fix: bound SQLite WAL growth and prevent worker hangs (#49)

The worker's SQLite WAL could grow unbounded (observed 19MB) and wedge the
DB, hanging Claude Code on every prompt. No checkpoint ever truncated the
WAL (only PASSIVE auto-checkpoint, which cannot reclaim the file), the
connection-scoped pragmas were set via a single Exec so only one pooled
connection received them (e.g. busy_timeout=0 on the rest), and the
maintenance service that would optimize/checkpoint was never wired up.

- Register a sqlite3 ConnectHook driver so all pragmas (busy_timeout,
  journal_mode, synchronous, cache_size, foreign_keys, journal_size_limit)
  apply to every pooled connection; enable safe connection recycling.
- Add Store.Checkpoint (TRUNCATE), checkpoint-on-Close, and a periodic
  size-gated checkpoint loop with configurable interval/threshold.
- Wire up the previously-dead maintenance service; make trigger_maintenance
  actually run DB maintenance instead of only recalculating scores.
- Harden the user-prompt hook to honor its deadline and fail open so a
  slow worker can never stall a prompt.
- Add regression tests for WAL truncation, checkpoint-on-close, and
  per-connection pragmas.

cmd/hooks/user-prompt/main.go

@@ -91,18 +91,21 @@ func handleUserPrompt(ctx *hooks.HookContext, input *Input) (string, error) {
 		observationCount int
 	)
 
-	// Start search in background
+	// Start search in background. Pass the deadline context so a wedged worker
+	// aborts the request at the deadline instead of blocking for the full
+	// hookClient timeout (10s). Errors are ignored -- fail open with no memory.
 	wg.Add(1)
 	go func() {
 		defer wg.Done()
-		searchResult, _ = hooks.GET(ctx.Port, searchURL)
+		searchResult, _ = hooks.GETWithContext(deadline, ctx.Port, searchURL)
 	}()
 
-	// Start session init in parallel (with observationCount=0; approximate is fine)
+	// Start session init in parallel (with observationCount=0; approximate is fine).
+	// Deadline context guards this call too.
 	wg.Add(1)
 	go func() {
 		defer wg.Done()
-		initResult, initErr = hooks.POST(ctx.Port, "/api/sessions/init", map[string]interface{}{
+		initResult, initErr = hooks.POSTWithContextResult(deadline, ctx.Port, "/api/sessions/init", map[string]interface{}{
 			"claudeSessionId":     ctx.SessionID,
 			"project":             ctx.Project,
 			"prompt":              input.Prompt,
@@ -113,7 +116,8 @@ func handleUserPrompt(ctx *hooks.HookContext, input *Input) (string, error) {
 	// Wait for both to complete
 	wg.Wait()
 
-	// Check deadline after network calls
+	// Check deadline after network calls -- if exceeded, fail open (proceed with
+	// no injected memory) rather than blocking or erroring the user's prompt.
 	if deadline.Err() != nil {
 		return "", nil
 	}
@@ -173,9 +177,11 @@ func handleUserPrompt(ctx *hooks.HookContext, input *Input) (string, error) {
 		contextToInject = contextBuilder
 	}
 
-	// Check session init result
+	// Check session init result. A session-init failure must never block the
+	// prompt: degrade gracefully and still inject any memory we found.
 	if initErr != nil {
-		return "", initErr
+		fmt.Fprintf(os.Stderr, "[user-prompt] Session init failed: %v\n", initErr)
+		return contextToInject, nil
 	}
 	if initResult == nil {
 		return contextToInject, nil // Non-JSON response from worker, skip session init
@@ -201,13 +207,15 @@ func handleUserPrompt(ctx *hooks.HookContext, input *Input) (string, error) {
 
 	fmt.Fprintf(os.Stderr, "[user-prompt] Session %d, prompt #%d\n", sessionID, promptNumber)
 
-	// Start SDK agent (depends on session init result, so kept sequential)
-	_, err := hooks.POST(ctx.Port, fmt.Sprintf("/sessions/%d/init", sessionID), map[string]interface{}{
+	// Start SDK agent (depends on session init result, so kept sequential).
+	// Deadline-guarded so a wedged worker cannot stall past the hook budget.
+	// Failure here must not block the prompt: degrade gracefully, still inject memory.
+	if _, err := hooks.POSTWithContextResult(deadline, ctx.Port, fmt.Sprintf("/sessions/%d/init", sessionID), map[string]interface{}{
 		"userPrompt":   input.Prompt,
 		"promptNumber": promptNumber,
-	})
-	if err != nil {
-		return "", err
+	}); err != nil {
+		fmt.Fprintf(os.Stderr, "[user-prompt] SDK agent init failed: %v\n", err)
+		return contextToInject, nil
 	}
 
 	// Return context if we found relevant observations

internal/config/config.go

@@ -39,44 +39,46 @@ var CriticalConcepts = []string{
 // Config holds the application configuration.
 // Field order optimized for memory alignment (fieldalignment).
 type Config struct {
-	ContextFullField          string   `json:"context_full_field"`
-	DBPath                    string   `json:"db_path"`
-	Model                     string   `json:"model"`
-	ClaudeCodePath            string   `json:"claude_code_path"`
-	EmbeddingModel            string   `json:"embedding_model"`
-	VectorStorageStrategy     string   `json:"vector_storage_strategy"`
-	ContextObsConcepts        []string `json:"context_obs_concepts"`
-	ContextObsTypes           []string `json:"context_obs_types"`
-	ContextFullCount          int      `json:"context_full_count"`
-	GraphBranchFactor         int      `json:"graph_branch_factor"`
-	GraphEdgeWeight           float64  `json:"graph_edge_weight"`
-	ContextRelevanceThreshold float64  `json:"context_relevance_threshold"`
-	RerankingCandidates       int      `json:"reranking_candidates"`
-	WorkerPort                int      `json:"worker_port"`
-	DeduplicationThreshold    float64  `json:"deduplication_threshold"`
-	RerankingMinImprovement   float64  `json:"reranking_min_improvement"`
-	ContextObservations       int      `json:"context_observations"`
-	ContextMaxPromptResults   int      `json:"context_max_prompt_results"`
-	ContextSessionCount       int      `json:"context_session_count"`
-	MaxConns                  int      `json:"max_conns"`
-	RerankingAlpha            float64  `json:"reranking_alpha"`
-	GraphMaxHops              int      `json:"graph_max_hops"`
-	RerankingResults          int      `json:"reranking_results"`
-	GraphRebuildIntervalMin   int      `json:"graph_rebuild_interval_min"`
-	HubThreshold              int      `json:"hub_threshold"`
-	ObservationRetentionDays  int      `json:"observation_retention_days"`
-	MaintenanceIntervalHours  int      `json:"maintenance_interval_hours"`
-	ContextMaxTokensStartup   int      `json:"context_max_tokens_startup"`
-	ContextMaxTokensPrompt    int      `json:"context_max_tokens_prompt"`
-	ContextShowWorkTokens     bool     `json:"context_show_work_tokens"`
-	ContextShowReadTokens     bool     `json:"context_show_read_tokens"`
-	RerankingPureMode         bool     `json:"reranking_pure_mode"`
-	GraphEnabled              bool     `json:"graph_enabled"`
-	DeduplicationEnabled      bool     `json:"deduplication_enabled"`
-	MaintenanceEnabled        bool     `json:"maintenance_enabled"`
-	RerankingEnabled          bool     `json:"reranking_enabled"`
-	ContextShowLastSummary    bool     `json:"context_show_last_summary"`
-	CleanupStaleObservations  bool     `json:"cleanup_stale_observations"`
+	ContextFullField             string   `json:"context_full_field"`
+	DBPath                       string   `json:"db_path"`
+	Model                        string   `json:"model"`
+	ClaudeCodePath               string   `json:"claude_code_path"`
+	EmbeddingModel               string   `json:"embedding_model"`
+	VectorStorageStrategy        string   `json:"vector_storage_strategy"`
+	ContextObsConcepts           []string `json:"context_obs_concepts"`
+	ContextObsTypes              []string `json:"context_obs_types"`
+	ContextFullCount             int      `json:"context_full_count"`
+	GraphBranchFactor            int      `json:"graph_branch_factor"`
+	GraphEdgeWeight              float64  `json:"graph_edge_weight"`
+	ContextRelevanceThreshold    float64  `json:"context_relevance_threshold"`
+	RerankingCandidates          int      `json:"reranking_candidates"`
+	WorkerPort                   int      `json:"worker_port"`
+	DeduplicationThreshold       float64  `json:"deduplication_threshold"`
+	RerankingMinImprovement      float64  `json:"reranking_min_improvement"`
+	ContextObservations          int      `json:"context_observations"`
+	ContextMaxPromptResults      int      `json:"context_max_prompt_results"`
+	ContextSessionCount          int      `json:"context_session_count"`
+	MaxConns                     int      `json:"max_conns"`
+	RerankingAlpha               float64  `json:"reranking_alpha"`
+	GraphMaxHops                 int      `json:"graph_max_hops"`
+	RerankingResults             int      `json:"reranking_results"`
+	GraphRebuildIntervalMin      int      `json:"graph_rebuild_interval_min"`
+	HubThreshold                 int      `json:"hub_threshold"`
+	ObservationRetentionDays     int      `json:"observation_retention_days"`
+	MaintenanceIntervalHours     int      `json:"maintenance_interval_hours"`
+	WALCheckpointIntervalSeconds int      `json:"wal_checkpoint_interval_seconds"`
+	WALCheckpointThresholdBytes  int64    `json:"wal_checkpoint_threshold_bytes"`
+	ContextMaxTokensStartup      int      `json:"context_max_tokens_startup"`
+	ContextMaxTokensPrompt       int      `json:"context_max_tokens_prompt"`
+	ContextShowWorkTokens        bool     `json:"context_show_work_tokens"`
+	ContextShowReadTokens        bool     `json:"context_show_read_tokens"`
+	RerankingPureMode            bool     `json:"reranking_pure_mode"`
+	GraphEnabled                 bool     `json:"graph_enabled"`
+	DeduplicationEnabled         bool     `json:"deduplication_enabled"`
+	MaintenanceEnabled           bool     `json:"maintenance_enabled"`
+	RerankingEnabled             bool     `json:"reranking_enabled"`
+	ContextShowLastSummary       bool     `json:"context_show_last_summary"`
+	CleanupStaleObservations     bool     `json:"cleanup_stale_observations"`
 }
 
