diff --git a/internal/retry/retry.go b/internal/retry/retry.go
index ed3d6f8ac..612623191 100644
--- a/internal/retry/retry.go
+++ b/internal/retry/retry.go
@@ -9,6 +9,7 @@ import (
 	"time"
 
 	"github.com/rs/zerolog"
+	"go.opentelemetry.io/otel/trace"
 
 	"github.com/pomerium/pomerium/internal/log"
 )
@@ -47,7 +48,10 @@ restart:
 	backoff:
 		for {
 			interval := backoff.NextBackOff()
-			log.Ctx(ctx).Info().Msgf("backing off for %s...", interval.String())
+			span := trace.SpanFromContext(ctx)
+			msg := fmt.Sprintf("backing off for %s...", interval.String())
+			span.AddEvent(msg)
+			log.Ctx(ctx).Info().Msg(msg)
 			timer := time.NewTimer(interval)
 			s := makeSelect(ctx, watches, name, timer.C, fn)
 			next, err := s.Exec(ctx)
diff --git a/internal/testenv/environment.go b/internal/testenv/environment.go
index 2cc6d50d7..0cc0d249a 100644
--- a/internal/testenv/environment.go
+++ b/internal/testenv/environment.go
@@ -412,10 +412,12 @@ func New(t testing.TB, opts ...EnvironmentOption) Environment {
 
 func (e *environment) debugf(format string, args ...any) {
 	e.t.Helper()
+	if e.rootSpan.IsRecording() {
+		e.rootSpan.AddEvent(fmt.Sprintf(format, args...))
+	}
 	if !e.debug {
 		return
 	}
-
 	e.t.Logf("\x1b[34m[debug] "+format+"\x1b[0m", args...)
 }