From: Anderson A. Giacomolli <redacted>
Date: Wed, 11 Nov 2026 14:49:23 +0000 (-0300)
Subject: Add local context to chat operation failures
X-Git-Url: https://git.giacomolli.uk/onechat/commitdiff_plain/bd7da3557dc7a17020931f5a49ed5007fa81a645

Add local context to chat operation failures

Daemon, chat, schedule, and worker failures identify their local
operation while wrapping the original cause. Successful results keep a
nil error. Privacy-safe causes and direct context errors retain their
existing handling, and shutdown and retry decisions do not change.

Issue: 3cdc678
---

diff --git a/chatgpt.go b/chatgpt.go
index 7748190..49be015 100644
--- a/chatgpt.go
+++ b/chatgpt.go
@@ -116,14 +116,14 @@ func (a *ChatGPTAuth) Authorize(ctx context.Context, header http.Header) error {
 
 	tokens, err := a.read()
 	if err != nil {
-		return err
+		return fmt.Errorf("read login tokens: %w", err)
 	}
 
 	expiry, found := chatgptTokenExpiry(tokens.AccessToken)
 	if !found || !time.Now().Before(expiry.Add(-chatgptRefreshMargin)) {
 		tokens, err = a.refresh(ctx, tokens)
 		if err != nil {
-			return err
+			return fmt.Errorf("refresh login tokens: %w", err)
 		}
 	}
 
@@ -184,7 +184,7 @@ func (a *ChatGPTAuth) refresh(ctx context.Context, tokens ChatGPTTokenFile) (Cha
 
 	err = a.write(tokens)
 	if err != nil {
-		return ChatGPTTokenFile{}, err
+		return ChatGPTTokenFile{}, fmt.Errorf("save refreshed tokens: %w", err)
 	}
 
 	return tokens, nil
@@ -199,8 +199,11 @@ func (a *ChatGPTAuth) postJSON(ctx context.Context, path string, body, result an
 	}
 
 	_, err = a.post(ctx, path, "application/json", data, result)
+	if err != nil {
+		return fmt.Errorf("post JSON request: %w", err)
+	}
 
-	return err
+	return nil
 }
 
 // write replaces the token file atomically. The file has mode 0600.
@@ -278,17 +281,17 @@ func (a *ChatGPTAuth) Login(ctx context.Context, out io.Writer) error {
 
 	grant, err := a.poll(ctx, code.DeviceAuthID, userCode, chatgptPollInterval(code.Interval))
 	if err != nil {
-		return err
+		return fmt.Errorf("wait for device grant: %w", err)
 	}
 
 	tokens, err := a.exchange(ctx, grant)
 	if err != nil {
-		return err
+		return fmt.Errorf("exchange device grant: %w", err)
 	}
 
 	err = a.write(tokens)
 	if err != nil {
-		return err
+		return fmt.Errorf("save login tokens: %w", err)
 	}
 
 	_, err = fmt.Fprintln(out, "Logged in.")
@@ -443,12 +446,12 @@ func chatgptDecodeClaims(token string, claims any) bool {
 func chatgptLogin(ctx context.Context, out io.Writer) (err error) {
 	dir, err := dataDir()
 	if err != nil {
-		return err
+		return fmt.Errorf("find data directory: %w", err)
 	}
 
 	tokens, err := lockTokens(dir)
 	if err != nil {
-		return err
+		return fmt.Errorf("lock login tokens: %w", err)
 	}
 
 	defer func() {
diff --git a/command.go b/command.go
index a49f1d9..02901e2 100644
--- a/command.go
+++ b/command.go
@@ -48,7 +48,7 @@ func parseCommand(ctx context.Context, args []string) error {
 	case len(args) == 1 && args[0] == "login":
 		err := chatgptLogin(ctx, os.Stdout)
 		if err != nil {
-			return err
+			return fmt.Errorf("log in: %w", err)
 		}
 