 var (
@@ -181,6 +183,10 @@ func Default() *Config {
 		MaintenanceIntervalHours:  6,     // Run every 6 hours
 		ObservationRetentionDays:  0,     // 0 = no age-based deletion (keep all)
 		CleanupStaleObservations:  false, // Don't auto-cleanup stale observations
+		// WAL checkpoint loop tunables (issue #49). Defaults mirror the worker constants:
+		// check the WAL every 60s and TRUNCATE-checkpoint once it reaches 4 MiB.
+		WALCheckpointIntervalSeconds: 60,
+		WALCheckpointThresholdBytes:  4 << 20, // 4 MiB
 	}
 }
 
@@ -284,6 +290,13 @@ func Load() (*Config, error) {
 	if v, ok := settings["CLAUDE_MNEMONIC_CONTEXT_MAX_TOKENS_PROMPT"].(float64); ok && v > 0 {
 		cfg.ContextMaxTokensPrompt = int(v)
 	}
+	// WAL checkpoint loop tunables (issue #49)
+	if v, ok := settings["CLAUDE_MNEMONIC_WAL_CHECKPOINT_INTERVAL_SECONDS"].(float64); ok && v > 0 {
+		cfg.WALCheckpointIntervalSeconds = int(v)
+	}
+	if v, ok := settings["CLAUDE_MNEMONIC_WAL_CHECKPOINT_THRESHOLD_BYTES"].(float64); ok && v > 0 {
+		cfg.WALCheckpointThresholdBytes = int64(v)
+	}
 	// Deduplication settings
 	if v, ok := settings["CLAUDE_MNEMONIC_DEDUP_ENABLED"].(bool); ok {
 		cfg.DeduplicationEnabled = v

internal/db/gorm/store.go

@@ -5,18 +5,80 @@ import (
 	"context"
 	"database/sql"
 	"fmt"
+	"os"
 	"slices"
 	"sync"
 	"time"
 
 	sqlite_vec "github.com/asg017/sqlite-vec-go-bindings/cgo"
-	_ "github.com/mattn/go-sqlite3" // Import SQLite driver with FTS5 support
+	sqlite3 "github.com/mattn/go-sqlite3" // SQLite driver with FTS5 support
 	"github.com/rs/zerolog/log"
 	"gorm.io/driver/sqlite"
 	"gorm.io/gorm"
 	"gorm.io/gorm/logger"
 )
 
+// driverName is the name of the custom mattn/go-sqlite3 driver registered with a
+// ConnectHook that applies ALL connection pragmas (correctness + best-effort) to EVERY
+// pooled connection at open time. The stock "sqlite3" driver has no hook, so pragmas set
+// via a single post-open Exec only reach one arbitrary pooled connection (issue #49, F6).
+const driverName = "sqlite3_mnemonic"
+
+// registerDriverOnce guards driver registration so it runs exactly once per process.
+// database/sql panics with "sql: Register called twice" on a duplicate name, and NewStore
+// may be called multiple times (e.g. after a config-change reinitialization).
+var registerDriverOnce sync.Once
+
+// correctnessPragmas MUST succeed on every connection: getting any of them wrong changes
+// transactional/locking semantics, not just performance. A failure here aborts the open.
+var correctnessPragmas = []string{
+	"PRAGMA foreign_keys=ON",
+	"PRAGMA journal_mode=WAL",
+	"PRAGMA synchronous=NORMAL",
+	"PRAGMA busy_timeout=5000",
+	"PRAGMA cache_size=-64000",
+}
+
+// bestEffortPragmas are per-connection or database-wide optimizations. A failure is logged
+// and tolerated: the connection is still correct, just less tuned. (page_size only takes
+// effect on an empty database / next VACUUM, but applying it per-connection is harmless.)
+var bestEffortPragmas = []string{
+	"PRAGMA temp_store=MEMORY",          // Store temp tables in memory
+	"PRAGMA mmap_size=268435456",        // 256MB memory-mapped I/O
+	"PRAGMA page_size=4096",             // 4KB pages (optimal for most systems)
+	"PRAGMA wal_autocheckpoint=1000",    // Auto-checkpoint (PASSIVE) every 1000 WAL frames
+	"PRAGMA journal_size_limit=8388608", // Backstop: cap -wal at 8MiB (issue #49)
+}
+
+// connectHook applies all pragmas to a freshly opened connection. mattn/go-sqlite3 calls
+// it at the very end of Open, after DSN params and extensions, so it is authoritative.
+func connectHook(c *sqlite3.SQLiteConn) error {
+	for _, pragma := range correctnessPragmas {
+		if _, err := c.Exec(pragma, nil); err != nil {
+			return fmt.Errorf("apply correctness pragma %q: %w", pragma, err)
+		}
+	}
+	for _, pragma := range bestEffortPragmas {
+		if _, err := c.Exec(pragma, nil); err != nil {
+			log.Warn().Str("pragma", pragma).Err(err).Msg("Failed to set pragma (non-fatal)")
+		}
+	}
+	return nil
+}
+
+// registerDriver registers the custom driver once. sqlite_vec.Auto() registers the vec
+// extension globally via sqlite3_auto_extension, which applies to connections from any
+// sqlite3-based driver, so the new driver still gets vec + FTS5.
+func registerDriver() {
+	registerDriverOnce.Do(func() {
+		sql.Register(driverName, &sqlite3.SQLiteDriver{
+			ConnectHook: func(c *sqlite3.SQLiteConn) error {
+				return connectHook(c)
+			},
+		})
+	})
+}
+
 // Store represents the GORM database connection with sqlite-vec support.
 type Store struct {
 	healthCacheTime time.Time
@@ -24,6 +86,7 @@ type Store struct {
 	sqlDB           *sql.DB
 	metrics         *PoolMetrics
 	cachedHealth    *HealthInfo
+	path            string
 	healthCacheTTL  time.Duration
 	healthCacheMu   sync.RWMutex
 }
@@ -36,22 +99,32 @@ type Config struct {
 }
 
