diff --git a/cli/cmd/configure_cmd.go b/cli/cmd/configure_cmd.go
index ef9d8582f0..c2e227fce8 100644
--- a/cli/cmd/configure_cmd.go
+++ b/cli/cmd/configure_cmd.go
@@ -27,6 +27,11 @@ var configureCmd = &cobra.Command{
 			CI: configParams.CI,
 		}
 
+		config, err := config.LoadConfig("")
+		if err != nil {
+			return "", err
+		}
+
 		if flagProvided(cmd, "server-url") || flagProvided(cmd, "endpoint") {
 			flags.ServerURL = configParams.ServerURL
 		}
@@ -43,7 +48,7 @@ var configureCmd = &cobra.Command{
 			flags.OrganizationID = configParams.OrganizationID
 		}
 
-		return "", configurator.Start(ctx, nil, flags)
+		return "", configurator.Start(ctx, &config, flags)
 	})),
 	PostRun: teardownCommand,
 }
diff --git a/cli/config/config.go b/cli/config/config.go
index 86f1a77343..d17513a645 100644
--- a/cli/config/config.go
+++ b/cli/config/config.go
@@ -126,7 +126,7 @@ func loadConfig(configFile string) (Config, error) {
 	return config, nil
 }
 
-func ValidateServerURL(serverURL string) error {
+func validateServerURL(serverURL string) error {
 	if !strings.HasPrefix(serverURL, "http://") && !strings.HasPrefix(serverURL, "https://") {
 		return fmt.Errorf(`the server URL must start with the scheme, either "http://" or "https://"`)
 	}
diff --git a/cli/config/configurator.go b/cli/config/configurator.go
index aa695bf224..0cc4797c9a 100644
--- a/cli/config/configurator.go
+++ b/cli/config/configurator.go
@@ -83,16 +83,21 @@ func (c Configurator) Start(ctx context.Context, prev *Config, flags agentConfig
 }
 
 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)
+	serverURL := flags.ServerURL
+
+	// if flag was passed, don't show prompt
+	if flags.ServerURL == "" {
+		possibleValues := []string{}
+		if prev != nil {
+			possibleValues = append(possibleValues, prev.UIEndpoint, prev.URL())
+		}
+		possibleValues = append(possibleValues, DefaultCloudEndpoint)
+
+		lastUsed := getFirstNonEmptyString(possibleValues)
+		serverURL = c.ui.TextInput("What tracetest server do you want to use?", lastUsed)
 	}
 
-	if err := ValidateServerURL(serverURL); err != nil {
+	if err := validateServerURL(serverURL); err != nil {
 		return "", err
 	}
 
@@ -163,9 +168,11 @@ func (c Configurator) populateConfigWithVersionInfo(ctx context.Context, cfg Con
 }
 
 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 prev != nil && cfg.URL() == prev.URL() {
+		if prev != nil && prev.Jwt != "" {
+			cfg.Jwt = prev.Jwt
+			cfg.Token = prev.Token
+		}
 	}
 
 	if flags.Token != "" {
@@ -178,17 +185,17 @@ func (c Configurator) handleOAuth(ctx context.Context, cfg Config, prev *Config,
 
 	if flags.AgentApiKey != "" {
 		cfg.AgentApiKey = flags.AgentApiKey
-		c.ShowOrganizationSelector(ctx, cfg, flags)
+		c.showOrganizationSelector(ctx, prev, cfg, flags)
 		return cfg, nil
 	}
 
 	if cfg.Jwt != "" {
-		c.ShowOrganizationSelector(ctx, cfg, flags)
+		c.showOrganizationSelector(ctx, prev, cfg, flags)
 		return cfg, nil
 	}
 
 	oauthServer := oauth.NewOAuthServer(cfg.OAuthEndpoint(), cfg.UIEndpoint)
-	err := oauthServer.WithOnSuccess(c.onOAuthSuccess(ctx, cfg)).
+	err := oauthServer.WithOnSuccess(c.onOAuthSuccess(ctx, cfg, prev)).
 		WithOnFailure(c.onOAuthFailure).
 		GetAuthJWT()
 	if err != nil {
@@ -225,7 +232,7 @@ func (c Configurator) exchangeToken(cfg Config, token string) (Config, error) {
 	return cfg, nil
 }
 
-func getFirstValidString(values ...string) string {
+func getFirstNonEmptyString(values []string) string {
 	for _, v := range values {
 		if v != "" {
 			return v
@@ -235,12 +242,12 @@ func getFirstValidString(values ...string) string {
 	return ""
 }
 
