diff --git a/Makefile b/Makefile
index 3a3905a646..d367f780f7 100644
--- a/Makefile
+++ b/Makefile
@@ -1,4 +1,5 @@
-VERSION?=dev
+export VERSION?=dev
+export TRACETEST_DEFAULT_CLOUD_ENDPOINT=https://app.tracetest.io
 TAG?=$(VERSION)
 GORELEASER_VERSION=1.23.0-pro
 
diff --git a/agent/config/flags.go b/agent/config/flags.go
index 44e5e3d62f..068de3a81f 100644
--- a/agent/config/flags.go
+++ b/agent/config/flags.go
@@ -8,7 +8,7 @@ const (
 )
 
 type Flags struct {
-	Endpoint       string
+	ServerURL      string
 	OrganizationID string
 	EnvironmentID  string
 	CI             bool
diff --git a/agent/runner/runner.go b/agent/runner/runner.go
index 49f7c8941f..6b753efd10 100644
--- a/agent/runner/runner.go
+++ b/agent/runner/runner.go
@@ -57,7 +57,7 @@ Once started, Tracetest Agent exposes OTLP ports 4317 and 4318 to ingest traces
 
 	s.logger = logger
 
-	return s.configurator.Start(ctx, cfg, flags)
+	return s.configurator.Start(ctx, &cfg, flags)
 }
 
 func (s *Runner) onStartAgent(ctx context.Context, cfg config.Config) {
diff --git a/cli/cmd/configure_cmd.go b/cli/cmd/configure_cmd.go
index 6417c46ae1..ef9d8582f0 100644
--- a/cli/cmd/configure_cmd.go
+++ b/cli/cmd/configure_cmd.go
@@ -26,13 +26,9 @@ var configureCmd = &cobra.Command{
 		flags := agentConfig.Flags{
 			CI: configParams.CI,
 		}
-		config, err := config.LoadConfig("")
-		if err != nil {
-			return "", err
-		}
 
 		if flagProvided(cmd, "server-url") || flagProvided(cmd, "endpoint") {
-			flags.Endpoint = configParams.ServerURL
+			flags.ServerURL = configParams.ServerURL
 		}
 
 		if flagProvided(cmd, "token") {
@@ -47,8 +43,7 @@ var configureCmd = &cobra.Command{
 			flags.OrganizationID = configParams.OrganizationID
 		}
 
-		err = configurator.Start(ctx, config, flags)
-		return "", err
+		return "", configurator.Start(ctx, nil, flags)
 	})),
 	PostRun: teardownCommand,
 }
diff --git a/cli/cmd/start_cmd.go b/cli/cmd/start_cmd.go
index 94a064c2f2..2a3a11af16 100644
--- a/cli/cmd/start_cmd.go
+++ b/cli/cmd/start_cmd.go
@@ -30,7 +30,7 @@ var startCmd = &cobra.Command{
 		flags := agentConfig.Flags{
 			OrganizationID: saveParams.organizationID,
 			EnvironmentID:  saveParams.environmentID,
-			Endpoint:       saveParams.endpoint,
+			ServerURL:      saveParams.endpoint,
 			AgentApiKey:    saveParams.agentApiKey,
 			Token:          saveParams.token,
 			Mode:           agentConfig.Mode(saveParams.mode),
diff --git a/cli/config/config.go b/cli/config/config.go
index 89ba800d98..2f9ab95645 100644
--- a/cli/config/config.go
+++ b/cli/config/config.go
@@ -38,6 +38,11 @@ type Config struct {
 	UIEndpoint       string `yaml:"uIEndpoint,omitempty"`
 }
 
+func (c Config) OAuthEndpoint() string {
+	return fmt.Sprintf("%s%s", c.URL(), c.Path())
+
+}
+
 func (c Config) URL() string {
 	if c.Scheme == "" || c.Endpoint == "" {
 		return ""
diff --git a/cli/config/configurator.go b/cli/config/configurator.go
index 71797a13d5..1f7caa9220 100644
--- a/cli/config/configurator.go
+++ b/cli/config/configurator.go
@@ -7,13 +7,10 @@ import (
 	"strings"
 
