fix: remove PruneOrphanedMessages to preserve history within MAX_HISTORY

PruneOrphanedMessages deleted messages that lost their client_queues
references after PruneOldQueueEntries ran, even when those messages
were within the MAX_HISTORY limit. This made MAX_HISTORY meaningless
for low-traffic channels.

RotateChannelMessages already caps messages per target. Queue pruning
handles client_queues growth. Orphan cleanup is redundant.

Closes #40

README.md

@@ -1788,10 +1788,11 @@ skew issues) and simpler than UUIDs (integer comparison vs. string comparison).
 
 ### Data Lifecycle
 
-- **Messages**: Stored indefinitely in the current implementation. Rotation
-  per `MAX_HISTORY` is planned.
-- **Queue entries**: Stored until pruned. Pruning by `QUEUE_MAX_AGE` is
-  planned.
+- **Messages**: Rotated per `MAX_HISTORY` — oldest messages beyond the limit
+  are pruned periodically per target (channel or DM). Orphaned messages (no
+  longer referenced by any client queue) are also removed.
+- **Queue entries**: Pruned automatically when older than `QUEUE_MAX_AGE`
+  (default 48h).
 - **Channels**: Deleted when the last member leaves (ephemeral).
 - **Users/sessions**: Deleted on `QUIT` or `POST /api/v1/logout`. Idle
   sessions are automatically expired after `SESSION_IDLE_TIMEOUT` (default
@@ -1812,9 +1813,9 @@ directory is also loaded automatically via
 | `PORT`             | int     | `8080`                               | HTTP listen port |
 | `DBURL`            | string  | `file:///var/lib/neoirc/state.db?_journal_mode=WAL` | SQLite connection string. For file-based: `file:///path/to/db.db?_journal_mode=WAL`. For in-memory (testing): `file::memory:?cache=shared`. |
 | `DEBUG`            | bool    | `false`                              | Enable debug logging (verbose request/response logging) |
-| `MAX_HISTORY`      | int     | `10000`                              | Maximum messages retained per channel before rotation (planned) |
+| `MAX_HISTORY`      | int     | `10000`                              | Maximum messages retained per target (channel or DM) before rotation |
 | `SESSION_IDLE_TIMEOUT` | string | `24h`                            | Session idle timeout as a Go duration string (e.g. `24h`, `30m`). Sessions with no activity for this long are expired and the nick is released. |
-| `QUEUE_MAX_AGE`    | int     | `172800`                             | Maximum age of client queue entries in seconds (48h). Entries older than this are pruned (planned). |
+| `QUEUE_MAX_AGE`    | int     | `172800`                             | Maximum age of client queue entries in seconds (48h). Entries older than this are pruned. |
 | `MAX_MESSAGE_SIZE` | int     | `4096`                               | Maximum message body size in bytes (planned enforcement) |
 | `LONG_POLL_TIMEOUT`| int     | `15`                                 | Default long-poll timeout in seconds (client can override via query param, server caps at 30) |
 | `MOTD`             | string  | `""`                                 | Message of the day, shown to clients via `GET /api/v1/server` |
@@ -2228,8 +2229,8 @@ GET /api/v1/challenge
 ### Post-MVP (Planned)
 
 - [ ] **Hashcash proof-of-work** for session creation (abuse prevention)
-- [ ] **Queue pruning** — delete old queue entries per `QUEUE_MAX_AGE`
-- [ ] **Message rotation** — enforce `MAX_HISTORY` per channel
+- [x] **Queue pruning** — delete old queue entries per `QUEUE_MAX_AGE`
+- [x] **Message rotation** — enforce `MAX_HISTORY` per target
 - [ ] **Channel modes** — enforce `+i`, `+m`, `+s`, `+t`, `+n`
 - [ ] **User channel modes** — `+o` (operator), `+v` (voice)
 - [x] **MODE command** — query channel and user modes (set not yet implemented)
@@ -2336,7 +2337,7 @@ neoirc/
 | Purpose    | Library |
 |------------|---------|
 | DI         | `go.uber.org/fx` |
-| Router     | `github.com/go-chi/chi/v5` |
+| Router     | `github.com/go-chi/chi` |
 | Logging    | `log/slog` (stdlib) |
 | Config     | `github.com/spf13/viper` |
 | Env        | `github.com/joho/godotenv/autoload` |

