diff --git a/backend/internal/service/openai_compat_model_test.go b/backend/internal/service/openai_compat_model_test.go
index a897e219..e222b093 100644
--- a/backend/internal/service/openai_compat_model_test.go
+++ b/backend/internal/service/openai_compat_model_test.go
@@ -480,6 +480,61 @@ func TestForwardAsAnthropic_AttachesPreviousResponseIDForCompatContinuation(t *t
 	require.Equal(t, "second", gjson.GetBytes(upstream.lastBody, "input.1.content.0.text").String())
 }
 
+func TestForwardAsAnthropic_PreviousResponseIDKeepsMultiToolCallContext(t *testing.T) {
+	t.Parallel()
+	gin.SetMode(gin.TestMode)
+
+	upstream := &httpUpstreamRecorder{}
+	svc := &OpenAIGatewayService{
+		httpUpstream: upstream,
+		cfg:          &config.Config{Security: config.SecurityConfig{URLAllowlist: config.URLAllowlistConfig{Enabled: false}}},
+	}
+	account := &Account{
+		ID:          1,
+		Name:        "openai-apikey",
+		Platform:    PlatformOpenAI,
+		Type:        AccountTypeAPIKey,
+		Concurrency: 1,
+		Credentials: map[string]any{
+			"api_key":  "sk-test",
+			"base_url": "https://api.openai.com/v1",
+		},
+	}
+
+	firstBody := []byte(`{"model":"claude-sonnet-4-5","max_tokens":16,"messages":[{"role":"user","content":"inspect files"}],"stream":false}`)
+	upstream.resp = openAICompatSSECompletedResponse("resp_first_tools", "gpt-5.3-codex")
+	firstRec := httptest.NewRecorder()
+	firstCtx, _ := gin.CreateTestContext(firstRec)
+	firstCtx.Request = httptest.NewRequest(http.MethodPost, "/v1/messages", bytes.NewReader(firstBody))
+	firstCtx.Request.Header.Set("Content-Type", "application/json")
+
+	firstResult, err := svc.ForwardAsAnthropic(context.Background(), firstCtx, account, firstBody, "stable-cache-key", "gpt-5.3-codex")
+	require.NoError(t, err)
+	require.NotNil(t, firstResult)
+
+	secondBody := []byte(`{"model":"claude-sonnet-4-5","max_tokens":16,"messages":[{"role":"user","content":"inspect files"},{"role":"assistant","content":[{"type":"tool_use","id":"call_one","name":"Read","input":{"file_path":"a.go"}},{"type":"tool_use","id":"call_two","name":"Read","input":{"file_path":"b.go"}}]},{"role":"user","content":[{"type":"tool_result","tool_use_id":"call_one","content":"package a"},{"type":"tool_result","tool_use_id":"call_two","content":"package b"},{"type":"text","text":"continue"}]}],"tools":[{"name":"Read","description":"read a file","input_schema":{"type":"object","properties":{"file_path":{"type":"string"}}}}],"stream":false}`)
+	upstream.resp = openAICompatSSECompletedResponse("resp_second_tools", "gpt-5.3-codex")
+	secondRec := httptest.NewRecorder()
+	secondCtx, _ := gin.CreateTestContext(secondRec)
+	secondCtx.Request = httptest.NewRequest(http.MethodPost, "/v1/messages", bytes.NewReader(secondBody))
+	secondCtx.Request.Header.Set("Content-Type", "application/json")
+
+	secondResult, err := svc.ForwardAsAnthropic(context.Background(), secondCtx, account, secondBody, "stable-cache-key", "gpt-5.3-codex")
+	require.NoError(t, err)
+	require.NotNil(t, secondResult)
+	require.Equal(t, "resp_first_tools", gjson.GetBytes(upstream.lastBody, "previous_response_id").String())
+
+	require.Equal(t, "function_call", gjson.GetBytes(upstream.lastBody, "input.1.type").String())
+	require.Equal(t, "call_one", gjson.GetBytes(upstream.lastBody, "input.1.call_id").String())
+	require.Equal(t, "function_call", gjson.GetBytes(upstream.lastBody, "input.2.type").String())
+	require.Equal(t, "call_two", gjson.GetBytes(upstream.lastBody, "input.2.call_id").String())
+	require.Equal(t, "function_call_output", gjson.GetBytes(upstream.lastBody, "input.3.type").String())
+	require.Equal(t, "call_one", gjson.GetBytes(upstream.lastBody, "input.3.call_id").String())
+	require.Equal(t, "function_call_output", gjson.GetBytes(upstream.lastBody, "input.4.type").String())
+	require.Equal(t, "call_two", gjson.GetBytes(upstream.lastBody, "input.4.call_id").String())
+	require.Equal(t, "continue", gjson.GetBytes(upstream.lastBody, "input.5.content.0.text").String())
+}
+
 func TestForwardAsAnthropic_ReplaysWithoutContinuationWhenPreviousResponseMissing(t *testing.T) {
 	t.Parallel()
 	gin.SetMode(gin.TestMode)
diff --git a/backend/internal/service/openai_messages_continuation.go b/backend/internal/service/openai_messages_continuation.go
index 57d04784..b3c900fb 100644
--- a/backend/internal/service/openai_messages_continuation.go
+++ b/backend/internal/service/openai_messages_continuation.go
@@ -37,10 +37,7 @@ func trimAnthropicCompatResponsesInputToLatestTurn(req *apicompat.ResponsesReque
 		return
 	}
 
