Fix context background and silent JWT

cmd/gateway/main.go

@@ -110,7 +110,7 @@ func main() {
 		Issuer:   cfg.Auth.Issuer,
 		Audience: cfg.Auth.Audience,
 	}
-	authMiddleware, err := auth.New(authConfig)
+	authMiddleware, err := auth.New(authConfig, logger)
 	if err != nil {
 		logger.Error("failed to initialize auth", slog.String("error", err.Error()))
 		os.Exit(1)

internal/auth/auth.go

@@ -6,6 +6,7 @@ import (
 	"encoding/base64"
 	"encoding/json"
 	"fmt"
+	"log/slog"
 	"math/big"
 	"net/http"
 	"strings"
@@ -28,12 +29,13 @@ type Middleware struct {
 	keys   map[string]*rsa.PublicKey
 	mu     sync.RWMutex
 	client *http.Client
+	logger *slog.Logger
 }
 
 // New creates an authentication middleware.
-func New(cfg Config) (*Middleware, error) {
+func New(cfg Config, logger *slog.Logger) (*Middleware, error) {
 	if !cfg.Enabled {
-		return &Middleware{cfg: cfg}, nil
+		return &Middleware{cfg: cfg, logger: logger}, nil
 	}
 
 	if cfg.Issuer == "" {
@@ -44,6 +46,7 @@ func New(cfg Config) (*Middleware, error) {
 		cfg:    cfg,
 		keys:   make(map[string]*rsa.PublicKey),
 		client: &http.Client{Timeout: 10 * time.Second},
+		logger: logger,
 	}
 
 	// Fetch JWKS on startup
@@ -255,6 +258,15 @@ func (m *Middleware) periodicRefresh() {
 	defer ticker.Stop()
 
 	for range ticker.C {
-		_ = m.refreshJWKS()
+		if err := m.refreshJWKS(); err != nil {
+			m.logger.Error("failed to refresh JWKS",
+				slog.String("issuer", m.cfg.Issuer),
+				slog.String("error", err.Error()),
+			)
+		} else {
+			m.logger.Debug("successfully refreshed JWKS",
+				slog.String("issuer", m.cfg.Issuer),
+			)
+		}
 	}
 }

internal/auth/auth_test.go

@@ -7,6 +7,7 @@ import (
 	"encoding/base64"
 	"encoding/json"
 	"fmt"
+	"log/slog"
 	"math/big"
 	"net/http"
 	"net/http/httptest"
@@ -213,7 +214,7 @@ func TestNew(t *testing.T) {
 				}
 			}
 
-			m, err := New(tt.config)
+			m, err := New(tt.config, slog.Default())
 
 			if tt.expectError {
 				assert.Error(t, err)
@@ -239,7 +240,7 @@ func TestMiddleware_Handler(t *testing.T) {
 		Issuer:   server.server.URL,
 		Audience: testAudience,
 	}
-	m, err := New(cfg)
+	m, err := New(cfg, slog.Default())
 	require.NoError(t, err)
 
 	// Create a test handler that echoes back claims
@@ -415,7 +416,7 @@ func TestMiddleware_Handler_DisabledAuth(t *testing.T) {
 	cfg := Config{
 		Enabled: false,
 	}
-	m, err := New(cfg)
+	m, err := New(cfg, slog.Default())
 	require.NoError(t, err)
 
 	testHandler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
@@ -442,7 +443,7 @@ func TestValidateToken(t *testing.T) {
 		Issuer:   server.server.URL,
 		Audience: testAudience,
 	}
-	m, err := New(cfg)
+	m, err := New(cfg, slog.Default())
 	require.NoError(t, err)
 
 	tests := []struct {
@@ -665,7 +666,7 @@ func TestValidateToken_NoAudienceConfigured(t *testing.T) {
 		Issuer:   server.server.URL,
 		Audience: "", // No audience required
 	}
-	m, err := New(cfg)
+	m, err := New(cfg, slog.Default())
 	require.NoError(t, err)
 