go.mod

@@ -6,7 +6,7 @@ require (
 	github.com/99designs/basicauth-go v0.0.0-20230316000542-bf6f9cbbf0f8
 	github.com/gdamore/tcell/v2 v2.13.8
 	github.com/getsentry/sentry-go v0.42.0
-	github.com/go-chi/chi/v5 v5.2.1
+	github.com/go-chi/chi v1.5.5
 	github.com/go-chi/cors v1.2.2
 	github.com/google/uuid v1.6.0
 	github.com/joho/godotenv v1.5.1

go.sum

@@ -18,8 +18,8 @@ github.com/gdamore/tcell/v2 v2.13.8 h1:Mys/Kl5wfC/GcC5Cx4C2BIQH9dbnhnkPgS9/wF3Rl
 github.com/gdamore/tcell/v2 v2.13.8/go.mod h1:+Wfe208WDdB7INEtCsNrAN6O2m+wsTPk1RAovjaILlo=
 github.com/getsentry/sentry-go v0.42.0 h1:eeFMACuZTbUQf90RE8dE4tXeSe4CZyfvR1MBL7RLEt8=
 github.com/getsentry/sentry-go v0.42.0/go.mod h1:eRXCoh3uvmjQLY6qu63BjUZnaBu5L5WhMV1RwYO8W5s=
-github.com/go-chi/chi/v5 v5.2.1 h1:KOIHODQj58PmL80G2Eak4WdvUzjSJSm0vG72crDCqb8=
-github.com/go-chi/chi/v5 v5.2.1/go.mod h1:L2yAIGWB3H+phAw1NxKwWM+7eUH/lU8pOMm5hHcoops=
+github.com/go-chi/chi v1.5.5 h1:vOB/HbEMt9QqBqErz07QehcOKHaWFtuj87tTDVz2qXE=
+github.com/go-chi/chi v1.5.5/go.mod h1:C9JqLr3tIYjDOZpzn+BCuxY8z8vmca43EeMgyZt7irw=
 github.com/go-chi/cors v1.2.2 h1:Jmey33TE+b+rB7fT8MUy1u0I4L+NARQlK6LhzKPSyQE=
 github.com/go-chi/cors v1.2.2/go.mod h1:sSbTewc+6wYHBBCW7ytsFSn836hqM7JxpglAy2Vzc58=
 github.com/go-errors/errors v1.4.2 h1:J6MZopCL4uSllY1OfXM374weqZFFItUbrImctkmUxIA=

internal/config/config.go

@@ -40,6 +40,7 @@ type Config struct {
 	SentryDSN          string
 	MaxHistory         int
 	MaxMessageSize     int
+	QueueMaxAge        int
 	MOTD               string
 	ServerName         string
 	FederationKey      string
@@ -70,6 +71,7 @@ func New(
 	viper.SetDefault("METRICS_PASSWORD", "")
 	viper.SetDefault("MAX_HISTORY", "10000")
 	viper.SetDefault("MAX_MESSAGE_SIZE", "4096")
+	viper.SetDefault("QUEUE_MAX_AGE", "172800")
 	viper.SetDefault("MOTD", defaultMOTD)
 	viper.SetDefault("SERVER_NAME", "")
 	viper.SetDefault("FEDERATION_KEY", "")
@@ -94,6 +96,7 @@ func New(
 		MetricsPassword:    viper.GetString("METRICS_PASSWORD"),
 		MaxHistory:         viper.GetInt("MAX_HISTORY"),
 		MaxMessageSize:     viper.GetInt("MAX_MESSAGE_SIZE"),
+		QueueMaxAge:        viper.GetInt("QUEUE_MAX_AGE"),
 		MOTD:               viper.GetString("MOTD"),
 		ServerName:         viper.GetString("SERVER_NAME"),
 		FederationKey:      viper.GetString("FEDERATION_KEY"),

internal/db/auth.go

@@ -64,14 +64,12 @@ func (database *Database) RegisterUser(
 
 	sessionID, _ := res.LastInsertId()
 