 	// A signal is the normal stop of the daemon and the client, so their
@@ -66,7 +66,7 @@ func parseCommand(ctx context.Context, args []string) error {
 	case len(args) > 0 && args[0] == "probe":
 		err := probe(ctx, args[1:], os.Stdout)
 		if err != nil {
-			return err
+			return fmt.Errorf("run probe: %w", err)
 		}
 	default:
 		return fmt.Errorf("unknown command %q\n\n%s", strings.Join(args, " "), strings.TrimSuffix(usage, "\n"))
diff --git a/daemon.go b/daemon.go
index d6aa6aa..962070a 100644
--- a/daemon.go
+++ b/daemon.go
@@ -213,8 +213,11 @@ func daemonRunRequest(l *TurnLoop, whatsapp *WhatsApp, request SocketRequest, an
 		}
 
 		_, err := l.Submit(terminalSource, request.Text)
+		if err != nil {
+			return fmt.Errorf("submit terminal message: %w", err)
+		}
 
-		return err
+		return nil
 	case "image":
 		if !filepath.IsAbs(request.Path) {
 			return errors.New("use /image PATH [caption]")
@@ -252,7 +255,11 @@ func daemonRunRequest(l *TurnLoop, whatsapp *WhatsApp, request SocketRequest, an
 			err = fmt.Errorf("no subagent %s runs", request.Text)
 		}
 
-		return err
+		if err != nil {
+			return fmt.Errorf("stop subagent: %w", err)
+		}
+
+		return nil
 	default:
 		return fmt.Errorf("unknown request %q", request.Type)
 	}
@@ -268,7 +275,7 @@ func daemonRunRequest(l *TurnLoop, whatsapp *WhatsApp, request SocketRequest, an
 func daemon(ctx context.Context, out io.Writer) (err error) {
 	dir, err := dataDir()
 	if err != nil {
-		return err
+		return fmt.Errorf("find data directory: %w", err)
 	}
 
 	// Check the socket path before the daemon writes a file, so that a data
@@ -276,22 +283,22 @@ func daemon(ctx context.Context, out io.Writer) (err error) {
 	socket := filepath.Join(dir, socketFileName)
 	err = checkSocketPath(socket)
 	if err != nil {
-		return err
+		return fmt.Errorf("check daemon socket path: %w", err)
 	}
 
 	config, err := loadConfig(dir)
 	if err != nil {
-		return err
+		return fmt.Errorf("load daemon config: %w", err)
 	}
 
 	botSettings, hasBot, err := loadTelegramConfig(dir)
 	if err != nil {
-		return err
+		return fmt.Errorf("load Telegram config: %w", err)
 	}
 
 	tokens, err := lockTokens(dir)
 	if err != nil {
-		return err
+		return fmt.Errorf("lock login tokens: %w", err)
 	}
 
 	defer func() {
@@ -303,7 +310,7 @@ func daemon(ctx context.Context, out io.Writer) (err error) {
 	logger := daemonLogger(out, "onechat: ")
 	whatsapp, err := openWhatsApp(ctx, dir, time.Now, daemonLogger(out, "whatsapp: "), whatsappNewClient)
 	if err != nil {
-		return err
+		return fmt.Errorf("open WhatsApp: %w", err)
 	}
 
 	defer func() {
@@ -312,12 +319,12 @@ func daemon(ctx context.Context, out io.Writer) (err error) {
 
 	address, auth, err := modelEndpoint(config, dir)
 	if err != nil {
-		return err
+		return fmt.Errorf("configure model endpoint: %w", err)
 	}
 
 	agents, err := openDaemonAgents(ctx, dir, address, auth, config.Compactor, time.Now, logger)
 	if err != nil {
-		return err
+		return fmt.Errorf("open daemon agents: %w", err)
 	}
 
 	defer func() {
@@ -332,7 +339,7 @@ func daemon(ctx context.Context, out io.Writer) (err error) {
 
 	listener, err := daemonListenSocket(socket)
 	if err != nil {
-		return err
+		return fmt.Errorf("listen for daemon clients: %w", err)
 	}
 
