diff --git a/internal/cmd/auth/login/login.go b/internal/cmd/auth/login/login.go
index 55f3663b0..3ba46f3d5 100644
--- a/internal/cmd/auth/login/login.go
+++ b/internal/cmd/auth/login/login.go
@@ -23,7 +23,7 @@ func NewCmd(p *print.Printer) *cobra.Command {
 				"$ stackit auth login"),
 		),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			err := auth.AuthorizeUser()
+			err := auth.AuthorizeUser(p, false)
 			if err != nil {
 				return fmt.Errorf("authorization failed: %w", err)
 			}
diff --git a/internal/pkg/auth/auth.go b/internal/pkg/auth/auth.go
index c7372599c..15f280b15 100644
--- a/internal/pkg/auth/auth.go
+++ b/internal/pkg/auth/auth.go
@@ -22,7 +22,7 @@ type tokenClaims struct {
 // It returns the configuration option that can be used to create an authenticated SDK client.
 //
 // If the user was logged in and the user session expired, reauthorizeUserRoutine is called to reauthenticate the user again.
-func AuthenticationConfig(p *print.Printer, reauthorizeUserRoutine func() error) (authCfgOption sdkConfig.ConfigurationOption, err error) {
+func AuthenticationConfig(p *print.Printer, reauthorizeUserRoutine func(p *print.Printer, isReauthentication bool) error) (authCfgOption sdkConfig.ConfigurationOption, err error) {
 	flow, err := GetAuthFlow()
 	if err != nil {
 		return nil, fmt.Errorf("get authentication flow: %w", err)
@@ -57,8 +57,7 @@ func AuthenticationConfig(p *print.Printer, reauthorizeUserRoutine func() error)
 		authCfgOption = sdkConfig.WithCustomAuth(keyFlow)
 	case AUTH_FLOW_USER_TOKEN:
 		if userSessionExpired {
-			p.Warn("Session expired, logging in again...\n")
-			err = reauthorizeUserRoutine()
+			err = reauthorizeUserRoutine(p, true)
 			if err != nil {
 				return nil, fmt.Errorf("user login: %w", err)
 			}
diff --git a/internal/pkg/auth/auth_test.go b/internal/pkg/auth/auth_test.go
index 18e61b158..9d4ee8778 100644
--- a/internal/pkg/auth/auth_test.go
+++ b/internal/pkg/auth/auth_test.go
@@ -192,7 +192,7 @@ func TestAuthenticationConfig(t *testing.T) {
 			}
 
 			reauthorizeUserCalled := false
-			reauthenticateUser := func() error {
+			reauthenticateUser := func(p *print.Printer, isReauthentication bool) error {
 				if reauthorizeUserCalled {
 					t.Errorf("user reauthorized more than once")
 				}
diff --git a/internal/pkg/auth/user_login.go b/internal/pkg/auth/user_login.go
index e3c0d3740..49dec2177 100644
--- a/internal/pkg/auth/user_login.go
+++ b/internal/pkg/auth/user_login.go
@@ -17,6 +17,8 @@ import (
 	"time"
 
 	"golang.org/x/oauth2"
+
+	"github.com/stackitcloud/stackit-cli/internal/pkg/print"
 )
 
 const (
@@ -36,7 +38,14 @@ type User struct {
 }
 
 // AuthorizeUser implements the PKCE OAuth2 flow.
-func AuthorizeUser() error {
+func AuthorizeUser(p *print.Printer, isReauthentication bool) error {
+	if isReauthentication {
+		err := p.PromptForEnter("Your session has expired, press Enter to login again...")
+		if err != nil {
+			return err
+		}
+	}
+
 	listener, err := net.Listen("tcp", ":0")
 	if err != nil {
 		return fmt.Errorf("bind port for login redirect: %w", err)
diff --git a/internal/pkg/auth/user_token_flow.go b/internal/pkg/auth/user_token_flow.go
index ab450d6f0..8abba51d0 100644
--- a/internal/pkg/auth/user_token_flow.go
+++ b/internal/pkg/auth/user_token_flow.go
@@ -14,7 +14,7 @@ import (
 
 type userTokenFlow struct {
 	printer                *print.Printer
-	reauthorizeUserRoutine func() error // Called if the user needs to login again
+	reauthorizeUserRoutine func(p *print.Printer, isReauthentication bool) error // Called if the user needs to login again
 	client                 *http.Client
 	authFlow               AuthFlow
 	accessToken            string
@@ -59,7 +59,6 @@ func (utf *userTokenFlow) RoundTrip(req *http.Request) (*http.Response, error) {
 	}
 
 	if !accessTokenValid {
-		utf.printer.Warn("Session expired, logging in again...")
 		err = reauthenticateUser(utf)
 		if err != nil {
 			return nil, fmt.Errorf("reauthenticate user: %w", err)
@@ -91,7 +90,7 @@ func loadVarsFromStorage(utf *userTokenFlow) error {
 }
 
 func reauthenticateUser(utf *userTokenFlow) error {
-	err := utf.reauthorizeUserRoutine()
+	err := utf.reauthorizeUserRoutine(utf.printer, true)
 	if err != nil {
 		return fmt.Errorf("authenticate user: %w", err)
 	}
diff --git a/internal/pkg/auth/user_token_flow_test.go b/internal/pkg/auth/user_token_flow_test.go
index 66831292f..b89f29bb8 100644
--- a/internal/pkg/auth/user_token_flow_test.go
+++ b/internal/pkg/auth/user_token_flow_test.go
@@ -271,7 +271,7 @@ func TestRoundTrip(t *testing.T) {
 				authorizeUserCalled: &authorizeUserCalled,
 				tokensRefreshed:     &tokensRefreshed,
 			}
-			authorizeUserRoutine := func() error {
+			authorizeUserRoutine := func(p *print.Printer, isReauthentication bool) error {
 				return reauthorizeUser(authorizeUserContext)
 			}
 
diff --git a/internal/pkg/print/print.go b/internal/pkg/print/print.go
index aadb64bed..3115a8d26 100644
--- a/internal/pkg/print/print.go
+++ b/internal/pkg/print/print.go
@@ -4,6 +4,7 @@ import (
 	"bufio"
 	"errors"
 	"fmt"
+
 	"log/slog"
 	"os"
 	"os/exec"
@@ -130,6 +131,26 @@ func (p *Printer) PromptForConfirmation(prompt string) error {
 	return fmt.Errorf("max number of wrong inputs")
 }
 
+// Prompts the user for confirmation by pressing Enter.
+//
+// Returns nil only if the user (explicitly) press directly enter.
+// Returns ErrAborted if the user press anything else before pressing enter.
+func (p *Printer) PromptForEnter(prompt string) error {
+	reader := bufio.NewReaderSize(p.Cmd.InOrStdin(), 1)
+
+	p.Cmd.PrintErr(prompt)
+	answer, err := reader.ReadByte()
+	if err != nil {
+		return fmt.Errorf("read user response: %w", err)
+	}
+
+	// ASCII code for Enter (newline) is 10.
+	if answer == 10 {
+		return nil
+	}
+	return errAborted
+}
+
 // Shows the content in the command's stdout using the "less" command
 // If output format is set to none, it does nothing
 func (p *Printer) PagerDisplay(content string) error {