Problem with sending mails with Modern Authentication with Microsoft

[cfreire]

Hi friends. I have configured Modern authentication with Outlook, and I have followed these steps in the link:

https://www.znuny.org/en/blog/modern-au ... -microsoft

I get mails successfully, but when I want to asnwer my ticktes I have the next error:

30/08/2023 - 12:04 (America/Guayaquil): Sending of this message has failed. SMTP authentication failed: 500, Command unknown: 'AUTH'!

In logs I watch too the erros attached in the image....

May anyone to helpme with this issued please?

Thanks by your attention.

[root]

Hi,

What are your settings for in the system configuration (Sendmail*)?

For sending it is also possible use classic authentication with username and password. Does this work?

- Roy

[cfreire]

Hi I have changed accordding at your recommendation SendmailModule::AuthenticationType to Password. The other settings im SendmailModule.. are the attached.

And I have the same error. I can´t send mails.

[root]

Hi,

What is the error when you try to send via command line with the application user?

Code: Select all

bin/otrs.Console.pl Maint::Email::MailQueue --send --verbose

- Roy

[cfreire]

Hi Roy, the error using commands are:

[otrs@znuny ~]$ bin/otrs.Console.pl Maint::Email::MailQueue --send --verbose
ERROR: OTRS-otrs.Console.pl-Maint::Email::MailQueue-19 Perl: 5.16.3 OS: linux Time: Wed Aug 30 20:24:09 2023

Message: CommunicationLog(ID:116925,AccountType:-,AccountID:-,Direction:Outgoing,Transport:Email,ObjectLogType:Connection,ObjectLogID:220248)::Kernel::System::Email::SMTPTLS => SMTP authentication failed (SMTP code: 500, ErrorMessage: 500, Command unknown: 'AUTH').

Traceback (29571):
Module: Kernel::System::CommunicationLog::_LogError Line: 535
Module: Kernel::System::CommunicationLog::ObjectLog Line: 297
Module: Kernel::System::Email::SMTP::Check Line: 241
Module: Kernel::System::Email::SMTP::Send Line: 291
Module: Kernel::System::Email::SendExecute Line: 758
Module: Kernel::System::MailQueue::Send Line: 675
Module: Kernel::System::Console::Command::Maint::Email::MailQueue::Send Line: 199
Module: Kernel::System::Console::Command::Maint::Email::MailQueue::Run Line: 147
Module: (eval) Line: 460
Module: Kernel::System::Console::BaseCommand::Execute Line: 454
Module: Kernel::System::Console::InterfaceConsole::Run Line: 81
Module: bin/otrs.Console.pl Line: 37

ERROR: OTRS-otrs.Console.pl-Maint::Email::MailQueue-19 Perl: 5.16.3 OS: linux Time: Wed Aug 30 20:24:09 2023

Message: CommunicationLog(ID:116925,AccountType:-,AccountID:-,Direction:Outgoing,Transport:Email,ObjectLogType:Message,ObjectLogID:220247)::Kernel::System::Email => Error sending message using backend 'Kernel::System::Email::SMTPTLS'.

Traceback (29571):
Module: Kernel::System::CommunicationLog::_LogError Line: 535
Module: Kernel::System::CommunicationLog::ObjectLog Line: 297
Module: Kernel::System::Email::SendExecute Line: 773
Module: Kernel::System::MailQueue::Send Line: 675
Module: Kernel::System::Console::Command::Maint::Email::MailQueue::Send Line: 199
Module: Kernel::System::Console::Command::Maint::Email::MailQueue::Run Line: 147
Module: (eval) Line: 460
Module: Kernel::System::Console::BaseCommand::Execute Line: 454
Module: Kernel::System::Console::InterfaceConsole::Run Line: 81
Module: bin/otrs.Console.pl Line: 37

ERROR: OTRS-otrs.Console.pl-Maint::Email::MailQueue-19 Perl: 5.16.3 OS: linux Time: Wed Aug 30 20:24:09 2023

Message: CommunicationLog(ID:116925,AccountType:-,AccountID:-,Direction:Outgoing,Transport:Email,ObjectLogType:Message,ObjectLogID:220247)::Kernel::System::MailQueue => Message could not be sent! Error message: SMTP authentication failed: 500, Command unknown: 'AUTH'!

