diff --git a/pkg/runner/job_executor.go b/pkg/runner/job_executor.go
index e1de6cbc7ab..b445708552f 100644
--- a/pkg/runner/job_executor.go
+++ b/pkg/runner/job_executor.go
@@ -95,21 +95,16 @@ func newJobExecutor(info jobInfo, sf stepFactory, rc *RunContext) common.Executo
 	}
 
 	postExecutor = postExecutor.Finally(func(ctx context.Context) error {
-		logger := common.Logger(ctx)
 		jobError := common.JobError(ctx)
-		if jobError != nil {
-			info.result("failure")
-			logger.WithField("jobResult", "failure").Infof("\U0001F3C1  Job failed")
-		} else {
-			err := info.stopContainer()(ctx)
-			if err != nil {
-				return err
-			}
-			info.result("success")
-			logger.WithField("jobResult", "success").Infof("\U0001F3C1  Job succeeded")
+		var err error
+		if rc.Config.AutoRemove || jobError == nil {
+			// always allow 1 min for stopping and removing the runner, even if we were cancelled
+			ctx, cancel := context.WithTimeout(common.WithLogger(context.Background(), common.Logger(ctx)), time.Minute)
+			defer cancel()
+			err = info.stopContainer()(ctx)
 		}
-
-		return nil
+		setJobResult(ctx, info, rc, jobError == nil)
+		return err
 	})
 
 	pipeline := make([]common.Executor, 0)
@@ -122,7 +117,7 @@ func newJobExecutor(info jobInfo, sf stepFactory, rc *RunContext) common.Executo
 			if ctx.Err() == context.Canceled {
 				// in case of an aborted run, we still should execute the
 				// post steps to allow cleanup.
-				ctx, cancel = context.WithTimeout(WithJobLogger(context.Background(), rc.Run.JobID, rc.String(), rc.Config, &rc.Masks, rc.Matrix), 5*time.Minute)
+				ctx, cancel = context.WithTimeout(common.WithLogger(context.Background(), common.Logger(ctx)), 5*time.Minute)
 				defer cancel()
 			}
 			return postExecutor(ctx)
@@ -131,6 +126,18 @@ func newJobExecutor(info jobInfo, sf stepFactory, rc *RunContext) common.Executo
 		Finally(info.closeContainer()))
 }
 
+func setJobResult(ctx context.Context, info jobInfo, rc *RunContext, success bool) {
+	logger := common.Logger(ctx)
+	jobResult := "success"
+	jobResultMessage := "succeeded"
+	if !success {
+		jobResult = "failure"
+		jobResultMessage = "failed"
+	}
+	info.result(jobResult)
+	logger.WithField("jobResult", jobResult).Infof("\U0001F3C1  Job %s", jobResultMessage)
+}
+
 func useStepLogger(rc *RunContext, stepModel *model.Step, stage stepStage, executor common.Executor) common.Executor {
 	return func(ctx context.Context) error {
 		ctx = withStepLogger(ctx, stepModel.ID, rc.ExprEval.Interpolate(ctx, stepModel.String()), stage.String())
diff --git a/pkg/runner/runner.go b/pkg/runner/runner.go
index 564814bc953..65f1897d78e 100644
--- a/pkg/runner/runner.go
+++ b/pkg/runner/runner.go
@@ -4,7 +4,6 @@ import (
 	"context"
 	"fmt"
 	"os"
-	"time"
 
 	log "github.com/sirupsen/logrus"
 
@@ -77,18 +76,15 @@ func New(runnerConfig *Config) (Runner, error) {
 }
 
 // NewPlanExecutor ...
-//
-//nolint:gocyclo
 func (runner *runnerImpl) NewPlanExecutor(plan *model.Plan) common.Executor {
 	maxJobNameLen := 0
 
 	stagePipeline := make([]common.Executor, 0)
 	for i := range plan.Stages {
-		s := i
 		stage := plan.Stages[i]
 		stagePipeline = append(stagePipeline, func(ctx context.Context) error {
 			pipeline := make([]common.Executor, 0)
-			for r, run := range stage.Runs {
+			for _, run := range stage.Runs {
 				stageExecutor := make([]common.Executor, 0)
 				job := run.Job()
 
@@ -123,29 +119,8 @@ func (runner *runnerImpl) NewPlanExecutor(plan *model.Plan) common.Executor {
 						maxJobNameLen = len(rc.String())
 					}
 					stageExecutor = append(stageExecutor, func(ctx context.Context) error {
-						logger := common.Logger(ctx)
 						jobName := fmt.Sprintf("%-*s", maxJobNameLen, rc.String())
-						return rc.Executor().Finally(func(ctx context.Context) error {
-							isLastRunningContainer := func(currentStage int, currentRun int) bool {
-								return currentStage == len(plan.Stages)-1 && currentRun == len(stage.Runs)-1
-							}
-
-							if runner.config.AutoRemove && isLastRunningContainer(s, r) {
-								var cancel context.CancelFunc
-								if ctx.Err() == context.Canceled {
-									ctx, cancel = context.WithTimeout(context.Background(), 5*time.Minute)
-									defer cancel()
-								}
-
-								log.Infof("Cleaning up container for job %s", rc.JobName)
-
-								if err := rc.stopJobContainer()(ctx); err != nil {
-									logger.Errorf("Error while cleaning container: %v", err)
-								}
-							}
-
-							return nil
-						})(common.WithJobErrorContainer(WithJobLogger(ctx, rc.Run.JobID, jobName, rc.Config, &rc.Masks, matrix)))
+						return rc.Executor()(common.WithJobErrorContainer(WithJobLogger(ctx, rc.Run.JobID, jobName, rc.Config, &rc.Masks, matrix)))
 					})
 				}
 				pipeline = append(pipeline, common.NewParallelExecutor(maxParallel, stageExecutor...))