diff --git a/CHANGELOG.md b/CHANGELOG.md
index 55e781a17..741755226 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,3 +1,7 @@
+## Release (2025-YY-XX)
+- `core`: [v0.17.2](core/CHANGELOG.md#v0172-2025-05-22)
+  - **Bugfix:** Access tokens generated via key flow authentication are refreshed 5 seconds before expiration to prevent timing issues with upstream systems which could lead to unexpected 401 error responses
+
 ## Release (2025-05-15)
 - `alb`:
   - [v0.4.0](services/alb/CHANGELOG.md#v040-2025-05-15)
diff --git a/core/CHANGELOG.md b/core/CHANGELOG.md
index c38237322..5b070c901 100644
--- a/core/CHANGELOG.md
+++ b/core/CHANGELOG.md
@@ -1,3 +1,6 @@
+## v0.17.2 (2025-05-22)
+- **Bugfix:** Access tokens generated via key flow authentication are refreshed 5 seconds before expiration to prevent timing issues with upstream systems which could lead to unexpected 401 error responses
+
 ## v0.17.1 (2025-04-09)
 - **Improvement:** Improve error message for key flow authentication
 
diff --git a/core/clients/key_flow.go b/core/clients/key_flow.go
index c529a6f80..589774314 100644
--- a/core/clients/key_flow.go
+++ b/core/clients/key_flow.go
@@ -32,6 +32,8 @@ const (
 	tokenAPI              = "https://service-account.api.stackit.cloud/token" //nolint:gosec // linter false positive
 	defaultTokenType      = "Bearer"
 	defaultScope          = ""
+
+	defaultTokenExpirationLeeway = time.Second * 5
 )
 
 // KeyFlow handles auth with SA key
@@ -45,6 +47,10 @@ type KeyFlow struct {
 
 	tokenMutex sync.RWMutex
 	token      *TokenResponseBody
+
+	// If the current access token would expire in less than TokenExpirationLeeway,
+	// the client will refresh it early to prevent clock skew or other timing issues.
+	tokenExpirationLeeway time.Duration
 }
 
 // KeyFlowConfig is the flow config
@@ -129,6 +135,8 @@ func (c *KeyFlow) Init(cfg *KeyFlowConfig) error {
 		c.config.TokenUrl = tokenAPI
 	}
 
+	c.tokenExpirationLeeway = defaultTokenExpirationLeeway
+
 	if c.rt = cfg.HTTPTransport; c.rt == nil {
 		c.rt = http.DefaultTransport
 	}
@@ -204,7 +212,7 @@ func (c *KeyFlow) GetAccessToken() (string, error) {
 	}
 	c.tokenMutex.RUnlock()
 
-	accessTokenExpired, err := tokenExpired(accessToken)
+	accessTokenExpired, err := tokenExpired(accessToken, c.tokenExpirationLeeway)
 	if err != nil {
 		return "", fmt.Errorf("check access token is expired: %w", err)
 	}
@@ -252,6 +260,10 @@ func (c *KeyFlow) validate() error {
 	}
 	c.privateKeyPEM = pem.EncodeToMemory(privKeyPEM)
 
+	if c.tokenExpirationLeeway < 0 {
+		return fmt.Errorf("token expiration leeway cannot be negative")
+	}
+
 	return nil
 }
 
@@ -268,7 +280,7 @@ func (c *KeyFlow) recreateAccessToken() error {
 	}
 	c.tokenMutex.RUnlock()
 
-	refreshTokenExpired, err := tokenExpired(refreshToken)
+	refreshTokenExpired, err := tokenExpired(refreshToken, c.tokenExpirationLeeway)
 	if err != nil {
 		return err
 	}
@@ -389,7 +401,7 @@ func (c *KeyFlow) parseTokenResponse(res *http.Response) error {
 	return nil
 }
 
-func tokenExpired(token string) (bool, error) {
+func tokenExpired(token string, tokenExpirationLeeway time.Duration) (bool, error) {
 	if token == "" {
 		return true, nil
 	}
@@ -400,11 +412,15 @@ func tokenExpired(token string) (bool, error) {
 	if err != nil {
 		return false, fmt.Errorf("parse token: %w", err)
 	}
+
 	expirationTimestampNumeric, err := tokenParsed.Claims.GetExpirationTime()
 	if err != nil {
 		return false, fmt.Errorf("get expiration timestamp: %w", err)
 	}
-	expirationTimestamp := expirationTimestampNumeric.Time
-	now := time.Now()
-	return now.After(expirationTimestamp), nil
+
+	// Pretend to be `tokenExpirationLeeway` into the future to avoid token expiring
+	// between retrieving the token and upstream systems validating it.
+	now := time.Now().Add(tokenExpirationLeeway)
+
+	return now.After(expirationTimestampNumeric.Time), nil
 }
diff --git a/core/clients/key_flow_test.go b/core/clients/key_flow_test.go
index b37b9593f..78dc43a3b 100644
--- a/core/clients/key_flow_test.go
+++ b/core/clients/key_flow_test.go
@@ -190,6 +190,7 @@ func TestSetToken(t *testing.T) {
 }
 
 func TestTokenExpired(t *testing.T) {
+	tokenExpirationLeeway := 5 * time.Second
 	tests := []struct {
 		desc              string
 		tokenInvalid      bool
@@ -209,6 +210,12 @@ func TestTokenExpired(t *testing.T) {
 			expectedErr:       false,
 			expectedIsExpired: true,
 		},
+		{
+			desc:              "token almost expired",
+			tokenExpiresAt:    time.Now().Add(tokenExpirationLeeway),
+			expectedErr:       false,
+			expectedIsExpired: true,
+		},
 		{
 			desc:         "token invalid",
 			tokenInvalid: true,
@@ -229,7 +236,7 @@ func TestTokenExpired(t *testing.T) {
 				}
 			}
 
-			isExpired, err := tokenExpired(token)
+			isExpired, err := tokenExpired(token, tokenExpirationLeeway)
 			if err != nil && !tt.expectedErr {
 				t.Fatalf("failed on valid input: %v", err)
 			}