diff --git a/corporate/lib/stripe.py b/corporate/lib/stripe.py
index ae20aa88de..2a7284c5ab 100644
--- a/corporate/lib/stripe.py
+++ b/corporate/lib/stripe.py
@@ -32,7 +32,6 @@ from corporate.models import (
     CustomerPlanOffer,
     Invoice,
     LicenseLedger,
-    PaymentIntent,
     Session,
     SponsoredPlanTypes,
     ZulipSponsorshipRequest,
@@ -529,14 +528,6 @@ class StripeCustomerData:
     metadata: Dict[str, Any]
 
 
-@dataclass
-class StripePaymentIntentData:
-    amount: int
-    description: str
-    plan_name: str
-    email: str
-
-
 @dataclass
 class UpgradeRequest:
     billing_modality: str
@@ -567,7 +558,7 @@ class UpdatePlanRequest:
 @dataclass
 class EventStatusRequest:
     stripe_session_id: Optional[str]
-    stripe_payment_intent_id: Optional[str]
+    stripe_invoice_id: Optional[str]
 
 
 class SupportType(Enum):
@@ -747,7 +738,7 @@ class BillingSession(ABC):
         pass
 
     @abstractmethod
-    def update_data_for_checkout_session_and_payment_intent(
+    def update_data_for_checkout_session_and_invoice_payment(
         self, metadata: Dict[str, Any]
     ) -> Dict[str, Any]:
         pass
@@ -787,7 +778,7 @@ class BillingSession(ABC):
             return_url=f"{self.billing_session_url}/billing/",
         ).url
 
-    def get_data_for_stripe_payment_intent(
+    def generate_invoice_for_upgrade(
         self,
         customer: Customer,
         price_per_license: Optional[int],
@@ -795,36 +786,77 @@ class BillingSession(ABC):
         licenses: int,
         plan_tier: int,
         billing_schedule: int,
-        email: str,
-    ) -> StripePaymentIntentData:
-        if hasattr(self, "support_session") and self.support_session:  # nocoverage
-            raise BillingError(
-                "invalid support session",
-                "Support requests do not set any stripe billing information.",
-            )
-
+        charge_automatically: bool,
+        license_management: Optional[str] = None,
+    ) -> stripe.Invoice:
         plan_name = CustomerPlan.name_from_tier(plan_tier)
         assert price_per_license is None or fixed_price is None
-        if price_per_license is not None:
-            amount = price_per_license * licenses
-            description = f"Upgrade to {plan_name}, ${price_per_license/100} x {licenses}"
+        price_args: PriceArgs = {}
+        if fixed_price is None:
+            assert price_per_license is not None
+            price_args = {
+                "quantity": licenses,
+                "unit_amount": price_per_license,
+            }
         else:
             assert fixed_price is not None
-            amount = get_amount_due_fixed_price_plan(fixed_price, billing_schedule)
-            description = plan_name
+            amount_due = get_amount_due_fixed_price_plan(fixed_price, billing_schedule)
+            price_args = {"amount": amount_due}
+
+        stripe.InvoiceItem.create(
+            currency="usd",
+            customer=customer.stripe_customer_id,
+            description=plan_name,
+            discountable=False,
+            **price_args,
+        )
 
         if fixed_price is None and customer.flat_discounted_months > 0:
             num_months = 12 if billing_schedule == CustomerPlan.BILLING_SCHEDULE_ANNUAL else 1
             flat_discounted_months = min(customer.flat_discounted_months, num_months)
-            amount -= customer.flat_discount * flat_discounted_months
-            description += f" - ${customer.flat_discount/100} x {flat_discounted_months}"
+            discount = customer.flat_discount * flat_discounted_months
+            customer.flat_discounted_months -= flat_discounted_months
+            customer.save(update_fields=["flat_discounted_months"])
 
-        return StripePaymentIntentData(
-            amount=amount,
-            description=description,
-            plan_name=plan_name,
-            email=email,
+            stripe.InvoiceItem.create(
+                currency="usd",
+                customer=customer.stripe_customer_id,
+                description=f"${cents_to_dollar_string(customer.flat_discount)}/month new customer discount",
+                # Negative value to apply discount.
+                amount=(-1 * discount),
+            )
+
+        if charge_automatically:
+            collection_method = "charge_automatically"
+            days_until_due = None
+        else:
+            collection_method = "send_invoice"
+            days_until_due = DEFAULT_INVOICE_DAYS_UNTIL_DUE
+
+        metadata = {
+            "plan_tier": plan_tier,
+            "billing_schedule": billing_schedule,
+            "licenses": licenses,
+            "license_management": license_management,
+        }
+
+        if hasattr(self, "user"):
+            metadata["user_id"] = self.user.id
+
+        # We only need to email customer about open invoice for manual billing.
+        # If automatic charge fails, we simply void the invoice.
+        # https://stripe.com/docs/invoicing/integration/automatic-advancement-collection
+        auto_advance = not charge_automatically
+        stripe_invoice = stripe.Invoice.create(
+            auto_advance=auto_advance,
+            collection_method=collection_method,
+            customer=customer.stripe_customer_id,
+            days_until_due=days_until_due,
+            statement_descriptor=plan_name,
+            metadata=metadata,
         )
+        stripe.Invoice.finalize_invoice(stripe_invoice)
+        return stripe_invoice
 
     @abstractmethod
     def update_or_create_customer(
@@ -1000,9 +1032,8 @@ class BillingSession(ABC):
     def update_or_create_stripe_customer(self, payment_method: Optional[str] = None) -> Customer:
         customer = self.get_customer()
         if customer is None or customer.stripe_customer_id is None:
-            # A stripe.PaymentMethod should be attached to a stripe.Customer via
-            # a stripe.SetupIntent or stripe.PaymentIntent. Here we just want to
-            # create a new stripe.Customer.
+            # A stripe.PaymentMethod should be attached to a stripe.Customer via replace_payment_method.
+            # Here we just want to create a new stripe.Customer.
             assert payment_method is None
             # We could do a better job of handling race conditions here, but if two
             # people try to upgrade at exactly the same time, the main bad thing that
@@ -1013,22 +1044,13 @@ class BillingSession(ABC):
             self.replace_payment_method(customer.stripe_customer_id, payment_method, True)
         return customer
 
-    def create_stripe_payment_intent(
+    def create_stripe_invoice_and_charge(
         self,
         metadata: Dict[str, Any],
     ) -> str:
         # NOTE: This charges users immediately.
         customer = self.get_customer()
         assert customer is not None and customer.stripe_customer_id is not None
-        payment_intent_data = self.get_data_for_stripe_payment_intent(
-            customer,
-            metadata["price_per_license"],
-            metadata["fixed_price"],
-            metadata["licenses"],
-            metadata["plan_tier"],
-            metadata["billing_schedule"],
-            self.get_email(),
-        )
         # Ensure customers have a default payment method set.
         stripe_customer = stripe_get_customer(customer.stripe_customer_id)
         if not stripe_customer_has_credit_card_as_default_payment_method(stripe_customer):
@@ -1039,29 +1061,42 @@ class BillingSession(ABC):
 
         assert stripe_customer.invoice_settings is not None
         assert stripe_customer.invoice_settings.default_payment_method is not None
+        stripe_invoice = None
         try:
-            # Try to charge user immediately, and if that fails, we inform the user about the failure.
-            stripe_payment_intent = stripe.PaymentIntent.create(
-                amount=payment_intent_data.amount,
-                currency="usd",
-                customer=customer.stripe_customer_id,
-                description=payment_intent_data.description,
-                receipt_email=payment_intent_data.email,
-                confirm=True,
-                statement_descriptor=payment_intent_data.plan_name,
-                metadata=metadata,
-                off_session=True,
-                payment_method=stripe_customer.invoice_settings.default_payment_method,
+            stripe_invoice = self.generate_invoice_for_upgrade(
+                customer,
+                metadata["price_per_license"],
+                metadata["fixed_price"],
+                metadata["licenses"],
+                metadata["plan_tier"],
+                metadata["billing_schedule"],
+                charge_automatically=True,
+                license_management=metadata["license_management"],
             )
-        except stripe.CardError as e:
-            raise StripeCardError("card error", e.user_message)
+            assert stripe_invoice.id is not None
+            invoice = Invoice.objects.create(
+                stripe_invoice_id=stripe_invoice.id,
+                customer=customer,
+                status=Invoice.SENT,
+            )
+            # Stripe takes its sweet hour to charge customers after creating an invoice.
+            # Since we want to charge customers immediately, we charge them manually.
+            # Then poll for the status of the invoice to see if the payment succeeded.
+            stripe_invoice = stripe.Invoice.pay(stripe_invoice.id)
+        except Exception as e:
+            if stripe_invoice is not None:
+                assert stripe_invoice.id is not None
+                # Void invoice to avoid double charging if customer tries to upgrade again.
+                stripe.Invoice.void_invoice(stripe_invoice.id)
+                invoice.status = Invoice.VOID
+                invoice.save(update_fields=["status"])
+            if isinstance(e, stripe.CardError):
+                raise StripeCardError("card error", e.user_message)
+            else:  # nocoverage
+                raise e
 
