diff --git a/main.go b/main.go
index fc2aeb6..1222c87 100644
--- a/main.go
+++ b/main.go
@@ -259,27 +259,31 @@ func newStripeCheckoutHandler(env *conf.Env, kc *keycloak.Keycloak, pc *stripeut
 
 		// No active payment - sign them up!
 		checkoutParams := &stripe.CheckoutSessionParams{
+			Mode:          stripe.String(string(stripe.CheckoutSessionModeSubscription)),
 			CustomerEmail: &user.Email,
 			SuccessURL:    stripe.String(env.SelfURL + "/profile?i=" + etag),
 			CancelURL:     stripe.String(env.SelfURL + "/profile"),
 		}
 		checkoutParams.Context = r.Context()
 
+		// Calculate specific pricing based on the member's profile
 		priceID := r.URL.Query().Get("price")
-		checkoutParams.Mode = stripe.String(string(stripe.CheckoutSessionModeSubscription))
+		checkoutParams.LineItems = calculateLineItems(user, priceID, pc)
 		checkoutParams.Discounts = calculateDiscount(user, priceID, pc)
 		if checkoutParams.Discounts == nil {
 			// Stripe API doesn't allow Discounts and AllowPromotionCodes to be set
 			checkoutParams.AllowPromotionCodes = stripe.Bool(true)
 		}
-		checkoutParams.LineItems = calculateLineItems(user, priceID, pc)
+
 		checkoutParams.SubscriptionData = &stripe.CheckoutSessionSubscriptionDataParams{
 			Metadata:           map[string]string{"etag": etag},
-			BillingCycleAnchor: calculateBillingCycleAnchor(user),
+			BillingCycleAnchor: calculateBillingCycleAnchor(user), // This enables migration from paypal
 		}
 		if checkoutParams.SubscriptionData.BillingCycleAnchor != nil {
+			// In this case, the member is already paid up - don't make them pay for the currenet period again
 			checkoutParams.SubscriptionData.ProrationBehavior = stripe.String("none")
 		}
+
 		s, err := session.New(checkoutParams)
 		if err != nil {
 			renderSystemError(w, "error while creating session: %s", err)
@@ -379,7 +383,6 @@ func newStripeWebhookHandler(env *conf.Env, kc *keycloak.Keycloak, pc *stripeuti
 			}
 		}
 
-		// TODO: Handle user 404s to avoid constantly failing webhooks?
 		err = kc.UpdateUserStripeInfo(r.Context(), customer, sub)
 		if err != nil {
 			log.Printf("error while updating Keycloak for Stripe subscription webhook event: %s", err)
@@ -405,91 +408,6 @@ func onlyLeadership(next http.HandlerFunc) http.HandlerFunc {
 	}
 }
 
