diff --git a/client/android/login.go b/client/android/login.go
index 0df78dbc3..16df24ba8 100644
--- a/client/android/login.go
+++ b/client/android/login.go
@@ -200,7 +200,7 @@ func (a *Auth) login(urlOpener URLOpener) error {
 }
 
 func (a *Auth) foregroundGetTokenInfo(urlOpener URLOpener) (*auth.TokenInfo, error) {
-	oAuthFlow, err := auth.NewOAuthFlow(a.ctx, a.config, false)
+	oAuthFlow, err := auth.NewOAuthFlow(a.ctx, a.config, false, "")
 	if err != nil {
 		return nil, err
 	}
diff --git a/client/cmd/login.go b/client/cmd/login.go
index 40b55f858..b0c877faa 100644
--- a/client/cmd/login.go
+++ b/client/cmd/login.go
@@ -106,6 +106,13 @@ func doDaemonLogin(ctx context.Context, cmd *cobra.Command, providedSetupKey str
 		Username:            &username,
 	}
 
+	profileState, err := pm.GetProfileState(activeProf.Name)
+	if err != nil {
+		log.Debugf("failed to get profile state for login hint: %v", err)
+	} else if profileState.Email != "" {
+		loginRequest.Hint = &profileState.Email
+	}
+
 	if rootCmd.PersistentFlags().Changed(preSharedKeyFlag) {
 		loginRequest.OptionalPreSharedKey = &preSharedKey
 	}
@@ -241,7 +248,7 @@ func doForegroundLogin(ctx context.Context, cmd *cobra.Command, setupKey string,
 		return fmt.Errorf("read config file %s: %v", configFilePath, err)
 	}
 
-	err = foregroundLogin(ctx, cmd, config, setupKey)
+	err = foregroundLogin(ctx, cmd, config, setupKey, activeProf.Name)
 	if err != nil {
 		return fmt.Errorf("foreground login failed: %v", err)
 	}
@@ -269,7 +276,7 @@ func handleSSOLogin(ctx context.Context, cmd *cobra.Command, loginResp *proto.Lo
 	return nil
 }
 
-func foregroundLogin(ctx context.Context, cmd *cobra.Command, config *profilemanager.Config, setupKey string) error {
+func foregroundLogin(ctx context.Context, cmd *cobra.Command, config *profilemanager.Config, setupKey, profileName string) error {
 	needsLogin := false
 
 	err := WithBackOff(func() error {
@@ -286,7 +293,7 @@ func foregroundLogin(ctx context.Context, cmd *cobra.Command, config *profileman
 
 	jwtToken := ""
 	if setupKey == "" && needsLogin {
-		tokenInfo, err := foregroundGetTokenInfo(ctx, cmd, config)
+		tokenInfo, err := foregroundGetTokenInfo(ctx, cmd, config, profileName)
 		if err != nil {
 			return fmt.Errorf("interactive sso login failed: %v", err)
 		}
@@ -315,8 +322,17 @@ func foregroundLogin(ctx context.Context, cmd *cobra.Command, config *profileman
 	return nil
 }
 
-func foregroundGetTokenInfo(ctx context.Context, cmd *cobra.Command, config *profilemanager.Config) (*auth.TokenInfo, error) {
-	oAuthFlow, err := auth.NewOAuthFlow(ctx, config, isUnixRunningDesktop())
+func foregroundGetTokenInfo(ctx context.Context, cmd *cobra.Command, config *profilemanager.Config, profileName string) (*auth.TokenInfo, error) {
+	hint := ""
+	pm := profilemanager.NewProfileManager()
+	profileState, err := pm.GetProfileState(profileName)
+	if err != nil {
+		log.Debugf("failed to get profile state for login hint: %v", err)
+	} else if profileState.Email != "" {
+		hint = profileState.Email
+	}
+
+	oAuthFlow, err := auth.NewOAuthFlow(ctx, config, isUnixRunningDesktop(), hint)
 	if err != nil {
 		return nil, err
 	}
diff --git a/client/cmd/up.go b/client/cmd/up.go
index d047c041e..80175f7be 100644
--- a/client/cmd/up.go
+++ b/client/cmd/up.go
@@ -185,7 +185,7 @@ func runInForegroundMode(ctx context.Context, cmd *cobra.Command, activeProf *pr
 