-func (c Configurator) onOAuthSuccess(ctx context.Context, cfg Config) func(token, jwt string) {
+func (c Configurator) onOAuthSuccess(ctx context.Context, cfg Config, prev *Config) func(token, jwt string) {
 	return func(token, jwt string) {
 		cfg.Jwt = jwt
 		cfg.Token = token
 
-		c.ShowOrganizationSelector(ctx, cfg, c.flags)
+		c.showOrganizationSelector(ctx, prev, cfg, c.flags)
 	}
 }
 
@@ -248,10 +255,10 @@ func (c Configurator) onOAuthFailure(err error) {
 	c.ui.Exit(err.Error())
 }
 
-func (c Configurator) ShowOrganizationSelector(ctx context.Context, cfg Config, flags agentConfig.Flags) {
+func (c Configurator) showOrganizationSelector(ctx context.Context, prev *Config, cfg Config, flags agentConfig.Flags) {
 	cfg.OrganizationID = flags.OrganizationID
 	if cfg.OrganizationID == "" && flags.AgentApiKey == "" {
-		orgID, err := c.organizationSelector(ctx, cfg)
+		orgID, err := c.organizationSelector(ctx, cfg, prev)
 		if err != nil {
 			c.ui.Exit(err.Error())
 			return
@@ -262,7 +269,7 @@ func (c Configurator) ShowOrganizationSelector(ctx context.Context, cfg Config,
 
 	cfg.EnvironmentID = flags.EnvironmentID
 	if cfg.EnvironmentID == "" && flags.AgentApiKey == "" {
-		envID, err := c.environmentSelector(ctx, cfg)
+		envID, err := c.environmentSelector(ctx, cfg, prev)
 		if err != nil {
 			c.ui.Exit(err.Error())
 			return
diff --git a/cli/config/selector.go b/cli/config/selector.go
index efedfaae22..c44b01e336 100644
--- a/cli/config/selector.go
+++ b/cli/config/selector.go
@@ -14,7 +14,7 @@ type Entry struct {
 	Name string `json:"name"`
 }
 
-func (c Configurator) organizationSelector(ctx context.Context, cfg Config) (string, error) {
+func (c Configurator) organizationSelector(ctx context.Context, cfg Config, prev *Config) (string, error) {
 	resource, err := c.resources.Get("organization")
 	if err != nil {
 		return "", err
@@ -33,6 +33,8 @@ Defaulting to only available Organization: %s`, elements[0].Name))
 
 	orgID := ""
 	options := make([]cliUI.Option, len(elements))
+
+	defaultIndex := 0
 	for i, org := range elements {
 		options[i] = cliUI.Option{
 			Text: fmt.Sprintf("%s (%s)", org.Name, org.ID),
@@ -42,16 +44,20 @@ Defaulting to only available Organization: %s`, elements[0].Name))
 				}
 			}(org),
 		}
+
+		// if we have a previous organization, set it as default
+		if prev != nil && prev.OrganizationID == org.ID {
+			defaultIndex = i
+		}
 	}
 
-	option := c.ui.Select(`
-What Organization do you want to use?`, options, 0)
+	option := c.ui.Select(`What Organization do you want to use?`, options, defaultIndex)
 	option.Fn(c.ui)
 
 	return orgID, nil
 }
 
-func (c Configurator) environmentSelector(ctx context.Context, cfg Config) (string, error) {
+func (c Configurator) environmentSelector(ctx context.Context, cfg Config, prev *Config) (string, error) {
 	resource, err := c.resources.Get("env")
 	if err != nil {
 		return "", err
@@ -72,6 +78,7 @@ func (c Configurator) environmentSelector(ctx context.Context, cfg Config) (stri
 
 	envID := ""
 	options := make([]cliUI.Option, len(elements))
+	defaultIndex := 0
 	for i, env := range elements {
 		options[i] = cliUI.Option{
 			Text: fmt.Sprintf("%s (%s)", env.Name, env.ID),
@@ -81,9 +88,13 @@ func (c Configurator) environmentSelector(ctx context.Context, cfg Config) (stri
 				}
 			}(env),
 		}
+		// if we have a previous env, set it as default
+		if prev != nil && prev.EnvironmentID == env.ID {
+			defaultIndex = i
+		}
 	}
 
-	option := c.ui.Select("What Environment do you want to use?", options, 0)
+	option := c.ui.Select("What Environment do you want to use?", options, defaultIndex)
 	option.Fn(c.ui)
 
 	return envID, err