 // NewStore creates a new Store with WAL mode enabled and sqlite-vec registered.
-// CRITICAL: WAL mode and foreign keys are enabled via pragmas for concurrent reads.
+// CRITICAL: all connection pragmas (WAL, foreign_keys, busy_timeout, etc.) are applied to
+// EVERY pooled connection via a driver ConnectHook (see registerDriver), so the pool is
+// uniformly configured and connections may be recycled safely (issue #49, F6).
 func NewStore(cfg Config) (*Store, error) {
-	// 1. Register sqlite-vec extension (must be done before opening database)
+	// 1. Register sqlite-vec extension (must be done before opening database).
+	// sqlite_vec.Auto() uses sqlite3_auto_extension, which is global to all sqlite3-based
+	// drivers, so connections from our custom driver also get the vec virtual table.
 	sqlite_vec.Auto()
 
-	// 2. Build connection string (foreign keys enabled in DSN)
-	// Use sqlite3 driver (mattn/go-sqlite3) which has FTS5 support
+	// 2. Register the custom driver whose ConnectHook applies ALL pragmas to EVERY pooled
+	// connection (issue #49, F6). Without this, pragmas set via a single post-open
+	// sqlDB.Exec reach only one arbitrary pooled connection. The hook is authoritative.
+	registerDriver()
+
+	// 3. Build a minimal DSN. _foreign_keys is kept as belt-and-suspenders (the hook sets
+	// it too); all other pragmas are applied per-connection by the ConnectHook, so they no
+	// longer need to live in the DSN.
 	dsn := cfg.Path + "?_foreign_keys=ON"
 
-	// 3. Open raw database connection with mattn/go-sqlite3 (has FTS5 support)
-	sqlDB, err := sql.Open("sqlite3", dsn)
+	// 4. Open raw database connection with the custom driver (FTS5 + per-connection pragmas).
+	sqlDB, err := sql.Open(driverName, dsn)
 	if err != nil {
 		return nil, fmt.Errorf("open database: %w", err)
 	}
 
-	// 4. Wrap with GORM using existing connection
+	// 5. Wrap with GORM using existing connection
 	db, err := gorm.Open(sqlite.Dialector{
 		Conn: sqlDB,
 	}, &gorm.Config{
@@ -66,16 +139,25 @@ func NewStore(cfg Config) (*Store, error) {
 		return nil, fmt.Errorf("open gorm: %w", err)
 	}
 
-	// 5. Configure connection pool (same settings as current implementation)
+	// 6. Configure connection pool.
 	maxConns := cfg.MaxConns
 	if maxConns <= 0 {
 		maxConns = 4
 	}
 	sqlDB.SetMaxOpenConns(maxConns)
 	sqlDB.SetMaxIdleConns(maxConns)
-	sqlDB.SetConnMaxLifetime(0) // Never expire (SQLite connections are cheap)
+	// Finite recycling (issue #49): previously SetConnMaxLifetime(0) meant connections
+	// NEVER recycled, so a long-lived read connection could pin an old WAL read-mark for the
+	// whole process lifetime and block TRUNCATE checkpoints from reclaiming the -wal file.
+	// Recycling is safe now because the ConnectHook reapplies every correctness pragma on
+	// each new connection — a recycled connection comes back fully configured, not with
+	// defaults. 1h lifetime bounds read-mark staleness without churning the pool; 30m idle
+	// time reclaims connections that sit unused (e.g. between sessions) so the pool shrinks
+	// back to one warm connection during quiet periods, dropping their WAL read-marks.
+	sqlDB.SetConnMaxLifetime(1 * time.Hour)
+	sqlDB.SetConnMaxIdleTime(30 * time.Minute)
 
-	// 6. Verify connection
+	// 7. Verify connection
 	if err := sqlDB.Ping(); err != nil {
 		return nil, fmt.Errorf("ping database: %w", err)
 	}
@@ -83,37 +165,18 @@ func NewStore(cfg Config) (*Store, error) {
 	store := &Store{
 		DB:             db,
 		sqlDB:          sqlDB,
+		path:           cfg.Path,
 		metrics:        NewPoolMetrics(100), // Track last 100 latency samples
 		healthCacheTTL: 5 * time.Second,     // Cache health checks for 5 seconds
 	}
 
-	// 7. Run migrations FIRST (before PRAGMA commands)
+	// 8. Run migrations. All pragmas (correctness + best-effort) are applied per-connection
+	// by the ConnectHook at open time, so there is no post-open pragma loop here anymore:
+	// such a loop only ever reached one arbitrary pooled connection (issue #49, F6).
 	if err := runMigrations(db, sqlDB); err != nil {
 		return nil, fmt.Errorf("run migrations: %w", err)
 	}
 
-	// 8. CRITICAL: Set WAL mode and other performance pragmas
-	// Use raw sqlDB to avoid GORM transaction issues
-	pragmas := []string{
-		"PRAGMA journal_mode=WAL",
-		"PRAGMA synchronous=NORMAL",
-		"PRAGMA cache_size=-64000",   // 64MB cache (negative = KB)
-		"PRAGMA temp_store=MEMORY",   // Store temp tables in memory
-		"PRAGMA mmap_size=268435456",    // 256MB memory-mapped I/O
-		"PRAGMA page_size=4096",         // 4KB pages (optimal for most systems)
-		"PRAGMA wal_autocheckpoint=1000", // Explicit default; checkpoint every 1000 WAL frames
-	}
-	for _, pragma := range pragmas {
-		if _, err := sqlDB.Exec(pragma); err != nil {
-			log.Warn().Str("pragma", pragma).Err(err).Msg("Failed to set pragma (non-fatal)")
-		}
-	}
-	// Set busy timeout to 5 seconds to handle concurrent writes
-	// This allows SQLite to retry when database is locked instead of failing immediately
-	if _, err := sqlDB.Exec("PRAGMA busy_timeout=5000"); err != nil {
-		return nil, fmt.Errorf("set busy timeout: %w", err)
-	}
-
 	// 9. Warm the connection pool
 	store.WarmPool(maxConns)
 
@@ -148,11 +211,55 @@ func (s *Store) WarmPool(numConns int) {
 	log.Debug().Int("connections", numConns).Msg("Connection pool warmed")
 }
 
-// Close closes the database connection.
+// Close checkpoints the WAL (TRUNCATE) before closing the connection. Checkpointing on
+// shutdown prevents the WAL file from persisting in a large, dirty state across restarts
+// and config-change reinitializations, which otherwise leaves a multi-megabyte -wal file
+// on disk (issue #49). The checkpoint is best-effort: a failure is logged, not fatal.
 func (s *Store) Close() error {
+	ctx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
+	defer cancel()
+	if err := s.Checkpoint(ctx); err != nil {
+		log.Warn().Err(err).Msg("WAL checkpoint on close failed (non-fatal)")
+	}
 	return s.sqlDB.Close()
 }
 