 	// Token without audience should be valid
@@ -897,7 +898,7 @@ func TestRefreshJWKS_Concurrency(t *testing.T) {
 		Issuer:   server.server.URL,
 		Audience: testAudience,
 	}
-	m, err := New(cfg)
+	m, err := New(cfg, slog.Default())
 	require.NoError(t, err)
 
 	// Trigger concurrent refreshes
@@ -982,7 +983,7 @@ func TestMiddleware_IssuerWithTrailingSlash(t *testing.T) {
 		Issuer:   server.server.URL + "/", // Trailing slash
 		Audience: testAudience,
 	}
-	m, err := New(cfg)
+	m, err := New(cfg, slog.Default())
 	require.NoError(t, err)
 	require.NotNil(t, m)
 	assert.Len(t, m.keys, 1)

internal/conversation/conversation.go

@@ -1,6 +1,7 @@
 package conversation
 
 import (
+	"context"
 	"sync"
 	"time"
 
@@ -9,10 +10,10 @@ import (
 
 // Store defines the interface for conversation storage backends.
 type Store interface {
-	Get(id string) (*Conversation, error)
+	Get(ctx context.Context, id string) (*Conversation, error)
-	Create(id string, model string, messages []api.Message) (*Conversation, error)
+	Create(ctx context.Context, id string, model string, messages []api.Message) (*Conversation, error)
-	Append(id string, messages ...api.Message) (*Conversation, error)
+	Append(ctx context.Context, id string, messages ...api.Message) (*Conversation, error)
-	Delete(id string) error
+	Delete(ctx context.Context, id string) error
 	Size() int
 	Close() error
 }
@@ -51,7 +52,7 @@ func NewMemoryStore(ttl time.Duration) *MemoryStore {
 }
 
 // Get retrieves a conversation by ID. Returns a deep copy to prevent data races.
-func (s *MemoryStore) Get(id string) (*Conversation, error) {
+func (s *MemoryStore) Get(ctx context.Context, id string) (*Conversation, error) {
 	s.mu.RLock()
 	defer s.mu.RUnlock()
 
@@ -74,7 +75,7 @@ func (s *MemoryStore) Get(id string) (*Conversation, error) {
 }
 
 // Create creates a new conversation with the given messages.
-func (s *MemoryStore) Create(id string, model string, messages []api.Message) (*Conversation, error) {
+func (s *MemoryStore) Create(ctx context.Context, id string, model string, messages []api.Message) (*Conversation, error) {
 	s.mu.Lock()
 	defer s.mu.Unlock()
 
@@ -105,7 +106,7 @@ func (s *MemoryStore) Create(id string, model string, messages []api.Message) (*
 }
 
 // Append adds new messages to an existing conversation.
-func (s *MemoryStore) Append(id string, messages ...api.Message) (*Conversation, error) {
+func (s *MemoryStore) Append(ctx context.Context, id string, messages ...api.Message) (*Conversation, error) {
 	s.mu.Lock()
 	defer s.mu.Unlock()
 
@@ -131,7 +132,7 @@ func (s *MemoryStore) Append(id string, messages ...api.Message) (*Conversation,
 }
 
 // Delete removes a conversation from the store.
-func (s *MemoryStore) Delete(id string) error {
+func (s *MemoryStore) Delete(ctx context.Context, id string) error {
 	s.mu.Lock()
 	defer s.mu.Unlock()
 

internal/conversation/conversation_test.go

@@ -1,6 +1,7 @@
 package conversation
 
 import (
+	"context"
 	"testing"
 	"time"
 
@@ -21,7 +22,7 @@ func TestMemoryStore_CreateAndGet(t *testing.T) {
 		},
 	}
 
-	conv, err := store.Create("test-id", "gpt-4", messages)
+	conv, err := store.Create(context.Background(),"test-id", "gpt-4", messages)
 	require.NoError(t, err)
 	require.NotNil(t, conv)
 	assert.Equal(t, "test-id", conv.ID)
@@ -29,7 +30,7 @@ func TestMemoryStore_CreateAndGet(t *testing.T) {
 	assert.Len(t, conv.Messages, 1)
 	assert.Equal(t, "Hello", conv.Messages[0].Content[0].Text)
 
