diff --git a/go.mod b/go.mod
index 8d2f9b481..fd2e50686 100644
--- a/go.mod
+++ b/go.mod
@@ -1,6 +1,6 @@
 module github.com/icinga/icinga-notifications
 
-go 1.20
+go 1.21
 
 require (
 	github.com/creasty/defaults v1.7.0
diff --git a/internal/incident/incident.go b/internal/incident/incident.go
index 661e1ff76..ef92c8b74 100644
--- a/internal/incident/incident.go
+++ b/internal/incident/incident.go
@@ -35,6 +35,14 @@ type Incident struct {
 
 	incidentRowID int64
 
+	// timer calls RetriggerEscalations the next time any escalation could be reached on the incident.
+	//
+	// For example, if there are escalations configured for incident_age>=1h and incident_age>=2h, if the incident
+	// is less than an hour old, timer will fire 1h after incident start, if the incident is between 1h and 2h
+	// old, timer will fire after 2h, and if the incident is already older than 2h, no future escalations can
+	// be reached solely based on the incident aging, so no more timer is necessary and timer stores nil.
+	timer *time.Timer
+
 	db            *icingadb.DB
 	logger        *zap.SugaredLogger
 	runtimeConfig *config.RuntimeConfig
@@ -147,7 +155,12 @@ func (i *Incident) ProcessEvent(ctx context.Context, ev *event.Event, created bo
 	}
 
 	// Re-evaluate escalations based on the newly evaluated rules.
-	if _, err := i.evaluateEscalations(ctx, tx, ev, causedBy); err != nil {
+	escalations, err := i.evaluateEscalations(ev.Time)
+	if err != nil {
+		return err
+	}
+
+	if err := i.triggerEscalations(ctx, tx, ev, causedBy, escalations); err != nil {
 		return err
 	}
 
@@ -165,6 +178,68 @@ func (i *Incident) ProcessEvent(ctx context.Context, ev *event.Event, created bo
 	return i.notifyContacts(ctx, ev, notifications)
 }
 
+// RetriggerEscalations tries to re-evaluate the escalations and notify contacts.
+func (i *Incident) RetriggerEscalations(ev *event.Event) {
+	i.Lock()
+	defer i.Unlock()
+
+	i.runtimeConfig.RLock()
+	defer i.runtimeConfig.RUnlock()
+
+	if !i.RecoveredAt.IsZero() {
+		// Incident is recovered in the meantime.
+		return
+	}
+
+	if !time.Now().After(ev.Time) {
+		i.logger.DPanicw("Event from the future", zap.Time("event_time", ev.Time), zap.Any("event", ev))
+		return
+	}
+
+	escalations, err := i.evaluateEscalations(ev.Time)
+	if err != nil {
+		i.logger.Errorw("Reevaluating time-based escalations failed", zap.Error(err))
+		return
+	}
+
+	if len(escalations) == 0 {
+		i.logger.Debug("Reevaluated escalations, no new escalations triggered")
+		return
+	}
+
+	var notifications []*NotificationEntry
+	ctx := context.Background()
+	err = utils.RunInTx(ctx, i.db, func(tx *sqlx.Tx) error {
+		err := ev.Sync(ctx, tx, i.db, i.Object.ID)
+		if err != nil {
+			return err
+		}
+
+		if err = i.triggerEscalations(ctx, tx, ev, types.Int{}, escalations); err != nil {
+			return err
+		}
+
+		channels := make(contactChannels)
+		for _, escalation := range escalations {
+			channels.loadEscalationRecipientsChannel(escalation, i, ev.Time)
+		}
+
+		notifications, err = i.addPendingNotifications(ctx, tx, ev, channels, types.Int{})
+
+		return err
+	})
+	if err != nil {
+		i.logger.Errorw("Reevaluating time-based escalations failed", zap.Error(err))
+	} else {
+		if err = i.notifyContacts(ctx, ev, notifications); err != nil {
+			i.logger.Errorw("Failed to notify reevaluated escalation recipients", zap.Error(err))
+			return
+		}
+
+		i.logger.Info("Successfully reevaluated time-based escalations")
+	}
+}
+
 func (i *Incident) processSeverityChangedEvent(ctx context.Context, tx *sqlx.Tx, ev *event.Event) (types.Int, error) {
 	var causedByHistoryId types.Int
 	oldSeverity := i.Severity
@@ -214,6 +289,10 @@ func (i *Incident) processSeverityChangedEvent(ctx context.Context, tx *sqlx.Tx,
 
 			return types.Int{}, errors.New("can't insert incident closed history to the database")
 		}
+
+		if i.timer != nil {
+			i.timer.Stop()
+		}
 	}
 
 	i.Severity = newSeverity
@@ -312,14 +391,25 @@ func (i *Incident) evaluateRules(ctx context.Context, tx *sqlx.Tx, eventID int64
 	return causedBy, nil
 }
 