 	_, _ = profilemanager.UpdateOldManagementURL(ctx, config, configFilePath)
 
-	err = foregroundLogin(ctx, cmd, config, providedSetupKey)
+	err = foregroundLogin(ctx, cmd, config, providedSetupKey, activeProf.Name)
 	if err != nil {
 		return fmt.Errorf("foreground login failed: %v", err)
 	}
@@ -286,6 +286,13 @@ func doDaemonUp(ctx context.Context, cmd *cobra.Command, client proto.DaemonServ
 	loginRequest.ProfileName = &activeProf.Name
 	loginRequest.Username = &username
 
+	profileState, err := pm.GetProfileState(activeProf.Name)
+	if err != nil {
+		log.Debugf("failed to get profile state for login hint: %v", err)
+	} else if profileState.Email != "" {
+		loginRequest.Hint = &profileState.Email
+	}
+
 	var loginErr error
 	var loginResp *proto.LoginResponse
 
diff --git a/client/internal/auth/device_flow.go b/client/internal/auth/device_flow.go
index da4f16c8d..8ca760742 100644
--- a/client/internal/auth/device_flow.go
+++ b/client/internal/auth/device_flow.go
@@ -128,9 +128,34 @@ func (d *DeviceAuthorizationFlow) RequestAuthInfo(ctx context.Context) (AuthFlow
 		deviceCode.VerificationURIComplete = deviceCode.VerificationURI
 	}
 
+	if d.providerConfig.LoginHint != "" {
+		deviceCode.VerificationURIComplete = appendLoginHint(deviceCode.VerificationURIComplete, d.providerConfig.LoginHint)
+		if deviceCode.VerificationURI != "" {
+			deviceCode.VerificationURI = appendLoginHint(deviceCode.VerificationURI, d.providerConfig.LoginHint)
+		}
+	}
+
 	return deviceCode, err
 }
 
+func appendLoginHint(uri, loginHint string) string {
+	if uri == "" || loginHint == "" {
+		return uri
+	}
+
+	parsedURL, err := url.Parse(uri)
+	if err != nil {
+		log.Debugf("failed to parse verification URI for login_hint: %v", err)
+		return uri
+	}
+
+	query := parsedURL.Query()
+	query.Set("login_hint", loginHint)
+	parsedURL.RawQuery = query.Encode()
+
+	return parsedURL.String()
+}
+
 func (d *DeviceAuthorizationFlow) requestToken(info AuthFlowInfo) (TokenRequestResponse, error) {
 	form := url.Values{}
 	form.Add("client_id", d.providerConfig.ClientID)
diff --git a/client/internal/auth/oauth.go b/client/internal/auth/oauth.go
index 4458f600c..9fbd6cf5f 100644
--- a/client/internal/auth/oauth.go
+++ b/client/internal/auth/oauth.go
@@ -66,32 +66,34 @@ func (t TokenInfo) GetTokenToUse() string {
 // and if that also fails, the authentication process is deemed unsuccessful
 //
 // On Linux distros without desktop environment support, it only tries to initialize the Device Code Flow
-func NewOAuthFlow(ctx context.Context, config *profilemanager.Config, isUnixDesktopClient bool) (OAuthFlow, error) {
+func NewOAuthFlow(ctx context.Context, config *profilemanager.Config, isUnixDesktopClient bool, hint string) (OAuthFlow, error) {
 	if (runtime.GOOS == "linux" || runtime.GOOS == "freebsd") && !isUnixDesktopClient {
-		return authenticateWithDeviceCodeFlow(ctx, config)
+		return authenticateWithDeviceCodeFlow(ctx, config, hint)
 	}
 
