diff --git a/Dockerfile b/Dockerfile
index 7a3c6f2b3..ccae6e06a 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,4 +1,4 @@
-FROM golang:1.17
+FROM golang:1.18
 LABEL maintainer="Victor Castell <victor@victorcastell.com>"
 
 EXPOSE 8080 8946
diff --git a/dkron/leader.go b/dkron/leader.go
index 94fa05352..89f2728c0 100644
--- a/dkron/leader.go
+++ b/dkron/leader.go
@@ -62,6 +62,31 @@ func (a *Agent) monitorLeadership() {
 	}
 }
 
+func (a *Agent) leadershipTransfer() error {
+	retryCount := 3
+	for i := 0; i < retryCount; i++ {
+		err := a.raft.LeadershipTransfer().Error()
+		if err == nil {
+			a.sched.Stop()
+			a.logger.Info("dkron: successfully transferred leadership")
+			return nil
+		}
+
+		// Don't retry if the Raft version doesn't support leadership transfer
+		// since this will never succeed.
+		if err == raft.ErrUnsupportedProtocol {
+			return fmt.Errorf("leadership transfer not supported with Raft version lower than 3")
+		}
+
+		a.logger.Error("failed to transfer leadership attempt, will retry",
+			"attempt", i,
+			"retry_limit", retryCount,
+			"error", err,
+		)
+	}
+	return fmt.Errorf("failed to transfer leadership in %d attempts", retryCount)
+}
+
 // leaderLoop runs as long as we are the leader to run various
 // maintenance activities
 func (a *Agent) leaderLoop(stopCh chan struct{}) {
@@ -85,16 +110,23 @@ RECONCILE:
 	// Check if we need to handle initial leadership actions
 	if !establishedLeader {
 		if err := a.establishLeadership(stopCh); err != nil {
+			a.logger.WithError(err).Error("dkron: failed to establish leadership")
+
 			// Immediately revoke leadership since we didn't successfully
 			// establish leadership.
 			if err := a.revokeLeadership(); err != nil {
 				a.logger.WithError(err).Error("dkron: failed to revoke leadership")
 			}
 
-			a.logger.WithError(err).Error("dkron: failed to establish leadership")
-
-			// TODO: review this code path
-			goto WAIT
+			// Attempt to transfer leadership. If successful, leave the
+			// leaderLoop since this node is no longer the leader. Otherwise
+			// try to establish leadership again after 5 seconds.
+			if err := a.leadershipTransfer(); err != nil {
+				a.logger.Error("failed to transfer leadership", "error", err)
+				interval = time.After(5 * time.Second)
+				goto WAIT
+			}
+			return
 		}
 
 		establishedLeader = true
@@ -125,10 +157,12 @@ RECONCILE:
 	}
 
 WAIT:
-	// Wait until leadership is lost
+	// Wait until leadership is lost or periodically reconcile as long as we
+	// are the leader, or when Serf events arrive.
 	for {
 		select {
 		case <-stopCh:
+			// Lost leadership.
 			return
 		case <-a.shutdownCh:
 			return
@@ -145,9 +179,6 @@ WAIT:
 func (a *Agent) reconcile() error {
 	defer metrics.MeasureSince([]string{"dkron", "leader", "reconcile"}, time.Now())
 
-	// TODO: Try to fix https://github.com/distribworks/dkron/issues/998
-	a.sched.Cron.Start()
-
 	members := a.serf.Members()
 	for _, member := range members {
 		if err := a.reconcileMember(member); err != nil {
diff --git a/dkron/scheduler.go b/dkron/scheduler.go
index ab19efea8..e2c581710 100644
--- a/dkron/scheduler.go
+++ b/dkron/scheduler.go
@@ -3,7 +3,6 @@ package dkron
 import (
 	"errors"
 	"expvar"
-	"fmt"
 	"strings"
 	"sync"
 
@@ -50,8 +49,10 @@ func (s *Scheduler) Start(jobs []*Job, agent *Agent) error {
 	defer s.mu.Unlock()
 
 	if s.Cron != nil {
-		// Creating a new cron is risky if not nil because the previous invocation is dirty
-		return fmt.Errorf("cron is already configured, can not start scheduler")
+		// Stop the cron scheduler first and wait for all jobs to finish
+		s.Stop()
+		// Clear the cron scheduler
+		s.Cron = nil
 	}
 
 	s.Cron = cron.New(cron.WithParser(extcron.NewParser()))