br><br>
+    {% include 'snippets/csrf.j2' %}
+    <button type="submit" class="green-button">Pay Now</button>
+    {% endif %}
+</fieldset>
+</form>
 
 <br>
 
-{{ stripe.saved_cards() }}
+{# Annual Subscription #}
+<form method="post" action="/billing/checkout">
+<fieldset>
+    <legend>Annual Subscription</legend>
+    <p>Support Remarkbox with a yearly contribution.</p>
 
-<label>New credit or debit card</label>
-<section class="new-card">
-<br>
-{{ stripe.new_card() }}
-</section>
+    <input type="hidden" name="payment_type" value="annual">
+    <input type="hidden" name="duration_months" value="12">
+
+    <label for="annual-amount">Annual Amount (USD)</label>
+    <select id="annual-amount" name="amount" style="width: 100%; max-width: 200px;">
+        <option value="36">$36/year ($3/month)</option>
+        <option value="60">$60/year ($5/month)</option>
+        <option value="120" selected>$120/year ($10/month)</option>
+        <option value="240">$240/year ($20/month)</option>
+        <option value="360">$360/year ($30/month)</option>
+    </select>
+
+    <br><br>
+    {% include 'snippets/csrf.j2' %}
+    <button type="submit" class="green-button">Subscribe Annually</button>
+</fieldset>
+</form>
 
-<br>
 <br>
 
-Or PayPal <a href="https://www.paypal.me/russellbal/" target="_blank">@russellbal</a>
+{# Top Up #}
+<form method="post" action="/billing/checkout">
+<fieldset>
+    <legend>Top Up</legend>
+    <p>Make an additional contribution anytime.</p>
+
+    <input type="hidden" name="payment_type" value="top_up">
+    <input type="hidden" name="duration_months" value="0">
+
+    <label for="topup-amount">Amount (USD)</label>
+    <input type="text"
+           id="topup-amount"
+           name="amount"
+           placeholder="$25.00"
+           required
+           style="width: 100%; max-width: 200px;">
+
+    <br><br>
+    {% include 'snippets/csrf.j2' %}
+    <button type="submit" class="green-button">Top Up</button>
+</fieldset>
+</form>
 
-<br>
 <br>
 
-<b>Thank you so much!</b>
+{# Payment History #}
+{% if payments %}
+<fieldset>
+    <legend>Payment History</legend>
+    <table style="width: 100%;">
+        <thead>
+            <tr>
+                <th style="text-align: left;">Date</th>
+                <th style="text-align: left;">Type</th>
+                <th style="text-align: right;">Amount</th>
+            </tr>
+        </thead>
+        <tbody>
+            {% for payment in payments %}
+            <tr>
+                <td>{{ payment.human_created_date }}</td>
+                <td>{{ payment.payment_type | replace("_", " ") | title }}</td>
+                <td style="text-align: right;">${{ "%.2f" | format(payment.amount_dollars) }}</td>
+            </tr>
+            {% endfor %}
+        </tbody>
+    </table>
+</fieldset>
+<br>
+{% endif %}
+
+<center>
+<p>
+    <small>
+        Payments are securely processed by <a href="https://stripe.com" target="_blank">Stripe</a>.
+        <br>
+        Or PayPal <a href="https://www.paypal.me/russellbal/" target="_blank">@russellbal</a>
+    </small>
+</p>
+</center>
 
