Problems with SMTPTLS and Gmail

[siraction]

Hello,

I'm evaluating OTRS for internal helpdesk use, so I downloaded the TRS appliance, inatalled in on a VM (HyperV) and was trying to set up the e-mail notification.

Since we use Google Apps for Business as e-mail provider I went into the sendmail configuration module and configured it accodring to FAQ/manual:

Module SMTPTLS

Host smtp.gmail.com

Port 587

AuthUser (a dedicated mailer account on Google apps, that I use for other similar programs as well)
AuthPassword (its password)

I then proceeded to send an e-mail to myself, the only agent defined, in the Admin Notification form and got the following error:

Oops! An Error occurred.
Error Message: No such binary: /usr/sbin/sendmail! EDIT: The actual error message is different, see posts below, this is the one from the sendmail test
.
You can Send a bugreport or go back to the previous page.

Backend ERROR: OTRS-CGI-48 Perl: 5.10.1 OS: linux Time: Thu Dec 19 12:28:50 2013 Message: No such binary: /usr/sbin/sendmail! RemoteAddress: 93.33.35.125 RequestURI: /otrs/index.pl Traceback (1684): Module: Kernel::System::Email::Sendmail::Send (OTRS 3.3.3) Line: 63 Module: Kernel::System::Email::Send (OTRS 3.3.3) Line: 725 Module: Kernel::Modules::AdminEmail::Run (OTRS 3.3.3) Line: 175 Module: Kernel::System::Web::InterfaceAgent::Run (OTRS 3.3.3) Line: 863 Module: ModPerl::ROOT::ModPerl::Registry::opt_otrs_bin_cgi_2dbin_index_2epl::handler (unknown version) Line: 41 Module: (eval) (v1.99) Line: 204 Module: ModPerl::RegistryCooker::run (v1.99) Line: 204 Module: ModPerl::RegistryCooker::default_handler (v1.99) Line: 170 Module: ModPerl::Registry::handler (v1.99) Line: 31

Trying with SMTPS and port 465 does not work either.

Can you help me solve this issue? I noticed on the forums a similar one but it was dated 2010 and referred to an older version of OTRS, but not sure if that applies to the current one.

[crythias]

No such binary: /usr/sbin/sendmail!

It means what it says.

But you don't want sendmail. You want SMTP (or SMTPTLS) ... check sysconfig sendmail for configuration changes.

[siraction]

My fault, got the error from one of the tries I made.

The actual error message is:

Oops! An Error occurred.
Error Message: Can't connect to smtp.gmail.com: Invalid argument!
.
You can Send a bugreport or go back to the previous page.

Backend ERROR: OTRS-CGI-48 Perl: 5.10.1 OS: linux Time: Thu Dec 19 15:20:53 2013 Message: Can't connect to smtp.gmail.com: Invalid argument! RemoteAddress: 93.33.35.125 RequestURI: /otrs/index.pl Traceback (1684): Module: Kernel::System::Email::SMTP::Send (OTRS 3.3.3) Line: 109 Module: Kernel::System::Email::Send (OTRS 3.3.3) Line: 725 Module: Kernel::Modules::AdminEmail::Run (OTRS 3.3.3) Line: 175 Module: Kernel::System::Web::InterfaceAgent::Run (OTRS 3.3.3) Line: 863 Module: ModPerl::ROOT::ModPerl::Registry::opt_otrs_bin_cgi_2dbin_index_2epl::handler (unknown version) Line: 41 Module: (eval) (v1.99) Line: 204 Module: ModPerl::RegistryCooker::run (v1.99) Line: 204 Module: ModPerl::RegistryCooker::default_handler (v1.99) Line: 170 Module: ModPerl::Registry::handler (v1.99) Line: 31

[crythias]

No help here?

[siraction]

Some info but none relevant to the problem.
I got info about a similar problem mentioning SMTP via SSL and port 445 (tried that too, same result, can't connect to smpt.gmail.com) but no particular insight about my issue.

[siraction]

I tried with SMTP (port25), with SMTPS (port445), with SMTPTLS (port 587) and with sendmail (not present in the OTRS appliance it seems)

[crythias]

http://wiki.otterhub.org/index.php?titl ... with_Gmail
Standard configuration instructions:

Incoming Mail (POP3) Server - requires SSL: pop.gmail.com
Use SSL: Yes
Port: 995
Outgoing Mail (SMTP) Server - requires TLS or SSL: smtp.gmail.com
Use Authentication: Yes
Port for TLS/STARTTLS: 587
Port for SSL: 465
Server timeouts Greater than 1 minute, we recommend 5
Full Name or Display Name: [your name]
Account Name or User Name: your full email address (including @gmail.com or @your_domain.com)
Email Address: your email address (username@gmail.com or username@your_domain.com)
Password: your Gmail password

[siraction]

Let me repeat myself:

I went into Edit Config Settings in Framework -> Core::Sendmail

I configured, following the instructions on manual and from the web, the parameters as follows:

SendmailModule SMTPTLS
SendmailModule::Host smtp.gmail.com
SendmailModule::Port 587
SendmailModule::AuthUser [username@mydomain.com]
SendmailModule::AuthPassword [my password]


I tried also with

SendmailModule SMTPS
SendmailModule::Host smtp.gmail.com
SendmailModule::Port 465
SendmailModule::AuthUser [username@mydomain.com]
SendmailModule::AuthPassword [my password]

But got in both cases the

Oops! An Error occurred.
Error Message: Can't connect to smtp.gmail.com: Invalid argument!
.

Backend ERROR: OTRS-CGI-48 Perl: 5.10.1 OS: linux Time: Thu Dec 19 16:23:24 2013 Message: Can't connect to smtp.gmail.com: Invalid argument! RemoteAddress: 93.33.35.125 RequestURI: /otrs/index.pl Traceback (1684): Module: Kernel::System::Email::SMTP::Send (OTRS 3.3.3) Line: 109 Module: Kernel::System::Email::Send (OTRS 3.3.3) Line: 725 Module: Kernel::Modules::AdminEmail::Run (OTRS 3.3.3) Line: 175 Module: Kernel::System::Web::InterfaceAgent::Run (OTRS 3.3.3) Line: 863 Module: ModPerl::ROOT::ModPerl::Registry::opt_otrs_bin_cgi_2dbin_index_2epl::handler (unknown version) Line: 41 Module: (eval) (v1.99) Line: 204 Module: ModPerl::RegistryCooker::run (v1.99) Line: 204 Module: ModPerl::RegistryCooker::default_handler (v1.99) Line: 170 Module: ModPerl::Registry::handler (v1.99) Line: 31

when trying to send an Admin Notification.

Edit: in your post you mention a "Use Authentication: Yes" that I can't find in the sendmail configuration fomr not in the wiki page you linked.