diff --git a/hscontrol/types/users.go b/hscontrol/types/users.go
index 55cd8fb1..8cae0016 100644
--- a/hscontrol/types/users.go
+++ b/hscontrol/types/users.go
@@ -10,6 +10,7 @@ import (
 
 	v1 "github.com/juanfont/headscale/gen/go/headscale/v1"
 	"github.com/juanfont/headscale/hscontrol/util"
+	"github.com/rs/zerolog/log"
 	"google.golang.org/protobuf/types/known/timestamppb"
 	"gorm.io/gorm"
 	"tailscale.com/tailcfg"
@@ -173,9 +174,11 @@ func (c *OIDCClaims) Identifier() string {
 // FromClaim overrides a User from OIDC claims.
 // All fields will be updated, except for the ID.
 func (u *User) FromClaim(claims *OIDCClaims) {
-	err := util.CheckForFQDNRules(claims.Username)
+	err := util.ValidateUsername(claims.Username)
 	if err == nil {
 		u.Name = claims.Username
+	} else {
+		log.Debug().Err(err).Msgf("Username %s is not valid", claims.Username)
 	}
 
 	if claims.EmailVerified {
diff --git a/hscontrol/util/dns.go b/hscontrol/util/dns.go
index c6861c9e..d55d6e8a 100644
--- a/hscontrol/util/dns.go
+++ b/hscontrol/util/dns.go
@@ -6,6 +6,7 @@ import (
 	"net/netip"
 	"regexp"
 	"strings"
+	"unicode"
 
 	"go4.org/netipx"
 	"tailscale.com/util/dnsname"
@@ -20,10 +21,40 @@ const (
 	LabelHostnameLength = 63
 )
 
+var invalidDNSRegex = regexp.MustCompile("[^a-z0-9-.]+")
 var invalidCharsInUserRegex = regexp.MustCompile("[^a-z0-9-.]+")
 
 var ErrInvalidUserName = errors.New("invalid user name")
 
+func ValidateUsername(username string) error {
+	// Ensure the username meets the minimum length requirement
+	if len(username) < 2 {
+		return errors.New("username must be at least 2 characters long")
+	}
+
+	// Ensure the username does not start with a number
+	if unicode.IsDigit(rune(username[0])) {
+		return errors.New("username cannot start with a number")
+	}
+
+	atCount := 0
+	for _, char := range username {
+		switch {
+		case unicode.IsLetter(char), unicode.IsDigit(char), char == '-':
+			// Valid characters
+		case char == '@':
+			atCount++
+			if atCount > 1 {
+				return errors.New("username cannot contain more than one '@'")
+			}
+		default:
+			return fmt.Errorf("username contains invalid character: '%c'", char)
+		}
+	}
+
+	return nil
+}
+
 func CheckForFQDNRules(name string) error {
 	if len(name) > LabelHostnameLength {
 		return fmt.Errorf(
@@ -39,7 +70,7 @@ func CheckForFQDNRules(name string) error {
 			ErrInvalidUserName,
 		)
 	}
-	if invalidCharsInUserRegex.MatchString(name) {
+	if invalidDNSRegex.MatchString(name) {
 		return fmt.Errorf(
 			"DNS segment should only be composed of lowercase ASCII letters numbers, hyphen and dots. %v doesn't comply with theses rules: %w",
 			name,
@@ -52,7 +83,7 @@ func CheckForFQDNRules(name string) error {
 
 func ConvertWithFQDNRules(name string) string {
 	name = strings.ToLower(name)
-	name = invalidCharsInUserRegex.ReplaceAllString(name, "")
+	name = invalidDNSRegex.ReplaceAllString(name, "")
 
 	return name
 }
@@ -197,7 +228,7 @@ func NormalizeToFQDNRules(name string, stripEmailDomain bool) (string, error) {
 	} else {
 		name = strings.ReplaceAll(name, "@", ".")
 	}
-	name = invalidCharsInUserRegex.ReplaceAllString(name, "-")
+	name = invalidDNSRegex.ReplaceAllString(name, "-")
 
 	for _, elt := range strings.Split(name, ".") {
 		if len(elt) > LabelHostnameLength {