+// Checkpoint runs a TRUNCATE WAL checkpoint: it flushes WAL frames into the main
+// database file and shrinks the -wal file back to zero. Unlike a PASSIVE checkpoint
+// (which never truncates the file and is all SQLite's auto-checkpoint ever performs), a
+// TRUNCATE checkpoint reclaims disk and is the mechanism that bounds WAL growth.
+// It waits up to the connection busy_timeout for the write lock and returns an error
+// rather than blocking indefinitely.
+func (s *Store) Checkpoint(ctx context.Context) error {
+	if _, err := s.sqlDB.ExecContext(ctx, "PRAGMA wal_checkpoint(TRUNCATE)"); err != nil {
+		return fmt.Errorf("wal checkpoint (truncate): %w", err)
+	}
+	return nil
+}
+
+// WALSize returns the size in bytes of the SQLite WAL sidecar file (<db>-wal), or 0 if
+// it does not exist or cannot be stat'd. Used to decide when a checkpoint is worthwhile.
+func (s *Store) WALSize() int64 {
+	if s.path == "" {
+		return 0
+	}
+	info, err := os.Stat(s.path + "-wal")
+	if err != nil {
+		return 0
+	}
+	return info.Size()
+}
+
+// CheckpointIfLarge performs a TRUNCATE checkpoint only when the WAL file has grown to or
+// beyond threshold bytes. Returns true if a checkpoint was performed. This keeps the
+// periodic checkpoint cheap: it does no work while the WAL is small.
+func (s *Store) CheckpointIfLarge(ctx context.Context, threshold int64) (bool, error) {
+	if s.WALSize() < threshold {
+		return false, nil
+	}
+	return true, s.Checkpoint(ctx)
+}
+
 // Ping verifies the database connection is alive.
 func (s *Store) Ping() error {
 	return s.sqlDB.Ping()
@@ -193,8 +300,9 @@ func (s *Store) Optimize(ctx context.Context) error {
 		log.Warn().Err(err).Msg("PRAGMA optimize failed (non-fatal)")
 	}
 
-	// Passive WAL checkpoint — doesn't block readers/writers
-	if _, err := s.sqlDB.ExecContext(ctx, "PRAGMA wal_checkpoint(PASSIVE)"); err != nil {
+	// TRUNCATE WAL checkpoint — reclaims the -wal file during low-activity optimization.
+	// (PASSIVE never shrinks the file, so it cannot bound WAL growth — see issue #49.)
+	if err := s.Checkpoint(ctx); err != nil {
 		log.Warn().Err(err).Msg("WAL checkpoint failed (non-fatal)")
 	}
 
@@ -519,7 +627,6 @@ func (s *Store) ExecWithTimeout(ctx context.Context, timeout time.Duration, quer
 	return nil
 }
 
-
 // TransactionWithTimeout wraps a transaction function with timeout handling.
 // The transaction is automatically rolled back if the context times out.
 func (s *Store) TransactionWithTimeout(ctx context.Context, timeout time.Duration, fn func(*gorm.DB) error) error {

internal/db/gorm/store_test.go

@@ -5,9 +5,12 @@ package gorm
 
 import (
 	"context"
+	"database/sql"
 	"os"
 	"path/filepath"
+	"strings"
 	"testing"
+	"time"
 