-<br>
-<br>
 {%- endblock -%}
diff --git a/remarkbox/templates/snippets/stripe.j2 b/remarkbox/templates/snippets/stripe.j2
deleted file mode 100644
index a7b5bc5..0000000
--- a/remarkbox/templates/snippets/stripe.j2
+++ /dev/null
@@ -1,133 +0,0 @@
-{% macro display_card(card, actions=True, change_card=False) %}
-  {%
-  set brand_logos = {
-    "Visa" : "https://js.stripe.com/v3/fingerprinted/img/visa-d6c6e0a636f7373e06d5fb896ad49475.svg",
-    "MasterCard" : "https://js.stripe.com/v3/fingerprinted/img/mastercard-a96ee3841a5e1e28d05ed3f0f4da62b8.svg",
-    "American Express" : "https://js.stripe.com/v3/fingerprinted/img/amex-edf6011de255d8a4c22904795c9d8770.svg",
-    "Discover" : "https://js.stripe.com/v3/fingerprinted/img/discover-8f3d8fc6ef836da1fcac12c095ee6fb8.svg",
-    "Diners Club" : "https://js.stripe.com/v3/fingerprinted/img/diners-fced9e136fd8c25f40a3e7b37a51dc1d.svg",
-    "JCB" : "https://js.stripe.com/v3/fingerprinted/img/jcb-1b12d588a1e9465d4d9fb84a610f9136.svg",
-    "UnionPay" : "https://js.stripe.com/v3/fingerprinted/img/unionpay-en-099cb6671310a54f640ac16d5f2a825c.svg",
-  }
-  %}
-
-  <section class="payment-card">
-    <img src="{{ brand_logos[card.brand] }}" style="width: 66px; float: left; margin-right: 20px;">
-    <b>{{ card.brand }}</b>
-    ending in
-    <b>{{ card.last4 }}</b>
-    <br/>
-    <span class="opacity-60">
-    expiring {{ card.exp_month }}/{{ card.exp_year }}
-    </span>
-    <br/>
-    <br/>
-    <div style="margin-top: -12px;">
-    {% if actions %}
-      <a href="/billing/confirm-update-card/delete-card/{{ card.id }}"><button type="button">delete</button></a>
-      <a href="/billing/confirm-update-card/make-card-active/{{ card.id }}" class="button button-small button-white"><button type="button">make active</button></a>
-    {% endif %}
-    {% if change_card %}
-      <a href="/billing"><button type="button">change card</button></a>
-    {% endif %}
-    </div>
-  </section>
-{% endmacro %}
-
-{% macro active_card(change_card=False) %}
-  {% if request.stripe_active_card %}
-    {{ display_card(request.stripe_active_card, actions=False, change_card=change_card) }}
-  {% endif %}
-{% endmacro %}
-
-{% macro saved_cards() %}
-  {% if request.stripe_saved_cards|length > 1 %}
-    <label>Saved Cards</label>
-    {% for card in request.stripe_saved_cards %}
-      {% if card != request.stripe_active_card %}
-        {{ display_card(card) }}
-        <br/>
-      {% endif %}
-    {% endfor %}
-    <br/>
-  {% endif %}
-{% endmacro %}
-
-{% macro new_card() %}
-<script src="https://js.stripe.com/v3/"></script>
-<form action="/billing/add-card" method="post" id="payment-form">
-  {% include 'snippets/csrf.j2' %}
-  <input type="hidden" name="return-to" value="{{ request.path_url }}">
-  <div class="form-row">
-
-    <center>
-    <div id="card-element">
-      <!-- A Stripe Element will be inserted here. -->
-    </div>
-    </center>
-
-
-    <center>
-    <button class="green-button button-max-width" style="margin-bottom: 0px; margin-top: 8px;">&#128274; Save Card</button>
-    <br>
-    <br>
-    <a href="https://stripe.com/docs/security/stripe" target="_blank"><img src="https://stripe.com/img/about/logos/badge/outline-dark.svg" style="margin-top: 8px;"></a>
-
-    <!-- Used to display Element errors. -->
-    <div id="card-errors" role="alert"></div>
-    </center>
-
-  </div>
-</form>
-
-<script>
-function stripeTokenHandler(token) {
-  // Insert the token ID into the form so it gets submitted to the server
-  var form = document.getElementById('payment-form');
-  var hiddenInput = document.createElement('input');
-  hiddenInput.setAttribute('type', 'hidden');
-  hiddenInput.setAttribute('name', 'stripeToken');
-  hiddenInput.setAttribute('value', token.id);
-  form.appendChild(hiddenInput);
-  
-  // Submit the form
-  form.submit();
-}
-
-var stripe;
-var elements;
-
-$(function () {
-  stripe = Stripe("{{ request.app.get("stripe.public") }}");
-  elements = stripe.elements();
-
-  var card = elements.create('card');
-  card.mount('#card-element');
-
-  card.addEventListener('change', function(event) {
-    var displayError = document.getElementById('card-errors');
-    if (event.error) {
-      displayError.textContent = event.error.message;
-    } else {
-      displayError.textContent = '';
-    }
-  });
-
-  var form = document.getElementById('payment-form');
-  form.addEventListener('submit', function(event) {
-    event.preventDefault();
-
-    stripe.createToken(card).then(function(result) {
-      if (result.error) {
-        // Inform the customer that there was an error.
-        var errorElement = document.getElementById('card-errors');
-        errorElement.textContent = result.error.message;
-      } else {
-        // Send the token to your server.
-        stripeTokenHandler(result.token);
-      }
-    });
-  });
-});
-</script>
-{% endmacro %}
diff --git a/remarkbox/templates/update-card.j2 b/remarkbox/templates/update-card.j2
deleted file mode 100644
index 48d6ac1..0000000
--- a/remarkbox/templates/update-card.j2
+++ /dev/null
@@ -1,23 +0,0 @@
-{% extends request.base_funnel_template -%}
-{%- import 'snippets/stripe.j2' as stripe with context -%}
-{% block title %}{{ the_title }} | {{ request.domain }}{%- endblock -%}
-{% block content -%}
-<h3>{{ the_title }}</h3>
-
-<label>Confirmation: <span style="font-weight: normal;">are you sure?</span></label>
-
-{{ stripe.display_card(card, actions=False) }}
-
-<br/>
-
-<div>
-<form action="/billing/update-card" method="post">
-  {% include 'snippets/csrf.j2' %}
-  <input type="hidden" name="action" value="{{ action }}">
-  <input type="hidden" name="card_id" value="{{ card_id }}">
-  <a href="/billing"><button type="button">Cancel</button></a>
-  <button type="submit" class="{{ button_class }}">Yes, {{ action_human }}</button>
-</form>
-</div>
-
-{%- endblock -%}
diff --git a/remarkbox/views/authenticated/stripe.py b/remarkbox/views/authenticated/stripe.py
index 66fa01d..fe7c799 100644
--- a/remarkbox/views/authenticated/stripe.py
+++ b/remarkbox/views/authenticated/stripe.py
@@ -1,94 +1,229 @@
-from pyramid.view import view_config
+"""
+Stripe payment views for Remarkbox.
 
