explicitly tell about enqueued email

bot/command.go

@@ -381,12 +381,17 @@ func (b *Bot) runSend(ctx context.Context) {
 	for _, to := range tos {
 		email := utils.NewEmail(ID, "", " "+ID, subject, from, to, body, "", nil)
 		data := email.Compose(b.getBotSettings().DKIMPrivateKey())
-		err = b.sendmail(from, to, data)
+		queued, err := b.Sendmail(evt.ID, from, to, data)
+		if queued {
+			b.log.Error("cannot send email: %v", err)
+			b.saveSentMetadata(ctx, queued, evt.ID, email, &cfg)
+			continue
+		}
 		if err != nil {
 			b.Error(ctx, evt.RoomID, "cannot send email to %s: %v", to, err)
-		} else {
-			b.saveSentMetadata(ctx, evt.ID, email, &cfg)
+			continue
 		}
+		b.saveSentMetadata(ctx, false, evt.ID, email, &cfg)
 	}
 	if len(tos) > 1 {
 		b.SendNotice(ctx, evt.RoomID, "All emails were sent.")

bot/email.go

@@ -37,17 +37,17 @@ func (b *Bot) SetSendmail(sendmail func(string, string, string) error) {
 
 // Sendmail tries to send email immediately, but if it gets 4xx error (greylisting),
 // the email will be added to the queue and retried several times after that
-func (b *Bot) Sendmail(eventID id.EventID, from, to, data string) error {
+func (b *Bot) Sendmail(eventID id.EventID, from, to, data string) (bool, error) {
 	err := b.sendmail(from, to, data)
 	if err != nil {
 		if strings.HasPrefix(err.Error(), "45") {
 			b.log.Debug("email %s (from=%s to=%s) was added to the queue: %v", eventID, from, to, err)
-			return b.enqueueEmail(eventID.String(), from, to, data)
+			return true, b.enqueueEmail(eventID.String(), from, to, data)
 		}
-		return err
+		return false, err
 	}
 
-	return nil
+	return false, nil
 }
 
 // GetDKIMprivkey returns DKIM private key
@@ -177,12 +177,19 @@ func (b *Bot) SendEmailReply(ctx context.Context) {
 	email := utils.NewEmail(ID, meta.InReplyTo, meta.References, meta.Subject, fromMailbox, meta.To, body, "", nil)
 	data := email.Compose(b.getBotSettings().DKIMPrivateKey())
 
-	err = b.Sendmail(evt.ID, meta.From, meta.To, data)
+	queued, err := b.Sendmail(evt.ID, meta.From, meta.To, data)
+	if queued {
+		b.log.Error("cannot send email: %v", err)
+		b.saveSentMetadata(ctx, queued, meta.ThreadID, email, &cfg)
+		return
+	}
+
 	if err != nil {
 		b.Error(ctx, evt.RoomID, "cannot send email: %v", err)
 		return
 	}
-	b.saveSentMetadata(ctx, meta.ThreadID, email, &cfg)
+
+	b.saveSentMetadata(ctx, queued, meta.ThreadID, email, &cfg)
 }
 
 type parentEmail struct {
@@ -264,10 +271,15 @@ func (b *Bot) getParentEmail(evt *event.Event) parentEmail {
 
 // saveSentMetadata used to save metadata from !pm sent and thread reply events to a separate notice message
 // because that metadata is needed to determine email thread relations
-func (b *Bot) saveSentMetadata(ctx context.Context, threadID id.EventID, email *utils.Email, cfg *roomSettings) {
+func (b *Bot) saveSentMetadata(ctx context.Context, queued bool, threadID id.EventID, email *utils.Email, cfg *roomSettings) {
+	text := "Email has been sent to " + email.To
+	if queued {
+		text = "Email to " + email.To + " has been queued"
+	}
+
 	evt := eventFromContext(ctx)
 	content := email.Content(threadID, cfg.ContentOptions())
-	notice := format.RenderMarkdown("Email has been sent to "+email.To, true, true)
+	notice := format.RenderMarkdown(text, true, true)
 	notice.MsgType = event.MsgNotice
 	msgContent, ok := content.Parsed.(event.MessageEventContent)
 	if !ok {

bot/queue.go

@@ -2,12 +2,11 @@ package bot
 
 import (
 	"strconv"
-	"time"
 )
 
 const (
 	defaultMaxQueueItems = 1
-	defaultMaxQueueTries = 100
+	defaultMaxQueueTries = 3
 )
 
 // ProcessQueue starts queue processing
@@ -67,6 +66,7 @@ func (b *Bot) processQueueItem(itemkey string, maxRetries int) bool {
 		b.log.Error("cannot retrieve a queue item %s: %v", itemkey, err)
 		return false
 	}
+	b.log.Debug("processing queue item %+v", item)
 	attempts, err := strconv.Atoi(item["attempts"])
 	if err != nil {
 		b.log.Error("cannot parse attempts of %s: %v", itemkey, err)
@@ -97,12 +97,11 @@ func (b *Bot) processQueueItem(itemkey string, maxRetries int) bool {
 func (b *Bot) enqueueEmail(id, from, to, data string) error {
 	itemkey := acQueueKey + "." + id
 	item := map[string]string{
-		"attemptedAt": time.Now().UTC().Format(time.RFC1123Z),
-		"attempts":    "0",
-		"data":        data,
-		"from":        from,
-		"to":          to,
-		"id":          id,
+		"attempts": "0",
+		"data":     data,
+		"from":     from,
+		"to":       to,
+		"id":       id,
 	}
 
 	b.lock(itemkey)

cmd/cmd.go

@@ -146,6 +146,7 @@ func startBot(statusMsg string) {
 
 func shutdown() {
 	log.Info("Shutting down...")
+	cron.Shutdown()
 	smtpm.Stop()
 	mxb.Stop()