diff --git a/token/jwt.go b/token/jwt.go
index a653e62..7073e27 100644
--- a/token/jwt.go
+++ b/token/jwt.go
@@ -247,8 +247,14 @@ func (j *Service) Set(w http.ResponseWriter, claims Claims) (Claims, error) {
 		return Claims{}, fmt.Errorf("failed to make token token: %w", err)
 	}
 
-	if j.SendJWTHeader {
+	// For OAuth handshake, always set cookies regardless of SendJWTHeader flag
+	// This allows the OAuth flow to complete successfully
+	needsCookies := claims.Handshake != nil
+
+	if j.SendJWTHeader && !needsCookies {
 		w.Header().Set(j.JWTHeaderKey, tokenString)
+		// reset cookies in case they were set by OAuth handshake
+		j.Reset(w)
 		return claims, nil
 	}
 
diff --git a/token/jwt_test.go b/token/jwt_test.go
index b1d5e81..cdb9986 100644
--- a/token/jwt_test.go
+++ b/token/jwt_test.go
@@ -258,13 +258,27 @@ func TestJWT_SendJWTHeader(t *testing.T) {
 		SendJWTHeader: true,
 	})
 
-	rr := httptest.NewRecorder()
-	_, err := j.Set(rr, testClaims)
-	assert.NoError(t, err)
-	cookies := rr.Result().Cookies()
-	t.Log(cookies)
-	require.Equal(t, 0, len(cookies), "no cookies set")
-	assert.Equal(t, testJwtValid, rr.Result().Header.Get("X-JWT"))
+	t.Run("with handshake", func(t *testing.T) {
+		rr := httptest.NewRecorder()
+		_, err := j.Set(rr, testClaims)
+		assert.NoError(t, err)
+		cookies := rr.Result().Cookies()
+		t.Log(cookies)
+		require.Equal(t, 2, len(cookies), "cookies are set for handshake")
+		assert.Equal(t, testJwtValid, rr.Result().Header.Get("X-JWT"))
+	})
+
+	t.Run("without handshake", func(t *testing.T) {
+		rr := httptest.NewRecorder()
+		claimsNoHandshake := testClaims
+		claimsNoHandshake.Handshake = nil
+		_, err := j.Set(rr, claimsNoHandshake)
+		assert.NoError(t, err)
+		cookies := rr.Result().Cookies()
+		t.Log(cookies)
+		require.Equal(t, 2, len(cookies), "empty cookies set for non-handshake")
+		assert.Equal(t, testJwtValidNoHandshake, rr.Result().Header.Get("X-JWT"))
+	})
 }
 
 func TestJWT_SetProlonged(t *testing.T) {
diff --git a/v2/token/jwt.go b/v2/token/jwt.go
index 22954ef..15b04d7 100644
--- a/v2/token/jwt.go
+++ b/v2/token/jwt.go
@@ -264,8 +264,14 @@ func (j *Service) Set(w http.ResponseWriter, claims Claims) (Claims, error) {
 		return Claims{}, fmt.Errorf("failed to make token token: %w", err)
 	}
 
-	if j.SendJWTHeader {
+	// For OAuth handshake, always set cookies regardless of SendJWTHeader flag
+	// This allows the OAuth flow to complete successfully
+	needsCookies := claims.Handshake != nil
+
+	if j.SendJWTHeader && !needsCookies {
 		w.Header().Set(j.JWTHeaderKey, tokenString)
+		// reset cookies in case they were set by OAuth handshake
+		j.Reset(w)
 		return claims, nil
 	}
 
@@ -274,6 +280,7 @@ func (j *Service) Set(w http.ResponseWriter, claims Claims) (Claims, error) {
 		cookieExpiration = int(j.CookieDuration.Seconds())
 	}
 
+	// Set cookies (always for OAuth handshake, or when SendJWTHeader is false)
 	jwtCookie := http.Cookie{Name: j.JWTCookieName, Value: tokenString, HttpOnly: true, Path: "/", Domain: j.JWTCookieDomain,
 		MaxAge: cookieExpiration, Secure: j.SecureCookies, SameSite: j.SameSite}
 	http.SetCookie(w, &jwtCookie)
diff --git a/v2/token/jwt_test.go b/v2/token/jwt_test.go
index ce71fde..d492b73 100644
--- a/v2/token/jwt_test.go
+++ b/v2/token/jwt_test.go
@@ -258,13 +258,27 @@ func TestJWT_SendJWTHeader(t *testing.T) {
 		SendJWTHeader: true,
 	})
 
-	rr := httptest.NewRecorder()
-	_, err := j.Set(rr, testClaims)
-	assert.NoError(t, err)
-	cookies := rr.Result().Cookies()
-	t.Log(cookies)
-	require.Equal(t, 0, len(cookies), "no cookies set")
-	assert.Equal(t, testJwtValid, rr.Result().Header.Get("X-JWT"))
+	t.Run("with handshake", func(t *testing.T) {
+		rr := httptest.NewRecorder()
+		_, err := j.Set(rr, testClaims)
+		assert.NoError(t, err)
+		cookies := rr.Result().Cookies()
+		t.Log(cookies)
+		require.Equal(t, 2, len(cookies), "cookies are set for handshake")
+		assert.Equal(t, testJwtValid, rr.Result().Header.Get("X-JWT"))
+	})
+
+	t.Run("without handshake", func(t *testing.T) {
+		rr := httptest.NewRecorder()
+		claimsNoHandshake := testClaims
+		claimsNoHandshake.Handshake = nil
+		_, err := j.Set(rr, claimsNoHandshake)
+		assert.NoError(t, err)
+		cookies := rr.Result().Cookies()
+		t.Log(cookies)
+		require.Equal(t, 2, len(cookies), "empty cookies set for non-handshake")
+		assert.Equal(t, testJwtValidNoHandshake, rr.Result().Header.Get("X-JWT"))
+	})
 }
 
 func TestJWT_SetProlonged(t *testing.T) {