+Supports:
+- Pay What You Want (custom amount, one-time payment)
+- Annual subscription (yearly payment with duration)
+- Top-up payments (extend subscription)
+"""
+
+from pyramid.view import view_config
 from pyramid.httpexceptions import HTTPFound, HTTPBadRequest
+from pyramid.response import Response
 
 from remarkbox.views import user_required
-
 from remarkbox.lib.mail import send_operator_email
+from remarkbox.stripe.checkout import (
+    configure_stripe,
+    create_checkout_session,
+    retrieve_checkout_session,
+    verify_webhook_signature,
+)
+from remarkbox.models import Payment, PayWhatYouCan, get_payment_by_session_id, create_payment
 
-from remarkbox.models import PayWhatYouCan
+import logging
+
+log = logging.getLogger(__name__)
 
 
 @view_config(route_name="billing", renderer="billing.j2")
 @user_required(
-    flash_msg="Thank you for helping us out, Please verify your email in the form below!",
+    flash_msg="Please verify your email to access billing.",
     flash_level="info",
-    return_to_route_name="billing"
+    return_to_route_name="billing",
 )
 def billing(request):
-    return {"the_title": "Payment Preferences"}
+    """Display the billing/payment page."""
+    # Get user's payment history
+    payments = request.user.payments.filter(Payment.status == "completed").limit(10).all()
 
-
-@view_config(route_name="add-card")
-@user_required()
-def add_card(request):
-    # try to get the return_to uri from posted parameters.
-    return_to = request.params.get("return-to", "/billing")
-    try:
-        source = request.stripe_customer.sources.create(
-            source=request.params.get("stripeToken")
-        )
-        request.stripe_customer.default_source = source
-        request.session.flash(("You saved a new card.", "success"))
-        # TODO: this is very temporary just as a stop gap for me to stay on top of new customers.
-        send_operator_email(
-            request,
-            "A user (hopefully a new one!) added a new card to their Stripe customer account. Log into Stripe and follow up to close the sale!",
-        )
-    except request.stripe.error.CardError as e:
-        body = e.json_body
-        err = body.get("error", {})
-        request.session.flash((err.get("message"), "error"))
-    request.stripe_customer.save()
-    return HTTPFound(return_to)
-
-
-@view_config(route_name="confirm-update-card", renderer="update-card.j2")
-@user_required()
-def confirm_update_card(request):
-    card_id = request.matchdict.get("card_id")
-    card = request.stripe_customer.sources.retrieve(card_id)
-    action = request.matchdict.get("action")
-    action_human = action.replace("-", " ")
-    button_class = "red-button" if action == "delete-card" else "blue-button"
     return {
-        "card": card,
-        "card_id": card_id,
-        "action": action,
-        "action_human": action_human,
-        "button_class": button_class,
-        "the_title": action_human.title(),
+        "the_title": "Billing",
+        "payments": payments,
     }
 
