diff --git a/backend/internal/repository/http_upstream_test.go b/backend/internal/repository/http_upstream_test.go
index 90cbd15ae3..d34e1df02c 100644
--- a/backend/internal/repository/http_upstream_test.go
+++ b/backend/internal/repository/http_upstream_test.go
@@ -15,6 +15,51 @@ import (
 	"github.com/stretchr/testify/suite"
 )
 
+func TestHTTPUpstreamDoAppliesGrokCLIIdentityBeforeRoundTrip(t *testing.T) {
+	t.Setenv("XAI_GROK_CLI_VERSION", "")
+
+	upstream := NewHTTPUpstream(nil)
+	svc, ok := upstream.(*httpUpstreamService)
+	require.True(t, ok)
+
+	const accountID int64 = 4079
+	isolation := svc.getIsolationMode()
+	profile := service.HTTPUpstreamProfileDefault
+	proxyKey := directProxyKey
+	protocolMode := svc.resolveProtocolMode(profile, proxyKey, nil)
+	settings := svc.resolvePoolSettings(isolation, 1)
+	settings = svc.applyProfilePoolSettings(settings, profile)
+	cacheKey := buildCacheKey(isolation, proxyKey, accountID, protocolMode)
+
+	var capturedHeaders http.Header
+	svc.clients[cacheKey] = &upstreamClientEntry{
+		client: &http.Client{Transport: roundTripFunc(func(req *http.Request) (*http.Response, error) {
+			capturedHeaders = req.Header.Clone()
+			return &http.Response{
+				StatusCode: http.StatusOK,
+				Header:     make(http.Header),
+				Body:       http.NoBody,
+				Request:    req,
+			}, nil
+		})},
+		proxyKey:     proxyKey,
+		poolKey:      buildPoolKey(settings, protocolMode),
+		protocolMode: protocolMode,
+	}
+
+	req, err := http.NewRequest(http.MethodPost, "https://cli-chat-proxy.grok.com/v1/responses", nil)
+	require.NoError(t, err)
+	req.Header.Set("User-Agent", "sub2api-grok/1.0")
+
+	resp, err := svc.Do(req, "", accountID, 1)
+	require.NoError(t, err)
+	require.NoError(t, resp.Body.Close())
+
+	require.Equal(t, "0.2.93", capturedHeaders.Get("x-grok-client-version"))
+	require.Equal(t, "xai-grok-cli", capturedHeaders.Get("X-XAI-Token-Auth"))
+	require.Equal(t, "xai-grok-workspace/0.2.93", capturedHeaders.Get("User-Agent"))
+}
+
 func TestApplyGrokCLIProxyHeaders(t *testing.T) {
 	t.Run("uses pinned stable version for the CLI proxy", func(t *testing.T) {
 		t.Setenv("XAI_GROK_CLI_VERSION", "")