[Fabio Macchia]

ello,

My Otobo installation cannot send outgoing emails. The system log shows Can’t connect to smtp.gmail.com: !, but the server itself can connect to Google’s SMTP without any issues.

 

Summary of Tests:

Here is what we have confirmed is working correctly on the server:

telnet smtp.gmail.com 587 -> Connects successfully.
openssl s_client … -> Handshake completes successfully (Verify return code: 0 (ok)). The server trusts the certificate.
sudo -u otobo dig smtp.gmail.com -> DNS resolves correctly for the otobo application user.
otobo.CheckModules.pl –all -> All required Perl modules for mail (Net::SMTP, IO::Socket::SSL, etc.) are installed and ok.
SELinux/AppArmor -> Checked and confirmed they are not blocking the connection.
The Core Problem: Even though all underlying system and dependency checks pass, the Otobo application log still shows a Can’t connect error.

We also noticed that a single otobo.Daemon.pl start command launches 6-7 separate daemon processes at once, which seems abnormal.

Question: Why would the Otobo Perl environment fail to connect when all system-level tools work perfectly? What could be the cause of the multiple daemon processes?

Any ideas for deeper debugging would be greatly appreciated. Thank you.

[Arnold]

Hi Fabio,

the OTOBO Deamon starting multiple processes is by design. It has multiple assignments to complete concurrently.

I think the wording of error message might be a bit misleading. Connecting to a host might not be the same as connecting a service.

Have you configured an application password for your OTOBO?
Are you using OAuth?
Does fetching emails work correctly?

You may get more information from the command line by running

./otobo.Console.pl Maint::Email::MailQueue --send --verbose

for fetching emails you may run:

./otobo.Console.pl Maint::PostMaster::MailAccountFetch --debug

Best regards,
Arnold

[Fabio Macchia]

Hi Arnold,

Thank you so much for your help and for providing that excellent diagnostic command. It has given us much more information.

To answer your questions:

Yes, we have configured and double-checked the 16-character Google App Password.

No, we are not using OAuth. We are using the standard SMTPTLS backend with username and password.

Regarding email fetching, we haven’t tested it yet. Our primary and critical problem is with sending emails, so we have focused all diagnostics on that first.

When I run the verbose console command to send mail, it fails with „Bad file descriptor“ and „Can’t connect“. I have the full log from that command.

[Fabio Macchia]

Here is the full output from the verbose command sudo -u otobo /opt/otobo/bin/otobo.Console.pl Maint::Email::MailQueue --send --verbose:

Traceback (399216) :
Module: Kernel: : System: : CommunicationLog ::_ LogError Line: 563
Module: Kernel: : System: : CommunicationLog: : ObjectLog Line: 321
Module: Kernel: : System: : MailQueue ::_ SendError Line: 966
Module: Kernel: : System: : MailQueue :: Send Line: 721
Module: Kernel: : System: : Console: : Command: : Maint : : Email : : MailQueue: : Send Line:
206
Module: Kernel: : System: : Console: : Command: : Maint : : Email : : MailQueue: : Run Line:

Module: (eval) Line: 480
Module: Kernel: : System: : Console: : BaseCommand: : Execute Line: 474
Module: Kernel: : System: : Console: : InterfaceConsole: : Run Line: 88
Module: /opt/otobo/bin/otobo. Console.pl Line: 35

Error:
Could not send message with ID ‚18220‘! Please refer to the log.

Sending has Failed.

No messages available for sending.
Error: Failed.

root@otrs-otobo:/opt/otobo/var/log/Daemon# _

[Mike Thumes]

Hi Fabio,

there should be a little more info in the /opt/otobo/var/log/otobo.log about what exactly went wrong when trying to send email. You might have to turn on full debugging by setting the System Configuration Variable ‚MinimumLogLevel‘ to ‚debug‘ in the Admin UI.

Hopes are this to shed some more light on the issue !?

kind regards,
-mike

[Fabio Macchia]

I can’t post the command output on the forum for you to help me because it says the message is spam.

How can I send it to you?

[Fabio Macchia]

ERROR: OTOBO-otobo. Console.pl-Maint : : Email: : MailQueue-19 Perl: 5.34.0 OS: linux
Time: Thu Sep 25 14:22:43 2025

Message: CommunicationLog (ID: 41067, Account Type :- , AccountID: -, Direction: Outgoing
, Transport : Email, ObjectLogType : Message, ObjectLogID : 72686) : : Kernel : : System: : MailQ
ueue => Temporary problem returned from server, requeuing message for sending. M
essage: SMTPCode: -, ErrorMessage: Can’t connect to smtp.gmail.com: !

Traceback (432358) :
Module: Kernel: : System: : CommunicationLog: : _LogError Line: 563
Module: Kernel: : System: : CommunicationLog: : ObjectLog Line: 321
Module: Kernel: : System: : MailQueue: : _SendError Line: 966
Module: Kernel: : System: : MailQueue: : Send Line: 721
Module: Kernel: : System: : Console: : Command: : Maint : : Email : : MailQueue: : Send Line:
206

[Arnold]

Hi Fabio,

after a little research I can not find one successful attempt to configure OTOBO against gmail.
I am very interested in the correct configuration if you are able to figure it out.

Godspeed!
Arnold

[Mike Thumes]

Hi Fabio,

after asking around a bit I got the following steps from a community member who has a working GMail setup for Otobo:

prerequisite: you have a valid gmail account with emailaddress and a password.

1) generate GMail app password:

• login to your gmail account
• goto  https://myaccount.google.com/apppasswords
• create a new app password one. name it anything you want, perhaps GMAIL ?

further info: https://support.google.com/accounts/answer/185833?hl=en

 

2) OTOBO Postmaster Setting IMAP

• Type: IMAPS
• username: full email address from gmail
• password: the app password from step 1)
• host: imap.gmail.com
• IMAP Folder: INBOX

 

3) OTOBO Admin UI Email Addresses

change email address to your full gmail email address to use for outgoing email

 

4) OTOBO SMTP: SysConfig -> Core -> Email

• SendmailModule: SMTPS
• AuthPassword: the app password from step 1)
• AuthUser: full email address from gmail
• Host: smtp.gmail.com
• Port: 465

Do not forget to deploy the changes to System Configuration!

Please let us know how if this works for you.

kind regards,
-mike

• Diese Antwort wurde vor 10 Monaten, 3 Wochen von Mike Thumes geändert.

[Autor]

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