-	pkceFlow, err := authenticateWithPKCEFlow(ctx, config)
+	pkceFlow, err := authenticateWithPKCEFlow(ctx, config, hint)
 	if err != nil {
-		// fallback to device code flow
 		log.Debugf("failed to initialize pkce authentication with error: %v\n", err)
 		log.Debug("falling back to device code flow")
-		return authenticateWithDeviceCodeFlow(ctx, config)
+		return authenticateWithDeviceCodeFlow(ctx, config, hint)
 	}
 	return pkceFlow, nil
 }
 
 // authenticateWithPKCEFlow initializes the Proof Key for Code Exchange flow auth flow
-func authenticateWithPKCEFlow(ctx context.Context, config *profilemanager.Config) (OAuthFlow, error) {
+func authenticateWithPKCEFlow(ctx context.Context, config *profilemanager.Config, hint string) (OAuthFlow, error) {
 	pkceFlowInfo, err := internal.GetPKCEAuthorizationFlowInfo(ctx, config.PrivateKey, config.ManagementURL, config.ClientCertKeyPair)
 	if err != nil {
 		return nil, fmt.Errorf("getting pkce authorization flow info failed with error: %v", err)
 	}
+
+	pkceFlowInfo.ProviderConfig.LoginHint = hint
+
 	return NewPKCEAuthorizationFlow(pkceFlowInfo.ProviderConfig)
 }
 
 // authenticateWithDeviceCodeFlow initializes the Device Code auth Flow
-func authenticateWithDeviceCodeFlow(ctx context.Context, config *profilemanager.Config) (OAuthFlow, error) {
+func authenticateWithDeviceCodeFlow(ctx context.Context, config *profilemanager.Config, hint string) (OAuthFlow, error) {
 	deviceFlowInfo, err := internal.GetDeviceAuthorizationFlowInfo(ctx, config.PrivateKey, config.ManagementURL)
 	if err != nil {
 		switch s, ok := gstatus.FromError(err); {
@@ -107,5 +109,7 @@ func authenticateWithDeviceCodeFlow(ctx context.Context, config *profilemanager.
 		}
 	}
 
+	deviceFlowInfo.ProviderConfig.LoginHint = hint
+
 	return NewDeviceAuthorizationFlow(deviceFlowInfo.ProviderConfig)
 }
diff --git a/client/internal/auth/pkce_flow.go b/client/internal/auth/pkce_flow.go
index 8741e8636..738d3e34f 100644
--- a/client/internal/auth/pkce_flow.go
+++ b/client/internal/auth/pkce_flow.go
@@ -109,6 +109,9 @@ func (p *PKCEAuthorizationFlow) RequestAuthInfo(ctx context.Context) (AuthFlowIn
 			params = append(params, oauth2.SetAuthURLParam("max_age", "0"))
 		}
 	}
+	if p.providerConfig.LoginHint != "" {
+		params = append(params, oauth2.SetAuthURLParam("login_hint", p.providerConfig.LoginHint))
+	}
 
 	authURL := p.oAuthConfig.AuthCodeURL(state, params...)
 
diff --git a/client/internal/device_auth.go b/client/internal/device_auth.go
index 6bd29801d..7f7d06130 100644
--- a/client/internal/device_auth.go
+++ b/client/internal/device_auth.go
@@ -38,6 +38,8 @@ type DeviceAuthProviderConfig struct {
 	Scope string
 	// UseIDToken indicates if the id token should be used for authentication
 	UseIDToken bool
+	// LoginHint is used to pre-fill the email/username field during authentication
+	LoginHint string
 }
 
