diff --git a/migrations/20230219_add_subscription_renewal.go b/migrations/20230219_add_subscription_renewal.go
new file mode 100644
index 0000000..6bb26ae
--- /dev/null
+++ b/migrations/20230219_add_subscription_renewal.go
@@ -0,0 +1,35 @@
+package migrations
+
+import (
+	"github.com/emvi/logbuch"
+	"github.com/muety/wakapi/config"
+	"github.com/muety/wakapi/models"
+	"gorm.io/gorm"
+)
+
+func init() {
+	const name = "20230219-add_subscription_renewal"
+	f := migrationFunc{
+		name: name,
+		f: func(db *gorm.DB, cfg *config.Config) error {
+			if hasRun(name, db) {
+				return nil
+			}
+
+			migrator := db.Migrator()
+
+			if migrator.HasColumn(&models.User{}, "subscription_renewal") {
+				logbuch.Info("running migration '%s'", name)
+
+				if err := db.Exec("UPDATE users SET subscription_renewal = subscribed_until WHERE subscribed_until is not null").Error; err != nil {
+					return err
+				}
+			}
+
+			setHasRun(name, db)
+			return nil
+		},
+	}
+
+	registerPostMigration(f)
+}
diff --git a/models/user.go b/models/user.go
index 43e2bb3..c46c88d 100644
--- a/models/user.go
+++ b/models/user.go
@@ -15,29 +15,30 @@ func init() {
 }
 
 type User struct {
-	ID                string      `json:"id" gorm:"primary_key"`
-	ApiKey            string      `json:"api_key" gorm:"unique; default:NULL"`
-	Email             string      `json:"email" gorm:"index:idx_user_email; size:255"`
-	Location          string      `json:"location"`
-	Password          string      `json:"-"`
-	CreatedAt         CustomTime  `gorm:"type:timestamp; default:CURRENT_TIMESTAMP" swaggertype:"string" format:"date" example:"2006-01-02 15:04:05.000"`
-	LastLoggedInAt    CustomTime  `gorm:"type:timestamp; default:CURRENT_TIMESTAMP" swaggertype:"string" format:"date" example:"2006-01-02 15:04:05.000"`
-	ShareDataMaxDays  int         `json:"-"`
-	ShareEditors      bool        `json:"-" gorm:"default:false; type:bool"`
-	ShareLanguages    bool        `json:"-" gorm:"default:false; type:bool"`
-	ShareProjects     bool        `json:"-" gorm:"default:false; type:bool"`
-	ShareOSs          bool        `json:"-" gorm:"default:false; type:bool; column:share_oss"`
-	ShareMachines     bool        `json:"-" gorm:"default:false; type:bool"`
-	ShareLabels       bool        `json:"-" gorm:"default:false; type:bool"`
-	IsAdmin           bool        `json:"-" gorm:"default:false; type:bool"`
-	HasData           bool        `json:"-" gorm:"default:false; type:bool"`
-	WakatimeApiKey    string      `json:"-"` // for relay middleware and imports
-	WakatimeApiUrl    string      `json:"-"` // for relay middleware and imports
-	ResetToken        string      `json:"-"`
-	ReportsWeekly     bool        `json:"-" gorm:"default:false; type:bool"`
-	PublicLeaderboard bool        `json:"-" gorm:"default:false; type:bool"`
-	SubscribedUntil   *CustomTime `json:"-" gorm:"type:timestamp" swaggertype:"string" format:"date" example:"2006-01-02 15:04:05.000"`
-	StripeCustomerId  string      `json:"-"`
+	ID                  string      `json:"id" gorm:"primary_key"`
+	ApiKey              string      `json:"api_key" gorm:"unique; default:NULL"`
+	Email               string      `json:"email" gorm:"index:idx_user_email; size:255"`
+	Location            string      `json:"location"`
+	Password            string      `json:"-"`
+	CreatedAt           CustomTime  `gorm:"type:timestamp; default:CURRENT_TIMESTAMP" swaggertype:"string" format:"date" example:"2006-01-02 15:04:05.000"`
+	LastLoggedInAt      CustomTime  `gorm:"type:timestamp; default:CURRENT_TIMESTAMP" swaggertype:"string" format:"date" example:"2006-01-02 15:04:05.000"`
+	ShareDataMaxDays    int         `json:"-"`
+	ShareEditors        bool        `json:"-" gorm:"default:false; type:bool"`
+	ShareLanguages      bool        `json:"-" gorm:"default:false; type:bool"`
+	ShareProjects       bool        `json:"-" gorm:"default:false; type:bool"`
+	ShareOSs            bool        `json:"-" gorm:"default:false; type:bool; column:share_oss"`
+	ShareMachines       bool        `json:"-" gorm:"default:false; type:bool"`
+	ShareLabels         bool        `json:"-" gorm:"default:false; type:bool"`
+	IsAdmin             bool        `json:"-" gorm:"default:false; type:bool"`
+	HasData             bool        `json:"-" gorm:"default:false; type:bool"`
+	WakatimeApiKey      string      `json:"-"` // for relay middleware and imports
+	WakatimeApiUrl      string      `json:"-"` // for relay middleware and imports
+	ResetToken          string      `json:"-"`
+	ReportsWeekly       bool        `json:"-" gorm:"default:false; type:bool"`
+	PublicLeaderboard   bool        `json:"-" gorm:"default:false; type:bool"`
+	SubscribedUntil     *CustomTime `json:"-" gorm:"type:timestamp" swaggertype:"string" format:"date" example:"2006-01-02 15:04:05.000"`
+	SubscriptionRenewal *CustomTime `json:"-" gorm:"type:timestamp" swaggertype:"string" format:"date" example:"2006-01-02 15:04:05.000"`
+	StripeCustomerId    string      `json:"-"`
 }
 