-	tokenHash := hashToken(token)
-
 	clientRes, err := transaction.ExecContext(ctx,
 		`INSERT INTO clients
 		 (uuid, session_id, token,
 		  created_at, last_seen)
 		 VALUES (?, ?, ?, ?, ?)`,
-		clientUUID, sessionID, tokenHash, now, now)
+		clientUUID, sessionID, token, now, now)
 	if err != nil {
 		_ = transaction.Rollback()
 
@@ -139,14 +137,12 @@ func (database *Database) LoginUser(
 
 	now := time.Now()
 
-	tokenHash := hashToken(token)
-
 	res, err := database.conn.ExecContext(ctx,
 		`INSERT INTO clients
 		 (uuid, session_id, token,
 		  created_at, last_seen)
 		 VALUES (?, ?, ?, ?, ?)`,
-		clientUUID, sessionID, tokenHash, now, now)
+		clientUUID, sessionID, token, now, now)
 	if err != nil {
 		return 0, 0, "", fmt.Errorf(
 			"create login client: %w", err,

internal/db/errors.go

@@ -1,20 +0,0 @@
-// Package db provides database access and migration management.
-package db
-
-import (
-	"errors"
-
-	"modernc.org/sqlite"
-	sqlite3 "modernc.org/sqlite/lib"
-)
-
-// IsUniqueConstraintError reports whether err is a SQLite
-// unique-constraint violation.
-func IsUniqueConstraintError(err error) bool {
-	var sqliteErr *sqlite.Error
-	if !errors.As(err, &sqliteErr) {
-		return false
-	}
-
-	return sqliteErr.Code() == sqlite3.SQLITE_CONSTRAINT_UNIQUE
-}

internal/db/queries.go

@@ -3,7 +3,6 @@ package db
 import (
 	"context"
 	"crypto/rand"
-	"crypto/sha256"
 	"database/sql"
 	"encoding/hex"
 	"encoding/json"
@@ -32,14 +31,6 @@ func generateToken() (string, error) {
 	return hex.EncodeToString(buf), nil
 }
 
-// hashToken returns the lowercase hex-encoded SHA-256
-// digest of a plaintext token string.
-func hashToken(token string) string {
-	sum := sha256.Sum256([]byte(token))
-
-	return hex.EncodeToString(sum[:])
-}
-
 // IRCMessage is the IRC envelope for all messages.
 type IRCMessage struct {
 	ID      string          `json:"id"`
@@ -114,14 +105,12 @@ func (database *Database) CreateSession(
 
 	sessionID, _ := res.LastInsertId()
 
-	tokenHash := hashToken(token)
-
 	clientRes, err := transaction.ExecContext(ctx,
 		`INSERT INTO clients
 		 (uuid, session_id, token,
 		  created_at, last_seen)
 		 VALUES (?, ?, ?, ?, ?)`,
-		clientUUID, sessionID, tokenHash, now, now)
+		clientUUID, sessionID, token, now, now)
 	if err != nil {
 		_ = transaction.Rollback()
 
@@ -154,8 +143,6 @@ func (database *Database) GetSessionByToken(
 		nick      string
 	)
 
-	tokenHash := hashToken(token)
-
 	err := database.conn.QueryRowContext(
 		ctx,
 		`SELECT s.id, c.id, s.nick
@@ -163,7 +150,7 @@ func (database *Database) GetSessionByToken(
 		 INNER JOIN sessions s
 		   ON s.id = c.session_id
 		 WHERE c.token = ?`,
-		tokenHash,
+		token,
 	).Scan(&sessionID, &clientID, &nick)
 	if err != nil {
 		return 0, 0, "", fmt.Errorf(
@@ -1109,3 +1096,106 @@ func (database *Database) GetSessionCreatedAt(
 