 // GetDeviceAuthorizationFlowInfo initialize a DeviceAuthorizationFlow instance and return with it
diff --git a/client/internal/pkce_auth.go b/client/internal/pkce_auth.go
index a713bb342..23c92e8af 100644
--- a/client/internal/pkce_auth.go
+++ b/client/internal/pkce_auth.go
@@ -44,6 +44,8 @@ type PKCEAuthProviderConfig struct {
 	DisablePromptLogin bool
 	// LoginFlag is used to configure the PKCE flow login behavior
 	LoginFlag common.LoginFlag
+	// LoginHint is used to pre-fill the email/username field during authentication
+	LoginHint string
 }
 
 // GetPKCEAuthorizationFlowInfo initialize a PKCEAuthorizationFlow instance and return with it
diff --git a/client/ios/NetBirdSDK/client.go b/client/ios/NetBirdSDK/client.go
index 2109d4b15..fa1c89aab 100644
--- a/client/ios/NetBirdSDK/client.go
+++ b/client/ios/NetBirdSDK/client.go
@@ -228,7 +228,7 @@ func (c *Client) LoginForMobile() string {
 		ConfigPath: c.cfgFile,
 	})
 
-	oAuthFlow, err := auth.NewOAuthFlow(ctx, cfg, false)
+	oAuthFlow, err := auth.NewOAuthFlow(ctx, cfg, false, "")
 	if err != nil {
 		return err.Error()
 	}
diff --git a/client/proto/daemon.pb.go b/client/proto/daemon.pb.go
index 841e3c0f7..02f09b08a 100644
--- a/client/proto/daemon.pb.go
+++ b/client/proto/daemon.pb.go
@@ -279,8 +279,10 @@ type LoginRequest struct {
 	ProfileName           *string `protobuf:"bytes,30,opt,name=profileName,proto3,oneof" json:"profileName,omitempty"`
 	Username              *string `protobuf:"bytes,31,opt,name=username,proto3,oneof" json:"username,omitempty"`
 	Mtu                   *int64  `protobuf:"varint,32,opt,name=mtu,proto3,oneof" json:"mtu,omitempty"`
-	unknownFields         protoimpl.UnknownFields
-	sizeCache             protoimpl.SizeCache
+	// hint is used to pre-fill the email/username field during SSO authentication
+	Hint          *string `protobuf:"bytes,33,opt,name=hint,proto3,oneof" json:"hint,omitempty"`
+	unknownFields protoimpl.UnknownFields
+	sizeCache     protoimpl.SizeCache
 }
 
 func (x *LoginRequest) Reset() {
@@ -538,6 +540,13 @@ func (x *LoginRequest) GetMtu() int64 {
 	return 0
 }
 