-        PaymentIntent.objects.create(
-            customer=customer,
-            stripe_payment_intent_id=stripe_payment_intent.id,
-            status=PaymentIntent.get_status_integer_from_status_text(stripe_payment_intent.status),
-        )
-        return stripe_payment_intent.id
+        assert stripe_invoice.id is not None
+        return stripe_invoice.id
 
     def create_card_update_session_for_upgrade(
         self,
@@ -1392,7 +1427,7 @@ class BillingSession(ABC):
             f"No current plan for {self.billing_entity_display_name}."
         )  # nocoverage
 
-    def setup_upgrade_payment_intent_and_charge(
+    def generate_stripe_invoice_and_charge_immediately(
         self,
         plan_tier: int,
         seat_count: int,
@@ -1423,11 +1458,10 @@ class BillingSession(ABC):
             general_metadata["price_per_license"] = price_per_license
         else:
             general_metadata["fixed_price"] = fixed_price_plan_offer.fixed_price
-        updated_metadata = self.update_data_for_checkout_session_and_payment_intent(
+        updated_metadata = self.update_data_for_checkout_session_and_invoice_payment(
             general_metadata
         )
-        stripe_payment_intent_id = self.create_stripe_payment_intent(updated_metadata)
-        return stripe_payment_intent_id
+        return self.create_stripe_invoice_and_charge(updated_metadata)
 
     def ensure_current_plan_is_upgradable(self, customer: Customer, new_plan_tier: int) -> None:
         # Upgrade for customers with an existing plan is only supported for remote realm / server right now.
@@ -1614,12 +1648,31 @@ class BillingSession(ABC):
                     plan=plan,
                     is_renewal=True,
                     event_time=event_time,
-                    licenses=billed_licenses,
-                    licenses_at_next_renewal=billed_licenses,
+                    licenses=licenses,
+                    licenses_at_next_renewal=licenses,
                 )
                 plan.invoiced_through = ledger_entry
                 plan.save(update_fields=["invoiced_through"])
 
+                # TODO: Do a check for max licenses for fixed price plans here after we add that.
+                if (
+                    stripe_invoice_paid
+                    and billed_licenses != licenses
+                    and not customer.exempt_from_license_number_check
+                    and not fixed_price_plan_offer
+                ):
+                    # Customer paid for less licenses than they have.
+                    # We need to create a new ledger entry to track the additional licenses.
+                    LicenseLedger.objects.create(
+                        plan=plan,
+                        is_renewal=False,
+                        event_time=event_time,
+                        licenses=billed_licenses,
+                        licenses_at_next_renewal=billed_licenses,
+                    )
+                    # Creates due today invoice for additional licenses.
+                    self.invoice_plan(plan, event_time)
+
             self.write_to_audit_log(
                 event_type=AuditLogEventType.CUSTOMER_PLAN_CREATED,
                 event_time=event_time,
@@ -1630,60 +1683,15 @@ class BillingSession(ABC):
             free_trial or should_schedule_upgrade_for_legacy_remote_server
         ):
             assert plan is not None
-            price_args: PriceArgs = {}
-            if plan.fixed_price is None:
-                price_args = {
-                    "quantity": billed_licenses,
-                    "unit_amount": price_per_license,
-                }
-            else:
-                assert plan.fixed_price is not None
-                amount_due = get_amount_due_fixed_price_plan(plan.fixed_price, billing_schedule)
-                price_args = {"amount": amount_due}
-            assert customer.stripe_customer_id is not None
-            stripe.InvoiceItem.create(
-                currency="usd",
-                customer=customer.stripe_customer_id,
-                description=plan.name,
-                discountable=False,
-                period={
-                    "start": datetime_to_timestamp(billing_cycle_anchor),
-                    "end": datetime_to_timestamp(period_end),
-                },
-                **price_args,
+            self.generate_invoice_for_upgrade(
+                customer,
+                price_per_license=price_per_license,
+                fixed_price=plan.fixed_price,
+                licenses=billed_licenses,
+                plan_tier=plan.tier,
+                billing_schedule=billing_schedule,
+                charge_automatically=False,
             )
-
-            if plan.fixed_price is None and customer.flat_discounted_months > 0:
-                num_months = 12 if billing_schedule == CustomerPlan.BILLING_SCHEDULE_ANNUAL else 1
-                flat_discounted_months = min(customer.flat_discounted_months, num_months)
-                discount = customer.flat_discount * flat_discounted_months
-                customer.flat_discounted_months -= flat_discounted_months
-                customer.save(update_fields=["flat_discounted_months"])
-
-                stripe.InvoiceItem.create(
-                    currency="usd",
-                    customer=customer.stripe_customer_id,
-                    description=f"${cents_to_dollar_string(customer.flat_discount)}/month new customer discount",
-                    # Negative value to apply discount.
-                    amount=(-1 * discount),
-                )
-
-            if charge_automatically:
-                collection_method = "charge_automatically"
-                days_until_due = None
-            else:
-                collection_method = "send_invoice"
-                days_until_due = DEFAULT_INVOICE_DAYS_UNTIL_DUE
-
-            stripe_invoice = stripe.Invoice.create(
-                auto_advance=True,
-                collection_method=collection_method,
-                customer=customer.stripe_customer_id,
-                days_until_due=days_until_due,
-                statement_descriptor=plan.name,
-            )
-            stripe.Invoice.finalize_invoice(stripe_invoice)
-
         if plan.status < CustomerPlan.LIVE_STATUS_THRESHOLD:
             # Tier and usage limit change will happen when plan becomes live.
             self.do_change_plan_type(tier=plan_tier)
@@ -1761,7 +1769,7 @@ class BillingSession(ABC):
             )
             data["organization_upgrade_successful"] = True
         else:
-            stripe_payment_intent_id = self.setup_upgrade_payment_intent_and_charge(
+            stripe_invoice_id = self.generate_stripe_invoice_and_charge_immediately(
                 upgrade_request.tier,
                 seat_count,
                 licenses,
@@ -1769,7 +1777,7 @@ class BillingSession(ABC):
                 billing_schedule,
                 billing_modality,
             )
-            data["stripe_payment_intent_id"] = stripe_payment_intent_id
+            data["stripe_invoice_id"] = stripe_invoice_id
         return data
 
     def do_change_schedule_after_free_trial(self, plan: CustomerPlan, schedule: int) -> None:
@@ -2827,18 +2835,18 @@ class BillingSession(ABC):
                 raise JsonableError(_("Must be a billing administrator or an organization owner"))
             return {"session": session.to_dict()}
 
-        stripe_payment_intent_id = event_status_request.stripe_payment_intent_id
-        if stripe_payment_intent_id is not None:
-            payment_intent = PaymentIntent.objects.filter(
-                stripe_payment_intent_id=stripe_payment_intent_id,
+        stripe_invoice_id = event_status_request.stripe_invoice_id
+        if stripe_invoice_id is not None:
+            stripe_invoice = Invoice.objects.filter(
+                stripe_invoice_id=stripe_invoice_id,
                 customer=customer,
             ).last()
 
-            if payment_intent is None:
+            if stripe_invoice is None:
                 raise JsonableError(_("Payment intent not found"))
-            return {"payment_intent": payment_intent.to_dict()}
+            return {"stripe_invoice": stripe_invoice.to_dict()}
 