-	retrieved, err := store.Get("test-id")
+	retrieved, err := store.Get(context.Background(),"test-id")
 	require.NoError(t, err)
 	require.NotNil(t, retrieved)
 	assert.Equal(t, conv.ID, retrieved.ID)
@@ -40,7 +41,7 @@ func TestMemoryStore_CreateAndGet(t *testing.T) {
 func TestMemoryStore_GetNonExistent(t *testing.T) {
 	store := NewMemoryStore(1 * time.Hour)
 
-	conv, err := store.Get("nonexistent")
+	conv, err := store.Get(context.Background(),"nonexistent")
 	require.NoError(t, err)
 	assert.Nil(t, conv, "should return nil for nonexistent conversation")
 }
@@ -57,7 +58,7 @@ func TestMemoryStore_Append(t *testing.T) {
 		},
 	}
 
-	_, err := store.Create("test-id", "gpt-4", initialMessages)
+	_, err := store.Create(context.Background(),"test-id", "gpt-4", initialMessages)
 	require.NoError(t, err)
 
 	newMessages := []api.Message{
@@ -75,7 +76,7 @@ func TestMemoryStore_Append(t *testing.T) {
 		},
 	}
 
-	conv, err := store.Append("test-id", newMessages...)
+	conv, err := store.Append(context.Background(),"test-id", newMessages...)
 	require.NoError(t, err)
 	require.NotNil(t, conv)
 	assert.Len(t, conv.Messages, 3, "should have all messages")
@@ -94,7 +95,7 @@ func TestMemoryStore_AppendNonExistent(t *testing.T) {
 		},
 	}
 
-	conv, err := store.Append("nonexistent", newMessage)
+	conv, err := store.Append(context.Background(),"nonexistent", newMessage)
 	require.NoError(t, err)
 	assert.Nil(t, conv, "should return nil when appending to nonexistent conversation")
 }
@@ -111,20 +112,20 @@ func TestMemoryStore_Delete(t *testing.T) {
 		},
 	}
 
-	_, err := store.Create("test-id", "gpt-4", messages)
+	_, err := store.Create(context.Background(),"test-id", "gpt-4", messages)
 	require.NoError(t, err)
 
 	// Verify it exists
-	conv, err := store.Get("test-id")
+	conv, err := store.Get(context.Background(),"test-id")
 	require.NoError(t, err)
 	assert.NotNil(t, conv)
 
 	// Delete it
-	err = store.Delete("test-id")
+	err = store.Delete(context.Background(),"test-id")
 	require.NoError(t, err)
 
 	// Verify it's gone
-	conv, err = store.Get("test-id")
+	conv, err = store.Get(context.Background(),"test-id")
 	require.NoError(t, err)
 	assert.Nil(t, conv, "conversation should be deleted")
 }
@@ -138,15 +139,15 @@ func TestMemoryStore_Size(t *testing.T) {
 		{Role: "user", Content: []api.ContentBlock{{Type: "input_text", Text: "Hello"}}},
 	}
 
-	_, err := store.Create("conv-1", "gpt-4", messages)
+	_, err := store.Create(context.Background(),"conv-1", "gpt-4", messages)
 	require.NoError(t, err)
 	assert.Equal(t, 1, store.Size())
 
-	_, err = store.Create("conv-2", "gpt-4", messages)
+	_, err = store.Create(context.Background(),"conv-2", "gpt-4", messages)
 	require.NoError(t, err)
 	assert.Equal(t, 2, store.Size())
 
-	err = store.Delete("conv-1")
+	err = store.Delete(context.Background(),"conv-1")
 	require.NoError(t, err)
 	assert.Equal(t, 1, store.Size())
 }
@@ -159,14 +160,14 @@ func TestMemoryStore_ConcurrentAccess(t *testing.T) {
 	}
 