Traceback (29571):
Module: Kernel::System::CommunicationLog::_LogError Line: 535
Module: Kernel::System::CommunicationLog::ObjectLog Line: 297
Module: Kernel::System::MailQueue::_SendError Line: 835
Module: Kernel::System::MailQueue::Send Line: 691
Module: Kernel::System::Console::Command::Maint::Email::MailQueue::Send Line: 199
Module: Kernel::System::Console::Command::Maint::Email::MailQueue::Run Line: 147
Module: (eval) Line: 460
Module: Kernel::System::Console::BaseCommand::Execute Line: 454
Module: Kernel::System::Console::InterfaceConsole::Run Line: 81
Module: bin/otrs.Console.pl Line: 37

ERROR: OTRS-otrs.Console.pl-Maint::Email::MailQueue-19 Perl: 5.16.3 OS: linux Time: Wed Aug 30 20:24:09 2023

Message: CommunicationLog(ID:116925,AccountType:-,AccountID:-,Direction:Outgoing,Transport:Email,ObjectLogType:Message,ObjectLogID:220247)::Kernel::System::MailQueue => Permanent sending problem or we reached the sending attempt limit. Message will be removed

Traceback (29571):
Module: Kernel::System::CommunicationLog::_LogError Line: 535
Module: Kernel::System::CommunicationLog::ObjectLog Line: 297
Module: Kernel::System::MailQueue::_SendError Line: 854
Module: Kernel::System::MailQueue::Send Line: 691
Module: Kernel::System::Console::Command::Maint::Email::MailQueue::Send Line: 199
Module: Kernel::System::Console::Command::Maint::Email::MailQueue::Run Line: 147
Module: (eval) Line: 460
Module: Kernel::System::Console::BaseCommand::Execute Line: 454
Module: Kernel::System::Console::InterfaceConsole::Run Line: 81
Module: bin/otrs.Console.pl Line: 37

Error:
Could not send message with ID '3355'! Please refer to the log.
Error:
Sending has Failed.

No messages available for sending.
Error: Failed.

[root]

Hi,

What version has the Perl module Net::SMTP? You can check this with bin/otrs.CheckModules.pl

- Roy

[cfreire]