 	linked := "not linked"
@@ -363,7 +370,7 @@ func daemon(ctx context.Context, out io.Writer) (err error) {
 func daemonListenSocket(path string) (net.Listener, error) {
 	err := checkSocketPath(path)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("check daemon socket path: %w", err)
 	}
 
 	err = os.Remove(path)
diff --git a/daemon_test.go b/daemon_test.go
index 6a4d98c..c6cc227 100644
--- a/daemon_test.go
+++ b/daemon_test.go
@@ -39,7 +39,7 @@ func TestClientsSeeTheTurnAsItHappens(t *testing.T) {
 	first.Type(stopCommand)
 	first.WaitFor(t, "[error] no turn runs")
 	first.Type(stopCommand + " BlueFox")
-	first.WaitFor(t, "[error] no subagent BlueFox runs")
+	first.WaitFor(t, "[error] stop subagent: no subagent BlueFox runs")
 	require.NotContains(t, second.Output(), "no turn runs")
 	require.NoError(t, first.Close())
 }
diff --git a/schedule.go b/schedule.go
index 7eb747f..23462d2 100644
--- a/schedule.go
+++ b/schedule.go
@@ -225,7 +225,7 @@ func (s *Schedules) deliver(ctx context.Context, l *TurnLoop) error {
 
 		err = s.Done(schedule, now)
 		if err != nil {
-			return err
+			return fmt.Errorf("acknowledge schedule run: %w", err)
 		}
 
 		attrs := []any{"id", schedule.ID}
@@ -352,7 +352,7 @@ func (s *Schedules) Set(text string, at, cron *string) (string, error) {
 	default:
 		parsed, err := scheduleParseCron(*cron)
 		if err != nil {
-			return "", err
+			return "", fmt.Errorf("parse schedule expression: %w", err)
 		}
 
 		next, found := parsed.Next(now)
@@ -372,7 +372,7 @@ func (s *Schedules) Set(text string, at, cron *string) (string, error) {
 	s.file.Schedules = append(s.file.Schedules, schedule)
 	err := s.save()
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("save new schedule: %w", err)
 	}
 
 	s.change()
@@ -430,7 +430,7 @@ func (s *Schedules) Remove(id int) (string, error) {
 	s.file.Schedules = slices.Delete(s.file.Schedules, index, index+1)
 	err := s.save()
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("save removed schedule: %w", err)
 	}
 
 	s.change()
diff --git a/schedule_cron.go b/schedule_cron.go
index b982f37..bf1424f 100644
--- a/schedule_cron.go
+++ b/schedule_cron.go
@@ -277,7 +277,7 @@ func scheduleCronField(field string, low, high int) (uint64, error) {
 
 			first, err = scheduleCronNumber(base, low, high)
 			if err != nil {
-				return 0, err
+				return 0, fmt.Errorf("parse cron field value: %w", err)
 			}
 
 			last = first
diff --git a/schedule_cron_test.go b/schedule_cron_test.go
index 06d23cf..33d861b 100644
--- a/schedule_cron_test.go
+++ b/schedule_cron_test.go
@@ -72,7 +72,7 @@ func TestScheduleParseCronRefuses(t *testing.T) {
 		{
 			name:       "rejects a day name",
 			expression: "0 8 * * MON",
-			message:    `the day of week field of "0 8 * * MON": "MON" is not a number from 0 to 7`,
+			message:    `the day of week field of "0 8 * * MON": parse cron field value: "MON" is not a number from 0 to 7`,
 		},
 		{
 			name:       "rejects a month name",
diff --git a/subagent_run.go b/subagent_run.go
index 24e4f82..e96975c 100644
--- a/subagent_run.go
+++ b/subagent_run.go
@@ -132,7 +132,7 @@ func (r *SubagentRuns) Spawn(ctx context.Context, tasks []string, effort *string
 