 	// Create initial conversation
-	_, err := store.Create("test-id", "gpt-4", messages)
+	_, err := store.Create(context.Background(),"test-id", "gpt-4", messages)
 	require.NoError(t, err)
 
 	// Simulate concurrent reads and writes
 	done := make(chan bool, 10)
 	for i := 0; i < 5; i++ {
 		go func() {
-			_, _ = store.Get("test-id")
+			_, _ = store.Get(context.Background(),"test-id")
 			done <- true
 		}()
 	}
@@ -176,7 +177,7 @@ func TestMemoryStore_ConcurrentAccess(t *testing.T) {
 				Role: "assistant",
 				Content: []api.ContentBlock{{Type: "output_text", Text: "Response"}},
 			}
-			_, _ = store.Append("test-id", newMsg)
+			_, _ = store.Append(context.Background(),"test-id", newMsg)
 			done <- true
 		}()
 	}
@@ -187,7 +188,7 @@ func TestMemoryStore_ConcurrentAccess(t *testing.T) {
 	}
 
 	// Verify final state
-	conv, err := store.Get("test-id")
+	conv, err := store.Get(context.Background(),"test-id")
 	require.NoError(t, err)
 	assert.NotNil(t, conv)
 	assert.GreaterOrEqual(t, len(conv.Messages), 1)
@@ -205,11 +206,11 @@ func TestMemoryStore_DeepCopy(t *testing.T) {
 		},
 	}
 
-	_, err := store.Create("test-id", "gpt-4", messages)
+	_, err := store.Create(context.Background(),"test-id", "gpt-4", messages)
 	require.NoError(t, err)
 
 	// Get conversation
-	conv1, err := store.Get("test-id")
+	conv1, err := store.Get(context.Background(),"test-id")
 	require.NoError(t, err)
 
 	// Note: Current implementation copies the Messages slice but not the Content blocks
@@ -225,7 +226,7 @@ func TestMemoryStore_DeepCopy(t *testing.T) {
 	assert.Equal(t, originalLen+1, len(conv1.Messages), "can modify returned message slice")
 
 	// Verify original is unchanged
-	conv2, err := store.Get("test-id")
+	conv2, err := store.Get(context.Background(),"test-id")
 	require.NoError(t, err)
 	assert.Equal(t, originalLen, len(conv2.Messages), "original conversation unaffected by slice modification")
 }
@@ -238,11 +239,11 @@ func TestMemoryStore_TTLCleanup(t *testing.T) {
 		{Role: "user", Content: []api.ContentBlock{{Type: "input_text", Text: "Hello"}}},
 	}
 
-	_, err := store.Create("test-id", "gpt-4", messages)
+	_, err := store.Create(context.Background(),"test-id", "gpt-4", messages)
 	require.NoError(t, err)
 
 	// Verify it exists
-	conv, err := store.Get("test-id")
+	conv, err := store.Get(context.Background(),"test-id")
 	require.NoError(t, err)
 	assert.NotNil(t, conv)
 	assert.Equal(t, 1, store.Size())
@@ -265,12 +266,12 @@ func TestMemoryStore_NoTTL(t *testing.T) {
 		{Role: "user", Content: []api.ContentBlock{{Type: "input_text", Text: "Hello"}}},
 	}
 
-	_, err := store.Create("test-id", "gpt-4", messages)
+	_, err := store.Create(context.Background(),"test-id", "gpt-4", messages)
 	require.NoError(t, err)
 	assert.Equal(t, 1, store.Size())
 
 	// Without TTL, conversation should persist indefinitely
-	conv, err := store.Get("test-id")
+	conv, err := store.Get(context.Background(),"test-id")
 	require.NoError(t, err)
 	assert.NotNil(t, conv)
 }
@@ -282,7 +283,7 @@ func TestMemoryStore_UpdatedAtTracking(t *testing.T) {
 		{Role: "user", Content: []api.ContentBlock{{Type: "input_text", Text: "Hello"}}},
 	}
 