-        raise JsonableError(_("Pass stripe_session_id or stripe_payment_intent_id"))
+        raise JsonableError(_("Pass stripe_session_id or stripe_invoice_id"))
 
     def get_sponsorship_plan_name(
         self, customer: Optional[Customer], is_remotely_hosted: bool
@@ -3378,7 +3386,7 @@ class RealmBillingSession(BillingSession):
         return realm_stripe_customer_data
 
     @override
-    def update_data_for_checkout_session_and_payment_intent(
+    def update_data_for_checkout_session_and_invoice_payment(
         self, metadata: Dict[str, Any]
     ) -> Dict[str, Any]:
         assert self.user is not None
@@ -3771,7 +3779,7 @@ class RemoteRealmBillingSession(BillingSession):
         return realm_stripe_customer_data
 
     @override
-    def update_data_for_checkout_session_and_payment_intent(
+    def update_data_for_checkout_session_and_invoice_payment(
         self, metadata: Dict[str, Any]
     ) -> Dict[str, Any]:
         assert self.remote_billing_user is not None
@@ -4194,7 +4202,7 @@ class RemoteServerBillingSession(BillingSession):
         return realm_stripe_customer_data
 
     @override
-    def update_data_for_checkout_session_and_payment_intent(
+    def update_data_for_checkout_session_and_invoice_payment(
         self, metadata: Dict[str, Any]
     ) -> Dict[str, Any]:
         assert self.remote_billing_user is not None
diff --git a/corporate/lib/stripe_event_handler.py b/corporate/lib/stripe_event_handler.py
index 104863c58b..7929fbc264 100644
--- a/corporate/lib/stripe_event_handler.py
+++ b/corporate/lib/stripe_event_handler.py
@@ -1,19 +1,19 @@
 import logging
-from typing import Any, Callable, Dict, Optional, Union
+from typing import Any, Callable, Optional, Union
 
 import stripe
 from django.conf import settings
 
 from corporate.lib.stripe import (
+    BILLING_SUPPORT_EMAIL,
     BillingError,
-    InvalidPlanUpgradeError,
     RealmBillingSession,
     RemoteRealmBillingSession,
     RemoteServerBillingSession,
-    UpgradeWithExistingPlanError,
     get_configured_fixed_price_plan_offer,
 )
-from corporate.models import Customer, CustomerPlan, Event, Invoice, PaymentIntent, Session
+from corporate.models import Customer, CustomerPlan, Event, Invoice, Session
+from zerver.lib.send_email import FromAddress, send_email
 from zerver.models.users import get_active_user_profile_by_id_in_realm
 
 billing_logger = logging.getLogger("corporate.stripe")
@@ -21,9 +21,9 @@ billing_logger = logging.getLogger("corporate.stripe")
 
 def error_handler(
     func: Callable[[Any, Any], None],
-) -> Callable[[Union[stripe.checkout.Session, stripe.PaymentIntent, stripe.Invoice], Event], None]:
+) -> Callable[[Union[stripe.checkout.Session, stripe.Invoice], Event], None]:
     def wrapper(
-        stripe_object: Union[stripe.checkout.Session, stripe.PaymentIntent, stripe.Invoice],
+        stripe_object: Union[stripe.checkout.Session, stripe.Invoice],
         event: Event,
     ) -> None:
         event.status = Event.EVENT_HANDLER_STARTED
@@ -32,7 +32,7 @@ def error_handler(
         try:
             func(stripe_object, event.content_object)
         except BillingError as e:
-            billing_logger.warning(
+            message = (
                 "BillingError in %s event handler: %s. stripe_object_id=%s, customer_id=%s metadata=%s",
                 event.type,
                 e.error_description,
@@ -40,12 +40,23 @@ def error_handler(
                 stripe_object.customer,
                 stripe_object.metadata,
             )
+            billing_logger.warning(message)
             event.status = Event.EVENT_HANDLER_FAILED
             event.handler_error = {
                 "message": e.msg,
                 "description": e.error_description,
             }
             event.save(update_fields=["status", "handler_error"])
+            if type(stripe_object) == stripe.Invoice:
+                # For Invoice processing errors, send email to billing support.
+                send_email(
+                    "zerver/emails/error_processing_invoice",
+                    to_emails=[BILLING_SUPPORT_EMAIL],
+                    from_address=FromAddress.tokenized_no_reply_address(),
+                    context={
+                        "message": message,
+                    },
+                )
         except Exception:
             billing_logger.exception(
                 "Uncaught exception in %s event handler:",
@@ -102,58 +113,6 @@ def handle_checkout_session_completed_event(
         billing_session.update_or_create_stripe_customer(payment_method)
 
 
-@error_handler
-def handle_payment_intent_succeeded_event(
-    stripe_payment_intent: stripe.PaymentIntent, payment_intent: PaymentIntent
-) -> None:
-    payment_intent.status = PaymentIntent.SUCCEEDED
-    payment_intent.save()
-    metadata: Dict[str, Any] = stripe_payment_intent.metadata
-
-    description = ""
-    charge: stripe.Charge
-    for charge in stripe_payment_intent.charges:  # type: ignore[attr-defined] # https://stripe.com/docs/upgrades#2022-11-15
-        assert charge.payment_method_details is not None
-        assert charge.payment_method_details.card is not None
-        description = f"Payment (Card ending in {charge.payment_method_details.card.last4})"
-        break
-
-    stripe.InvoiceItem.create(
-        amount=stripe_payment_intent.amount * -1,
-        currency="usd",
-        customer=stripe_payment_intent.customer,
-        description=description,
-        discountable=False,
-    )
-    billing_session = get_billing_session_for_stripe_webhook(
-        payment_intent.customer, metadata.get("user_id")
-    )
-    plan_tier = int(metadata["plan_tier"])
-    try:
-        billing_session.ensure_current_plan_is_upgradable(payment_intent.customer, plan_tier)
-    except (UpgradeWithExistingPlanError, InvalidPlanUpgradeError) as e:
-        stripe_invoice = stripe.Invoice.create(
-            auto_advance=True,
-            collection_method="charge_automatically",
-            customer=stripe_payment_intent.customer,
-            days_until_due=None,
-            statement_descriptor=CustomerPlan.name_from_tier(plan_tier).replace("Zulip ", "")
-            + " Credit",
-        )
-        stripe.Invoice.finalize_invoice(stripe_invoice)
-        raise e
-
-    billing_session.process_initial_upgrade(
-        plan_tier,
-        int(metadata["licenses"]),
-        metadata["license_management"] == "automatic",
-        int(metadata["billing_schedule"]),
-        True,
-        False,
-        billing_session.get_remote_server_legacy_plan(payment_intent.customer),
-    )
-
-
 @error_handler
 def handle_invoice_paid_event(stripe_invoice: stripe.Invoice, invoice: Invoice) -> None:
     invoice.status = Invoice.PAID
@@ -183,3 +142,35 @@ def handle_invoice_paid_event(stripe_invoice: stripe.Invoice, invoice: Invoice)
             remote_server_legacy_plan=remote_server_legacy_plan,
             stripe_invoice_paid=True,
         )
+    elif stripe_invoice.collection_method == "charge_automatically":
+        metadata = stripe_invoice.metadata
+        assert metadata is not None
+        billing_session = get_billing_session_for_stripe_webhook(customer, metadata.get("user_id"))
+        remote_server_legacy_plan = billing_session.get_remote_server_legacy_plan(customer)
+        billing_schedule = int(metadata["billing_schedule"])
+        plan_tier = int(metadata["plan_tier"])
+        if configured_fixed_price_plan and customer.required_plan_tier == plan_tier:
+            assert customer.required_plan_tier is not None
+            billing_session.process_initial_upgrade(
+                plan_tier=customer.required_plan_tier,
+                # TODO: Currently licenses don't play any role for fixed price plan.
+                # We plan to introduce max_licenses allowed soon.
+                licenses=0,
+                automanage_licenses=True,
+                billing_schedule=billing_schedule,
+                charge_automatically=True,
+                free_trial=False,
+                remote_server_legacy_plan=remote_server_legacy_plan,
+                stripe_invoice_paid=True,
+            )
+        else:
+            billing_session.process_initial_upgrade(
+                plan_tier,
+                int(metadata["licenses"]),
+                metadata["license_management"] == "automatic",
+                billing_schedule=billing_schedule,
+                charge_automatically=True,
+                free_trial=False,
+                remote_server_legacy_plan=remote_server_legacy_plan,
+                stripe_invoice_paid=True,
+            )
diff --git a/corporate/models.py b/corporate/models.py
index 2ce8296c52..e6a1d40e42 100644
--- a/corporate/models.py
+++ b/corporate/models.py
@@ -113,7 +113,7 @@ class Event(models.Model):
 
 
 def get_last_associated_event_by_type(
-    content_object: Union["PaymentIntent", "Session"], event_type: str
+    content_object: Union["Invoice", "PaymentIntent", "Session"], event_type: str
 ) -> Optional[Event]:
     content_type = ContentType.objects.get_for_model(type(content_object))
     return Event.objects.filter(
@@ -168,7 +168,7 @@ class Session(models.Model):
         return get_last_associated_event_by_type(self, "checkout.session.completed")
 