 	"gorm.io/gorm/logger"
 )
@@ -239,3 +242,321 @@ func TestOptimize_RespectsContextCancellation(t *testing.T) {
 		t.Error("expected error with cancelled context, got nil")
 	}
 }
+
+// growWAL inserts sizeable rows to push the SQLite WAL well past a few hundred KB so
+// checkpoint behaviour can be observed. Returns the WAL file size after the inserts.
+func growWAL(t *testing.T, store *Store, rows int) int64 {
+	t.Helper()
+	bigTitle := strings.Repeat("x", 2048)
+	for i := 0; i < rows; i++ {
+		_, err := store.GetRawDB().Exec(
+			"INSERT INTO observations (sdk_session_id, title, scope, project, type, created_at, created_at_epoch) "+
+				"VALUES (?, ?, 'project', '/tmp/test', 'decision', '2026-01-01T00:00:00Z', 1735689600)",
+			"sess", bigTitle)
+		if err != nil {
+			t.Fatalf("insert row %d: %v", i, err)
+		}
+	}
+	return store.WALSize()
+}
+
+func countObservations(t *testing.T, store *Store) int64 {
+	t.Helper()
+	var n int64
+	if err := store.GetRawDB().QueryRow("SELECT COUNT(*) FROM observations").Scan(&n); err != nil {
+		t.Fatalf("count observations: %v", err)
+	}
+	return n
+}
+
+// TestCheckpoint_TruncateShrinksWAL verifies Checkpoint() performs a TRUNCATE checkpoint
+// that actually reclaims the -wal file. This is the load-bearing fix for issue #49: a
+// PASSIVE checkpoint drains frames but never shrinks the file, so reverting Checkpoint to
+// PASSIVE would leave the WAL grown and fail this test.
+func TestCheckpoint_TruncateShrinksWAL(t *testing.T) {
+	tmpDir, err := os.MkdirTemp("", "gorm_checkpoint_truncate_*")
+	if err != nil {
+		t.Fatalf("create temp dir: %v", err)
+	}
+	defer os.RemoveAll(tmpDir)
+
+	dbPath := filepath.Join(tmpDir, "test.db")
+	store, err := NewStore(Config{Path: dbPath, MaxConns: 2, LogLevel: logger.Silent})
+	if err != nil {
+		t.Fatalf("NewStore failed: %v", err)
+	}
+	defer store.Close()
+
+	walBefore := growWAL(t, store, 1000)
+	if walBefore < 64*1024 {
+		t.Fatalf("expected WAL to grow above 64KiB, got %d bytes", walBefore)
+	}
+
+	if err := store.Checkpoint(context.Background()); err != nil {
+		t.Fatalf("Checkpoint failed: %v", err)
+	}
+
+	walAfter := store.WALSize()
+	if walAfter >= walBefore {
+		t.Errorf("expected WAL to shrink after TRUNCATE checkpoint: before=%d after=%d", walBefore, walAfter)
+	}
+	if walAfter > 64*1024 {
+		t.Errorf("expected WAL truncated to near-zero, got %d bytes", walAfter)
+	}
+}
+
+// TestCheckpointIfLarge_GatesOnThreshold verifies the size-gated periodic checkpoint used
+// by the worker's walCheckpointLoop: a no-op below the threshold, a truncating checkpoint
+// at/above it.
+func TestCheckpointIfLarge_GatesOnThreshold(t *testing.T) {
+	tmpDir, err := os.MkdirTemp("", "gorm_checkpoint_gated_*")
+	if err != nil {
+		t.Fatalf("create temp dir: %v", err)
+	}
+	defer os.RemoveAll(tmpDir)
+
+	dbPath := filepath.Join(tmpDir, "test.db")
+	store, err := NewStore(Config{Path: dbPath, MaxConns: 2, LogLevel: logger.Silent})
+	if err != nil {
+		t.Fatalf("NewStore failed: %v", err)
+	}
+	defer store.Close()
+
+	// Below an enormous threshold -> no checkpoint.
+	done, err := store.CheckpointIfLarge(context.Background(), 1<<30) // 1 GiB
+	if err != nil {
+		t.Fatalf("CheckpointIfLarge (small) failed: %v", err)
+	}
+	if done {
+		t.Errorf("expected no checkpoint below threshold, but one was performed")
+	}
+
+	// Grow the WAL, then a low threshold triggers a truncating checkpoint.
+	walBefore := growWAL(t, store, 1000)
+	if walBefore < 64*1024 {
+		t.Fatalf("expected WAL to grow above 64KiB, got %d bytes", walBefore)
+	}
+
+	done, err = store.CheckpointIfLarge(context.Background(), 64*1024)
+	if err != nil {
+		t.Fatalf("CheckpointIfLarge (large) failed: %v", err)
+	}
+	if !done {
+		t.Errorf("expected checkpoint above threshold, but none was performed")
+	}
+	if walAfter := store.WALSize(); walAfter >= walBefore {
+		t.Errorf("expected WAL to shrink after gated checkpoint: before=%d after=%d", walBefore, walAfter)
+	}
+}
+
+// TestClose_CheckpointsWAL verifies Close() reclaims the WAL and leaves the data intact on
+// the next open (issue #49: shutdown must not leave a large dirty WAL on disk).
+func TestClose_CheckpointsWAL(t *testing.T) {
+	tmpDir, err := os.MkdirTemp("", "gorm_close_checkpoint_*")
+	if err != nil {
+		t.Fatalf("create temp dir: %v", err)
+	}
+	defer os.RemoveAll(tmpDir)
+
+	dbPath := filepath.Join(tmpDir, "test.db")
+	store, err := NewStore(Config{Path: dbPath, MaxConns: 2, LogLevel: logger.Silent})
+	if err != nil {
+		t.Fatalf("NewStore failed: %v", err)
+	}
+
+	if walBefore := growWAL(t, store, 800); walBefore == 0 {
+		t.Fatalf("expected WAL to grow before close, got 0")
+	}
+	count := countObservations(t, store)
+	if count < 800 {
+		t.Fatalf("expected >=800 observations before close, got %d", count)
+	}
+
+	if err := store.Close(); err != nil {
+		t.Fatalf("Close failed: %v", err)
+	}
+
+	// The -wal file must not persist large on disk after a clean shutdown.
+	if info, statErr := os.Stat(dbPath + "-wal"); statErr == nil && info.Size() > 64*1024 {
+		t.Errorf("expected WAL reclaimed on close, -wal still %d bytes", info.Size())
+	}
+
+	// Reopen and verify data survived the checkpoint.
+	store2, err := NewStore(Config{Path: dbPath, MaxConns: 2, LogLevel: logger.Silent})
+	if err != nil {
+		t.Fatalf("reopen NewStore failed: %v", err)
+	}
+	defer store2.Close()
+
+	if count2 := countObservations(t, store2); count2 != count {
+		t.Errorf("expected %d observations after reopen, got %d", count, count2)
+	}
+}
+
+// TestBusyTimeoutAppliedToAllConnections verifies the issue #49 DSN fix: busy_timeout is
+// applied to EVERY pooled connection (not just one arbitrary connection as happened when
+// it was set via a single post-open sqlDB.Exec).
+func TestBusyTimeoutAppliedToAllConnections(t *testing.T) {
+	tmpDir, err := os.MkdirTemp("", "gorm_busy_timeout_*")
+	if err != nil {
+		t.Fatalf("create temp dir: %v", err)
+	}
+	defer os.RemoveAll(tmpDir)
+
+	dbPath := filepath.Join(tmpDir, "test.db")
+	const maxConns = 4
+	store, err := NewStore(Config{Path: dbPath, MaxConns: maxConns, LogLevel: logger.Silent})
+	if err != nil {
+		t.Fatalf("NewStore failed: %v", err)
+	}
+	defer store.Close()
+
+	// Pin all connections concurrently so each distinct connection is inspected, then
+	// assert every one reports busy_timeout=5000.
+	raw := store.GetRawDB()
+	conns := make([]*sql.Conn, 0, maxConns)
+	defer func() {
+		for _, c := range conns {
+			_ = c.Close()
+		}
+	}()
+	for i := 0; i < maxConns; i++ {
+		c, err := raw.Conn(context.Background())
+		if err != nil {
+			t.Fatalf("acquire conn %d: %v", i, err)
+		}
+		conns = append(conns, c)
+	}
+	for i, c := range conns {
+		var timeout int
+		if err := c.QueryRowContext(context.Background(), "PRAGMA busy_timeout").Scan(&timeout); err != nil {
+			t.Fatalf("query busy_timeout on conn %d: %v", i, err)
+		}
+		if timeout != 5000 {
+			t.Errorf("conn %d: expected busy_timeout=5000, got %d", i, timeout)
+		}
+	}
+}
+
+// TestAllPragmasAppliedToAllConnections verifies the issue #49 (F6) ConnectHook fix: not
+// just busy_timeout but the full pragma set — including the best-effort pragmas that used
+// to be set via a single post-open sqlDB.Exec (journal_size_limit, temp_store,
+// wal_autocheckpoint) — is applied to EVERY pooled connection. It pins all connections so
+// each distinct connection is inspected, then asserts each reports the expected value.
+func TestAllPragmasAppliedToAllConnections(t *testing.T) {
+	tmpDir, err := os.MkdirTemp("", "gorm_all_pragmas_*")
+	if err != nil {
+		t.Fatalf("create temp dir: %v", err)
+	}
+	defer os.RemoveAll(tmpDir)
+
+	dbPath := filepath.Join(tmpDir, "test.db")
+	const maxConns = 4
+	store, err := NewStore(Config{Path: dbPath, MaxConns: maxConns, LogLevel: logger.Silent})
+	if err != nil {
+		t.Fatalf("NewStore failed: %v", err)
+	}
+	defer store.Close()
+
+	// Expected per-connection pragma values. temp_store=MEMORY reports as 2; the others are
+	// numeric. foreign_keys/journal_mode/synchronous are covered by TestNewStore and the
+	// busy_timeout test; here we focus on the previously single-connection pragmas.
+	checks := []struct {
+		name string
+		want int64
+	}{
+		{"busy_timeout", 5000},
+		{"journal_size_limit", 8388608},
+		{"temp_store", 2}, // 2 == MEMORY
+		{"wal_autocheckpoint", 1000},
+		{"foreign_keys", 1},
+	}
+
+	raw := store.GetRawDB()
+	conns := make([]*sql.Conn, 0, maxConns)
+	defer func() {
+		for _, c := range conns {
+			_ = c.Close()
+		}
+	}()
+	for i := 0; i < maxConns; i++ {
+		c, err := raw.Conn(context.Background())
+		if err != nil {
+			t.Fatalf("acquire conn %d: %v", i, err)
+		}
+		conns = append(conns, c)
+	}
+
+	for i, c := range conns {
+		for _, chk := range checks {
+			var got int64
+			query := "PRAGMA " + chk.name
+			if err := c.QueryRowContext(context.Background(), query).Scan(&got); err != nil {
+				t.Fatalf("conn %d: query %q: %v", i, chk.name, err)
+			}
+			if got != chk.want {
+				t.Errorf("conn %d: %s = %d, want %d", i, chk.name, got, chk.want)
+			}
+		}
+	}
+}
+
+// TestRecycledConnectionRetainsPragmas verifies that recycling a connection (which now
+// happens because SetConnMaxLifetime is finite, not 0) does NOT drop the correctness
+// pragmas: the ConnectHook reapplies them on every new connection. We force recycling by
+// setting a near-zero max lifetime so the next acquisition opens a fresh connection, then
+// assert the new connection still reports the safe values rather than SQLite defaults
+// (busy_timeout would default to 0 and journal_mode to "delete" without the hook).
+func TestRecycledConnectionRetainsPragmas(t *testing.T) {
+	tmpDir, err := os.MkdirTemp("", "gorm_recycle_pragmas_*")
+	if err != nil {
+		t.Fatalf("create temp dir: %v", err)
+	}
+	defer os.RemoveAll(tmpDir)
+
+	dbPath := filepath.Join(tmpDir, "test.db")
+	store, err := NewStore(Config{Path: dbPath, MaxConns: 2, LogLevel: logger.Silent})
+	if err != nil {
+		t.Fatalf("NewStore failed: %v", err)
+	}
+	defer store.Close()
+
+	raw := store.GetRawDB()
+
+	// Force aggressive recycling: any connection older than 1ns is expired on next use, so
+	// database/sql opens a brand-new connection (running the ConnectHook again).
+	raw.SetConnMaxLifetime(time.Nanosecond)
+	time.Sleep(5 * time.Millisecond)
+
+	// Acquire a connection that is necessarily freshly opened (all prior ones are expired),
+	// and verify the hook reapplied the correctness pragmas.
+	conn, err := raw.Conn(context.Background())
+	if err != nil {
+		t.Fatalf("acquire recycled conn: %v", err)
+	}
+	defer conn.Close()
+
+	var busyTimeout int
+	if err := conn.QueryRowContext(context.Background(), "PRAGMA busy_timeout").Scan(&busyTimeout); err != nil {
+		t.Fatalf("query busy_timeout: %v", err)
+	}
+	if busyTimeout != 5000 {
+		t.Errorf("recycled conn: busy_timeout = %d, want 5000 (hook did not reapply)", busyTimeout)
+	}
+
+	var journalMode string
+	if err := conn.QueryRowContext(context.Background(), "PRAGMA journal_mode").Scan(&journalMode); err != nil {
+		t.Fatalf("query journal_mode: %v", err)
+	}
+	if journalMode != "wal" {
+		t.Errorf("recycled conn: journal_mode = %q, want \"wal\" (hook did not reapply)", journalMode)
+	}
+
+	var foreignKeys int
+	if err := conn.QueryRowContext(context.Background(), "PRAGMA foreign_keys").Scan(&foreignKeys); err != nil {
+		t.Fatalf("query foreign_keys: %v", err)
+	}
+	if foreignKeys != 1 {
+		t.Errorf("recycled conn: foreign_keys = %d, want 1 (hook did not reapply)", foreignKeys)
+	}
+}