 	"github.com/golang-jwt/jwt"
-
 	agentConfig "github.com/kubeshop/tracetest/agent/config"
-
 	"github.com/kubeshop/tracetest/cli/analytics"
 	"github.com/kubeshop/tracetest/cli/pkg/oauth"
 	"github.com/kubeshop/tracetest/cli/pkg/resourcemanager"
-
 	cliUI "github.com/kubeshop/tracetest/cli/ui"
 )
 
@@ -42,111 +39,167 @@ func (c Configurator) WithOnFinish(onFinish onFinishFn) Configurator {
 	return c
 }
 
-func (c Configurator) Start(ctx context.Context, prev Config, flags agentConfig.Flags) error {
+func (c Configurator) Start(ctx context.Context, prev *Config, flags agentConfig.Flags) error {
 	c.flags = flags
-	serverURL := getFirstValidString(flags.Endpoint, prev.UIEndpoint, DefaultCloudEndpoint)
-	if serverURL == "" {
-		path := ""
-		if prev.ServerPath != nil {
-			path = *prev.ServerPath
+	serverURL, err := c.getServerURL(prev, flags)
+	if err != nil {
+		return err
+	}
+
+	cfg, err := c.createConfig(serverURL)
+	if err != nil {
+		return err
+	}
+
+	cfg, err, isOSS := c.populateConfigWithVersionInfo(ctx, cfg)
+	if err != nil {
+		return err
+	}
+
+	if isOSS {
+		// we don't need anything else for OSS
+		return nil
+	}
+
+	if flags.CI {
+		err = Save(cfg)
+		if err != nil {
+			return err
 		}
-		serverURL = c.ui.TextInput("Enter your Tracetest server URL", fmt.Sprintf("%s%s", prev.URL(), path))
+		return nil
 	}
 
-	if err := ValidateServerURL(serverURL); err != nil {
+	_, err = c.handleOAuth(ctx, cfg, prev, flags)
+	if err != nil {
 		return err
 	}
 
+	return nil
+}
+
+func (c Configurator) getServerURL(prev *Config, flags agentConfig.Flags) (string, error) {
+	var prevUIEndpoint string
+	if prev != nil {
+		prevUIEndpoint = prev.UIEndpoint
+	}
+	serverURL := getFirstValidString(flags.ServerURL, prevUIEndpoint)
+	if serverURL == "" {
+		serverURL = c.ui.TextInput("What tracetest server do you want to use?", DefaultCloudEndpoint)
+	}
+
+	if err := ValidateServerURL(serverURL); err != nil {
+		return "", err
+	}
+
+	return serverURL, nil
+}
+
+func (c Configurator) createConfig(serverURL string) (Config, error) {
 	scheme, endpoint, path, err := ParseServerURL(serverURL)
 	if err != nil {
-		return err
+		return Config{}, err
 	}
 
 	if strings.Contains(serverURL, DefaultCloudDomain) {
 		path = &DefaultCloudPath
 	}
 
-	cfg := Config{
+	return Config{
 		Scheme:     scheme,
 		Endpoint:   endpoint,
 		ServerPath: path,
-	}
+	}, nil
+}
 