+func (x *LoginRequest) GetHint() string {
+	if x != nil && x.Hint != nil {
+		return *x.Hint
+	}
+	return ""
+}
+
 type LoginResponse struct {
 	state                   protoimpl.MessageState `protogen:"open.v1"`
 	NeedsSSOLogin           bool                   `protobuf:"varint,1,opt,name=needsSSOLogin,proto3" json:"needsSSOLogin,omitempty"`
@@ -4608,7 +4617,7 @@ var File_daemon_proto protoreflect.FileDescriptor
 const file_daemon_proto_rawDesc = "" +
 	"\n" +
 	"\fdaemon.proto\x12\x06daemon\x1a google/protobuf/descriptor.proto\x1a\x1fgoogle/protobuf/timestamp.proto\x1a\x1egoogle/protobuf/duration.proto\"\x0e\n" +
-	"\fEmptyRequest\"\xc3\x0e\n" +
+	"\fEmptyRequest\"\xe5\x0e\n" +
 	"\fLoginRequest\x12\x1a\n" +
 	"\bsetupKey\x18\x01 \x01(\tR\bsetupKey\x12&\n" +
 	"\fpreSharedKey\x18\x02 \x01(\tB\x02\x18\x01R\fpreSharedKey\x12$\n" +
@@ -4645,7 +4654,8 @@ const file_daemon_proto_rawDesc = "" +
 	"\rblock_inbound\x18\x1d \x01(\bH\x10R\fblockInbound\x88\x01\x01\x12%\n" +
 	"\vprofileName\x18\x1e \x01(\tH\x11R\vprofileName\x88\x01\x01\x12\x1f\n" +
 	"\busername\x18\x1f \x01(\tH\x12R\busername\x88\x01\x01\x12\x15\n" +
-	"\x03mtu\x18  \x01(\x03H\x13R\x03mtu\x88\x01\x01B\x13\n" +
+	"\x03mtu\x18  \x01(\x03H\x13R\x03mtu\x88\x01\x01\x12\x17\n" +
+	"\x04hint\x18! \x01(\tH\x14R\x04hint\x88\x01\x01B\x13\n" +
 	"\x11_rosenpassEnabledB\x10\n" +
 	"\x0e_interfaceNameB\x10\n" +
 	"\x0e_wireguardPortB\x17\n" +
@@ -4665,7 +4675,8 @@ const file_daemon_proto_rawDesc = "" +
 	"\x0e_block_inboundB\x0e\n" +
 	"\f_profileNameB\v\n" +
 	"\t_usernameB\x06\n" +
-	"\x04_mtu\"\xb5\x01\n" +
+	"\x04_mtuB\a\n" +
+	"\x05_hint\"\xb5\x01\n" +
 	"\rLoginResponse\x12$\n" +
 	"\rneedsSSOLogin\x18\x01 \x01(\bR\rneedsSSOLogin\x12\x1a\n" +
 	"\buserCode\x18\x02 \x01(\tR\buserCode\x12(\n" +
diff --git a/client/proto/daemon.proto b/client/proto/daemon.proto
index 5b27b4d98..8d1080051 100644
--- a/client/proto/daemon.proto
+++ b/client/proto/daemon.proto
@@ -158,6 +158,9 @@ message LoginRequest {
   optional string username = 31;
 
   optional int64 mtu = 32;
+
+  // hint is used to pre-fill the email/username field during SSO authentication
+  optional string hint = 33;
 }
 
 message LoginResponse {
diff --git a/client/server/server.go b/client/server/server.go
index 3641e6f92..6699cdadc 100644
--- a/client/server/server.go
+++ b/client/server/server.go
@@ -483,7 +483,11 @@ func (s *Server) Login(callerCtx context.Context, msg *proto.LoginRequest) (*pro
 	state.Set(internal.StatusConnecting)
 
 	if msg.SetupKey == "" {
-		oAuthFlow, err := auth.NewOAuthFlow(ctx, config, msg.IsUnixDesktopClient)
+		hint := ""
+		if msg.Hint != nil {
+			hint = *msg.Hint
+		}
+		oAuthFlow, err := auth.NewOAuthFlow(ctx, config, msg.IsUnixDesktopClient, hint)
 		if err != nil {
 			state.Set(internal.StatusLoginFailed)
 			return nil, err
diff --git a/client/ui/client_ui.go b/client/ui/client_ui.go
index f4350b251..e580be56d 100644
--- a/client/ui/client_ui.go
+++ b/client/ui/client_ui.go
@@ -610,11 +610,20 @@ func (s *serviceClient) login(ctx context.Context, openURL bool) (*proto.LoginRe
 		return nil, fmt.Errorf("get current user: %w", err)
 	}
 
-	loginResp, err := conn.Login(ctx, &proto.LoginRequest{
+	loginReq := &proto.LoginRequest{
 		IsUnixDesktopClient: runtime.GOOS == "linux" || runtime.GOOS == "freebsd",
 		ProfileName:         &activeProf.Name,
 		Username:            &currUser.Username,
-	})
+	}
+
+	profileState, err := s.profileManager.GetProfileState(activeProf.Name)
+	if err != nil {
+		log.Debugf("failed to get profile state for login hint: %v", err)
+	} else if profileState.Email != "" {
+		loginReq.Hint = &profileState.Email
+	}
+
+	loginResp, err := conn.Login(ctx, loginReq)
 	if err != nil {
 		return nil, fmt.Errorf("login to management: %w", err)
 	}