internal/maintenance/service.go

@@ -83,8 +83,20 @@ func (s *Service) Start(ctx context.Context) {
 		Bool("cleanup_stale", s.config.CleanupStaleObservations).
 		Msg("Starting maintenance scheduler")
 
-	// Initial run after 5 minutes (allow system to stabilize)
-	time.Sleep(5 * time.Minute)
+	// Initial run after 5 minutes (allow system to stabilize).
+	// Use a cancellable timer so shutdown (ctx cancel / Stop) is not blocked for up to 5m.
+	initialDelay := time.NewTimer(5 * time.Minute)
+	select {
+	case <-ctx.Done():
+		initialDelay.Stop()
+		s.log.Info().Msg("Maintenance shutting down before initial run (context cancellation)")
+		return
+	case <-s.stopCh:
+		initialDelay.Stop()
+		s.log.Info().Msg("Maintenance shutting down before initial run (stop signal)")
+		return
+	case <-initialDelay.C:
+	}
 	s.runMaintenance(ctx)
 
 	ticker := time.NewTicker(interval)
@@ -288,7 +300,13 @@ func (s *Service) Stats() map[string]any {
 	}
 }
 
-// RunNow triggers an immediate maintenance run.
+// RunNow triggers an immediate maintenance run in the background.
 func (s *Service) RunNow(ctx context.Context) {
 	go s.runMaintenance(ctx)
 }
+
+// RunNowSync triggers an immediate maintenance run and blocks until it completes.
+// Use this when the caller needs to report a synchronous result (e.g. an HTTP handler).
+func (s *Service) RunNowSync(ctx context.Context) {
+	s.runMaintenance(ctx)
+}

internal/mcp/server.go

@@ -534,7 +534,7 @@ func (s *Server) handleToolsList(req *Request) *Response {
 		},
 		{
 			Name:        "trigger_maintenance",
-			Description: "Trigger an immediate maintenance run (cleanup old observations, optimize database).",
+			Description: "Trigger an immediate database maintenance run: optimize/checkpoint the database, clean up old prompts, apply any configured observation retention/stale cleanup, and recalculate importance scores.",
 			InputSchema: map[string]any{
 				"type":       "object",
 				"properties": map[string]any{},
@@ -917,7 +917,7 @@ func (s *Server) callTool(ctx context.Context, name string, args json.RawMessage
 			"project": s.project,
 		})
 	case "trigger_maintenance":
-		return s.proxyPostRaw(ctx, "/api/scoring/recalculate", nil)
+		return s.proxyPostRaw(ctx, "/api/maintenance/run", nil)
 	case "analyze_observation_importance":
 		return s.handleAnalyzeImportanceProxy(ctx, args)
 	case "analyze_search_patterns":

internal/worker/handlers_scoring.go

@@ -314,6 +314,49 @@ func (s *Service) handleTriggerRecalculation(w http.ResponseWriter, r *http.Requ
 	writeJSON(w, map[string]string{"status": "recalculation triggered"})
 }
 
+// handleRunMaintenance triggers an immediate, synchronous database maintenance run
+// (Optimize/TRUNCATE checkpoint + prompt cleanup + any enabled retention/stale cleanup)
+// and also kicks off an importance-score recalculation in the background so the behavior
+// of the previous trigger_maintenance tool is preserved (issue #49).
+func (s *Service) handleRunMaintenance(w http.ResponseWriter, r *http.Request) {
+	// initMu.RLock held by requireReady middleware
+	maintSvc := s.maintenanceSvc
+	recalculator := s.recalculator
+
+	if maintSvc == nil {
+		http.Error(w, "maintenance service not available", http.StatusServiceUnavailable)
+		return
+	}
+
+	// Run maintenance synchronously with an independent, bounded context so the caller
+	// receives a real completion status. Use context.Background so an HTTP client timeout
+	// does not abort an in-progress DB maintenance pass.
+	mctx, cancel := context.WithTimeout(context.Background(), 60*time.Second)
+	defer cancel()
+	maintSvc.RunNowSync(mctx)
+
+	// Preserve prior trigger_maintenance behavior: also recalculate importance scores.
+	recalcTriggered := false
+	if recalculator != nil {
+		recalcTriggered = true
+		s.wg.Add(1)
+		go func() {
+			defer s.wg.Done()
+			ctx, cancel := context.WithTimeout(context.Background(), 60*time.Second)
+			defer cancel()
+			if err := recalculator.RecalculateNow(ctx); err != nil {
+				log.Error().Err(err).Msg("Background recalculation during maintenance failed")
+			}
+		}()
+	}
+
+	writeJSON(w, map[string]any{
+		"status":            "maintenance completed",
+		"recalc_triggered":  recalcTriggered,
+		"maintenance_stats": maintSvc.Stats(),
+	})
+}
+
 // parseIntParam parses an integer query parameter with a default value.
 func parseIntParam(r *http.Request, name string, defaultVal int) int {
 	if val := r.URL.Query().Get(name); val != "" {

internal/worker/service.go

@@ -16,6 +16,7 @@ import (
 	"github.com/lukaszraczylo/claude-mnemonic/internal/config"
 	"github.com/lukaszraczylo/claude-mnemonic/internal/db/gorm"
 	"github.com/lukaszraczylo/claude-mnemonic/internal/embedding"
+	"github.com/lukaszraczylo/claude-mnemonic/internal/maintenance"
 	"github.com/lukaszraczylo/claude-mnemonic/internal/pattern"
 	"github.com/lukaszraczylo/claude-mnemonic/internal/reranking"
 	"github.com/lukaszraczylo/claude-mnemonic/internal/scoring"
@@ -44,6 +45,14 @@ const (
 	// QueueProcessInterval is how often the background queue processor runs.
 	QueueProcessInterval = 2 * time.Second
 