-	conv, err := store.Create("test-id", "gpt-4", messages)
+	conv, err := store.Create(context.Background(),"test-id", "gpt-4", messages)
 	require.NoError(t, err)
 	createdAt := conv.CreatedAt
 	updatedAt := conv.UpdatedAt
@@ -296,7 +297,7 @@ func TestMemoryStore_UpdatedAtTracking(t *testing.T) {
 		Role: "assistant",
 		Content: []api.ContentBlock{{Type: "output_text", Text: "Response"}},
 	}
-	conv, err = store.Append("test-id", newMsg)
+	conv, err = store.Append(context.Background(),"test-id", newMsg)
 	require.NoError(t, err)
 
 	assert.Equal(t, createdAt, conv.CreatedAt, "created time should not change")
@@ -313,7 +314,7 @@ func TestMemoryStore_MultipleConversations(t *testing.T) {
 		messages := []api.Message{
 			{Role: "user", Content: []api.ContentBlock{{Type: "input_text", Text: "Hello " + id}}},
 		}
-		_, err := store.Create(id, model, messages)
+		_, err := store.Create(context.Background(),id, model, messages)
 		require.NoError(t, err)
 	}
 
@@ -322,7 +323,7 @@ func TestMemoryStore_MultipleConversations(t *testing.T) {
 	// Verify each conversation is independent
 	for i := 0; i < 10; i++ {
 		id := "conv-" + string(rune('0'+i))
-		conv, err := store.Get(id)
+		conv, err := store.Get(context.Background(),id)
 		require.NoError(t, err)
 		require.NotNil(t, conv)
 		assert.Equal(t, id, conv.ID)

internal/conversation/redis_store.go

@@ -13,7 +13,6 @@ import (
 type RedisStore struct {
 	client *redis.Client
 	ttl    time.Duration
-	ctx    context.Context
 }
 
 // NewRedisStore creates a Redis-backed conversation store.
@@ -21,7 +20,6 @@ func NewRedisStore(client *redis.Client, ttl time.Duration) *RedisStore {
 	return &RedisStore{
 		client: client,
 		ttl:    ttl,
-		ctx:    context.Background(),
 	}
 }
 
@@ -31,8 +29,8 @@ func (s *RedisStore) key(id string) string {
 }
 
 // Get retrieves a conversation by ID from Redis.
-func (s *RedisStore) Get(id string) (*Conversation, error) {
+func (s *RedisStore) Get(ctx context.Context, id string) (*Conversation, error) {
-	data, err := s.client.Get(s.ctx, s.key(id)).Bytes()
+	data, err := s.client.Get(ctx, s.key(id)).Bytes()
 	if err == redis.Nil {
 		return nil, nil
 	}
@@ -49,7 +47,7 @@ func (s *RedisStore) Get(id string) (*Conversation, error) {
 }
 
 // Create creates a new conversation with the given messages.
-func (s *RedisStore) Create(id string, model string, messages []api.Message) (*Conversation, error) {
+func (s *RedisStore) Create(ctx context.Context, id string, model string, messages []api.Message) (*Conversation, error) {
 	now := time.Now()
 	conv := &Conversation{
 		ID:        id,
@@ -64,7 +62,7 @@ func (s *RedisStore) Create(id string, model string, messages []api.Message) (*C
 		return nil, err
 	}
 
-	if err := s.client.Set(s.ctx, s.key(id), data, s.ttl).Err(); err != nil {
+	if err := s.client.Set(ctx, s.key(id), data, s.ttl).Err(); err != nil {
 		return nil, err
 	}
 
@@ -72,8 +70,8 @@ func (s *RedisStore) Create(id string, model string, messages []api.Message) (*C
 }
 
