diff --git a/internal/frontend/grpc/service_methods.go b/internal/frontend/grpc/service_methods.go
index c63203c6..e0f27b2b 100644
--- a/internal/frontend/grpc/service_methods.go
+++ b/internal/frontend/grpc/service_methods.go
@@ -670,12 +670,7 @@ func (s *Service) SetMailServerSettings(_ context.Context, settings *ImapSmtpSet
 		}
 	}
 
-	_ = s.SendEvent(NewMailServerSettingsChangedEvent(&ImapSmtpSettings{
-		ImapPort:      int32(s.bridge.GetIMAPPort()),
-		SmtpPort:      int32(s.bridge.GetSMTPPort()),
-		UseSSLForImap: s.bridge.GetIMAPSSL(),
-		UseSSLForSmtp: s.bridge.GetSMTPSSL(),
-	}))
+	_ = s.SendEvent(NewMailServerSettingsChangedEvent(s.getMailServerSettings()))
 
 	return &emptypb.Empty{}, nil
 }
@@ -744,3 +739,12 @@ func base64Decode(in []byte) ([]byte, error) {
 
 	return out[:n], nil
 }
+
+func (s *Service) getMailServerSettings() *ImapSmtpSettings {
+	return &ImapSmtpSettings{
+		ImapPort:      int32(s.bridge.GetIMAPPort()),
+		SmtpPort:      int32(s.bridge.GetSMTPPort()),
+		UseSSLForImap: s.bridge.GetIMAPSSL(),
+		UseSSLForSmtp: s.bridge.GetSMTPSSL(),
+	}
+}
diff --git a/internal/frontend/grpc/service_user.go b/internal/frontend/grpc/service_user.go
index b54b3fb7..45fb1119 100644
--- a/internal/frontend/grpc/service_user.go
+++ b/internal/frontend/grpc/service_user.go
@@ -131,10 +131,17 @@ func (s *Service) RemoveUser(ctx context.Context, userID *wrapperspb.StringValue
 func (s *Service) ConfigureUserAppleMail(ctx context.Context, request *ConfigureAppleMailRequest) (*emptypb.Empty, error) {
 	s.log.WithField("UserID", request.UserID).WithField("Address", request.Address).Debug("ConfigureUserAppleMail")
 
+	sslWasEnabled := s.bridge.GetSMTPSSL()
+
 	if err := s.bridge.ConfigureAppleMail(request.UserID, request.Address); err != nil {
 		s.log.WithField("userID", request.UserID).Error("Cannot configure AppleMail for user")
 		return nil, status.Error(codes.Internal, "Apple Mail config failed")
 	}
 
+	if s.bridge.GetSMTPSSL() != sslWasEnabled {
+		// we've changed SMTP SSL settings. This will happen if SSL was off and macOS >= Catalina. We must inform gRPC clients.
+		_ = s.SendEvent(NewMailServerSettingsChangedEvent(s.getMailServerSettings()))
+	}
+
 	return &emptypb.Empty{}, nil
 }