 
-class PaymentIntent(models.Model):
+class PaymentIntent(models.Model):  # nocoverage
     customer = models.ForeignKey(Customer, on_delete=CASCADE)
     stripe_payment_intent_id = models.CharField(max_length=255, unique=True)
 
@@ -221,8 +221,32 @@ class Invoice(models.Model):
 
     SENT = 1
     PAID = 2
+    VOID = 3
     status = models.SmallIntegerField()
 
+    def get_status_as_string(self) -> str:
+        return {
+            Invoice.SENT: "sent",
+            Invoice.PAID: "paid",
+            Invoice.VOID: "void",
+        }[self.status]
+
+    def get_last_associated_event(self) -> Optional[Event]:
+        if self.status == Invoice.PAID:
+            event_type = "invoice.paid"
+        # TODO: Add test for this case. Not sure how to trigger naturally.
+        else:  # nocoverage
+            return None  # nocoverage
+        return get_last_associated_event_by_type(self, event_type)
+
+    def to_dict(self) -> Dict[str, Any]:
+        stripe_invoice_dict: Dict[str, Any] = {}
+        stripe_invoice_dict["status"] = self.get_status_as_string()
+        event = self.get_last_associated_event()
+        if event is not None:
+            stripe_invoice_dict["event_handler"] = event.get_event_handler_details_as_dict()
+        return stripe_invoice_dict
+
 
 class AbstractCustomerPlan(models.Model):
     # A customer can only have one ACTIVE / CONFIGURED plan,
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diff --git a/corporate/tests/stripe_fixtures/void_all_open_invoices--Invoice.void_invoice.2.json b/corporate/tests/stripe_fixtures/void_all_open_invoices--Invoice.void_invoice.2.json
index 7b97f38856..2270c03ac6 100644
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diff --git a/corporate/tests/test_stripe.py b/corporate/tests/test_stripe.py
index 765ae85d51..f06774cc0a 100644
--- a/corporate/tests/test_stripe.py
+++ b/corporate/tests/test_stripe.py
@@ -86,7 +86,6 @@ from corporate.models import (
     Event,
     Invoice,
     LicenseLedger,
-    PaymentIntent,
     ZulipSponsorshipRequest,
     get_current_plan_by_customer,
     get_current_plan_by_realm,
@@ -169,6 +168,12 @@ def generate_and_save_stripe_fixture(
             with open(fixture_path, "w") as f:
                 assert e.headers is not None
                 error_dict = {**vars(e), "headers": dict(e.headers)}
+                # Add http_body to the error_dict, since it's not included in the vars(e) output.
+                # It should be same as e.json_body, but we include it since stripe expects it.
+                if e.http_body is None:
+                    assert e.json_body is not None
+                    # Convert e.json_body to be a JSON string, since that's what stripe expects.
+                    error_dict["http_body"] = json.dumps(e.json_body)
                 f.write(
                     json.dumps(error_dict, indent=2, separators=(",", ": "), sort_keys=True) + "\n"
                 )
@@ -320,10 +325,6 @@ MOCKED_STRIPE_FUNCTION_NAMES = [
         "Invoice.void_invoice",
         "InvoiceItem.create",
         "InvoiceItem.list",
-        "PaymentIntent.confirm",
-        "PaymentIntent.create",
-        "PaymentIntent.list",
-        "PaymentIntent.retrieve",
         "PaymentMethod.attach",
         "PaymentMethod.create",
         "PaymentMethod.detach",
@@ -478,19 +479,19 @@ class StripeTestCase(ZulipTestCase):
         response_dict = self.assert_json_success(json_response)
         self.assertEqual(response_dict["session"], expected_details)
 
-    def assert_details_of_valid_payment_intent_from_event_status_endpoint(
+    def assert_details_of_valid_invoice_payment_from_event_status_endpoint(
         self,
-        stripe_payment_intent_id: str,
+        stripe_invoice_id: str,
         expected_details: Dict[str, Any],
     ) -> None:
         json_response = self.client_billing_get(
             "/billing/event/status",
             {
-                "stripe_payment_intent_id": stripe_payment_intent_id,
+                "stripe_invoice_id": stripe_invoice_id,
             },
         )
         response_dict = self.assert_json_success(json_response)
-        self.assertEqual(response_dict["payment_intent"], expected_details)
+        self.assertEqual(response_dict["stripe_invoice"], expected_details)
 
     def trigger_stripe_checkout_session_completed_webhook(
         self,
@@ -635,19 +636,20 @@ class StripeTestCase(ZulipTestCase):
             # upgrade for legacy remote servers.
             return upgrade_json_response
 
-        last_stripe_payment_intent = PaymentIntent.objects.last()
-        assert last_stripe_payment_intent is not None
+        last_sent_invoice = Invoice.objects.last()
+        assert last_sent_invoice is not None
 
         response_dict = self.assert_json_success(upgrade_json_response)
         self.assertEqual(
-            response_dict["stripe_payment_intent_id"],
-            last_stripe_payment_intent.stripe_payment_intent_id,
+            response_dict["stripe_invoice_id"],
+            last_sent_invoice.stripe_invoice_id,
         )
 
-        # Verify that the payment was successful.
-        self.assert_details_of_valid_payment_intent_from_event_status_endpoint(
-            last_stripe_payment_intent.stripe_payment_intent_id,
-            {"status": "succeeded"},
+        # Verify that the Invoice was sent.
+        # Invoice is only marked as paid in our db after we receive `invoice.paid` event.
+        self.assert_details_of_valid_invoice_payment_from_event_status_endpoint(
+            last_sent_invoice.stripe_invoice_id,
+            {"status": "sent"},
         )
 
         # Upgrade the organization.
@@ -828,10 +830,7 @@ class StripeTest(StripeTestCase):
         # Check Charges in Stripe
         [charge] = iter(stripe.Charge.list(customer=stripe_customer.id))
         self.assertEqual(charge.amount, 8000 * self.seat_count)
-        # TODO: fix Decimal
-        self.assertEqual(
-            charge.description, f"Upgrade to Zulip Cloud Standard, $80.0 x {self.seat_count}"
-        )
+        self.assertEqual(charge.description, "Payment for Invoice")
         self.assertEqual(charge.receipt_email, user.delivery_email)
         self.assertEqual(charge.statement_descriptor, "Zulip Cloud Standard")
         # Check Invoices in Stripe
@@ -839,26 +838,22 @@ class StripeTest(StripeTestCase):
         self.assertIsNotNone(invoice.status_transitions.finalized_at)
         invoice_params = {
             # auto_advance is False because the invoice has been paid
-            "amount_due": 0,
-            "amount_paid": 0,
+            "amount_due": 48000,
+            "amount_paid": 48000,
             "auto_advance": False,
             "collection_method": "charge_automatically",
-            "charge": None,
             "status": "paid",
-            "total": 0,
+            "total": 48000,
         }
+        self.assertIsNotNone(invoice.charge)
         for key, value in invoice_params.items():
             self.assertEqual(invoice.get(key), value)
         # Check Line Items on Stripe Invoice
-        [item0, item1] = iter(invoice.lines)
+        [item0] = iter(invoice.lines)
         line_item_params = {
             "amount": 8000 * self.seat_count,
             "description": "Zulip Cloud Standard",
             "discountable": False,
-            "period": {
-                "end": datetime_to_timestamp(self.next_year),
-                "start": datetime_to_timestamp(self.now),
-            },
             # There's no unit_amount on Line Items, probably because it doesn't show up on the
             # user-facing invoice. We could pull the Invoice Item instead and test unit_amount there,
             # but testing the amount and quantity seems sufficient.
@@ -868,16 +863,6 @@ class StripeTest(StripeTestCase):
         }
         for key, value in line_item_params.items():
             self.assertEqual(item0.get(key), value)
-        line_item_params = {
-            "amount": -8000 * self.seat_count,
-            "description": "Payment (Card ending in 4242)",
-            "discountable": False,
-            "plan": None,
-            "proration": False,
-            "quantity": 1,
-        }
-        for key, value in line_item_params.items():
-            self.assertEqual(item1.get(key), value)
 