 	view, err := r.layout.Split(r.memory.ViewLines(nil))
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("split worker view: %w", err)
 	}
 
 	names := make([]string, 0, len(tasks))
@@ -143,7 +143,7 @@ func (r *SubagentRuns) Spawn(ctx context.Context, tasks []string, effort *string
 		}
 
 		if err != nil {
-			return "", err
+			return "", fmt.Errorf("create worker: %w", err)
 		}
 
 		names = append(names, name)
@@ -157,19 +157,19 @@ func (r *SubagentRuns) Spawn(ctx context.Context, tasks []string, effort *string
 func (r *SubagentRuns) create(ctx context.Context, note, task string, view []string, effort string) (string, error) {
 	subagent, err := r.subagents.Create(ctx)
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("create worker log: %w", err)
 	}
 
 	for _, message := range [][2]string{{"note", note}, {"user", task}} {
 		_, err = subagent.Append(message[0], message[1])
 		if err != nil {
-			return "", err
+			return "", fmt.Errorf("append worker message: %w", err)
 		}
 	}
 
 	err = subagent.Flush(ctx)
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("flush worker log: %w", err)
 	}
 
 	err = os.MkdirAll(subagent.WorkDir(), 0o700)
@@ -210,7 +210,11 @@ func (r *SubagentRuns) start(ctx context.Context, run *SubagentRun) error {
 		r.mutex.Unlock()
 		run.cancel()
 
-		return err
+		if err != nil {
+			return fmt.Errorf("save running workers: %w", err)
+		}
+
+		return nil
 	}
 
 	r.workers.Add(1)
@@ -329,12 +333,12 @@ func (r *SubagentRuns) workPath() string {
 func (r *SubagentRuns) chain(ctx context.Context, run *SubagentRun) (string, error) {
 	instructions, err := r.agent.SubagentPrompt()
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("read worker instructions: %w", err)
 	}
 
 	log, err := run.subagent.Show()
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("read worker log: %w", err)
 	}
 
 	input := make([]any, 0, len(run.view)+2)
@@ -410,13 +414,17 @@ func (r *SubagentRuns) Stop(name string) (bool, error) {
 func (r *SubagentRuns) Resume(ctx context.Context) error {
 	names, err := r.load()
 	if err != nil || len(names) == 0 {
-		return err
+		if err != nil {
+			return fmt.Errorf("load interrupted workers: %w", err)
+		}
+
+		return nil
 	}
 
 	text := "The daemon restarted, cutting " + strings.Join(names, ", ") + "; nothing was lost: go on."
 	err = r.note(text)
 	if err != nil {
-		return err
+		return fmt.Errorf("record interrupted workers: %w", err)
 	}
 
 	for _, name := range names {
@@ -468,7 +476,7 @@ func (r *SubagentRuns) Tell(ctx context.Context, name, message string) (string,
 
 		told, err := run.subagent.Append("user", message)
 		if err != nil {
-			return "", err
+			return "", fmt.Errorf("append running worker message: %w", err)
 		}
 
 		run.pending = append(run.pending, told)
@@ -485,12 +493,12 @@ func (r *SubagentRuns) Tell(ctx context.Context, name, message string) (string,
 
 	subagent, err := r.subagents.Get(ctx, name)
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("open worker log: %w", err)
 	}
 
 	effort, err := r.effort(subagent)
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("read worker effort: %w", err)
 	}
 
 	err = r.memory.Settle(ctx)
@@ -500,7 +508,7 @@ func (r *SubagentRuns) Tell(ctx context.Context, name, message string) (string,
 
 	view, err := r.layout.Split(r.memory.ViewLines(nil))
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("split worker view: %w", err)
 	}
 
 	_, err = subagent.Append("user", message)
@@ -509,7 +517,7 @@ func (r *SubagentRuns) Tell(ctx context.Context, name, message string) (string,
 	}
 