 // Append adds new messages to an existing conversation.
-func (s *RedisStore) Append(id string, messages ...api.Message) (*Conversation, error) {
+func (s *RedisStore) Append(ctx context.Context, id string, messages ...api.Message) (*Conversation, error) {
-	conv, err := s.Get(id)
+	conv, err := s.Get(ctx, id)
 	if err != nil {
 		return nil, err
 	}
@@ -89,7 +87,7 @@ func (s *RedisStore) Append(id string, messages ...api.Message) (*Conversation,
 		return nil, err
 	}
 
-	if err := s.client.Set(s.ctx, s.key(id), data, s.ttl).Err(); err != nil {
+	if err := s.client.Set(ctx, s.key(id), data, s.ttl).Err(); err != nil {
 		return nil, err
 	}
 
@@ -97,17 +95,18 @@ func (s *RedisStore) Append(id string, messages ...api.Message) (*Conversation,
 }
 
 // Delete removes a conversation from Redis.
-func (s *RedisStore) Delete(id string) error {
+func (s *RedisStore) Delete(ctx context.Context, id string) error {
-	return s.client.Del(s.ctx, s.key(id)).Err()
+	return s.client.Del(ctx, s.key(id)).Err()
 }
 
 // Size returns the number of active conversations in Redis.
 func (s *RedisStore) Size() int {
 	var count int
 	var cursor uint64
+	ctx := context.Background()
 
 	for {
-		keys, nextCursor, err := s.client.Scan(s.ctx, cursor, "conv:*", 100).Result()
+		keys, nextCursor, err := s.client.Scan(ctx, cursor, "conv:*", 100).Result()
 		if err != nil {
 			return 0
 		}

internal/conversation/sql_store.go

@@ -1,6 +1,7 @@
 package conversation
 
 import (
+	"context"
 	"database/sql"
 	"encoding/json"
 	"time"
@@ -71,8 +72,8 @@ func NewSQLStore(db *sql.DB, driver string, ttl time.Duration) (*SQLStore, error
 	return s, nil
 }
 
-func (s *SQLStore) Get(id string) (*Conversation, error) {
+func (s *SQLStore) Get(ctx context.Context, id string) (*Conversation, error) {
-	row := s.db.QueryRow(s.dialect.getByID, id)
+	row := s.db.QueryRowContext(ctx, s.dialect.getByID, id)
 
 	var conv Conversation
 	var msgJSON string
@@ -91,14 +92,14 @@ func (s *SQLStore) Get(id string) (*Conversation, error) {
 	return &conv, nil
 }
 
-func (s *SQLStore) Create(id string, model string, messages []api.Message) (*Conversation, error) {
+func (s *SQLStore) Create(ctx context.Context, id string, model string, messages []api.Message) (*Conversation, error) {
 	now := time.Now()
 	msgJSON, err := json.Marshal(messages)
 	if err != nil {
 		return nil, err
 	}
 
-	if _, err := s.db.Exec(s.dialect.upsert, id, model, string(msgJSON), now, now); err != nil {
+	if _, err := s.db.ExecContext(ctx, s.dialect.upsert, id, model, string(msgJSON), now, now); err != nil {
 		return nil, err
 	}
 
@@ -111,8 +112,8 @@ func (s *SQLStore) Create(id string, model string, messages []api.Message) (*Con
 	}, nil
 }
 
-func (s *SQLStore) Append(id string, messages ...api.Message) (*Conversation, error) {
+func (s *SQLStore) Append(ctx context.Context, id string, messages ...api.Message) (*Conversation, error) {
-	conv, err := s.Get(id)
+	conv, err := s.Get(ctx, id)
 	if err != nil {
 		return nil, err
 	}
@@ -128,15 +129,15 @@ func (s *SQLStore) Append(id string, messages ...api.Message) (*Conversation, er
 		return nil, err
 	}
 
