diff --git a/agent/runner.go b/agent/runner.go
index 4f815c1a3..605275640 100644
--- a/agent/runner.go
+++ b/agent/runner.go
@@ -81,17 +81,20 @@ func (r *Runner) Run(ctx context.Context) error {
 		timeout = time.Duration(minutes) * time.Minute
 	}
 
+	repoName := extractRepositoryName(work.Config) // hack
+	buildNumber := extractBuildNumber(work.Config) // hack
+
 	r.counter.Add(
 		work.ID,
 		timeout,
-		extractRepositoryName(work.Config), // hack
-		extractBuildNumber(work.Config),    // hack
+		repoName,
+		buildNumber,
 	)
 	defer r.counter.Done(work.ID)
 
 	logger := log.With().
-		Str("repo", extractRepositoryName(work.Config)). // hack
-		Str("build", extractBuildNumber(work.Config)).   // hack
+		Str("repo", repoName).
+		Str("build", buildNumber).
 		Str("id", work.ID).
 		Logger()
 
@@ -308,6 +311,11 @@ func (r *Runner) Run(ctx context.Context) error {
 		pipeline.WithLogger(defaultLogger),
 		pipeline.WithTracer(defaultTracer),
 		pipeline.WithEngine(*r.engine),
+		pipeline.WithDescription(map[string]string{
+			"ID":    work.ID,
+			"Repo":  repoName,
+			"Build": buildNumber,
+		}),
 	).Run()
 
 	state.Finished = time.Now().Unix()
diff --git a/cli/exec/exec.go b/cli/exec/exec.go
index 10fee160d..7ce62445d 100644
--- a/cli/exec/exec.go
+++ b/cli/exec/exec.go
@@ -201,6 +201,9 @@ func execWithAxis(c *cli.Context, file, repoPath string, axis matrix.Axis) error
 		pipeline.WithTracer(pipeline.DefaultTracer),
 		pipeline.WithLogger(defaultLogger),
 		pipeline.WithEngine(engine),
+		pipeline.WithDescription(map[string]string{
+			"CLI": "exec",
+		}),
 	).Run()
 }
 
diff --git a/pipeline/option.go b/pipeline/option.go
index a31c1fa36..4d380af66 100644
--- a/pipeline/option.go
+++ b/pipeline/option.go
@@ -36,3 +36,9 @@ func WithContext(ctx context.Context) Option {
 		r.ctx = ctx
 	}
 }
+
+func WithDescription(desc map[string]string) Option {
+	return func(r *Runtime) {
+		r.Description = desc
+	}
+}
diff --git a/pipeline/pipeline.go b/pipeline/pipeline.go
index e27061f9e..3b810e3c2 100644
--- a/pipeline/pipeline.go
+++ b/pipeline/pipeline.go
@@ -5,6 +5,7 @@ import (
 	"strings"
 	"time"
 
+	"github.com/rs/zerolog"
 	"github.com/rs/zerolog/log"
 	"golang.org/x/sync/errgroup"
 
@@ -40,12 +41,15 @@ type Runtime struct {
 	ctx    context.Context
 	tracer Tracer
 	logger Logger
+
+	Description map[string]string // The runtime descriptors.
 }
 
 // New returns a new runtime using the specified runtime
 // configuration and runtime engine.
 func New(spec *backend.Config, opts ...Option) *Runtime {
 	r := new(Runtime)
+	r.Description = map[string]string{}
 	r.spec = spec
 	r.ctx = context.Background()
 	for _, opts := range opts {
@@ -54,11 +58,33 @@ func New(spec *backend.Config, opts ...Option) *Runtime {
 	return r
 }
 
+func (r *Runtime) MakeLogger() zerolog.Logger {
+	logCtx := log.With()
+	for key, val := range r.Description {
+		logCtx = logCtx.Str(key, val)
+	}
+	return logCtx.Logger()
+}
+
 // Starts the execution of the pipeline and waits for it to complete
 func (r *Runtime) Run() error {
+	logger := r.MakeLogger()
+	logger.Debug().Msgf("Executing %d stages, in order of:", len(r.spec.Stages))
+	for _, stage := range r.spec.Stages {
+		steps := []string{}
+		for _, step := range stage.Steps {
+			steps = append(steps, step.Name)
+		}
+
+		logger.Debug().
+			Str("Stage", stage.Name).
+			Str("Steps", strings.Join(steps, ",")).
+			Msg("stage")
+	}
+
 	defer func() {
 		if err := r.engine.Destroy(r.ctx, r.spec); err != nil {
-			log.Error().Err(err).Msg("could not destroy pipeline")
+			logger.Error().Err(err).Msg("could not destroy engine")
 		}
 	}()
 
@@ -104,13 +130,17 @@ func (r *Runtime) traceStep(processState *backend.State, err error, step *backen
 	state.Process = processState // empty
 	state.Pipeline.Error = r.err
 
-	return r.tracer.Trace(state)
+	if traceErr := r.tracer.Trace(state); traceErr != nil {
+		return traceErr
+	}
+	return err
 }
 
 // Executes a set of parallel steps
 func (r *Runtime) execAll(steps []*backend.Step) <-chan error {
 	var g errgroup.Group
 	done := make(chan error)
+	logger := r.MakeLogger()
 
 	for _, step := range steps {
 		// required since otherwise the loop variable
@@ -119,10 +149,21 @@ func (r *Runtime) execAll(steps []*backend.Step) <-chan error {
 		step := step
 		g.Go(func() error {
 			// Case the pipeline was already complete.
+			logger.Debug().
+				Str("Step", step.Name).
+				Msg("Prepare")
+
 			switch {
 			case r.err != nil && !step.OnFailure:
+				logger.Debug().
+					Str("Step", step.Name).
+					Err(r.err).
+					Msgf("Skipped due to OnFailure=%t", step.OnFailure)
 				return nil
 			case r.err == nil && !step.OnSuccess:
+				logger.Debug().
+					Str("Step", step.Name).
+					Msgf("Skipped due to OnSuccess=%t", step.OnSuccess)
 				return nil
 			}
 
@@ -132,15 +173,26 @@ func (r *Runtime) execAll(steps []*backend.Step) <-chan error {
 				return err
 			}
 
+			logger.Debug().
+				Str("Step", step.Name).
+				Msg("Executing")
+
 			processState, err := r.exec(step)
 
-			// Return the error after tracing it.
-			traceErr := r.traceStep(processState, err, step)
-			if traceErr != nil {
-				return traceErr
+			logger.Debug().
+				Str("Step", step.Name).
+				Msg("Complete")
+
+			// if we got a nil process but an error state
+			// then we need to log the internal error to the step.
+			if r.logger != nil && err != nil && processState == nil {
+				_ = r.logger.Log(step, multipart.New(strings.NewReader(
+					"Backend engine error while running step: "+err.Error(),
+				)))
 			}
 
-			return err
+			// Return the error after tracing it.
+			return r.traceStep(processState, err, step)
 		})
 	}
 
@@ -171,8 +223,10 @@ func (r *Runtime) exec(step *backend.Step) (*backend.State, error) {
 		}
 
 		go func() {
+			logger := r.MakeLogger()
+
 			if err := r.logger.Log(step, multipart.New(rc)); err != nil {
-				log.Error().Err(err).Msg("process logging failed")
+				logger.Error().Err(err).Msg("process logging failed")
 			}
 			_ = rc.Close()
 		}()