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("save worker message: %w", err)
 	}
 
 	err = r.start(ctx, &SubagentRun{
@@ -518,7 +526,7 @@ func (r *SubagentRuns) Tell(ctx context.Context, name, message string) (string,
 		effort:   effort,
 	})
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("start told worker: %w", err)
 	}
 
 	return "Sent. " + name + "'s reply will reach you as a message.", nil
@@ -529,7 +537,7 @@ func (r *SubagentRuns) Tell(ctx context.Context, name, message string) (string,
 func (r *SubagentRuns) effort(subagent *Subagent) (string, error) {
 	note, err := subagent.First()
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("read worker note: %w", err)
 	}
 
 	effort, own := strings.CutPrefix(note.Text, subagentNote+subagentNoteEffort)
diff --git a/subagent_run_test.go b/subagent_run_test.go
index 708b515..8c9205f 100644
--- a/subagent_run_test.go
+++ b/subagent_run_test.go
@@ -357,7 +357,7 @@ func TestTellToAFinishedSubagentGoesOnFromItsLog(t *testing.T) {
 	require.Equal(t, "work: "+subagentReport(name, []string{"Reply 2."}), test.Log(t)[2])
 
 	_, err = runs.Tell(t.Context(), "BlueFox", "Hello.")
-	require.EqualError(t, err, "no agent BlueFox")
+	require.EqualError(t, err, "open worker log: no agent BlueFox")
 }
 
 func TestStopEndsASubagentAndItsCommand(t *testing.T) {
@@ -522,12 +522,12 @@ func TestRestartReportsASubagentThatCannotGoOn(t *testing.T) {
 	events.WaitFor(t, "idle", 1)
 	require.Equal(t, []string{
 		"note: The daemon restarted, cutting BlueFox; nothing was lost: go on.",
-		"work: " + subagentReport("BlueFox", []string{"failed: no agent BlueFox"}),
+		"work: " + subagentReport("BlueFox", []string{"failed: open worker log: no agent BlueFox"}),
 		"reply: a line",
 	}, subagentTestChat(t, memory))
 
 	require.Equal(t, subagentFailed, events.LastEvent("work").Status)
-	require.Equal(t, "<3>subagent lost at restart name=BlueFox: no agent BlueFox\n", logs.String())
+	require.Equal(t, "<3>subagent lost at restart name=BlueFox: open worker log: no agent BlueFox\n", logs.String())
 
 	data, err := os.ReadFile(filepath.Join(agent.dir, subagentWorkFileName))
 	require.NoError(t, err)
diff --git a/telegram.go b/telegram.go
index 306f8f5..85b0f44 100644
--- a/telegram.go
+++ b/telegram.go
@@ -264,7 +264,7 @@ func (b *TelegramBot) send(ctx context.Context) {
 func (b *TelegramBot) poll(ctx context.Context, l *TurnLoop, whatsapp *WhatsApp) error {
 	offset, err := telegramLoadOffset(b.offsetPath)
 	if err != nil {
-		return err
+		return fmt.Errorf("load Telegram offset: %w", err)
 	}
 
 	outage := &TelegramOutage{
@@ -313,7 +313,11 @@ poll:
 					continue poll
 				}
 
-				return err
+				if err != nil {
+					return fmt.Errorf("handle Telegram update: %w", err)
+				}
+
+				return nil
 			}
 
 			imageOutage.End()
@@ -323,7 +327,7 @@ poll:
 			offset = update.UpdateID + 1
 			err = telegramSaveOffset(b.offsetPath, offset)
 			if err != nil {
-				return err
+				return fmt.Errorf("save Telegram offset: %w", err)
 			}
 		}
 	}
@@ -476,7 +480,7 @@ func (b *TelegramBot) handle(ctx context.Context, l *TurnLoop, whatsapp *WhatsAp
 	default:
 		_, err := l.Submit(telegramSource, message.Text)
 		if err != nil {
-			return err
+			return fmt.Errorf("submit Telegram text: %w", err)
 		}
 