         # Check that we correctly populated Customer, CustomerPlan, and LicenseLedger in Zulip
         customer = Customer.objects.get(stripe_customer_id=stripe_customer.id, realm=user.realm)
@@ -1016,10 +1001,6 @@ class StripeTest(StripeTestCase):
             "amount": 8000 * 123,
             "description": "Zulip Cloud Standard",
             "discountable": False,
-            "period": {
-                "end": datetime_to_timestamp(self.next_year),
-                "start": datetime_to_timestamp(self.now),
-            },
             "plan": None,
             "proration": False,
             "quantity": 123,
@@ -1123,7 +1104,7 @@ class StripeTest(StripeTestCase):
 
             stripe_customer = self.add_card_and_upgrade(user)
 
-            self.assertEqual(PaymentIntent.objects.count(), 0)
+            self.assertEqual(Invoice.objects.count(), 0)
             self.assertEqual(stripe_customer.description, "zulip (Zulip Dev)")
             self.assertEqual(stripe_customer.discount, None)
             self.assertEqual(stripe_customer.email, user.delivery_email)
@@ -1499,13 +1480,19 @@ class StripeTest(StripeTestCase):
         [charge] = iter(stripe.Charge.list(customer=stripe_customer_id))
         self.assertEqual(8000 * self.seat_count, charge.amount)
         # Check that the invoice has a credit for the old amount and a charge for the new one
-        [stripe_invoice] = iter(stripe.Invoice.list(customer=stripe_customer_id))
+        [additional_license_invoice, upgrade_invoice] = iter(
+            stripe.Invoice.list(customer=stripe_customer_id)
+        )
         self.assertEqual(
-            [8000 * new_seat_count, -8000 * self.seat_count],
-            [item.amount for item in stripe_invoice.lines],
+            [8000 * self.seat_count],
+            [item.amount for item in upgrade_invoice.lines],
+        )
+        self.assertEqual(
+            [8000 * (new_seat_count - self.seat_count)],
+            [item.amount for item in additional_license_invoice.lines],
         )
         # Check LicenseLedger has the new amount
-        ledger_entry = LicenseLedger.objects.first()
+        ledger_entry = LicenseLedger.objects.last()
         assert ledger_entry is not None
         self.assertEqual(ledger_entry.licenses, new_seat_count)
         self.assertEqual(ledger_entry.licenses_at_next_renewal, new_seat_count)
@@ -1526,6 +1513,7 @@ class StripeTest(StripeTestCase):
         self.login_user(hamlet)
         hamlet_upgrade_page_response = self.client_get("/upgrade/")
         self.add_card_to_customer_for_upgrade()
+        [stripe_event_before_upgrade] = iter(stripe.Event.list(limit=1))
         self.client_billing_post(
             "/billing/upgrade",
             {
@@ -1538,23 +1526,24 @@ class StripeTest(StripeTestCase):
                 "license_management": "automatic",
             },
         )
-        # Hamlet already paid to upgrade the org but we haven't received a success event for it yet.
-        [hamlet_payment_success_event] = iter(
-            stripe.Event.list(type="payment_intent.succeeded", limit=1)
-        )
-        [hamlet_payment_intent] = iter(stripe.PaymentIntent.list(limit=1))
+
+        # Get the last generated invoice for Hamlet
+        customer = get_customer_by_realm(get_realm("zulip"))
+        assert customer is not None
+        [hamlet_invoice] = iter(stripe.Invoice.list(customer=customer.stripe_customer_id))
 
         self.login_user(othello)
         # Othello completed the upgrade while we were waiting on success payment event for Hamlet.
         self.upgrade()
 
         with self.assertLogs("corporate.stripe", "WARNING"):
-            self.send_stripe_webhook_event(hamlet_payment_success_event)
+            self.send_stripe_webhook_events(stripe_event_before_upgrade)
 
-        self.assert_details_of_valid_payment_intent_from_event_status_endpoint(
-            hamlet_payment_intent.id,
+        assert hamlet_invoice.id is not None
+        self.assert_details_of_valid_invoice_payment_from_event_status_endpoint(
+            hamlet_invoice.id,
             {
-                "status": "succeeded",
+                "status": "paid",
                 "event_handler": {
                     "status": "failed",
                     "error": {
@@ -1564,14 +1553,17 @@ class StripeTest(StripeTestCase):
                 },
             },
         )
-        charged_amount = self.seat_count * 8000
-        customer = get_customer_by_realm(get_realm("zulip"))
-        assert customer is not None
-        assert customer.stripe_customer_id is not None
-        [invoice, _] = iter(stripe.Invoice.list(customer=customer.stripe_customer_id))
-        self.assertEqual(invoice.total, -1 * charged_amount)
-        stripe_customer = stripe.Customer.retrieve(customer.stripe_customer_id)
-        self.assertEqual(stripe_customer.balance, -1 * charged_amount)
+
+        # Check that we informed the support team about the failure.
+        from django.core.mail import outbox
+
+        self.assert_length(outbox, 1)
+
+        for message in outbox:
+            self.assert_length(message.to, 1)
+            self.assertEqual(message.to[0], "sales@zulip.com")
+            self.assertEqual(message.subject, "Error processing paid customer invoice")
+            self.assertEqual(self.email_envelope_from(message), settings.NOREPLY_EMAIL_ADDRESS)
 
     def test_upgrade_race_condition_during_invoice_upgrade(self) -> None:
         hamlet = self.example_user("hamlet")
@@ -1704,8 +1696,8 @@ class StripeTest(StripeTestCase):
                 upgrade_params["licenses"] = licenses
             with patch("corporate.lib.stripe.BillingSession.process_initial_upgrade"):
                 with patch(
-                    "corporate.lib.stripe.BillingSession.create_stripe_payment_intent",
-                    return_value="fake_payment_intent_id",
+                    "corporate.lib.stripe.BillingSession.create_stripe_invoice_and_charge",
+                    return_value="fake_stripe_invoice_id",
                 ):
                     response = self.upgrade(
                         invoice=invoice, talk_to_stripe=False, del_args=del_args, **upgrade_params
@@ -1759,7 +1751,7 @@ class StripeTest(StripeTestCase):
         self.login_user(hamlet)
         self.add_card_to_customer_for_upgrade()
         with patch(
-            "corporate.lib.stripe.BillingSession.create_stripe_payment_intent",
+            "corporate.lib.stripe.BillingSession.create_stripe_invoice_and_charge",
             side_effect=Exception,
         ), self.assertLogs("corporate.stripe", "WARNING") as m:
             response = self.upgrade(talk_to_stripe=False)
@@ -1773,7 +1765,7 @@ class StripeTest(StripeTestCase):
         )
 
     @mock_stripe(tested_timestamp_fields=["created"])
-    def test_payment_intent_succeeded_event_with_uncaught_exception(self, *mock_args: Any) -> None:
+    def test_invoice_payment_succeeded_event_with_uncaught_exception(self, *mock_args: Any) -> None:
         hamlet = self.example_user("hamlet")
         self.login_user(hamlet)
         self.add_card_to_customer_for_upgrade()
@@ -1785,15 +1777,15 @@ class StripeTest(StripeTestCase):
 
         response_dict = self.assert_json_success(response)
 