 
-@view_config(route_name="update-card")
-@user_required()
-def update_card(request):
-    action = request.params.get("action", None)
-    card_id = request.params.get("card_id")
-    if action not in ["make-card-active", "delete-card"]:
-        return HTTPBadRequest
-    if "delete-card" == action:
-        request.stripe_customer.sources.retrieve(card_id).delete()
-        request.session.flash(("You deleted that card.", "success"))
-    if "make-card-active" == action:
-        request.stripe_customer.default_source = card_id
-        request.session.flash(("You set the active card.", "success"))
-    request.stripe_customer.save()
-    return HTTPFound("/billing")
-
-
-@view_config(route_name="pay-what-you-can")
+@view_config(route_name="pay-what-you-can", request_method="POST")
 @user_required()
 def pay_what_you_can(request):
+    """Save user's pay-what-you-can preferences (frequency and amount)."""
     frequency = request.params.get("frequency", None)
     amount = request.params.get("amount", None)
+
     if frequency is None or amount is None:
-        request.session.flash(("You must put a value for both frequency and amount.", "error"))
+        request.session.flash(("You must set both frequency and amount.", "error"))
     elif request.user.pay_what_you_can:
         request.user.pay_what_you_can.update(frequency, amount)
-        request.session.flash(("You updated your contribution preferences.", "success"))
+        request.session.flash(("Your contribution preferences have been saved.", "success"))
     else:
         request.user.pay_what_you_can = PayWhatYouCan(request.user, frequency, amount)
-        request.session.flash(("You updated your contribution preferences.", "success"))
+        request.session.flash(("Your contribution preferences have been saved.", "success"))
+
     return HTTPFound("/billing")
+
+
+@view_config(route_name="create-checkout", request_method="POST")
+@user_required()
+def create_checkout(request):
+    """Create a Stripe Checkout session and redirect to it."""
+    configure_stripe(request.app.get("stripe.secret"))
+
+    # Get form parameters
+    payment_type = request.params.get("payment_type", "pay_what_you_want")
+    amount_str = request.params.get("amount", "0")
+    duration_str = request.params.get("duration_months", "12")
+
+    # Parse amount (convert dollars to cents)
+    try:
+        amount_dollars = float(amount_str.replace("$", "").replace(",", "").strip())
+        amount_cents = int(amount_dollars * 100)
+    except (ValueError, AttributeError):
+        request.session.flash(("Invalid amount specified.", "error"))
+        return HTTPFound("/billing")
+
+    # Parse duration
+    try:
+        duration_months = int(duration_str)
+    except (ValueError, AttributeError):
+        duration_months = 12
+
+    if amount_cents < 100:
+        request.session.flash(("Minimum payment is $1.00.", "error"))
+        return HTTPFound("/billing")
+
+    # Build URLs
+    base_url = request.app.get("app_url", request.host_url)
+    success_url = f"{base_url}/billing/success?session_id={{CHECKOUT_SESSION_ID}}"
+    cancel_url = f"{base_url}/billing"
+
+    # Create checkout session
+    session, error = create_checkout_session(
+        amount_cents=amount_cents,
+        payment_type=payment_type,
+        duration_months=duration_months,
+        email=request.user.email,
+        success_url=success_url,
+        cancel_url=cancel_url,
+        metadata={"user_id": str(request.user.id)},
+    )
+
+    if error:
+        log.error(f"Checkout creation failed for user {request.user.id}: {error}")
+        request.session.flash((f"Payment error: {error}", "error"))
+        return HTTPFound("/billing")
+
+    # Create pending payment record
+    create_payment(
+        dbsession=request.dbsession,
+        user=request.user,
+        stripe_session_id=session.id,
+        payment_type=payment_type,
+        amount_cents=amount_cents,
+        duration_months=duration_months,
+    )
+
+    # Redirect to Stripe Checkout
+    return HTTPFound(session.url)
+
+
+@view_config(route_name="billing-success", renderer="billing-success.j2")
+@user_required()
+def billing_success(request):
+    """Handle successful payment return from Stripe."""
+    configure_stripe(request.app.get("stripe.secret"))
+
+    session_id = request.params.get("session_id")
+    if not session_id:
+        request.session.flash(("Missing session information.", "error"))