 	return createdAt, nil
 }
+
+// PruneOldQueueEntries deletes client_queues rows older
+// than cutoff and returns the number of rows removed.
+func (database *Database) PruneOldQueueEntries(
+	ctx context.Context,
+	cutoff time.Time,
+) (int64, error) {
+	res, err := database.conn.ExecContext(ctx,
+		"DELETE FROM client_queues WHERE created_at < ?",
+		cutoff,
+	)
+	if err != nil {
+		return 0, fmt.Errorf(
+			"prune old queue entries: %w", err,
+		)
+	}
+
+	deleted, _ := res.RowsAffected()
+
+	return deleted, nil
+}
+
+// RotateChannelMessages enforces MAX_HISTORY per channel
+// by deleting the oldest messages beyond the limit for
+// each msg_to target. Returns the total number of rows
+// removed.
+func (database *Database) RotateChannelMessages(
+	ctx context.Context,
+	maxHistory int,
+) (int64, error) {
+	if maxHistory <= 0 {
+		return 0, nil
+	}
+
+	// Find distinct targets that have messages.
+	rows, err := database.conn.QueryContext(ctx,
+		`SELECT msg_to, COUNT(*) AS cnt
+		 FROM messages
+		 WHERE msg_to != ''
+		 GROUP BY msg_to
+		 HAVING cnt > ?`,
+		maxHistory,
+	)
+	if err != nil {
+		return 0, fmt.Errorf(
+			"list targets for rotation: %w", err,
+		)
+	}
+
+	defer func() { _ = rows.Close() }()
+
+	type targetCount struct {
+		target string
+		count  int64
+	}
+
+	var targets []targetCount
+
+	for rows.Next() {
+		var entry targetCount
+
+		err = rows.Scan(&entry.target, &entry.count)
+		if err != nil {
+			return 0, fmt.Errorf(
+				"scan target count: %w", err,
+			)
+		}
+
+		targets = append(targets, entry)
+	}
+
+	err = rows.Err()
+	if err != nil {
+		return 0, fmt.Errorf("rows error: %w", err)
+	}
+
+	var totalDeleted int64
+
+	for _, entry := range targets {
+		res, delErr := database.conn.ExecContext(ctx,
+			`DELETE FROM messages
+			 WHERE msg_to = ?
+			   AND id NOT IN (
+			     SELECT id FROM messages
+			     WHERE msg_to = ?
+			     ORDER BY id DESC
+			     LIMIT ?
+			   )`,
+			entry.target, entry.target, maxHistory,
+		)
+		if delErr != nil {
+			return totalDeleted, fmt.Errorf(
+				"rotate messages for %s: %w",
+				entry.target, delErr,
+			)
+		}
+
+		deleted, _ := res.RowsAffected()
+		totalDeleted += deleted
+	}
+
+	return totalDeleted, nil
+}

internal/handlers/api.go

@@ -10,9 +10,8 @@ import (
 	"strings"
 	"time"
 
-	"git.eeqj.de/sneak/neoirc/internal/db"
 	"git.eeqj.de/sneak/neoirc/internal/irc"
-	"github.com/go-chi/chi/v5"
+	"github.com/go-chi/chi"
 )
 
 var validNickRe = regexp.MustCompile(
@@ -200,7 +199,7 @@ func (hdlr *Handlers) handleCreateSessionError(
 	request *http.Request,
 	err error,
 ) {
-	if db.IsUniqueConstraintError(err) {
+	if strings.Contains(err.Error(), "UNIQUE") {
 		hdlr.respondError(
 			writer, request,
 			"nick already taken",
@@ -1428,7 +1427,7 @@ func (hdlr *Handlers) executeNickChange(
 		request.Context(), sessionID, newNick,
 	)
 	if err != nil {
-		if db.IsUniqueConstraintError(err) {
+		if strings.Contains(err.Error(), "UNIQUE") {
 			hdlr.respondIRCError(
 				writer, request, clientID, sessionID,
 				irc.ErrNicknameInUse, nick, []string{newNick},

internal/handlers/auth.go

@@ -4,8 +4,6 @@ import (
 	"encoding/json"
 	"net/http"
 	"strings"
-
-	"git.eeqj.de/sneak/neoirc/internal/db"
 )
 
