diff --git a/agent/initialization/start.go b/agent/initialization/start.go
index 6b876f36cd..44dbe3810d 100644
--- a/agent/initialization/start.go
+++ b/agent/initialization/start.go
@@ -2,6 +2,7 @@ package initialization
 
 import (
 	"context"
+	"errors"
 	"fmt"
 
 	"github.com/kubeshop/tracetest/agent/client"
@@ -13,6 +14,8 @@ import (
 	"go.opentelemetry.io/otel/trace"
 )
 
+var ErrOtlpServerStart = errors.New("OTLP server start error")
+
 func NewClient(ctx context.Context, config config.Config, traceCache collector.TraceCache) (*client.Client, error) {
 	client, err := client.Connect(ctx, config.ServerURL,
 		client.WithAPIKey(config.APIKey),
@@ -72,7 +75,7 @@ func StartCollector(ctx context.Context, config config.Config, traceCache collec
 
 	_, err := collector.Start(ctx, collectorConfig, noopTracer, collector.WithTraceCache(traceCache), collector.WithStartRemoteServer(false))
 	if err != nil {
-		return err
+		return ErrOtlpServerStart
 	}
 
 	return nil
diff --git a/cli/pkg/starter/starter.go b/cli/pkg/starter/starter.go
index dd8bef56d6..dcc89060bf 100644
--- a/cli/pkg/starter/starter.go
+++ b/cli/pkg/starter/starter.go
@@ -3,6 +3,7 @@ package starter
 import (
 	"context"
 	"encoding/json"
+	"errors"
 	"fmt"
 
 	"github.com/golang-jwt/jwt/v4"
@@ -106,11 +107,29 @@ func (s *Starter) StartAgent(ctx context.Context, endpoint, agentApiKey, uiEndpo
 		cfg.APIKey = agentApiKey
 	}
 
-	s.ui.Println(fmt.Sprintf(`
-Starting Agent with name %s...`, cfg.Name))
-	session, err := initialization.Start(ctx, cfg)
-	if err != nil {
-		return err
+	s.ui.Info(fmt.Sprintf("Starting Agent with name %s...", cfg.Name))
+
+	isStarted := false
+	session := &initialization.Session{}
+	for !isStarted {
+		session, err = initialization.Start(ctx, cfg)
+		if err != nil && errors.Is(err, initialization.ErrOtlpServerStart) {
+			s.ui.Error("Tracetest Agent binds to the OpenTelemetry ports 4317 and 4318 which are used to receive trace information from your system. The agent tried to bind to these ports, but failed.")
+			shouldRetry := s.ui.Enter("Please stop the process currently listening on these ports and press enter to try again.")
+
+			if !shouldRetry {
+				s.ui.Finish()
+				return err
+			}
+
+			continue
+		}
+
+		if err != nil {
+			return err
+		}
+
+		isStarted = true
 	}
 
 	claims, err := s.getTokenClaims(session.Token)