 		err = l.Flush(context.WithoutCancel(ctx))
diff --git a/terminal.go b/terminal.go
index da0d78a..db259fb 100644
--- a/terminal.go
+++ b/terminal.go
@@ -30,13 +30,13 @@ var errTerminalDaemonClosed = errors.New("the daemon closed the connection")
 func terminal(ctx context.Context, in io.Reader, out io.Writer) error {
 	dir, err := dataDir()
 	if err != nil {
-		return err
+		return fmt.Errorf("find data directory: %w", err)
 	}
 
 	path := filepath.Join(dir, socketFileName)
 	err = checkSocketPath(path)
 	if err != nil {
-		return err
+		return fmt.Errorf("check terminal socket path: %w", err)
 	}
 
 	var dialer net.Dialer
diff --git a/tools.go b/tools.go
index 191bb25..24e0fdb 100644
--- a/tools.go
+++ b/tools.go
@@ -419,7 +419,7 @@ func (b *Toolbox) zoomAgent(ctx context.Context, name string) (string, error) {
 
 	subagent, err := b.subagents.Get(ctx, name)
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("open worker log: %w", err)
 	}
 
 	return subagent.Show()
diff --git a/tools_test.go b/tools_test.go
index 3075cbf..c03e7fc 100644
--- a/tools_test.go
+++ b/tools_test.go
@@ -185,7 +185,7 @@ func TestZoomWithANameGivesTheWholeChatOfTheAgent(t *testing.T) {
 	output := box.run(t.Context(), "zoom", `{"id":0,"n":1,"name":"`+subagent.name+`"}`)
 	require.Equal(t, "0|note: subagent\n\n1|user: Count the files.", output)
 
-	require.Equal(t, "error: no agent BlueFox", box.run(t.Context(), "zoom", `{"id":0,"n":1,"name":"BlueFox"}`))
+	require.Equal(t, "error: open worker log: no agent BlueFox", box.run(t.Context(), "zoom", `{"id":0,"n":1,"name":"BlueFox"}`))
 	require.Equal(t, "error: line 0+1 goes past the last message, -1", box.run(t.Context(), "zoom", `{"id":0,"n":1,"name":null}`))
 }
 
diff --git a/whatsapp.go b/whatsapp.go
index df43e8e..27dd3c3 100644
--- a/whatsapp.go
+++ b/whatsapp.go
@@ -197,7 +197,7 @@ func openWhatsApp(ctx context.Context, dir string, clock func() time.Time, logge
 
 	w.state, err = openWhatsAppState(filepath.Join(w.dir, whatsappStateFileName))
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("open WhatsApp state: %w", err)
 	}
 
 	w.inbox = newWhatsAppInbox(w.state, clock, w.groups, &ImageStore{dir: filepath.Join(dir, imageDirName)}, logger)
@@ -217,7 +217,7 @@ func openWhatsApp(ctx context.Context, dir string, clock func() time.Time, logge
 
 	err = w.openSession(ctx)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("open WhatsApp session: %w", err)
 	}
 
 	if w.device.ID != nil {
@@ -239,7 +239,7 @@ func (w *WhatsApp) sessionPath() string {
 func (w *WhatsApp) openSession(ctx context.Context) error {
 	address, err := whatsappSessionAddress(w.sessionPath())
 	if err != nil {
-		return err
+		return fmt.Errorf("find WhatsApp session address: %w", err)
 	}
 
 	container, err := sqlstore.New(ctx, "sqlite", address, waLog.Noop)
@@ -323,14 +323,18 @@ func (w *WhatsApp) Run(ctx context.Context, l *TurnLoop, notify func(Event)) err
 	for {
 		err := w.inbox.deliver(ctx, l, w.link(), false)
 		if err != nil {
-			return err
+			return fmt.Errorf("deliver WhatsApp inbox: %w", err)
 		}
 