-	if _, err := s.db.Exec(s.dialect.update, string(msgJSON), conv.UpdatedAt, id); err != nil {
+	if _, err := s.db.ExecContext(ctx, s.dialect.update, string(msgJSON), conv.UpdatedAt, id); err != nil {
 		return nil, err
 	}
 
 	return conv, nil
 }
 
-func (s *SQLStore) Delete(id string) error {
+func (s *SQLStore) Delete(ctx context.Context, id string) error {
-	_, err := s.db.Exec(s.dialect.deleteByID, id)
+	_, err := s.db.ExecContext(ctx, s.dialect.deleteByID, id)
 	return err
 }
 

internal/observability/store_wrapper.go

@@ -42,9 +42,7 @@ func NewInstrumentedStore(s conversation.Store, backend string, registry *promet
 }
 
 // Get wraps the store's Get method with metrics and tracing.
-func (s *InstrumentedStore) Get(id string) (*conversation.Conversation, error) {
+func (s *InstrumentedStore) Get(ctx context.Context, id string) (*conversation.Conversation, error) {
-	ctx := context.Background()
-
 	// Start span if tracing is enabled
 	if s.tracer != nil {
 		var span trace.Span
@@ -61,7 +59,7 @@ func (s *InstrumentedStore) Get(id string) (*conversation.Conversation, error) {
 	start := time.Now()
 
 	// Call underlying store
-	conv, err := s.base.Get(id)
+	conv, err := s.base.Get(ctx, id)
 
 	// Record metrics
 	duration := time.Since(start).Seconds()
@@ -95,9 +93,7 @@ func (s *InstrumentedStore) Get(id string) (*conversation.Conversation, error) {
 }
 
 // Create wraps the store's Create method with metrics and tracing.
-func (s *InstrumentedStore) Create(id string, model string, messages []api.Message) (*conversation.Conversation, error) {
+func (s *InstrumentedStore) Create(ctx context.Context, id string, model string, messages []api.Message) (*conversation.Conversation, error) {
-	ctx := context.Background()
-
 	// Start span if tracing is enabled
 	if s.tracer != nil {
 		var span trace.Span
@@ -116,7 +112,7 @@ func (s *InstrumentedStore) Create(id string, model string, messages []api.Messa
 	start := time.Now()
 
 	// Call underlying store
-	conv, err := s.base.Create(id, model, messages)
+	conv, err := s.base.Create(ctx, id, model, messages)
 
 	// Record metrics
 	duration := time.Since(start).Seconds()
@@ -146,9 +142,7 @@ func (s *InstrumentedStore) Create(id string, model string, messages []api.Messa
 }
 
 // Append wraps the store's Append method with metrics and tracing.
-func (s *InstrumentedStore) Append(id string, messages ...api.Message) (*conversation.Conversation, error) {
+func (s *InstrumentedStore) Append(ctx context.Context, id string, messages ...api.Message) (*conversation.Conversation, error) {
-	ctx := context.Background()
-
 	// Start span if tracing is enabled
 	if s.tracer != nil {
 		var span trace.Span
@@ -166,7 +160,7 @@ func (s *InstrumentedStore) Append(id string, messages ...api.Message) (*convers
 	start := time.Now()
 
 	// Call underlying store
-	conv, err := s.base.Append(id, messages...)
+	conv, err := s.base.Append(ctx, id, messages...)
 
 	// Record metrics
 	duration := time.Since(start).Seconds()
@@ -199,9 +193,7 @@ func (s *InstrumentedStore) Append(id string, messages ...api.Message) (*convers
 }
 
 // Delete wraps the store's Delete method with metrics and tracing.
-func (s *InstrumentedStore) Delete(id string) error {
+func (s *InstrumentedStore) Delete(ctx context.Context, id string) error {
-	ctx := context.Background()
-
 	// Start span if tracing is enabled
 	if s.tracer != nil {
 		var span trace.Span
@@ -218,7 +210,7 @@ func (s *InstrumentedStore) Delete(id string) error {
 	start := time.Now()
 
 	// Call underlying store
-	err := s.base.Delete(id)
+	err := s.base.Delete(ctx, id)
 