Last failed login: Wed Aug 30 16:50:56 -05 2023 from 190.63.65.249 on ssh:notty
There were 2 failed login attempts since the last successful login.
Last login: Wed Aug 30 15:23:59 2023 from 190.63.171.162
[root@znuny ~]# su - otrs
Last login: Wed Aug 30 15:24:08 -05 2023 on pts/1
[otrs@znuny ~]$ bin/otrs.CheckModules.pl
o Apache::DBI......................ok (v1.12)
o Apache2::Reload..................ok (v0.13)
o Archive::Tar.....................ok (v1.92)
o Archive::Zip.....................ok (v1.30)
o Authen::SASL.....................ok (v2.15)
o Crypt::Eksblowfish::Bcrypt.......ok (v0.009)
o Crypt::JWT.......................Not installed! To install, you can use: 'yum install "perl(Crypt::JWT)"'. (optional - JSON web token support.)
o Crypt::OpenSSL::X509.............Not installed! To install, you can use: 'yum install "perl(Crypt::OpenSSL::X509)"'. (optional - X509 certificate support.)
o CSS::Minifier::XS................ok (v0.13)
o Data::UUID.......................ok (v1.226)
o Date::Format.....................ok (v2.24)
o DateTime.........................ok (v1.04)
o DateTime::TimeZone.............ok (v1.70)
Please consider updating to version 2.20 or higher: This version includes recent time zone changes for Chile.
o DBI..............................ok (v1.627)
o DBD::mysql.......................ok (v4.023)
o DBD::ODBC........................Not installed! (optional - Required to connect to a MS-SQL database.)
o DBD::Oracle......................Not installed! (optional - Required to connect to a Oracle database.)
o DBD::Pg..........................ok (v2.19.3)
o Digest::SHA......................ok (v5.85)
o Encode::HanExtra.................ok (v0.23)
o Excel::Writer::XLSX..............ok (v0.95)
o Hash::Merge......................ok (v0.302)
o IO::Socket::SSL..................ok (v1.94)
Please consider updating to version 2.066 or higher: This version fixes email sending (bug#14357).
o JavaScript::Minifier::XS.........ok (v0.15)
o Jq...............................Not installed! To install, you can use: 'yum install "perl(Jq)"'. (optional - Support for extended condition checking via Jq for the generic interface.)
o JSON::XS.........................ok (v3.01)
o List::Util::XS...................ok (v1.27)
o LWP::UserAgent...................ok (v6.53)
o Mail::IMAPClient.................ok (v3.37)
o IO::Socket::SSL................ok (v1.94)
Please consider updating to version 2.066 or higher: This version fixes email sending (bug#14357).
o Authen::NTLM...................Not installed! To install, you can use: 'yum install "perl(Authen::NTLM)"'. (optional - Required for NTLM authentication mechanism in IMAP connections.)
o ModPerl::Util....................ok (v2.000011)
o Moo..............................ok (v2.005004)
o Net::DNS.........................ok (v0.72)
o Net::LDAP........................ok (v0.56)
o Net::LDAP::Constant..............ok (v0.20)
o Net::SMTP........................ok (v2.31)
Please consider updating to version 3.11 or higher: This version fixes email sending (bug#14357).
o Spreadsheet::XLSX................ok (v0.17)
o Template.........................ok (v2.24)
o Template::Stash::XS..............ok (undef)
o Text::Diff::FormattedHTML........ok (v0.08)
o Text::CSV_XS.....................ok (v1.00)
o Time::HiRes......................ok (v1.9725)
o XML::LibXML......................ok (v2.0018)
o XML::LibXSLT.....................ok (v1.80)
o XML::Parser......................ok (v2.41)
o YAML::XS.........................ok (v0.54)
[otrs@znuny ~]$

[root]

Hi,

Update Net::SMTP and try then sending again

- Roy

[cfreire]

Hi Roy, I hope that you bi fine..... I have upgrade 2 modules NET::SMTP and IO::Socket::SSL, but I dont now if upgrade IO::Socket::SSL was an error , because since this upgrade, I can't receive mails and I have the next error:

outlook.office365.com (IMAPTLS)...
ERROR: OTRS-otrs.Console.pl-Maint::PostMaster::MailAccountFetch-19 Perl: 5.16.3 OS: linux Time: Thu Aug 31 16:17:02 2023

Message: CommunicationLog(ID:118459,AccountType:-,AccountID:-,Direction:Incoming,Transport:Email,ObjectLogType:Connection,ObjectLogID:223869)::Kernel::System::MailAccount::IMAPTLS => Auth error: 2 NO AUTHENTICATE failed.


Traceback (13847):
Module: Kernel::System::CommunicationLog::_LogError Line: 535
Module: Kernel::System::CommunicationLog::ObjectLog Line: 297
Module: Kernel::System::MailAccount::IMAP::_Fetch Line: 270
Module: Kernel::System::MailAccount::IMAP::Fetch Line: 157
Module: Kernel::System::MailAccount::MailAccountFetch Line: 649
Module: (eval) Line: 170
Module: Kernel::System::Console::Command::Maint::PostMaster::MailAccountFetch::Run Line: 162
Module: (eval) Line: 460
Module: Kernel::System::Console::BaseCommand::Execute Line: 454
Module: Kernel::System::Console::InterfaceConsole::Run Line: 81
Module: /opt/otrs/bin/otrs.Console.pl Line: 37

