diff --git a/backend/internal/handler/concurrency_error_response.go b/backend/internal/handler/concurrency_error_response.go
new file mode 100644
index 00000000..52abf735
--- /dev/null
+++ b/backend/internal/handler/concurrency_error_response.go
@@ -0,0 +1,27 @@
+package handler
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"net/http"
+)
+
+const statusClientClosedRequest = 499
+
+func concurrencyErrorResponse(err error, slotType string) (int, string, string) {
+	var concurrencyErr *ConcurrencyError
+	if errors.As(err, &concurrencyErr) {
+		if concurrencyErr.SlotType != "" {
+			slotType = concurrencyErr.SlotType
+		}
+		return http.StatusTooManyRequests, "rate_limit_error",
+			fmt.Sprintf("Concurrency limit exceeded for %s, please retry later", slotType)
+	}
+
+	if errors.Is(err, context.Canceled) {
+		return statusClientClosedRequest, "api_error", "context canceled"
+	}
+
+	return http.StatusServiceUnavailable, "api_error", "Service temporarily unavailable, please retry later"
+}
diff --git a/backend/internal/handler/concurrency_error_response_test.go b/backend/internal/handler/concurrency_error_response_test.go
new file mode 100644
index 00000000..a2e6b9ab
--- /dev/null
+++ b/backend/internal/handler/concurrency_error_response_test.go
@@ -0,0 +1,63 @@
+package handler
+
+import (
+	"context"
+	"errors"
+	"net/http"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestConcurrencyErrorResponse(t *testing.T) {
+	tests := []struct {
+		name        string
+		err         error
+		slotType    string
+		wantStatus  int
+		wantType    string
+		wantMessage string
+	}{
+		{
+			name:        "true concurrency timeout remains rate limit",
+			err:         &ConcurrencyError{SlotType: "account", IsTimeout: true},
+			slotType:    "user",
+			wantStatus:  http.StatusTooManyRequests,
+			wantType:    "rate_limit_error",
+			wantMessage: "Concurrency limit exceeded for account, please retry later",
+		},
+		{
+			name:        "client cancellation is not classified as concurrency limit",
+			err:         context.Canceled,
+			slotType:    "user",
+			wantStatus:  statusClientClosedRequest,
+			wantType:    "api_error",
+			wantMessage: "context canceled",
+		},
+		{
+			name:        "deadline exceeded is service unavailable",
+			err:         context.DeadlineExceeded,
+			slotType:    "user",
+			wantStatus:  http.StatusServiceUnavailable,
+			wantType:    "api_error",
+			wantMessage: "Service temporarily unavailable, please retry later",
+		},
+		{
+			name:        "redis acquire error is service unavailable",
+			err:         errors.New("redis unavailable"),
+			slotType:    "user",
+			wantStatus:  http.StatusServiceUnavailable,
+			wantType:    "api_error",
+			wantMessage: "Service temporarily unavailable, please retry later",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			status, errType, message := concurrencyErrorResponse(tt.err, tt.slotType)
+			require.Equal(t, tt.wantStatus, status)
+			require.Equal(t, tt.wantType, errType)
+			require.Equal(t, tt.wantMessage, message)
+		})
+	}
+}
diff --git a/backend/internal/handler/gateway_handler.go b/backend/internal/handler/gateway_handler.go
index 4695a791..a24611f9 100644
--- a/backend/internal/handler/gateway_handler.go
+++ b/backend/internal/handler/gateway_handler.go
@@ -1471,10 +1471,10 @@ func (h *GatewayHandler) calculateSubscriptionRemaining(group *service.Group, su
 	return min
 }
 
