diff --git a/go.mod b/go.mod
index d45b5115..0ab63dc0 100644
--- a/go.mod
+++ b/go.mod
@@ -5,7 +5,7 @@ go 1.20
 require (
 	github.com/0xAX/notificator v0.0.0-20220220101646-ee9b8921e557
 	github.com/Masterminds/semver/v3 v3.2.0
-	github.com/ProtonMail/gluon v0.17.1-0.20230817061728-c2e6c5429251
+	github.com/ProtonMail/gluon v0.17.1-0.20230829112217-5d5c25c504b5
 	github.com/ProtonMail/go-autostart v0.0.0-20210130080809-00ed301c8e9a
 	github.com/ProtonMail/go-proton-api v0.4.1-0.20230829100923-d12b1baf9bf3
 	github.com/ProtonMail/gopenpgp/v2 v2.7.1-proton
diff --git a/go.sum b/go.sum
index fb22db7c..0ea8fdd8 100644
--- a/go.sum
+++ b/go.sum
@@ -25,6 +25,8 @@ github.com/ProtonMail/docker-credential-helpers v1.1.0 h1:+kvUIpwWcbtP3WFv5sSvkF
 github.com/ProtonMail/docker-credential-helpers v1.1.0/go.mod h1:mK0aBveCxhnQ756AmaTfXMZDeULvheYVhF/MWMErN5g=
 github.com/ProtonMail/gluon v0.17.1-0.20230817061728-c2e6c5429251 h1:WjVsvfisn0B0LdDCIncggk3KMAz0uaEyj7nI+f0dU/0=
 github.com/ProtonMail/gluon v0.17.1-0.20230817061728-c2e6c5429251/go.mod h1:Og5/Dz1MiGpCJn51XujZwxiLG7WzvvjE5PRpZBQmAHo=
+github.com/ProtonMail/gluon v0.17.1-0.20230829112217-5d5c25c504b5 h1:C/8P5NHAKi2yCKez+OZ5rSR8SsL7k8si4pK4SE2QtV8=
+github.com/ProtonMail/gluon v0.17.1-0.20230829112217-5d5c25c504b5/go.mod h1:Og5/Dz1MiGpCJn51XujZwxiLG7WzvvjE5PRpZBQmAHo=
 github.com/ProtonMail/go-autostart v0.0.0-20210130080809-00ed301c8e9a h1:D+aZah+k14Gn6kmL7eKxoo/4Dr/lK3ChBcwce2+SQP4=
 github.com/ProtonMail/go-autostart v0.0.0-20210130080809-00ed301c8e9a/go.mod h1:oTGdE7/DlWIr23G0IKW3OXK9wZ5Hw1GGiaJFccTvZi4=
 github.com/ProtonMail/go-crypto v0.0.0-20230321155629-9a39f2531310/go.mod h1:8TI4H3IbrackdNgv+92dI+rhpCaLqM0IfpgCgenFvRE=
diff --git a/internal/services/smtp/service.go b/internal/services/smtp/service.go
index ede91e57..1705c389 100644
--- a/internal/services/smtp/service.go
+++ b/internal/services/smtp/service.go
@@ -22,6 +22,7 @@ import (
 	"errors"
 	"fmt"
 	"io"
+	"time"
 
 	"github.com/ProtonMail/gluon/async"
 	"github.com/ProtonMail/gluon/logging"
@@ -254,6 +255,13 @@ type sendMailReq struct {
 
 func (s *Service) sendMail(ctx context.Context, req *sendMailReq) error {
 	defer async.HandlePanic(s.panicHandler)
+	start := time.Now()
+	s.log.Debug("Received send mail request")
+	defer func() {
+		end := time.Now()
+		s.log.Debugf("Send mail request finished in %v", end.Sub(start))
+	}()
+
 	if err := s.smtpSendMail(ctx, req.authID, req.from, req.to, req.r); err != nil {
 		if apiErr := new(proton.APIError); errors.As(err, &apiErr) {
 			s.log.WithError(apiErr).WithField("Details", apiErr.DetailsToString()).Error("failed to send message")
diff --git a/internal/services/smtp/smtp.go b/internal/services/smtp/smtp.go
index 8a19c04e..58730228 100644
--- a/internal/services/smtp/smtp.go
+++ b/internal/services/smtp/smtp.go
@@ -75,6 +75,7 @@ func (s *Service) smtpSendMail(ctx context.Context, authID string, from string,
 	}
 
 	// Check if we already tried to send this message recently.
+	s.log.Debug("Checking for duplicate message")
 	srID, ok, err := s.recorder.TryInsertWait(ctx, hash, to, time.Now().Add(90*time.Second))
 	if err != nil {
 		return fmt.Errorf("failed to check send hash: %w", err)
@@ -83,12 +84,11 @@ func (s *Service) smtpSendMail(ctx context.Context, authID string, from string,
 		return nil
 	}
 
-	// If we fail to send this message, we should remove the hash from the send recorder.
-	defer s.recorder.RemoveOnFail(hash, srID)
-
 	// Create a new message parser from the reader.
 	parser, err := parser.New(bytes.NewReader(b))
 	if err != nil {
+		s.log.Debug("Message failed to send, removing from send recorder")
+		s.recorder.RemoveOnFail(hash, srID)
 		return fmt.Errorf("failed to create parser: %w", err)
 	}
 
@@ -100,10 +100,12 @@ func (s *Service) smtpSendMail(ctx context.Context, authID string, from string,
 	// Load the user's mail settings.
 	settings, err := s.client.GetMailSettings(ctx)
 	if err != nil {
+		s.log.Debug("Message failed to send, removing from send recorder")
+		s.recorder.RemoveOnFail(hash, srID)
 		return fmt.Errorf("failed to get mail settings: %w", err)
 	}
 
-	return usertypes.WithAddrKR(s.identityState.User, fromAddr, s.keyPassProvider.KeyPass(), func(userKR, addrKR *crypto.KeyRing) error {
+	if err := usertypes.WithAddrKR(s.identityState.User, fromAddr, s.keyPassProvider.KeyPass(), func(userKR, addrKR *crypto.KeyRing) error {
 		// Use the first key for encrypting the message.
 		addrKR, err := addrKR.FirstKey()
 		if err != nil {
@@ -150,10 +152,17 @@ func (s *Service) smtpSendMail(ctx context.Context, authID string, from string,
 		}
 
 		// If the message was successfully sent, we can update the message ID in the record.
+		s.log.Debug("Message sent successfully, signaling recorder")
 		s.recorder.SignalMessageSent(hash, srID, sent.ID)
 
 		return nil
-	})
+	}); err != nil {
+		s.log.Debug("Message failed to send, removing from send recorder")
+		s.recorder.RemoveOnFail(hash, srID)
+		return err
+	}
+
+	return nil
 }
 
 // sendWithKey sends the message with the given address key.