diff --git a/internal/wrench/scheduler.go b/internal/wrench/scheduler.go
index ff7e406..a5d51f5 100644
--- a/internal/wrench/scheduler.go
+++ b/internal/wrench/scheduler.go
@@ -184,7 +184,7 @@ func (b *Bot) schedulerWork(ctx context.Context) error {
 	}
 
 	for _, schedule := range b.schedule {
-		if _, err := b.scheduleJob(ctx, schedule, runners, false); err != nil {
+		if _, err := b.ensureJobScheduled(ctx, schedule, runners, false); err != nil {
 			b.idLogf(schedulerLogID, "%v", err)
 			continue
 		}
@@ -203,10 +203,10 @@ func (b *Bot) scheduleJobNow(ctx context.Context, scheduledJobID api.JobID, runn
 	if found == nil {
 		return "", errors.New("scheduled job not found")
 	}
-	return b.scheduleJob(ctx, *found, runners, true)
+	return b.ensureJobScheduled(ctx, *found, runners, true)
 }
 
-func (b *Bot) scheduleJob(ctx context.Context, schedule ScheduledJob, runners []api.Runner, force bool) (api.JobID, error) {
+func (b *Bot) ensureJobScheduled(ctx context.Context, schedule ScheduledJob, runners []api.Runner, force bool) (api.JobID, error) {
 	if schedule.Job.TargetRunnerID == "*" {
 		for _, runner := range runners {
 			schedule.Job.TargetRunnerID = runner.ID
@@ -223,44 +223,30 @@ func (b *Bot) scheduleJob(ctx context.Context, schedule ScheduledJob, runners []
 		return "", errors.Wrap(err, "failed to query last job")
 	}
 
-	startable := lastJob == nil || (lastJob.State != api.JobStateReady &&
-		lastJob.State != api.JobStateStarting &&
-		lastJob.State != api.JobStateRunning &&
-		lastJob.State != api.JobStateError)
+	// We can start the existing job if it exists and it is ready to start
+	lastJobDoesNotExist := lastJob == nil
 	lastJobErrored := lastJob != nil && lastJob.State == api.JobStateError
-	shouldStart := startable || lastJobErrored
-	if startable && schedule.Every == 0 {
-		shouldStart = false // Job can be started, but is not scheduled to start automatically.
-	}
+	lastJobSucceeded := lastJob != nil && lastJob.State == api.JobStateSuccess
+	lastJobDone := lastJob != nil && (lastJobErrored || lastJobSucceeded)
 
-	if force {
-		if startable {
-			lastJob.ScheduledStart = time.Time{}
-			if err := b.store.UpsertRunnerJob(ctx, *lastJob); err != nil {
-				return "", errors.Wrap(err, "failed to update job")
-			}
-			return lastJob.ID, nil
-		} else {
-			schedule.Job.ScheduledStart = time.Time{}
-			jobID, err := b.store.NewRunnerJob(ctx, schedule.Job)
-			if err != nil {
-				return "", errors.Wrap(err, "failed to create job")
-			}
-			b.idLogf(schedulerLogID, "job created: %v", schedule.Job.Title)
-			return jobID, nil
-		}
-	}
-	if !shouldStart {
+	jobSchedulesAutomatically := schedule.Every != 0 // If zero, job can be started manually only
+	shouldStartNow := force || (jobSchedulesAutomatically && (lastJobDoesNotExist || lastJobDone))
+
+	if !shouldStartNow {
+		// There is already a job for this running
 		return "", nil
 	}
 
-	// Job is not running/scheduled, and is set to Always run OR is a ScheduledStart.
-	if !schedule.Always {
-		if lastJob == nil || lastJobErrored {
-			schedule.Job.ScheduledStart = time.Now().Add(30 * time.Second)
-		} else {
-			schedule.Job.ScheduledStart = time.Now().Add(schedule.Every)
-		}
+	// Create a new job
+	if schedule.Always || force {
+		// Job should be running right now, so ScheduledStart should be zero.
+		schedule.Job.ScheduledStart = time.Time{}
+	} else if lastJob == nil || lastJobErrored {
+		// If there is no last job, or the last job errored, schedule it to run again soon.
+		schedule.Job.ScheduledStart = time.Now().Add(30 * time.Second)
+	} else {
+		// If the job ran successfully, schedule it to run again at the desired interval.
+		schedule.Job.ScheduledStart = time.Now().Add(schedule.Every)
 	}
 
 	jobID, err := b.store.NewRunnerJob(ctx, schedule.Job)