-	start := len(items) - 1
-	for start > 0 && items[start].Type == "function_call_output" {
-		start--
-	}
+	start := latestAnthropicCompatResponsesInputTurnStart(items)
 	trimmed := append([]apicompat.ResponsesInputItem(nil), items[start:]...)
 	if len(trimmed) == len(items) {
 		return
@@ -50,6 +47,63 @@ func trimAnthropicCompatResponsesInputToLatestTurn(req *apicompat.ResponsesReque
 	}
 }
 
+func latestAnthropicCompatResponsesInputTurnStart(items []apicompat.ResponsesInputItem) int {
+	if len(items) == 0 {
+		return 0
+	}
+
+	start := len(items) - 1
+	last := items[start]
+	switch {
+	case last.Type == "function_call_output":
+		for start > 0 && items[start-1].Type == "function_call_output" {
+			start--
+		}
+	case last.Type == "message" && last.Role == "user":
+		for start > 0 && items[start-1].Type == "function_call_output" {
+			start--
+		}
+	default:
+		return start
+	}
+
+	return expandAnthropicCompatResponsesInputToolCallStart(items, start)
+}
+
+func expandAnthropicCompatResponsesInputToolCallStart(items []apicompat.ResponsesInputItem, start int) int {
+	if start < 0 || start >= len(items) {
+		return start
+	}
+
+	needed := make(map[string]struct{})
+	for i := start; i < len(items); i++ {
+		if items[i].Type != "function_call_output" {
+			continue
+		}
+		callID := strings.TrimSpace(items[i].CallID)
+		if callID != "" {
+			needed[callID] = struct{}{}
+		}
+	}
+	if len(needed) == 0 {
+		return start
+	}
+
+	expandedStart := start
+	for i := start - 1; i >= 0 && len(needed) > 0; i-- {
+		if items[i].Type != "function_call" {
+			continue
+		}
+		callID := strings.TrimSpace(items[i].CallID)
+		if _, ok := needed[callID]; !ok {
+			continue
+		}
+		delete(needed, callID)
+		expandedStart = i
+	}
+	return expandedStart
+}
+
 func isOpenAICompatPreviousResponseNotFound(statusCode int, upstreamMsg string, upstreamBody []byte) bool {
 	if statusCode != http.StatusBadRequest && statusCode != http.StatusNotFound {
 		return false