-        self.assert_details_of_valid_payment_intent_from_event_status_endpoint(
-            response_dict["stripe_payment_intent_id"],
+        self.assert_details_of_valid_invoice_payment_from_event_status_endpoint(
+            response_dict["stripe_invoice_id"],
             {
-                "status": "succeeded",
+                "status": "paid",
                 "event_handler": {
                     "status": "failed",
                     "error": {
                         "message": "Something went wrong. Please contact desdemona+admin@zulip.com.",
-                        "description": "uncaught exception in payment_intent.succeeded event handler",
+                        "description": "uncaught exception in invoice.paid event handler",
                     },
                 },
             },
@@ -4139,19 +4131,19 @@ class StripeWebhookEndpointTest(ZulipTestCase):
         self.assertEqual(result.status_code, 200)
         m.assert_not_called()
 
-    def test_stripe_webhook_for_payment_intent_events(self) -> None:
+    def test_stripe_webhook_for_invoice_payment_events(self) -> None:
         customer = Customer.objects.create(realm=get_realm("zulip"))
 
         stripe_event_id = "stripe_event_id"
-        stripe_payment_intent_id = "stripe_payment_intent_id"
+        stripe_invoice_id = "stripe_invoice_id"
         valid_session_event_data = {
             "id": stripe_event_id,
-            "type": "payment_intent.succeeded",
+            "type": "invoice.paid",
             "api_version": STRIPE_API_VERSION,
-            "data": {"object": {"object": "payment_intent", "id": stripe_payment_intent_id}},
+            "data": {"object": {"object": "invoice", "id": stripe_invoice_id}},
         }
 
-        with patch("corporate.views.webhook.handle_payment_intent_succeeded_event") as m:
+        with patch("corporate.views.webhook.handle_invoice_paid_event") as m:
             result = self.client_post(
                 "/stripe/webhook/",
                 valid_session_event_data,
@@ -4161,14 +4153,14 @@ class StripeWebhookEndpointTest(ZulipTestCase):
         self.assertEqual(result.status_code, 200)
         m.assert_not_called()
 
-        PaymentIntent.objects.create(
-            stripe_payment_intent_id=stripe_payment_intent_id,
+        Invoice.objects.create(
+            stripe_invoice_id=stripe_invoice_id,
             customer=customer,
-            status=PaymentIntent.REQUIRES_PAYMENT_METHOD,
+            status=Invoice.SENT,
         )
 
         self.assert_length(Event.objects.filter(stripe_event_id=stripe_event_id), 0)
-        with patch("corporate.views.webhook.handle_payment_intent_succeeded_event") as m:
+        with patch("corporate.views.webhook.handle_invoice_paid_event") as m:
             result = self.client_post(
                 "/stripe/webhook/",
                 valid_session_event_data,
@@ -4179,7 +4171,7 @@ class StripeWebhookEndpointTest(ZulipTestCase):
         strip_event = stripe.Event.construct_from(valid_session_event_data, stripe.api_key)
         m.assert_called_once_with(strip_event.data.object, event)
 
-        with patch("corporate.views.webhook.handle_payment_intent_succeeded_event") as m:
+        with patch("corporate.views.webhook.handle_invoice_paid_event") as m:
             result = self.client_post(
                 "/stripe/webhook/",
                 valid_session_event_data,
@@ -4254,16 +4246,14 @@ class EventStatusTest(StripeTestCase):
         self.assert_json_error_contains(response, "Session not found")
 
         response = self.client_get(
-            "/json/billing/event/status", {"stripe_payment_intent_id": "invalid_payment_intent_id"}
+            "/json/billing/event/status", {"stripe_invoice_id": "invalid_invoice_id"}
         )
         self.assert_json_error_contains(response, "Payment intent not found")
 
         response = self.client_get(
             "/json/billing/event/status",
         )
-        self.assert_json_error_contains(
-            response, "Pass stripe_session_id or stripe_payment_intent_id"
-        )
+        self.assert_json_error_contains(response, "Pass stripe_session_id or stripe_invoice_id")
 
     def test_event_status_page(self) -> None:
         self.login_user(self.example_user("polonius"))
@@ -4274,13 +4264,11 @@ class EventStatusTest(StripeTestCase):
         )
         self.assert_in_success_response([f'data-stripe-session-id="{stripe_session_id}"'], response)
 
-        stripe_payment_intent_id = "pi_1JGLpnA4KHR4JzRvUfkF9Tn7"
+        stripe_invoice_id = "pi_1JGLpnA4KHR4JzRvUfkF9Tn7"
         response = self.client_get(
-            "/billing/event_status/", {"stripe_payment_intent_id": stripe_payment_intent_id}
-        )
-        self.assert_in_success_response(
-            [f'data-stripe-payment-intent-id="{stripe_payment_intent_id}"'], response
+            "/billing/event_status/", {"stripe_invoice_id": stripe_invoice_id}
         )
+        self.assert_in_success_response([f'data-stripe-invoice-id="{stripe_invoice_id}"'], response)
 
 
 class RequiresBillingAccessTest(StripeTestCase):
@@ -5411,7 +5399,7 @@ class TestSupportBillingHelpers(StripeTestCase):
         assert stripe_customer_id is not None
         [invoice] = iter(stripe.Invoice.list(customer=stripe_customer_id))
         self.assertEqual(
-            [1200 * self.seat_count, -1200 * self.seat_count],
+            [1200 * self.seat_count],
             [item.amount for item in invoice.lines],
         )
         # Check CustomerPlan reflects the discount
@@ -5432,7 +5420,7 @@ class TestSupportBillingHelpers(StripeTestCase):
         assert stripe_customer_id is not None
         [invoice, _] = iter(stripe.Invoice.list(customer=stripe_customer_id))
         self.assertEqual(
-            [6000 * self.seat_count, -6000 * self.seat_count],
+            [6000 * self.seat_count],
             [item.amount for item in invoice.lines],
         )
         plan = CustomerPlan.objects.get(price_per_license=6000, discount=Decimal(25))
@@ -6069,7 +6057,7 @@ class TestRemoteRealmBillingFlow(StripeTestCase, RemoteRealmBillingTestCase):
                     tier=CustomerPlan.TIER_SELF_HOSTED_BASIC, schedule="monthly"
                 )
 
-            self.assertEqual(PaymentIntent.objects.count(), 0)
+            self.assertEqual(Invoice.objects.count(), 0)
             customer = Customer.objects.get(stripe_customer_id=stripe_customer.id)
             plan = CustomerPlan.objects.get(customer=customer)
             LicenseLedger.objects.get(plan=plan)
@@ -6146,7 +6134,7 @@ class TestRemoteRealmBillingFlow(StripeTestCase, RemoteRealmBillingTestCase):
 
     @responses.activate
     @mock_stripe()
-    def test_upgrade_user_to_monthly_basic_plan(self, *mocks: Mock) -> None:
+    def test_upgrade_remote_realm_user_to_monthly_basic_plan(self, *mocks: Mock) -> None:
         self.login("hamlet")
         hamlet = self.example_user("hamlet")
 
@@ -6950,7 +6938,7 @@ class TestRemoteRealmBillingFlow(StripeTestCase, RemoteRealmBillingTestCase):
 
         [invoice0] = iter(stripe.Invoice.list(customer=stripe_customer.id))
 
-        [invoice_item0, invoice_item1, invoice_item2] = iter(invoice0.lines)
+        [invoice_item0, invoice_item1] = iter(invoice0.lines)
         invoice_item_params = {
             "amount": -2000,
             "description": "$20.00/month new customer discount",
@@ -6967,14 +6955,6 @@ class TestRemoteRealmBillingFlow(StripeTestCase, RemoteRealmBillingTestCase):
         for key, value in invoice_item_params.items():
             self.assertEqual(invoice_item1[key], value)
 
-        invoice_item_params = {
-            "amount": -1 * (realm_user_count * 3.5 * 100 - 2000),
-            "description": "Payment (Card ending in 4242)",
-            "quantity": 1,
-        }
-        for key, value in invoice_item_params.items():
-            self.assertEqual(invoice_item2[key], value)
-
     @responses.activate
     @mock_stripe()
     def test_invoice_plans_as_needed(self, *mocks: Mock) -> None:
@@ -7130,15 +7110,12 @@ class TestRemoteRealmBillingFlow(StripeTestCase, RemoteRealmBillingTestCase):
             self.billing_session.min_licenses_for_plan(CustomerPlan.TIER_SELF_HOSTED_BUSINESS),
         )
 