 type Login struct {
diff --git a/routes/subscription.go b/routes/subscription.go
index 5aa4fc4..f9e9f51 100644
--- a/routes/subscription.go
+++ b/routes/subscription.go
@@ -278,14 +278,17 @@ func (h *SubscriptionHandler) handleSubscriptionEvent(subscription *stripe.Subsc
 		if user.SubscribedUntil == nil || !user.SubscribedUntil.T().Equal(until.T()) {
 			hasSubscribed = true
 			user.SubscribedUntil = &until
+			user.SubscriptionRenewal = &until
 			logbuch.Info("user %s got active subscription %s until %v", user.ID, subscription.ID, user.SubscribedUntil)
 		}
 
 		if cancelAt := time.Unix(subscription.CancelAt, 0); !cancelAt.IsZero() && cancelAt.After(time.Now()) {
+			user.SubscriptionRenewal = nil
 			logbuch.Info("user %s chose to cancel subscription %s by %v", user.ID, subscription.ID, cancelAt)
 		}
-	case "canceled", "unpaid":
+	case "canceled", "unpaid", "incomplete_expired":
 		user.SubscribedUntil = nil
+		user.SubscriptionRenewal = nil
 		logbuch.Info("user %s's subscription %s got canceled, because of status update to '%s'", user.ID, subscription.ID, subscription.Status)
 	default:
 		logbuch.Info("got subscription (%s) status update to '%s' for user '%s'", subscription.ID, subscription.Status, user.ID)
diff --git a/services/misc.go b/services/misc.go
index a1c628d..90a9bf9 100644
--- a/services/misc.go
+++ b/services/misc.go
@@ -180,6 +180,7 @@ func (srv *MiscService) ComputeOldestHeartbeats() {
 // - Subscriptions are enabled on the server (aka. users can do something about their old data getting cleaned up)
 // - User has an e-mail address configured
 // - User's subscription has expired or is about to expire soon
+// - User doesn't have upcoming auto-renewal (i.e. chose to cancel at some date in the future)
 // - The user has gotten no such e-mail before recently
 // Note: only one mail will be sent for either "expired" or "about to expire" state.
 func (srv *MiscService) NotifyExpiringSubscription() {
@@ -187,6 +188,7 @@ func (srv *MiscService) NotifyExpiringSubscription() {
 		return
 	}
 
+	now := time.Now()
 	logbuch.Info("notifying users about soon to expire subscriptions")
 
 	users, err := srv.userService.GetAll()
@@ -210,10 +212,22 @@ func (srv *MiscService) NotifyExpiringSubscription() {
 			config.Log().Warn("invalid state: user '%s' has active subscription but no e-mail address set", u.ID)
 		}
 
+		var alreadySent bool
+		if kvs, ok := subscriptionReminders[u.ID]; ok && len(kvs) > 0 {
+			// don't send again while subscription hasn't had chance to have been renewed
+			if sendDate, err := time.Parse(time.RFC822Z, kvs[0].Value); err == nil && now.Sub(sendDate) <= notifyBeforeSubscriptionExpiry {
+				alreadySent = true
+			} else if err != nil {
+				config.Log().Error("failed to parse date for last sent subscription notification mail for user '%s', %v", u.ID, err)
+				alreadySent = true
+			}
+		}
+
 		// skip users without e-mail address
 		// skip users who already received a notification before
 		// skip users who either never had a subscription before or intentionally deleted it
-		if _, ok := subscriptionReminders[u.ID]; ok || u.Email == "" || u.SubscribedUntil == nil {
+		// skip users who have upcoming auto-renewal (everyone except users who chose to cancel subscription at later date)
+		if alreadySent || u.Email == "" || u.SubscribedUntil == nil || (u.SubscriptionRenewal != nil && u.SubscriptionRenewal.T().After(now)) {
 			continue
 		}
 
diff --git a/views/settings.tpl.html b/views/settings.tpl.html
index afa7d58..b2df66c 100644
--- a/views/settings.tpl.html
+++ b/views/settings.tpl.html
@@ -729,7 +729,12 @@
                 <span class="font-semibold text-gray-300">Subscription status:</span>
                 <span class="text-gray-600 ml-1 text-sm">
                     {{ if .User.HasActiveSubscription }}
-                    <span class="font-semibold text-green-500 text-base">Active</span> (until {{ .User.SubscribedUntil.T | date }})
+                    <span class="font-semibold text-green-500 text-base">Active</span>
+                    {{ if .User.SubscriptionRenewal }}
+                    (automatically renews at {{ .User.SubscriptionRenewal.T | date }})
+                    {{ else }}
+                    (until {{ .User.SubscribedUntil.T | date }})
+                    {{ end }}
                     {{ else }}
                     <span class="font-semibold text-red-500 text-base">Inactive</span>
                     {{ end }}
@@ -746,7 +751,7 @@
                 </form>
                 {{ else }}
                 <form action="subscription/portal" method="post" class="mt-8 mb-8" id="form-subscription-portal">
-                    <button type="submit" class="btn-danger">Cancel subscription</button>
+                    <button type="submit" class="btn-primary">Manage subscription</button>
                 </form>
                 {{ end }}
             </div>