 		select {
 		case <-ctx.Done():
 			return nil
 		case err = <-w.inbox.failures:
-			return err
+			if err != nil {
+				return fmt.Errorf("receive WhatsApp inbox: %w", err)
+			}
+
+			return nil
 		case <-w.inbox.wake:
 		case <-w.inbox.due():
 		case <-retry:
@@ -340,7 +344,7 @@ func (w *WhatsApp) Run(ctx context.Context, l *TurnLoop, notify func(Event)) err
 
 			err = w.loggedOut(ctx, l)
 			if err != nil {
-				return err
+				return fmt.Errorf("handle WhatsApp logout: %w", err)
 			}
 		case request := <-w.requests:
 			cancel()
@@ -355,7 +359,7 @@ func (w *WhatsApp) Run(ctx context.Context, l *TurnLoop, notify func(Event)) err
 
 				err = w.unlink(ctx, l, request.answer)
 				if err != nil {
-					return err
+					return fmt.Errorf("unlink WhatsApp: %w", err)
 				}
 			case w.isLinked():
 				request.answer("WhatsApp is linked already. Run /whatsapp unlink first.")
@@ -885,7 +889,7 @@ func (w *WhatsApp) newDevice(ctx context.Context) (*store.Device, error) {
 
 		err = w.openSession(ctx)
 		if err != nil {
-			return nil, err
+			return nil, fmt.Errorf("open new WhatsApp session: %w", err)
 		}
 	}
 
diff --git a/whatsapp_inbox.go b/whatsapp_inbox.go
index 5010a74..8bf8a97 100644
--- a/whatsapp_inbox.go
+++ b/whatsapp_inbox.go
@@ -129,7 +129,7 @@ func (i *WhatsAppInbox) deliver(ctx context.Context, l *TurnLoop, link WhatsAppL
 	}
 
 	if err != nil {
-		return err
+		return fmt.Errorf("close due WhatsApp batches: %w", err)
 	}
 
 	batches := i.state.Closed()
@@ -183,7 +183,7 @@ func (i *WhatsAppInbox) deliver(ctx context.Context, l *TurnLoop, link WhatsAppL
 
 		err = i.state.Remove(batch.Number)
 		if err != nil {
-			return err
+			return fmt.Errorf("remove delivered WhatsApp batch: %w", err)
 		}
 
 		if batch.Turn() {
diff --git a/whatsapp_send.go b/whatsapp_send.go
index b3bbe95..dbbf862 100644
--- a/whatsapp_send.go
+++ b/whatsapp_send.go
@@ -51,7 +51,7 @@ func whatsappSend(ctx context.Context, link WhatsAppLink, groups *WhatsAppGroups
 
 	jid, err := whatsappSendCheck(id, chat, text, image, link.own)
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("check WhatsApp send: %w", err)
 	}
 
 	digest := sha256.Sum256([]byte(text))
@@ -88,7 +88,7 @@ func whatsappSend(ctx context.Context, link WhatsAppLink, groups *WhatsAppGroups
 	record.MessageID = link.client.GenerateMessageID()
 	err = state.PutSend(record)
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("save pending WhatsApp send: %w", err)
 	}
 
 	message := &waE2E.Message{Conversation: new(text)}
@@ -128,7 +128,7 @@ func whatsappSend(ctx context.Context, link WhatsAppLink, groups *WhatsAppGroups
 
 	err = state.PutSend(record)
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("save completed WhatsApp send: %w", err)
 	}
 
 	return record.Answer, nil
diff --git a/whatsapp_send_test.go b/whatsapp_send_test.go
index df82e3c..977d06b 100644
--- a/whatsapp_send_test.go
+++ b/whatsapp_send_test.go
@@ -190,7 +190,7 @@ func TestWhatsAppSendRefuses(t *testing.T) {
 	for _, tc := range testCases {
 		t.Run(tc.name, func(t *testing.T) {
 			_, err := whatsapp.Send(t.Context(), tc.id, tc.chat, tc.text, "")
-			require.EqualError(t, err, tc.err)
+			require.EqualError(t, err, "check WhatsApp send: "+tc.err)
 		})
 	}