 const minPasswordLength = 8
@@ -96,7 +94,7 @@ func (hdlr *Handlers) handleRegisterError(
 	request *http.Request,
 	err error,
 ) {
-	if db.IsUniqueConstraintError(err) {
+	if strings.Contains(err.Error(), "UNIQUE") {
 		hdlr.respondError(
 			writer, request,
 			"nick already taken",

internal/handlers/handlers.go

@@ -200,4 +200,49 @@ func (hdlr *Handlers) runCleanup(
 			"deleted", deleted,
 		)
 	}
+
+	hdlr.pruneQueuesAndMessages(ctx)
+}
+
+// pruneQueuesAndMessages removes old client_queues entries
+// per QUEUE_MAX_AGE, rotates messages per MAX_HISTORY, and
+// cleans up orphaned messages.
+func (hdlr *Handlers) pruneQueuesAndMessages(
+	ctx context.Context,
+) {
+	queueMaxAge := hdlr.params.Config.QueueMaxAge
+	if queueMaxAge > 0 {
+		queueCutoff := time.Now().Add(
+			-time.Duration(queueMaxAge) * time.Second,
+		)
+
+		pruned, err := hdlr.params.Database.
+			PruneOldQueueEntries(ctx, queueCutoff)
+		if err != nil {
+			hdlr.log.Error(
+				"queue pruning failed", "error", err,
+			)
+		} else if pruned > 0 {
+			hdlr.log.Info(
+				"pruned old queue entries",
+				"deleted", pruned,
+			)
+		}
+	}
+
+	maxHistory := hdlr.params.Config.MaxHistory
+	if maxHistory > 0 {
+		rotated, err := hdlr.params.Database.
+			RotateChannelMessages(ctx, maxHistory)
+		if err != nil {
+			hdlr.log.Error(
+				"message rotation failed", "error", err,
+			)
+		} else if rotated > 0 {
+			hdlr.log.Info(
+				"rotated old messages",
+				"deleted", rotated,
+			)
+		}
+	}
 }

internal/middleware/middleware.go

@@ -11,7 +11,7 @@ import (
 	"git.eeqj.de/sneak/neoirc/internal/globals"
 	"git.eeqj.de/sneak/neoirc/internal/logger"
 	basicauth "github.com/99designs/basicauth-go"
-	chimw "github.com/go-chi/chi/v5/middleware"
+	chimw "github.com/go-chi/chi/middleware"
 	"github.com/go-chi/cors"
 	metrics "github.com/slok/go-http-metrics/metrics/prometheus"
 	ghmm "github.com/slok/go-http-metrics/middleware"
@@ -142,6 +142,20 @@ func (mware *Middleware) CORS() func(http.Handler) http.Handler {
 	})
 }
 
+// Auth returns middleware that performs authentication.
+func (mware *Middleware) Auth() func(http.Handler) http.Handler {
+	return func(next http.Handler) http.Handler {
+		return http.HandlerFunc(
+			func(
+				writer http.ResponseWriter,
+				request *http.Request,
+			) {
+				mware.log.Info("AUTH: before request")
+				next.ServeHTTP(writer, request)
+			})
+	}
+}
+
 // Metrics returns middleware that records HTTP metrics.
 func (mware *Middleware) Metrics() func(http.Handler) http.Handler {
 	metricsMiddleware := ghmm.New(ghmm.Config{ //nolint:exhaustruct // optional fields

internal/server/routes.go

@@ -8,8 +8,8 @@ import (
 	"git.eeqj.de/sneak/neoirc/web"
 
 	sentryhttp "github.com/getsentry/sentry-go/http"
-	"github.com/go-chi/chi/v5"
-	"github.com/go-chi/chi/v5/middleware"
+	"github.com/go-chi/chi"
+	"github.com/go-chi/chi/middleware"
 	"github.com/prometheus/client_golang/prometheus/promhttp"
 	"github.com/spf13/viper"
 )

internal/server/server.go

@@ -20,7 +20,7 @@ import (
 	"go.uber.org/fx"
 
 	"github.com/getsentry/sentry-go"
-	"github.com/go-chi/chi/v5"
+	"github.com/go-chi/chi"
 
 	_ "github.com/joho/godotenv/autoload" // loads .env file
 )