+	// WALCheckpointInterval is how often the worker checks whether the SQLite WAL needs a
+	// TRUNCATE checkpoint to reclaim disk and prevent unbounded growth (issue #49).
+	WALCheckpointInterval = 60 * time.Second
+
+	// WALCheckpointThreshold is the WAL file size at or above which the periodic check
+	// performs a TRUNCATE checkpoint. Keeps the steady-state WAL bounded to a few MB.
+	WALCheckpointThreshold = 4 << 20 // 4 MiB
+
 	// reinitializationDrainDelay is the delay after marking the service as not ready
 	// to allow in-flight requests to complete before reinitializing.
 	reinitializationDrainDelay = 200 * time.Millisecond
@@ -121,6 +130,7 @@ type Service struct {
 	patternStore       *gorm.PatternStore
 	relationStore      *gorm.RelationStore
 	patternDetector    *pattern.Detector
+	maintenanceSvc     *maintenance.Service
 	sessionManager     *session.Manager
 	sseBroadcaster     *sse.Broadcaster
 	processor          *sdk.Processor
@@ -570,6 +580,34 @@ func (s *Service) initializeAsync() {
 		go s.processQueue()
 	}
 
+	// Start periodic WAL checkpoint loop to bound SQLite WAL file growth (issue #49).
+	s.wg.Add(1)
+	go s.walCheckpointLoop()
+
+	// Start the scheduled maintenance service (issue #49: was dead code, never instantiated).
+	// vectorCleanupFn mirrors the observation store's cleanup hook so age/stale deletions done
+	// directly via GORM still remove their vectors from sqlite-vec.
+	var vectorCleanupFn func(ctx context.Context, deletedIDs []int64)
+	if vectorSync != nil {
+		vectorCleanupFn = func(ctx context.Context, deletedIDs []int64) {
+			if err := retryWithBackoff(ctx, VectorSyncMaxRetries, VectorSyncInitialBackoff, func() error {
+				return vectorSync.DeleteObservations(ctx, deletedIDs)
+			}); err != nil {
+				log.Warn().Err(err).Ints64("ids", deletedIDs).Msg("Failed to delete observations from sqlite-vec during maintenance")
+			}
+		}
+	}
+	maintSvc := maintenance.NewService(store, observationStore, summaryStore, promptStore, vectorCleanupFn, s.config, log.Logger)
+	s.initMu.Lock()
+	s.maintenanceSvc = maintSvc
+	s.initMu.Unlock()
+	s.wg.Add(1)
+	go func() {
+		defer s.wg.Done()
+		maintSvc.Start(s.ctx)
+	}()
+	log.Info().Msg("Maintenance scheduler started")
+
 	// Start file watchers for auto-recreation on deletion
 	s.startWatchers()
 
@@ -1290,6 +1328,9 @@ func (s *Service) setupRoutes() {
 		r.Put("/api/scoring/concepts/{concept}", s.handleUpdateConceptWeight)
 		r.Post("/api/scoring/recalculate", s.handleTriggerRecalculation)
 
+		// Maintenance: run an immediate synchronous DB maintenance pass (issue #49)
+		r.Post("/api/maintenance/run", s.handleRunMaintenance)
+
 		// Context injection
 		r.Get("/api/context/count", s.handleContextCount)
 		r.Get("/api/context/inject", s.handleContextInject)
@@ -1621,6 +1662,52 @@ func (s *Service) processQueue() {
 	}
 }
 
+// walCheckpointLoop periodically checkpoints the SQLite WAL so it cannot grow unbounded
+// during long-lived sessions. SQLite's internal auto-checkpoint is PASSIVE and never
+// shrinks the -wal file; under sustained writes with overlapping readers it can leave the
+// WAL growing without limit (issue #49). This loop performs a TRUNCATE checkpoint whenever
+// the WAL has grown to WALCheckpointThreshold, and does nothing while it is small.
+func (s *Service) walCheckpointLoop() {
+	defer s.wg.Done()
+
+	// Tunable via config; fall back to the package constants when unset/<=0 (issue #49).
+	interval := WALCheckpointInterval
+	if s.config != nil && s.config.WALCheckpointIntervalSeconds > 0 {
+		interval = time.Duration(s.config.WALCheckpointIntervalSeconds) * time.Second
+	}
+	threshold := int64(WALCheckpointThreshold)
+	if s.config != nil && s.config.WALCheckpointThresholdBytes > 0 {
+		threshold = s.config.WALCheckpointThresholdBytes
+	}
+
+	ticker := time.NewTicker(interval)
+	defer ticker.Stop()
+
+	for {
+		select {
+		case <-s.ctx.Done():
+			return
+		case <-ticker.C:
+			s.initMu.RLock()
+			store := s.store
+			s.initMu.RUnlock()
+			if store == nil {
+				continue
+			}
+
+			ctx, cancel := context.WithTimeout(s.ctx, 15*time.Second)
+			done, err := store.CheckpointIfLarge(ctx, threshold)
+			cancel()
+			switch {
+			case err != nil:
+				log.Warn().Err(err).Msg("Periodic WAL checkpoint failed (non-fatal)")
+			case done:
+				log.Debug().Msg("Periodic WAL checkpoint (TRUNCATE) completed")
+			}
+		}
+	}
+}
+
 // processAllSessions processes pending messages for all active sessions.
 // Messages are processed in parallel using goroutines, with concurrency
 // limited by a channel-based semaphore.
@@ -1748,6 +1835,9 @@ func (s *Service) Shutdown(ctx context.Context) error {
 	if s.patternDetector != nil {
 		s.patternDetector.Stop()
 	}
+	if s.maintenanceSvc != nil {
+		s.maintenanceSvc.Stop()
+	}
 
 	// Phase 4: Shutdown sessions (flush pending work)
 	log.Debug().Msg("Phase 4: Shutting down sessions...")

pkg/hooks/worker.go

@@ -564,6 +564,44 @@ func POSTWithContext(ctx context.Context, port int, path string, body interface{
 	return nil
 }
 
+// POSTWithContextResult sends a POST request using the provided context and
+// decodes the JSON response body, mirroring POST but honoring ctx for
+// cancellation/deadline. Used on the prompt critical path so a wedged worker
+// aborts at the hook deadline instead of blocking for the full client timeout.
+// A non-JSON body is returned as (nil, nil), matching POST's behavior.
+func POSTWithContextResult(ctx context.Context, port int, path string, body interface{}) (map[string]interface{}, error) {
+	jsonBody, err := json.Marshal(body)
+	if err != nil {
+		return nil, err
+	}
+
+	req, err := http.NewRequestWithContext(ctx, http.MethodPost,
+		fmt.Sprintf("http://127.0.0.1:%d%s", port, path),
+		bytes.NewReader(jsonBody))
+	if err != nil {
+		return nil, err
+	}
+	req.Header.Set("Content-Type", "application/json")
+
+	resp, err := hookClient.Do(req)
+	if err != nil {
+		return nil, err
+	}
+	defer func() { _ = resp.Body.Close() }()
+
+	if resp.StatusCode >= 400 {
+		return nil, fmt.Errorf("request failed: %s", resp.Status)
+	}
+
+	var result map[string]interface{}
+	if err := json.NewDecoder(resp.Body).Decode(&result); err != nil {
+		// Not all endpoints return JSON
+		return nil, nil
+	}
+
+	return result, nil
+}
+
 // GET sends a GET request to the worker.
 func GET(port int, path string) (map[string]interface{}, error) {
 	resp, err := hookClient.Get(fmt.Sprintf("http://127.0.0.1:%d%s", port, path))
@@ -584,6 +622,35 @@ func GET(port int, path string) (map[string]interface{}, error) {
 	return result, nil
 }
 