-// evaluateEscalations evaluates this incidents rule escalations if they aren't already.
-// Returns whether a new escalation triggered or an error on database failure.
-func (i *Incident) evaluateEscalations(ctx context.Context, tx *sqlx.Tx, ev *event.Event, causedBy types.Int) (bool, error) {
+// evaluateEscalations evaluates this incidents rule escalations to be triggered if they aren't already.
+// Returns the newly evaluated escalations to be triggered or an error on database failure.
+func (i *Incident) evaluateEscalations(eventTime time.Time) ([]*rule.Escalation, error) {
 	if i.EscalationState == nil {
 		i.EscalationState = make(map[int64]*EscalationState)
 	}
 
-	newEscalationMatched := false
+	// Escalations are reevaluated now, reset any existing timer, if there might be future time-based escalations,
+	// this function will start a new timer.
+	if i.timer != nil {
+		i.logger.Info("Stopping reevaluate timer due to escalation evaluation")
+		i.timer.Stop()
+		i.timer = nil
+	}
+
+	filterContext := &rule.EscalationFilter{IncidentAge: eventTime.Sub(i.StartedAt), IncidentSeverity: i.Severity}
+
+	var escalations []*rule.Escalation
+	retryAfter := rule.RetryNever
 
 	for rID := range i.Rules {
 		r := i.runtimeConfig.Rules[rID]
@@ -336,13 +426,8 @@ func (i *Incident) evaluateEscalations(ctx context.Context, tx *sqlx.Tx, ev *eve
 				if escalation.Condition == nil {
 					matched = true
 				} else {
-					cond := &rule.EscalationFilter{
-						IncidentAge:      time.Since(i.StartedAt),
-						IncidentSeverity: i.Severity,
-					}
-
 					var err error
-					matched, err = escalation.Condition.Eval(cond)
+					matched, err = escalation.Condition.Eval(filterContext)
 					if err != nil {
 						i.logger.Warnw(
 							"Failed to evaluate escalation condition", zap.String("rule", r.Name),
@@ -350,53 +435,80 @@ func (i *Incident) evaluateEscalations(ctx context.Context, tx *sqlx.Tx, ev *eve
 						)
 
 						matched = false
+					} else if !matched {
+						incidentAgeFilter := filterContext.ReevaluateAfter(escalation.Condition)
+						retryAfter = min(retryAfter, incidentAgeFilter)
 					}
 				}
 
 				if matched {
-					newEscalationMatched = true
+					escalations = append(escalations, escalation)
+				}
+			}
+		}
+	}
 
-					state := &EscalationState{RuleEscalationID: escalation.ID, TriggeredAt: types.UnixMilli(time.Now())}
-					i.EscalationState[escalation.ID] = state
+	if retryAfter != rule.RetryNever {
+		nextEvalAt := eventTime.Add(retryAfter)
 
-					i.logger.Infof("Rule %q reached escalation %q", r.Name, escalation.DisplayName())
+		i.logger.Infow("Scheduling escalation reevaluation", zap.Duration("after", retryAfter), zap.Time("at", nextEvalAt))
+		i.timer = time.AfterFunc(retryAfter, func() {
+			i.logger.Info("Reevaluating escalations")
 
-					if err := i.AddEscalationTriggered(ctx, tx, state); err != nil {
-						i.logger.Errorw(
-							"Failed to upsert escalation state", zap.String("rule", r.Name),
-							zap.String("escalation", escalation.DisplayName()), zap.Error(err),
-						)
+			i.RetriggerEscalations(&event.Event{
+				Type:    event.TypeInternal,
+				Time:    nextEvalAt,
+				Message: fmt.Sprintf("Incident reached age %v", retryAfter),
+			})
+		})
+	}
 
-						return false, errors.New("failed to upsert escalation state")
-					}
+	return escalations, nil
+}
 
-					history := &HistoryRow{
-						Time:                      state.TriggeredAt,
-						EventID:                   utils.ToDBInt(ev.ID),
-						RuleEscalationID:          utils.ToDBInt(state.RuleEscalationID),
-						RuleID:                    utils.ToDBInt(r.ID),
-						Type:                      EscalationTriggered,
-						CausedByIncidentHistoryID: causedBy,
-					}
+// triggerEscalations triggers the given escalations and generates incident history items for each of them.
+// Returns an error on database failure.
+func (i *Incident) triggerEscalations(ctx context.Context, tx *sqlx.Tx, ev *event.Event, causedBy types.Int, escalations []*rule.Escalation) error {
+	for _, escalation := range escalations {
+		r := i.runtimeConfig.Rules[escalation.RuleID]
+		i.logger.Infof("Rule %q reached escalation %q", r.Name, escalation.DisplayName())
 