-        with mock.patch("stripe.Invoice.create") as invoice_create, time_machine.travel(
-            end_date, tick=False
-        ):
+        with time_machine.travel(end_date, tick=False):
             send_server_data_to_push_bouncer(consider_usage_statistics=False)
             invoice_plans_as_needed()
             # 'invoice_plan()' is called with both legacy & new plan, but
             # invoice is created only for new plan. The legacy plan only goes
             # through the end of cycle updates.
-            invoice_create.assert_called_once()
 
         realm_legacy_plan.refresh_from_db()
         new_plan.refresh_from_db()
@@ -7572,7 +7549,7 @@ class TestRemoteServerBillingFlow(StripeTestCase, RemoteServerTestCase):
                 stripe_customer = self.add_card_and_upgrade(
                     tier=CustomerPlan.TIER_SELF_HOSTED_BASIC, schedule="monthly"
                 )
-            self.assertEqual(PaymentIntent.objects.count(), 0)
+            self.assertEqual(Invoice.objects.count(), 0)
 
             customer = Customer.objects.get(stripe_customer_id=stripe_customer.id)
             plan = CustomerPlan.objects.get(customer=customer)
@@ -7650,7 +7627,7 @@ class TestRemoteServerBillingFlow(StripeTestCase, RemoteServerTestCase):
 
     @responses.activate
     @mock_stripe()
-    def test_upgrade_user_to_monthly_basic_plan(self, *mocks: Mock) -> None:
+    def test_upgrade_server_user_to_monthly_basic_plan(self, *mocks: Mock) -> None:
         self.login("hamlet")
         hamlet = self.example_user("hamlet")
 
@@ -8233,7 +8210,7 @@ class TestRemoteServerBillingFlow(StripeTestCase, RemoteServerTestCase):
 
         [invoice0] = iter(stripe.Invoice.list(customer=stripe_customer.id))
 
-        [invoice_item0, invoice_item1, invoice_item2] = iter(invoice0.lines)
+        [invoice_item0, invoice_item1] = iter(invoice0.lines)
         invoice_item_params = {
             "amount": -2000,
             "description": "$20.00/month new customer discount",
@@ -8250,13 +8227,8 @@ class TestRemoteServerBillingFlow(StripeTestCase, RemoteServerTestCase):
         for key, value in invoice_item_params.items():
             self.assertEqual(invoice_item1[key], value)
 
-        invoice_item_params = {
-            "amount": -1 * (server_user_count * 3.5 * 100 - 2000),
-            "description": "Payment (Card ending in 4242)",
-            "quantity": 1,
-        }
-        for key, value in invoice_item_params.items():
-            self.assertEqual(invoice_item2[key], value)
+        self.assertEqual(invoice0.total, server_user_count * 3.5 * 100 - 2000)
+        self.assertEqual(invoice0.status, "paid")
 
     @responses.activate
     @mock_stripe()
@@ -8448,15 +8420,12 @@ class TestRemoteServerBillingFlow(StripeTestCase, RemoteServerTestCase):
         )
         licenses = max(min_licenses, server_user_count)
 
-        with mock.patch("stripe.Invoice.create") as invoice_create, time_machine.travel(
-            end_date, tick=False
-        ):
+        with time_machine.travel(end_date, tick=False):
             send_server_data_to_push_bouncer(consider_usage_statistics=False)
             invoice_plans_as_needed()
             # 'invoice_plan()' is called with both legacy & new plan, but
             # invoice is created only for new plan. The legacy plan only
             # goes through the end of cycle updates.
-            invoice_create.assert_called_once()
 
         legacy_plan.refresh_from_db()
         new_plan.refresh_from_db()
diff --git a/corporate/views/event_status.py b/corporate/views/event_status.py
index b0fe77315e..70c87470e4 100644
--- a/corporate/views/event_status.py
+++ b/corporate/views/event_status.py
@@ -30,10 +30,10 @@ def event_status(
     user: UserProfile,
     *,
     stripe_session_id: Optional[str] = None,
-    stripe_payment_intent_id: Optional[str] = None,
+    stripe_invoice_id: Optional[str] = None,
 ) -> HttpResponse:
     event_status_request = EventStatusRequest(
-        stripe_session_id=stripe_session_id, stripe_payment_intent_id=stripe_payment_intent_id
+        stripe_session_id=stripe_session_id, stripe_invoice_id=stripe_invoice_id
     )
     billing_session = RealmBillingSession(user)
     data = billing_session.get_event_status(event_status_request)
@@ -47,10 +47,10 @@ def remote_realm_event_status(
     billing_session: RemoteRealmBillingSession,
     *,
     stripe_session_id: Optional[str] = None,
-    stripe_payment_intent_id: Optional[str] = None,
+    stripe_invoice_id: Optional[str] = None,
 ) -> HttpResponse:
     event_status_request = EventStatusRequest(
-        stripe_session_id=stripe_session_id, stripe_payment_intent_id=stripe_payment_intent_id
+        stripe_session_id=stripe_session_id, stripe_invoice_id=stripe_invoice_id
     )
     data = billing_session.get_event_status(event_status_request)
     return json_success(request, data)
@@ -63,10 +63,10 @@ def remote_server_event_status(
     billing_session: RemoteServerBillingSession,
     *,
     stripe_session_id: Optional[str] = None,
-    stripe_payment_intent_id: Optional[str] = None,
+    stripe_invoice_id: Optional[str] = None,
 ) -> HttpResponse:  # nocoverage
     event_status_request = EventStatusRequest(
-        stripe_session_id=stripe_session_id, stripe_payment_intent_id=stripe_payment_intent_id
+        stripe_session_id=stripe_session_id, stripe_invoice_id=stripe_invoice_id
     )
     data = billing_session.get_event_status(event_status_request)
     return json_success(request, data)
@@ -78,11 +78,11 @@ def event_status_page(
     request: HttpRequest,
     *,
     stripe_session_id: str = "",
-    stripe_payment_intent_id: str = "",
+    stripe_invoice_id: str = "",
 ) -> HttpResponse:
     context = {
         "stripe_session_id": stripe_session_id,
-        "stripe_payment_intent_id": stripe_payment_intent_id,
+        "stripe_invoice_id": stripe_invoice_id,
         "billing_base_url": "",
     }
     return render(request, "corporate/billing/event_status.html", context=context)
@@ -96,11 +96,11 @@ def remote_realm_event_status_page(
     realm_uuid: str = "",
     server_uuid: str = "",
     stripe_session_id: str = "",
-    stripe_payment_intent_id: str = "",
+    stripe_invoice_id: str = "",
 ) -> HttpResponse:  # nocoverage
     context = {
         "stripe_session_id": stripe_session_id,
-        "stripe_payment_intent_id": stripe_payment_intent_id,
+        "stripe_invoice_id": stripe_invoice_id,
         "billing_base_url": f"/realm/{realm_uuid}",
     }
     return render(request, "corporate/billing/event_status.html", context=context)
@@ -114,11 +114,11 @@ def remote_server_event_status_page(
     realm_uuid: str = "",
     server_uuid: str = "",
     stripe_session_id: str = "",
-    stripe_payment_intent_id: str = "",
+    stripe_invoice_id: str = "",
 ) -> HttpResponse:  # nocoverage
     context = {
         "stripe_session_id": stripe_session_id,
-        "stripe_payment_intent_id": stripe_payment_intent_id,
+        "stripe_invoice_id": stripe_invoice_id,
         "billing_base_url": f"/server/{server_uuid}",
     }
     return render(request, "corporate/billing/event_status.html", context=context)
diff --git a/corporate/views/webhook.py b/corporate/views/webhook.py
index 2987f3a572..28b6dd1b46 100644
--- a/corporate/views/webhook.py
+++ b/corporate/views/webhook.py
@@ -11,9 +11,8 @@ from corporate.lib.stripe import STRIPE_API_VERSION
 from corporate.lib.stripe_event_handler import (
     handle_checkout_session_completed_event,
     handle_invoice_paid_event,
-    handle_payment_intent_succeeded_event,
 )
-from corporate.models import Event, Invoice, PaymentIntent, Session
+from corporate.models import Event, Invoice, Session
 from zproject.config import get_secret
 