-func calculateLineItems(user *keycloak.User, priceID string, pc *stripeutil.PriceCache) []*stripe.CheckoutSessionLineItemParams {
-	// Migrate existing paypal users at their current rate
-	if priceID == "paypal" {
-		interval := "month"
-		if user.LastPaypalTransactionPrice > 50 {
-			interval = "year"
-		}
-
-		cents := user.LastPaypalTransactionPrice * 100
-		productID := pc.GetPrices()[0].ProductID // all prices reference the same product
-		return []*stripe.CheckoutSessionLineItemParams{{
-			Quantity: stripe.Int64(1),
-			PriceData: &stripe.CheckoutSessionLineItemPriceDataParams{
-				Currency:          stripe.String("usd"),
-				Product:           &productID,
-				UnitAmountDecimal: &cents,
-				Recurring: &stripe.CheckoutSessionLineItemPriceDataRecurringParams{
-					Interval: &interval,
-				},
-			},
-		}}
-	}
-
-	return []*stripe.CheckoutSessionLineItemParams{{
-		Price:    stripe.String(priceID),
-		Quantity: stripe.Int64(1),
-	}}
-}
-
-func calculateDiscount(user *keycloak.User, priceID string, pc *stripeutil.PriceCache) []*stripe.CheckoutSessionDiscountParams {
-	if user.DiscountType == "" || priceID == "" {
-		return nil
-	}
-	for _, price := range pc.GetPrices() {
-		if price.ID == priceID && price.CouponIDs != nil && price.CouponIDs[user.DiscountType] != "" {
-			return []*stripe.CheckoutSessionDiscountParams{{
-				Coupon: stripe.String(price.CouponIDs[user.DiscountType]),
-			}}
-		}
-	}
-	return nil
-}
-
-func calculateDiscounts(user *keycloak.User, prices []*stripeutil.Price) []*stripeutil.Price {
-	if user.DiscountType == "" {
-		return prices
-	}
-	out := make([]*stripeutil.Price, len(prices))
-	for i, price := range prices {
-		amountOff := price.CouponAmountsOff[user.DiscountType]
-		out[i] = &stripeutil.Price{
-			ID:               price.ID,
-			ProductID:        price.ProductID,
-			Annual:           price.Annual,
-			Price:            price.Price - (float64(amountOff) / 100),
-			CouponIDs:        price.CouponIDs,
-			CouponAmountsOff: price.CouponAmountsOff,
-		}
-	}
-	return out
-}
-
-func calculateBillingCycleAnchor(user *keycloak.User) *int64 {
-	if user.LastPaypalTransactionPrice == 0 {
-		return nil
-	}
-
-	var end time.Time
-	if user.LastPaypalTransactionPrice > 41 {
-		// Annual
-		end = user.LastPaypalTransactionTime.Add(time.Hour * 24 * 365)
-	} else {
-		// Monthly
-		end = user.LastPaypalTransactionTime.Add(time.Hour * 24 * 30)
-	}
-
-	// Stripe will throw an error if the cycle anchor is before the current time
-	if time.Until(end) < time.Minute {
-		return nil
-	}
-
-	ts := end.Unix()
-	return &ts
-}
-
 // getUserID allows the oauth2proxy header to be overridden for testing.
 func getUserID(r *http.Request) string {
 	user := r.Header.Get("X-Forwarded-Preferred-Username")
diff --git a/pricing.go b/pricing.go
new file mode 100644
index 0000000..ba90f2c
--- /dev/null
+++ b/pricing.go
@@ -0,0 +1,95 @@
+package main
+
+import (
+	"time"
+
+	"github.com/stripe/stripe-go/v75"
+
+	"github.com/TheLab-ms/profile/internal/keycloak"
+	"github.com/TheLab-ms/profile/internal/stripeutil"
+)
+
+func calculateLineItems(user *keycloak.User, priceID string, pc *stripeutil.PriceCache) []*stripe.CheckoutSessionLineItemParams {
+	// Migrate existing paypal users at their current rate
+	if priceID == "paypal" {
+		interval := "month"
+		if user.LastPaypalTransactionPrice > 50 {
+			interval = "year"
+		}
+
+		cents := user.LastPaypalTransactionPrice * 100
+		productID := pc.GetPrices()[0].ProductID // all prices reference the same product
+		return []*stripe.CheckoutSessionLineItemParams{{
+			Quantity: stripe.Int64(1),
+			PriceData: &stripe.CheckoutSessionLineItemPriceDataParams{
+				Currency:          stripe.String("usd"),
+				Product:           &productID,
+				UnitAmountDecimal: &cents,
+				Recurring: &stripe.CheckoutSessionLineItemPriceDataRecurringParams{
+					Interval: &interval,
+				},
+			},
+		}}
+	}
+
+	return []*stripe.CheckoutSessionLineItemParams{{
+		Price:    stripe.String(priceID),
+		Quantity: stripe.Int64(1),
+	}}
+}
+
+func calculateDiscount(user *keycloak.User, priceID string, pc *stripeutil.PriceCache) []*stripe.CheckoutSessionDiscountParams {
+	if user.DiscountType == "" || priceID == "" {
+		return nil
+	}
+	for _, price := range pc.GetPrices() {
+		if price.ID == priceID && price.CouponIDs != nil && price.CouponIDs[user.DiscountType] != "" {
+			return []*stripe.CheckoutSessionDiscountParams{{
+				Coupon: stripe.String(price.CouponIDs[user.DiscountType]),
+			}}
+		}
+	}
+	return nil
+}
+
+func calculateDiscounts(user *keycloak.User, prices []*stripeutil.Price) []*stripeutil.Price {
+	if user.DiscountType == "" {
+		return prices
+	}
+	out := make([]*stripeutil.Price, len(prices))
+	for i, price := range prices {
+		amountOff := price.CouponAmountsOff[user.DiscountType]
+		out[i] = &stripeutil.Price{
+			ID:               price.ID,
+			ProductID:        price.ProductID,
+			Annual:           price.Annual,
+			Price:            price.Price - (float64(amountOff) / 100),
+			CouponIDs:        price.CouponIDs,
+			CouponAmountsOff: price.CouponAmountsOff,
+		}
+	}
+	return out
+}
+
+func calculateBillingCycleAnchor(user *keycloak.User) *int64 {
+	if user.LastPaypalTransactionPrice == 0 {
+		return nil
+	}
+
+	var end time.Time
+	if user.LastPaypalTransactionPrice > 41 {
+		// Annual
+		end = user.LastPaypalTransactionTime.Add(time.Hour * 24 * 365)
+	} else {
+		// Monthly
+		end = user.LastPaypalTransactionTime.Add(time.Hour * 24 * 30)
+	}
+
+	// Stripe will throw an error if the cycle anchor is before the current time
+	if time.Until(end) < time.Minute {
+		return nil
+	}
+
+	ts := end.Unix()
+	return &ts
+}