-					if _, err := i.AddHistory(ctx, tx, history, false); err != nil {
-						i.logger.Errorw(
-							"Failed to insert escalation triggered incident history", zap.String("rule", r.Name),
-							zap.String("escalation", escalation.DisplayName()), zap.Error(err),
-						)
+		state := &EscalationState{RuleEscalationID: escalation.ID, TriggeredAt: types.UnixMilli(time.Now())}
+		i.EscalationState[escalation.ID] = state
 
-						return false, errors.New("failed to insert escalation triggered incident history")
-					}
+		if err := i.AddEscalationTriggered(ctx, tx, state); err != nil {
+			i.logger.Errorw(
+				"Failed to upsert escalation state", zap.String("rule", r.Name),
+				zap.String("escalation", escalation.DisplayName()), zap.Error(err),
+			)
 
-					if err := i.AddRecipient(ctx, tx, escalation, ev.ID); err != nil {
-						return false, err
-					}
-				}
-			}
+			return errors.New("failed to upsert escalation state")
+		}
+
+		history := &HistoryRow{
+			Time:                      state.TriggeredAt,
+			EventID:                   utils.ToDBInt(ev.ID),
+			RuleEscalationID:          utils.ToDBInt(state.RuleEscalationID),
+			RuleID:                    utils.ToDBInt(r.ID),
+			Type:                      EscalationTriggered,
+			CausedByIncidentHistoryID: causedBy,
+		}
+
+		if _, err := i.AddHistory(ctx, tx, history, false); err != nil {
+			i.logger.Errorw(
+				"Failed to insert escalation triggered incident history", zap.String("rule", r.Name),
+				zap.String("escalation", escalation.DisplayName()), zap.Error(err),
+			)
+
+			return errors.New("failed to insert escalation triggered incident history")
+		}
+
+		if err := i.AddRecipient(ctx, tx, escalation, ev.ID); err != nil {
+			return err
 		}
 	}
 
-	return newEscalationMatched, nil
+	return nil
 }
 
 // notifyContacts executes all the given pending notifications of the current incident.
diff --git a/internal/incident/incidents.go b/internal/incident/incidents.go
index 640ef5a21..56d0b1663 100644
--- a/internal/incident/incidents.go
+++ b/internal/incident/incidents.go
@@ -45,34 +45,11 @@ func LoadOpenIncidents(ctx context.Context, db *icingadb.DB, logger *logging.Log
 			continue
 		}
 
-		evaluateRulesAndEscalations := func(ctx context.Context) error {
-			ev := &event.Event{Time: time.Now(), Type: event.TypeEscalation}
-			if !incident.evaluateEscalations() {
-				return nil
-			}
-
-			tx, err := db.BeginTxx(ctx, nil)
-			if err != nil {
-				return err
-			}
-			defer func() { _ = tx.Rollback() }()
-
-			err = incident.notifyContacts(ctx, tx, ev, types.Int{})
-			if err != nil {
-				return err
-			}
-
-			if err = tx.Commit(); err != nil {
-				incident.logger.Errorw("Failed to commit database transaction", zap.Error(err))
-				return err
-			}
-
-			return nil
-		}
-
-		if evaluateRulesAndEscalations(ctx) != nil {
-			continue
-		}
+		incident.RetriggerEscalations(&event.Event{
+			Time:    time.Now(),
+			Type:    event.TypeInternal,
+			Message: "Incident reevaluation at daemon startup",
+		})
 	}
 
 	return nil
diff --git a/internal/utils/utils.go b/internal/utils/utils.go
index 7bf6b53b0..a809bbe3b 100644
--- a/internal/utils/utils.go
+++ b/internal/utils/utils.go
@@ -30,6 +30,26 @@ func BuildInsertStmtWithout(db *icingadb.DB, into interface{}, withoutColumn str
 	)
 }
 
+// RunInTx allows running a function in a database transaction without requiring manual transaction handling.
+//
+// A new transaction is started on db which is then passed to fn. After fn returns, the transaction is
+// committed unless an error was returned. If fn returns an error, that error is returned, otherwise an
+// error is returned if a database operation fails.
+func RunInTx(ctx context.Context, db *icingadb.DB, fn func(tx *sqlx.Tx) error) error {
+	tx, err := db.BeginTxx(ctx, nil)
+	if err != nil {
+		return err
+	}
+	defer func() { _ = tx.Rollback() }()
+
+	err = fn(tx)
+	if err != nil {
+		return err
+	}
+
+	return tx.Commit()
+}
+
 // InsertAndFetchId executes the given query and fetches the last inserted ID.
 func InsertAndFetchId(ctx context.Context, tx *sqlx.Tx, stmt string, args any) (int64, error) {
 	var lastInsertId int64