+// GETWithContext sends a GET request using the provided context and decodes the
+// JSON response body, mirroring GET but honoring ctx for cancellation/deadline.
+// Used on the prompt critical path so a wedged worker aborts at the hook
+// deadline instead of blocking for the full client timeout.
+func GETWithContext(ctx context.Context, port int, path string) (map[string]interface{}, error) {
+	req, err := http.NewRequestWithContext(ctx, http.MethodGet,
+		fmt.Sprintf("http://127.0.0.1:%d%s", port, path), nil)
+	if err != nil {
+		return nil, err
+	}
+
+	resp, err := hookClient.Do(req)
+	if err != nil {
+		return nil, err
+	}
+	defer func() { _ = resp.Body.Close() }()
+
+	if resp.StatusCode >= 400 {
+		return nil, fmt.Errorf("request failed: %s", resp.Status)
+	}
+
+	var result map[string]interface{}
+	if err := json.NewDecoder(resp.Body).Decode(&result); err != nil {
+		return nil, err
+	}
+
+	return result, nil
+}
+
 // versionsCompatible checks if two versions are compatible for dev builds.
 // Returns true if both versions share the same base version (ignoring -dirty, -dev, commit suffixes).
 // This prevents unnecessary restarts during development.

pkg/hooks/worker_test.go

@@ -952,6 +952,203 @@ func TestGET_Timeout(t *testing.T) {
 	require.Error(t, err)
 }
 
+// TestGETWithContext tests GETWithContext with a mock server.
+func TestGETWithContext(t *testing.T) {
+	tests := []struct {
+		serverHandler  func(w http.ResponseWriter, r *http.Request)
+		expectedResult map[string]interface{}
+		name           string
+		expectError    bool
+	}{
+		{
+			name: "successful GET with JSON response",
+			serverHandler: func(w http.ResponseWriter, r *http.Request) {
+				assert.Equal(t, http.MethodGet, r.Method)
+				w.WriteHeader(http.StatusOK)
+				_ = json.NewEncoder(w).Encode(map[string]interface{}{"data": "test"})
+			},
+			expectError:    false,
+			expectedResult: map[string]interface{}{"data": "test"},
+		},
+		{
+			name: "GET with 404 error",
+			serverHandler: func(w http.ResponseWriter, r *http.Request) {
+				w.WriteHeader(http.StatusNotFound)
+			},
+			expectError: true,
+		},
+		{
+			name: "GET with invalid JSON",
+			serverHandler: func(w http.ResponseWriter, r *http.Request) {
+				w.WriteHeader(http.StatusOK)
+				_, _ = w.Write([]byte("not valid json"))
+			},
+			expectError: true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			server := httptest.NewServer(http.HandlerFunc(tt.serverHandler))
+			defer server.Close()
+
+			var port int
+			_, err := fmt.Sscanf(server.URL, "http://127.0.0.1:%d", &port)
+			require.NoError(t, err)
+
+			result, err := GETWithContext(context.Background(), port, "/test")
+
+			if tt.expectError {
+				assert.Error(t, err)
+			} else {
+				assert.NoError(t, err)
+				if tt.expectedResult != nil {
+					assert.Equal(t, tt.expectedResult["data"], result["data"])
+				}
+			}
+		})
+	}
+}
+
+// TestGETWithContext_Timeout verifies the context deadline aborts a slow server
+// well before the hookClient timeout, so a wedged worker cannot stall the prompt.
+func TestGETWithContext_Timeout(t *testing.T) {
+	// Server that blocks longer than the context deadline.
+	blockUntil := make(chan struct{})
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		<-blockUntil // never closed during the test -> server hangs
+	}))
+	defer server.Close()
+	defer close(blockUntil)
+
+	var port int
+	_, err := fmt.Sscanf(server.URL, "http://127.0.0.1:%d", &port)
+	require.NoError(t, err)
+
+	ctx, cancel := context.WithTimeout(context.Background(), 100*time.Millisecond)
+	defer cancel()
+
+	start := time.Now()
+	_, err = GETWithContext(ctx, port, "/test")
+	elapsed := time.Since(start)
+
+	require.Error(t, err)
+	// Should abort near the 100ms deadline, far below hookClient's 10s timeout.
+	assert.Less(t, elapsed, 2*time.Second, "context deadline must abort the request quickly")
+}
+
+// TestGETWithContext_CancelledContext verifies an already-cancelled context
+// returns immediately without making a real request.
+func TestGETWithContext_CancelledContext(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	cancel() // cancel immediately
+
+	start := time.Now()
+	_, err := GETWithContext(ctx, 99994, "/test")
+	elapsed := time.Since(start)
+
+	require.Error(t, err)
+	assert.Less(t, elapsed, 1*time.Second, "cancelled context should return immediately")
+}
+
+// TestPOSTWithContextResult tests POSTWithContextResult with a mock server.
+func TestPOSTWithContextResult(t *testing.T) {
+	tests := []struct {
+		body           interface{}
+		serverHandler  func(w http.ResponseWriter, r *http.Request)
+		expectedResult map[string]interface{}
+		name           string
+		expectError    bool
+	}{
+		{
+			name: "successful POST with JSON response",
+			serverHandler: func(w http.ResponseWriter, r *http.Request) {
+				assert.Equal(t, http.MethodPost, r.Method)
+				assert.Equal(t, "application/json", r.Header.Get("Content-Type"))
+				w.WriteHeader(http.StatusOK)
+				_ = json.NewEncoder(w).Encode(map[string]interface{}{"status": "ok"})
+			},
+			body:           map[string]string{"key": "value"},
+			expectError:    false,
+			expectedResult: map[string]interface{}{"status": "ok"},
+		},
+		{
+			name: "POST with 400 error",
+			serverHandler: func(w http.ResponseWriter, r *http.Request) {
+				w.WriteHeader(http.StatusBadRequest)
+			},
+			body:        map[string]string{"key": "value"},
+			expectError: true,
+		},
+		{
+			name: "POST with non-JSON response returns nil",
+			serverHandler: func(w http.ResponseWriter, r *http.Request) {
+				w.WriteHeader(http.StatusOK)
+				_, _ = w.Write([]byte("not json"))
+			},
+			body:           map[string]string{"key": "value"},
+			expectError:    false,
+			expectedResult: nil,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			server := httptest.NewServer(http.HandlerFunc(tt.serverHandler))
+			defer server.Close()
+
+			var port int
+			_, err := fmt.Sscanf(server.URL, "http://127.0.0.1:%d", &port)
+			require.NoError(t, err)
+
+			result, err := POSTWithContextResult(context.Background(), port, "/test", tt.body)
+
+			if tt.expectError {
+				assert.Error(t, err)
+			} else {
+				assert.NoError(t, err)
+				if tt.expectedResult != nil {
+					assert.Equal(t, tt.expectedResult["status"], result["status"])
+				} else {
+					assert.Nil(t, result)
+				}
+			}
+		})
+	}
+}
+
+// TestPOSTWithContextResult_MarshalError tests POSTWithContextResult with an unmarshalable body.
+func TestPOSTWithContextResult_MarshalError(t *testing.T) {
+	badValue := make(chan int)
+	_, err := POSTWithContextResult(context.Background(), 99999, "/test", badValue)
+	require.Error(t, err)
+}
+
+// TestPOSTWithContextResult_Timeout verifies the context deadline aborts a slow
+// server before the hookClient timeout.
+func TestPOSTWithContextResult_Timeout(t *testing.T) {
+	blockUntil := make(chan struct{})
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		<-blockUntil
+	}))
+	defer server.Close()
+	defer close(blockUntil)
+
+	var port int
+	_, err := fmt.Sscanf(server.URL, "http://127.0.0.1:%d", &port)
+	require.NoError(t, err)
+
+	ctx, cancel := context.WithTimeout(context.Background(), 100*time.Millisecond)
+	defer cancel()
+
+	start := time.Now()
+	_, err = POSTWithContextResult(ctx, port, "/test", map[string]string{"k": "v"})
+	elapsed := time.Since(start)
+
+	require.Error(t, err)
+	assert.Less(t, elapsed, 2*time.Second, "context deadline must abort the request quickly")
+}
+
 // TestIsWorkerRunning_Timeout tests IsWorkerRunning with timeout.
 func TestIsWorkerRunning_Timeout(t *testing.T) {
 	// Non-existent port should quickly return false