diff --git a/cmd/rig/cmd/auth/login.go b/cmd/rig/cmd/auth/login.go
index 715c6ab4b..a9c8afbd5 100644
--- a/cmd/rig/cmd/auth/login.go
+++ b/cmd/rig/cmd/auth/login.go
@@ -2,6 +2,7 @@ package auth
 
 import (
 	"context"
+	"fmt"
 
 	"github.com/bufbuild/connect-go"
 	"github.com/rigdev/rig-go-api/api/v1/authentication"
@@ -10,41 +11,13 @@ import (
 	"github.com/rigdev/rig/cmd/common"
 	"github.com/rigdev/rig/cmd/rig/cmd/base"
 	"github.com/rigdev/rig/pkg/auth"
+	"github.com/rigdev/rig/pkg/errors"
 	"github.com/rigdev/rig/pkg/uuid"
 	"github.com/spf13/cobra"
 )
 
 func AuthLogin(ctx context.Context, cmd *cobra.Command, client rig.Client, cfg *base.Config) error {
-	var identifier *model.UserIdentifier
-	var err error
-	if authUserIdentifier == "" {
-		identifier, err = common.PromptUserIndentifier()
-		if err != nil {
-			return err
-		}
-	} else {
-		identifier, err = common.ParseUserIdentifier(authUserIdentifier)
-	}
-
-	if authPassword == "" {
-		pw, err := common.GetPasswordPrompt("Enter Password")
-		if err != nil {
-			return err
-		}
-		authPassword = string(pw)
-	}
-
-	res, err := client.Authentication().Login(ctx, &connect.Request[authentication.LoginRequest]{
-		Msg: &authentication.LoginRequest{
-			Method: &authentication.LoginRequest_UserPassword{
-				UserPassword: &authentication.UserPassword{
-					Identifier: identifier,
-					Password:   authPassword,
-					ProjectId:  auth.RigProjectID.String(),
-				},
-			},
-		},
-	})
+	res, err := loginWithRetry(ctx, client, authUserIdentifier, authPassword, auth.RigProjectID.String())
 	if err != nil {
 		return err
 	}
@@ -65,3 +38,59 @@ func AuthLogin(ctx context.Context, cmd *cobra.Command, client rig.Client, cfg *
 
 	return nil
 }
+
+func loginWithRetry(ctx context.Context, client rig.Client, identifierStr, password, project string) (*connect.Response[authentication.LoginResponse], error) {
+	shouldPromptIdentifier := identifierStr == ""
+	shouldPromptPassword := password == ""
+	var identifier *model.UserIdentifier
+	for {
+		var err error
+		if shouldPromptIdentifier {
+			identifier, err = common.PromptUserIndentifier()
+		} else if identifier == nil {
+			identifier, err = common.ParseUserIdentifier(authUserIdentifier)
+		}
+		if err != nil {
+			return nil, err
+		}
+
+		if shouldPromptPassword {
+			password, err = common.GetPasswordPrompt("Enter Password")
+			if err != nil {
+				return nil, err
+			}
+		}
+
+		res, err := client.Authentication().Login(ctx, &connect.Request[authentication.LoginRequest]{
+			Msg: &authentication.LoginRequest{
+				Method: &authentication.LoginRequest_UserPassword{
+					UserPassword: &authentication.UserPassword{
+						Identifier: identifier,
+						Password:   password,
+						ProjectId:  project,
+					},
+				},
+			},
+		})
+		if err == nil {
+			return res, nil
+		}
+
+		if errors.IsNotFound(err) {
+			if !shouldPromptIdentifier {
+				return nil, err
+			}
+			fmt.Println("User not found")
+			continue
+		}
+
+		if errors.IsUnauthenticated(err) {
+			if !shouldPromptPassword {
+				return nil, err
+			}
+			shouldPromptIdentifier = false
+			fmt.Println("Wrong password")
+			continue
+		}
+	}
+}