Concernig to sending mails I have the nex error In the web:

31/08/2023 - 11:30 (America/Guayaquil): Sending of this message has failed. Could not send message to server: 554, 5.2.252 SendAsDenied; soporteunidadesmedicas@espoltel.com not allowed to send as soporteunidadesmedicas@espoltel.net; STOREDRV.Submission.Exception:SendAsDeniedException.MapiExceptionSendAsDenied; Failed to process message due to a permanent exception with message [BeginDiagnosticData]Cannot submit message. 0.35250:80030400, 1.36674:0A000000, 1.61250:00000000, 1.45378:02000000, 1.44866:0B3D0000, 1.36674:0E000000, 1.61250:00000000, 1.45378:103D0000, 1.44866:30010000, 16.55847:A81B0000, 17.43559:0000000024020000000000000000000000000000, 20.52176:140F599A0D00103100000000, 20.50032:140F599A7D17000000000000, 0.53414:140F599A, 0.35180:00000000, 255.23226:140F599A, 255.27962:0A000000, 255.27962:0E000000, 255.31418:0F000000, 0.35250:0A004881, 1.36674:0A000000, 1.61250:00000000, 1.45378:02000000, 1.44866:5E000000, 1.36674:32000000, 1.61250:00000000, 1.45378:63000000, 1.44866:01000000, 16.55847:D9000000, 17.43559:00000000B8030000000000000000000000000000, 20.52176:140F599A0D00101065000000, 20.50032:140F599A7D17000003000136, 0.53414:6A000000, 0.35180:4800D13D, 255.23226:0A00DA36, 255.27962:0A000000, 255.27962:32000000, 255.17082:DC040000, 0.27745:80000000, 4.21921:DC040000, 255.27962:FA000000, 255.1494:85000000, 0.38698:05000780, 1.41134:46000000, 0.37692:86000000, 0.37948:86000000, 5.33852:00000000534D545000000000, 7.36354:010000000000010986000000, 4.56248:DC040000, 7.40748:010000000000010B86000000, 7.57132:00000000000000001B010000, 4.39640:DC040000, 1.63016:32000000, 8.45434:DF014700BE58F04FA97CA045FF758D5430354D42, 1.46798:04000000, 5.10786:0000000031352E32302E363734352E3031333A444D34505230354D42393535393A61336666666264632D666565332D343233362D613533612D3037626436666565303162323A3131383337363A2E4E455420362E302E323000000000, 7.51330:6BC9198A3FAADB0800000000, 0.39570:02000000, 1.55954:0A000000, 1.33010:0A000000, 2.54258:00000000, 0.40002:00000000, 1.56562:00000000, 1.33010:0A000000, 2.54258:00000000, 0.40002:00000000, 1.56562:00000000, 1.64146:32000000, 1.33010:32000000, 2.54258:DC040000, 1.33010:32000000, 2.54258:DC040000, 255.1750:0A006136, 255.31418:0A005636, 0.22753:D2000000, 255.21817:DC040000, 0.64418:0A006136, 4.39842:DC040000, 0.41586:03000336, 4.60547:DC040000, 0.21966:DC000000, 4.30158:DC040000[EndDiagnosticData] [Hostname=DM4PR05MB9559.namprd05.prod.outlook.com] !


I dont know why It try to use my old account .net instead to use the actual domain .com....

Thanks,

[cfreire]

Hi Roy, I have corrected the error of use my old mail account, now I can send mails successfully. But now I have the error to get mails, any way to downgrade the IO::Socket::SSL to (v1.94) or another way to recovery the inbound mails?

thanks by your attention and patience.

[cfreire]

Hi ROy, I have solved all my problems, abouy inbound mail it was by the token was expired, I renewed it and I received mails normally.
Actually I receive and send mails normally. Thanks for your help. This case was solved. Thank you very much.

Regards.