+func (c Configurator) populateConfigWithVersionInfo(ctx context.Context, cfg Config) (_ Config, _ error, isOSS bool) {
 	client := GetAPIClient(cfg)
 	version, err := getVersionMetadata(ctx, client)
 	if err != nil {
-		return fmt.Errorf("cannot get version metadata: %w", err)
+		return Config{}, fmt.Errorf("cannot get version metadata: %w", err), false
 	}
 
 	serverType := version.GetType()
 	if serverType == "oss" {
 		err := Save(cfg)
 		if err != nil {
-			return fmt.Errorf("could not save configuration: %w", err)
+			return Config{}, fmt.Errorf("could not save configuration: %w", err), false
 		}
 
 		c.ui.Success("Successfully configured Tracetest CLI")
-		return nil
+		return cfg, nil, true
 	}
 
 	cfg.AgentEndpoint = version.GetAgentEndpoint()
 	cfg.UIEndpoint = version.GetUiEndpoint()
 	cfg.Scheme, cfg.Endpoint, cfg.ServerPath, err = ParseServerURL(version.GetApiEndpoint())
 	if err != nil {
-		return fmt.Errorf("cannot parse server url: %w", err)
+		return Config{}, fmt.Errorf("cannot parse server url: %w", err), false
 	}
 
-	if flags.CI {
-		return Save(cfg)
-	}
-
-	oauthEndpoint := fmt.Sprintf("%s%s", cfg.URL(), cfg.Path())
+	return cfg, nil, false
+}
 
-	if prev.Jwt != "" {
+func (c Configurator) handleOAuth(ctx context.Context, cfg Config, prev *Config, flags agentConfig.Flags) (Config, error) {
+	if prev != nil && prev.Jwt != "" {
 		cfg.Jwt = prev.Jwt
 		cfg.Token = prev.Token
 	}
 
 	if flags.Token != "" {
-		jwt, err := oauth.ExchangeToken(oauthEndpoint, flags.Token)
-		if err != nil {
-			return err
-		}
-
-		cfg.Jwt = jwt
-		cfg.Token = flags.Token
-
-		claims, err := GetTokenClaims(jwt)
+		var err error
+		cfg, err = c.exchangeToken(cfg, flags.Token)
 		if err != nil {
-			return err
-		}
-
-		organizationId := claims["organization_id"].(string)
-		environmentId := claims["environment_id"].(string)
-
-		if organizationId != "" {
-			flags.OrganizationID = organizationId
-		}
-		if environmentId != "" {
-			flags.EnvironmentID = environmentId
+			return Config{}, err
 		}
 	}
 
 	if flags.AgentApiKey != "" {
 		cfg.AgentApiKey = flags.AgentApiKey
 		c.ShowOrganizationSelector(ctx, cfg, flags)
-		return nil
+		return cfg, nil
 	}
 
 	if cfg.Jwt != "" {
 		c.ShowOrganizationSelector(ctx, cfg, flags)
-		return nil
+		return cfg, nil
 	}
 
-	oauthServer := oauth.NewOAuthServer(oauthEndpoint, cfg.UIEndpoint)
-	return oauthServer.WithOnSuccess(c.onOAuthSuccess(ctx, cfg)).
+	oauthServer := oauth.NewOAuthServer(cfg.OAuthEndpoint(), cfg.UIEndpoint)
+	err := oauthServer.WithOnSuccess(c.onOAuthSuccess(ctx, cfg)).
 		WithOnFailure(c.onOAuthFailure).
 		GetAuthJWT()
+	if err != nil {
+		return Config{}, err
+	}
+
+	return cfg, nil
+}
+
+func (c Configurator) exchangeToken(cfg Config, token string) (Config, error) {
+	jwt, err := oauth.ExchangeToken(cfg.OAuthEndpoint(), token)
+	if err != nil {
+		return Config{}, err
+	}
+
+	cfg.Jwt = jwt
+	cfg.Token = token
+
+	claims, err := GetTokenClaims(jwt)
+	if err != nil {
+		return Config{}, err
+	}
+
+	organizationId := claims["organization_id"].(string)
+	environmentId := claims["environment_id"].(string)
+
+	if organizationId != "" {
+		c.flags.OrganizationID = organizationId
+	}
+	if environmentId != "" {
+		c.flags.EnvironmentID = environmentId
+	}
+
+	return cfg, nil
 }
 
 func getFirstValidString(values ...string) string {