 	// Record metrics
 	duration := time.Since(start).Seconds()

internal/server/health.go

@@ -51,7 +51,7 @@ func (s *GatewayServer) handleReady(w http.ResponseWriter, r *http.Request) {
 
 	// Test conversation store by attempting a simple operation
 	testID := "health_check_test"
-	_, err := s.convs.Get(testID)
+	_, err := s.convs.Get(ctx, testID)
 	if err != nil {
 		checks["conversation_store"] = "unhealthy: " + err.Error()
 		allHealthy = false

internal/server/mocks_test.go

@@ -156,7 +156,7 @@ func newMockConversationStore() *mockConversationStore {
 	}
 }
 
-func (m *mockConversationStore) Get(id string) (*conversation.Conversation, error) {
+func (m *mockConversationStore) Get(ctx context.Context, id string) (*conversation.Conversation, error) {
 	m.mu.Lock()
 	defer m.mu.Unlock()
 
@@ -170,7 +170,7 @@ func (m *mockConversationStore) Get(id string) (*conversation.Conversation, erro
 	return conv, nil
 }
 
-func (m *mockConversationStore) Create(id string, model string, messages []api.Message) (*conversation.Conversation, error) {
+func (m *mockConversationStore) Create(ctx context.Context, id string, model string, messages []api.Message) (*conversation.Conversation, error) {
 	m.mu.Lock()
 	defer m.mu.Unlock()
 
@@ -187,7 +187,7 @@ func (m *mockConversationStore) Create(id string, model string, messages []api.M
 	return conv, nil
 }
 
-func (m *mockConversationStore) Append(id string, messages ...api.Message) (*conversation.Conversation, error) {
+func (m *mockConversationStore) Append(ctx context.Context, id string, messages ...api.Message) (*conversation.Conversation, error) {
 	m.mu.Lock()
 	defer m.mu.Unlock()
 
@@ -203,7 +203,7 @@ func (m *mockConversationStore) Append(id string, messages ...api.Message) (*con
 	return conv, nil
 }
 
-func (m *mockConversationStore) Delete(id string) error {
+func (m *mockConversationStore) Delete(ctx context.Context, id string) error {
 	m.mu.Lock()
 	defer m.mu.Unlock()
 

internal/server/server.go

@@ -107,7 +107,7 @@ func (s *GatewayServer) handleResponses(w http.ResponseWriter, r *http.Request)
 	// Build full message history from previous conversation
 	var historyMsgs []api.Message
 	if req.PreviousResponseID != nil && *req.PreviousResponseID != "" {
-		conv, err := s.convs.Get(*req.PreviousResponseID)
+		conv, err := s.convs.Get(r.Context(), *req.PreviousResponseID)
 		if err != nil {
 			s.logger.ErrorContext(r.Context(), "failed to retrieve conversation",
 				logger.LogAttrsWithTrace(r.Context(),
@@ -186,7 +186,7 @@ func (s *GatewayServer) handleSyncResponse(w http.ResponseWriter, r *http.Reques
 		ToolCalls: result.ToolCalls,
 	}
 	allMsgs := append(storeMsgs, assistantMsg)
-	if _, err := s.convs.Create(responseID, result.Model, allMsgs); err != nil {
+	if _, err := s.convs.Create(r.Context(), responseID, result.Model, allMsgs); err != nil {
 		s.logger.ErrorContext(r.Context(), "failed to store conversation",
 			logger.LogAttrsWithTrace(r.Context(),
 				slog.String("request_id", logger.FromContext(r.Context())),
@@ -543,7 +543,7 @@ loop:
 			ToolCalls: toolCalls,
 		}
 		allMsgs := append(storeMsgs, assistantMsg)
-		if _, err := s.convs.Create(responseID, model, allMsgs); err != nil {
+		if _, err := s.convs.Create(r.Context(), responseID, model, allMsgs); err != nil {
 			s.logger.ErrorContext(r.Context(), "failed to store conversation",
 				slog.String("request_id", logger.FromContext(r.Context())),
 				slog.String("response_id", responseID),