+        return HTTPFound("/billing")
+
+    # Retrieve the session from Stripe
+    session, error = retrieve_checkout_session(session_id)
+    if error:
+        log.error(f"Failed to retrieve session {session_id}: {error}")
+        request.session.flash(("Could not verify payment.", "error"))
+        return HTTPFound("/billing")
+
+    # Check payment status
+    if session.payment_status != "paid":
+        log.warning(f"Session {session_id} not paid: {session.payment_status}")
+        request.session.flash(("Payment not completed.", "error"))
+        return HTTPFound("/billing")
+
+    # Update payment record
+    payment = get_payment_by_session_id(request.dbsession, session_id)
+    if payment and payment.status == "pending":
+        payment.mark_completed()
+        request.dbsession.add(payment)
+
+        # Send notification to operator
+        send_operator_email(
+            request,
+            f"New payment received! User: {request.user.email}, "
+            f"Amount: ${payment.amount_cents/100:.2f}, Type: {payment.payment_type}",
+        )
+
+    return {
+        "the_title": "Payment Successful",
+        "session": session,
+        "payment": payment,
+    }
+
+
+@view_config(route_name="stripe-webhook", request_method="POST")
+def stripe_webhook(request):
+    """Handle Stripe webhook events."""
+    webhook_secret = request.app.get("stripe.webhook_secret")
+    if not webhook_secret:
+        log.error("Stripe webhook secret not configured")
+        return Response(status=500, json_body={"error": "Webhook not configured"})
+
+    configure_stripe(request.app.get("stripe.secret"))
+
+    # Get the raw body and signature
+    payload = request.body
+    sig_header = request.headers.get("Stripe-Signature")
+
+    if not sig_header:
+        return Response(status=400, json_body={"error": "Missing signature"})
+
+    # Verify webhook signature
+    event, error = verify_webhook_signature(payload, sig_header, webhook_secret)
+    if error:
+        log.error(f"Webhook signature verification failed: {error}")
+        return Response(status=400, json_body={"error": error})
+
+    log.info(f"Received Stripe webhook: {event.type}")
+
+    # Handle the event
+    if event.type == "checkout.session.completed":
+        session = event.data.object
+        _handle_checkout_completed(request.dbsession, session)
+    elif event.type == "payment_intent.payment_failed":
+        payment_intent = event.data.object
+        log.warning(f"Payment failed: {payment_intent.id}")
+    else:
+        log.debug(f"Unhandled webhook event type: {event.type}")
+
+    return Response(status=200, json_body={"received": True})
+
+
+def _handle_checkout_completed(dbsession, session):
+    """Process a completed checkout session from webhook."""
+    session_id = session.id
+
+    if session.payment_status != "paid":
+        log.info(f"Session {session_id} not paid yet: {session.payment_status}")
+        return
+
+    # Find and update the payment record
+    payment = get_payment_by_session_id(dbsession, session_id)
+    if payment:
+        if payment.status == "pending":
+            payment.mark_completed()
+            dbsession.add(payment)
+            log.info(f"Payment {payment.id} marked as completed via webhook")
+        else:
+            log.info(f"Payment {payment.id} already processed: {payment.status}")
+    else:
+        log.warning(f"No payment record found for session {session_id}")
diff --git a/requirements.txt b/requirements.txt
index 4cbd5f1..4ab428b 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -63,8 +63,8 @@ requests[security]
 # request library pins this dependency too low.
 # idna==2.6
 
-# credit card storage and processing.
-stripe==3.5.0
+# Stripe Checkout payment processing.
+stripe>=5.0.0
 
 # slack: bot notifications.
 slacker
diff --git a/test.ini b/test.ini
index a2a3e7c..bc805bf 100644
--- a/test.ini
+++ b/test.ini
@@ -76,10 +76,11 @@ app.theme = meta
 # related to billing and registering Namespaces. Defaults to False
 #app.stand_alone_mode = enabled
 
-# stripe: credit card storage and processing.
+# stripe: Stripe Checkout payment processing.
 # This syntax will automatically expand an ENV var of the same name.
 app.stripe.secret = ${REMARKBOX_APP_STRIPE_SECRET}
 app.stripe.public = ${REMARKBOX_APP_STRIPE_PUBLIC}
+app.stripe.webhook_secret = ${REMARKBOX_APP_STRIPE_WEBHOOK_SECRET:-}
 
 # slack: bot notifications.
 app.slack.secret = ${REMARKBOX_APP_SLACK_SECRET}