diff --git a/cmd/init.go b/cmd/init.go
index 9494aa4..0fbb4d6 100644
--- a/cmd/init.go
+++ b/cmd/init.go
@@ -47,8 +47,16 @@ func stage1LocalReqs() error {
 	return nil
 }
 
-func stage2Login(server string) (*ssh.Client, string, error) {
-	users := []string{"root", "sidekick"}
+func stage2Login(server string, customUser string) (*ssh.Client, string, error) {
+	var users []string
+
+	if customUser != "" {
+		users = append(users, customUser)
+	} else {
+		users = append(users, "root")
+	}
+	users = append(users, "sidekick")
+
 	for _, user := range users {
 		client, err := utils.Login(server, user)
 		if err == nil {
@@ -70,8 +78,8 @@ func stage3UserSetup(client *ssh.Client, loggedInUser string) error {
 		}
 	}
 
-	if !hasSidekickUser && loggedInUser == "root" {
-		if err := utils.RunStage(client, utils.UsersetupStage); err != nil {
+	if !hasSidekickUser {
+		if err := utils.RunStage(client, utils.UsersetupStage(loggedInUser)); err != nil {
 			return err
 		}
 	}
@@ -179,6 +187,7 @@ var InitCmd = &cobra.Command{
 		skipPromptsFlag, _ := cmd.Flags().GetBool("yes")
 		server, _ := cmd.Flags().GetString("server")
 		certEmail, _ := cmd.Flags().GetString("email")
+		sshUser, _ := cmd.Flags().GetString("user")
 
 		if server == "" {
 			server = render.GenerateTextQuestion("Please enter the IPv4 Address of your VPS", "", "")
@@ -194,6 +203,10 @@ var InitCmd = &cobra.Command{
 			}
 		}
 
+		if sshUser == "" && !skipPromptsFlag {
+			sshUser = render.GenerateTextQuestion("Please enter the SSH username", "root", "default: root")
+		}
+
 		publicKey := viper.GetString("publicKey")
 		if publicKey != "" && server != viper.GetString("serverAddress") && !skipPromptsFlag {
 			confirm := render.GenerateTextQuestion("A server was previously setup with Sidekick. Would you like to override the settings? (y/n)", "n", "")
@@ -223,7 +236,7 @@ var InitCmd = &cobra.Command{
 			AllDone:     false,
 		})
 
-		utils.Login(server, "root")
+		utils.Login(server, sshUser)
 
 		go func() {
 			if err := stage1LocalReqs(); err != nil {
@@ -233,7 +246,7 @@ var InitCmd = &cobra.Command{
 			time.Sleep(time.Millisecond * 100)
 			p.Send(render.NextStageMsg{})
 
-			sshClient, loggedInUser, err := stage2Login(server)
+			sshClient, loggedInUser, err := stage2Login(server, sshUser)
 			if err != nil {
 				p.Send(render.ErrorMsg{ErrorStr: fmt.Sprintf("Login failed: %s", err)})
 				return
@@ -318,5 +331,6 @@ func init() {
 
 	InitCmd.Flags().StringP("server", "s", "", "Set the IP address of your Server")
 	InitCmd.Flags().StringP("email", "e", "", "An email address to be used for SSL certs")
+	InitCmd.Flags().StringP("user", "u", "", "SSH username to use for initial connection")
 	InitCmd.Flags().BoolP("yes", "y", false, "Skip all validation prompts")
 }
diff --git a/utils/stages.go b/utils/stages.go
index db921d7..945ea53 100644
--- a/utils/stages.go
+++ b/utils/stages.go
@@ -20,17 +20,26 @@ import (
 	"strings"
 )
 
-var UsersetupStage = CommandsStage{
-	SpinnerSuccessMessage: "New user created successfully",
-	SpinnerFailMessage:    "Error creating a new user for the machine",
-	Commands: []string{
-		"sudo useradd -m -s /bin/bash -G sudo sidekick",
-		`echo "sidekick ALL=(ALL) NOPASSWD: ALL" >> /etc/sudoers.d/sidekick`,
-		"mkdir -p /home/sidekick/.ssh/",
-		"sudo cat /root/.ssh/authorized_keys | sudo tee -a /home/sidekick/.ssh/authorized_keys",
-		"sudo chown sidekick:sidekick /home/sidekick/.ssh/authorized_keys",
-		"sudo chmod 600 /home/sidekick/.ssh/authorized_keys",
-	},
+func UsersetupStage(currentUser string) CommandsStage {
+	// Determine the source of SSH keys based on current user
+	sshKeysSource := "~/.ssh/authorized_keys"
+	if currentUser == "root" {
+		sshKeysSource = "/root/.ssh/authorized_keys"
+	}
+
+	return CommandsStage{
+		SpinnerSuccessMessage: "New user created successfully",
+		SpinnerFailMessage:    "Error creating a new user for the machine",
+		Commands: []string{
+			"sudo useradd -m -s /bin/bash -G sudo sidekick || true",
+			`echo "sidekick ALL=(ALL) NOPASSWD: ALL" | sudo tee /etc/sudoers.d/sidekick`,
+			"sudo mkdir -p /home/sidekick/.ssh/",
+			fmt.Sprintf("sudo cp %s /home/sidekick/.ssh/authorized_keys", sshKeysSource),
+			"sudo chown -R sidekick:sidekick /home/sidekick/.ssh/",
+			"sudo chmod 700 /home/sidekick/.ssh/",
+			"sudo chmod 600 /home/sidekick/.ssh/authorized_keys",
+		},
+	}
 }
 
 var SetupStage = CommandsStage{