 billing_logger = logging.getLogger("corporate.stripe")
@@ -50,7 +49,6 @@ def stripe_webhook(request: HttpRequest) -> HttpResponse:
 
     if stripe_event.type not in [
         "checkout.session.completed",
-        "payment_intent.succeeded",
         "invoice.paid",
     ]:
         return HttpResponse(status=200)
@@ -71,21 +69,6 @@ def stripe_webhook(request: HttpRequest) -> HttpResponse:
         event.object_id = session.id
         event.save()
         handle_checkout_session_completed_event(stripe_session, event)
-    elif stripe_event.type == "payment_intent.succeeded":
-        stripe_payment_intent = stripe_event.data.object
-        assert isinstance(stripe_payment_intent, stripe.PaymentIntent)
-        try:
-            payment_intent = PaymentIntent.objects.get(
-                stripe_payment_intent_id=stripe_payment_intent.id
-            )
-        except PaymentIntent.DoesNotExist:
-            # PaymentIntent that was not manually created from the billing system.
-            # Could be an Invoice getting paid which is not an event we are interested in.
-            return HttpResponse(status=200)
-        event.content_type = ContentType.objects.get_for_model(PaymentIntent)
-        event.object_id = payment_intent.id
-        event.save()
-        handle_payment_intent_succeeded_event(stripe_payment_intent, event)
     elif stripe_event.type == "invoice.paid":
         stripe_invoice = stripe_event.data.object
         assert isinstance(stripe_invoice, stripe.Invoice)
diff --git a/templates/corporate/billing/event_status.html b/templates/corporate/billing/event_status.html
index 28ade3a096..b4244c4010 100644
--- a/templates/corporate/billing/event_status.html
+++ b/templates/corporate/billing/event_status.html
@@ -18,7 +18,7 @@
         <div class="page-content">
             <div class="main">
                 <br />
-                <div id="data" data-stripe-session-id="{{ stripe_session_id}}" data-stripe-payment-intent-id="{{ stripe_payment_intent_id }}" data-billing-base-url="{{ billing_base_url }}"></div>
+                <div id="data" data-stripe-session-id="{{ stripe_session_id}}" data-stripe-invoice-id="{{ stripe_invoice_id }}" data-billing-base-url="{{ billing_base_url }}"></div>
                 <div class="alert alert-success" id="webhook-success"></div>
                 <div class="alert alert-danger" id="webhook-error"></div>
                 <div id="webhook-loading">
@@ -32,7 +32,7 @@
                 </div>
 
                 <form id="restartsession-form">
-                    <input type="hidden" name="stripe_payment_intent_id" value="{{ stripe_payment_intent_id }}" />
+                    <input type="hidden" name="stripe_invoice_id" value="{{ stripe_invoice_id }}" />
                     <input type="hidden" name="csrfmiddlewaretoken" value="{{ csrf_token }}" />
                 </form>
                 <div class="alert alert-success" id="restartsession-success">Redirecting to Stripe Checkout</div>
diff --git a/templates/zerver/emails/error_processing_invoice.html b/templates/zerver/emails/error_processing_invoice.html
new file mode 100644
index 0000000000..f233330e2d
--- /dev/null
+++ b/templates/zerver/emails/error_processing_invoice.html
@@ -0,0 +1,7 @@
+{% extends "zerver/emails/email_base_messages.html" %}
+
+{% block content %}
+
+{{ message }}
+
+{% endblock %}
diff --git a/templates/zerver/emails/error_processing_invoice.subject.txt b/templates/zerver/emails/error_processing_invoice.subject.txt
new file mode 100644
index 0000000000..a07ff52140
--- /dev/null
+++ b/templates/zerver/emails/error_processing_invoice.subject.txt
@@ -0,0 +1 @@
+Error processing paid customer invoice
diff --git a/templates/zerver/emails/error_processing_invoice.txt b/templates/zerver/emails/error_processing_invoice.txt
new file mode 100644
index 0000000000..414c17f26b
--- /dev/null
+++ b/templates/zerver/emails/error_processing_invoice.txt
@@ -0,0 +1 @@
+{{ message }}
diff --git a/web/src/billing/event_status.ts b/web/src/billing/event_status.ts
index 5ef9474d8f..f463b6168e 100644
--- a/web/src/billing/event_status.ts
+++ b/web/src/billing/event_status.ts
@@ -10,7 +10,6 @@ const billing_base_url = $("#data").attr("data-billing-base-url")!;
 const stripe_response_schema = z.object({
     session: z.object({
         type: z.string(),
-        stripe_payment_intent_id: z.string().optional(),
         status: z.string(),
         is_manual_license_management_upgrade_session: z.boolean().optional(),
         tier: z.number().nullable().optional(),
@@ -80,15 +79,13 @@ async function stripe_checkout_session_status_check(stripe_session_id: string):
     return false;
 }
 
-export async function stripe_payment_intent_status_check(
-    stripe_payment_intent_id: string,
-): Promise<boolean> {
+export async function stripe_invoice_status_check(stripe_invoice_id: string): Promise<boolean> {
     const response: unknown = await $.get(`/json${billing_base_url}/billing/event/status`, {
-        stripe_payment_intent_id,
+        stripe_invoice_id,
     });
 
     const response_schema = z.object({
-        payment_intent: z.object({
+        stripe_invoice: z.object({
             status: z.string(),
             event_handler: z
                 .object({
@@ -100,25 +97,16 @@ export async function stripe_payment_intent_status_check(
                         .optional(),
                 })
                 .optional(),
-            last_payment_error: z
-                .object({
-                    message: z.string(),
-                })
-                .optional(),
         }),
     });
     const response_data = response_schema.parse(response);
 
-    switch (response_data.payment_intent.status) {
-        case "succeeded":
-            if (response_data.payment_intent.event_handler!.status === "succeeded") {
+    switch (response_data.stripe_invoice.status) {
+        case "paid":
+            if (response_data.stripe_invoice.event_handler!.status === "succeeded") {
                 helpers.redirect_to_billing_with_successful_upgrade(billing_base_url);
                 return true;
             }
-            if (response_data.payment_intent.event_handler!.status === "failed") {
-                show_error_message(response_data.payment_intent.event_handler!.error!.message);
-                return true;
-            }
             return false;
         default:
             return false;
@@ -131,9 +119,7 @@ export async function check_status(): Promise<boolean> {
             $("#data").attr("data-stripe-session-id")!,
         );
     }
-    return await stripe_payment_intent_status_check(
-        $("#data").attr("data-stripe-payment-intent-id")!,
-    );
+    return await stripe_invoice_status_check($("#data").attr("data-stripe-invoice-id")!);
 }
 
 async function start_status_polling(): Promise<void> {
diff --git a/web/src/billing/upgrade.ts b/web/src/billing/upgrade.ts
index 6bf78fd7e4..99008333e9 100644
--- a/web/src/billing/upgrade.ts
+++ b/web/src/billing/upgrade.ts
@@ -38,7 +38,7 @@ let current_license_count = page_params.seat_count;
 
 const upgrade_response_schema = z.object({
     // Returned if we charged the user and need to verify.
-    stripe_payment_intent_id: z.string().optional(),
+    stripe_invoice_id: z.string().optional(),
     // Returned if we directly upgraded the org (for free trial or invoice payments).
     organization_upgrade_successful: z.boolean().optional(),
 });
@@ -146,9 +146,9 @@ export const initialize = (): void => {
             "POST",
             (response) => {
                 const response_data = upgrade_response_schema.parse(response);
-                if (response_data.stripe_payment_intent_id) {
+                if (response_data.stripe_invoice_id) {
                     window.location.replace(
-                        `${page_params.billing_base_url}/billing/event_status?stripe_payment_intent_id=${response_data.stripe_payment_intent_id}`,
+                        `${page_params.billing_base_url}/billing/event_status?stripe_invoice_id=${response_data.stripe_invoice_id}`,
                     );
                 } else if (response_data.organization_upgrade_successful) {
                     helpers.redirect_to_billing_with_successful_upgrade(