-// handleConcurrencyError handles concurrency-related errors with proper 429 response
+// handleConcurrencyError handles concurrency-related acquire errors.
 func (h *GatewayHandler) handleConcurrencyError(c *gin.Context, err error, slotType string, streamStarted bool) {
-	h.handleStreamingAwareError(c, http.StatusTooManyRequests, "rate_limit_error",
-		fmt.Sprintf("Concurrency limit exceeded for %s, please retry later", slotType), streamStarted)
+	status, errType, message := concurrencyErrorResponse(err, slotType)
+	h.handleStreamingAwareError(c, status, errType, message, streamStarted)
 }
 
 func (h *GatewayHandler) handleFailoverExhausted(c *gin.Context, failoverErr *service.UpstreamFailoverError, platform string, streamStarted bool) {
diff --git a/backend/internal/handler/gateway_helper.go b/backend/internal/handler/gateway_helper.go
index 09e6c09b..e4897502 100644
--- a/backend/internal/handler/gateway_helper.go
+++ b/backend/internal/handler/gateway_helper.go
@@ -336,6 +336,9 @@ func (h *ConcurrencyHelper) waitForSlotWithPingTimeout(c *gin.Context, slotType
 	for {
 		select {
 		case <-ctx.Done():
+			if parentErr := c.Request.Context().Err(); parentErr != nil {
+				return nil, parentErr
+			}
 			return nil, &ConcurrencyError{
 				SlotType:  slotType,
 				IsTimeout: true,
diff --git a/backend/internal/handler/gateway_helper_hotpath_test.go b/backend/internal/handler/gateway_helper_hotpath_test.go
index 4a677199..d57c396c 100644
--- a/backend/internal/handler/gateway_helper_hotpath_test.go
+++ b/backend/internal/handler/gateway_helper_hotpath_test.go
@@ -280,6 +280,25 @@ func TestWaitForSlotWithPingTimeout_TimeoutAndStreamPing(t *testing.T) {
 	})
 }
 
+func TestWaitForSlotWithPingTimeout_ParentContextCanceled(t *testing.T) {
+	cache := &helperConcurrencyCacheStub{
+		accountSeq: []bool{false},
+	}
+	concurrency := service.NewConcurrencyService(cache)
+	helper := NewConcurrencyHelper(concurrency, SSEPingFormatNone, 5*time.Millisecond)
+	c, _ := newHelperTestContext(http.MethodPost, "/v1/messages")
+	reqCtx, cancel := context.WithCancel(c.Request.Context())
+	c.Request = c.Request.WithContext(reqCtx)
+	cancel()
+
+	streamStarted := false
+	release, err := helper.waitForSlotWithPingTimeout(c, "account", 101, 2, time.Second, false, &streamStarted, true)
+	require.Nil(t, release)
+	require.ErrorIs(t, err, context.Canceled)
+	var cErr *ConcurrencyError
+	require.False(t, errors.As(err, &cErr))
+}
+
 func TestWaitForSlotWithPingTimeout_AcquireError(t *testing.T) {
 	errCache := &helperConcurrencyCacheStubWithError{
 		err: errors.New("redis unavailable"),
diff --git a/backend/internal/handler/openai_gateway_handler.go b/backend/internal/handler/openai_gateway_handler.go
index 1d661748..979aaa1c 100644
--- a/backend/internal/handler/openai_gateway_handler.go
+++ b/backend/internal/handler/openai_gateway_handler.go
@@ -1688,10 +1688,10 @@ func (h *OpenAIGatewayHandler) acquireImageGenerationSlot(c *gin.Context, stream
 	return nil, false
 }
 
-// handleConcurrencyError handles concurrency-related errors with proper 429 response
+// handleConcurrencyError handles concurrency-related acquire errors.
 func (h *OpenAIGatewayHandler) handleConcurrencyError(c *gin.Context, err error, slotType string, streamStarted bool) {
-	h.handleStreamingAwareError(c, http.StatusTooManyRequests, "rate_limit_error",
-		fmt.Sprintf("Concurrency limit exceeded for %s, please retry later", slotType), streamStarted)
+	status, errType, message := concurrencyErrorResponse(err, slotType)
+	h.handleStreamingAwareError(c, status, errType, message, streamStarted)
 }
 
 func (h *OpenAIGatewayHandler) handleFailoverExhausted(c *gin.Context, failoverErr *service.UpstreamFailoverError, streamStarted bool) {