diff --git a/cli/config/configurator.go b/cli/config/configurator.go
index f8523fc637..8e112c90dc 100644
--- a/cli/config/configurator.go
+++ b/cli/config/configurator.go
@@ -41,10 +41,10 @@ func (c Configurator) WithOnFinish(onFinish onFinishFn) Configurator {
 func (c Configurator) Start(ctx context.Context, prev Config, flags ConfigFlags) error {
 	c.flags = flags
 	var serverURL string
-	if prev.UIEndpoint != "" {
-		serverURL = prev.UIEndpoint
-	} else if flags.Endpoint != "" {
+	if flags.Endpoint != "" {
 		serverURL = flags.Endpoint
+	} else if prev.UIEndpoint != "" {
+		serverURL = prev.UIEndpoint
 	} else {
 		path := ""
 		if prev.ServerPath != nil {
diff --git a/go.work.sum b/go.work.sum
index 5ba68739dc..481badd06e 100644
--- a/go.work.sum
+++ b/go.work.sum
@@ -573,6 +573,7 @@ github.com/aws/aws-sdk-go-v2/service/s3 v1.16.1 h1:z+P3r4LrwdudLKBoEVWxIORrk4sVg
 github.com/aws/aws-sdk-go-v2/service/sso v1.4.2 h1:pZwkxZbspdqRGzddDB92bkZBoB7lg85sMRE7OqdB3V0=
 github.com/aws/aws-sdk-go-v2/service/sts v1.7.2 h1:ol2Y5DWqnJeKqNd8th7JWzBtqu63xpOfs1Is+n1t8/4=
 github.com/aws/smithy-go v1.8.0 h1:AEwwwXQZtUwP5Mz506FeXXrKBe0jA8gVM+1gEcSRooc=
+github.com/benbjohnson/clock v1.3.0/go.mod h1:J11/hYXuz8f4ySSvYwY0FKfm+ezbsZBKZxNJlLklBHA=
 github.com/benbjohnson/immutable v0.2.1 h1:EVv7H1ju7cDg/a8HUF4hAH4DBrMJh6RWWFwq9JfoO9I=
 github.com/benbjohnson/tmpl v1.0.0 h1:T5QPGJD0W6JJxyEEAlVnX3co/IkUrfHen1/42nlgAHo=
 github.com/bgentry/speakeasy v0.1.0 h1:ByYyxL9InA1OWqxJqqp2A5pYHUrCiAL6K3J+LKSsQkY=