Hello everyone,
I saw a lot of topics about that but didn’t find the issue 
I have a fresh new install of debian 9 and passbolt. Everything is working fine except the mails. I enabled the access for the less secured apps on gmail.
When I want to send a test, I have an error :
root@passbolt:/var/www/passbolt# ./bin/cake passbolt send_test_email
____ __ ____
/ __ \____ _____ ____/ /_ ____ / / /_
/ // / __ `/ / / __ / __ / / _/
/ / // ( | ) // / // / / /
// _,///.__/__//_/
Open source password manager for teams
Debug email shell
Email configuration
Host: smtp.gmail.com
Port: 587
Username: my@gmail.com
Password: *********
TLS: true
Sending email from: Passbolt my@gmail.com
Sending email to: doesnotexist@passboltdummydomain.com
Trace
A test email could not be sent.
Error: Connection timed out
This is the passbolt.php :
'EmailTransport' => [
'default' => [
'host' => 'smtp.gmail.com',
'port' => 587,
'username' => 'theoallin1991@gmail.com',
'password' => 'mypassword',
// Is this a secure connection? true if yes, null if no.
'tls' => true,
'timeout' => 30,
'client' => null,
'url' => null,
],
],
'Email' => [
'default' => [
// Defines the default name and email of the sender of the emails.
'from' => ['informatique@see.com' => 'Passbolt'],
//'charset' => 'utf-8',
//'headerCharset' => 'utf-8',
],
],
I can ping the smtp relay :
root@passbolt:/var/www/passbolt# ping smtp.gmail.com
PING gmail-smtp-msa.l.google.com (74.125.71.108) 56(84) bytes of data.
64 bytes from wn-in-f108.1e100.net (74.125.71.108): icmp_seq=1 ttl=46 time=11.8 ms
64 bytes from wn-in-f108.1e100.net (74.125.71.108): icmp_seq=2 ttl=46 time=11.9 ms
64 bytes from wn-in-f108.1e100.net (74.125.71.108): icmp_seq=3 ttl=46 time=11.9 ms
^C
— gmail-smtp-msa.l.google.com ping statistics —
3 packets transmitted, 3 received, 0% packet loss, time 2003ms
rtt min/avg/max/mdev = 11.878/11.909/11.935/0.023 ms
No error found with the healthcheck command.
This is the logs :
www-data@passbolt:~/passbolt/logs$ cat cli-debug.log
2018-07-04 07:41:30 Notice: Notice (8): Trying to get property of non-object in [/var/www/passbolt/src/Template/Email/html/AN/user_register_self.ctp, line 22]
www-data@passbolt:~/passbolt/logs$ cat cli-debug.log
2018-07-04 07:41:30 Notice: Notice (8): Trying to get property of non-object in [/var/www/passbolt/src/Template/Email/html/AN/user_register_self.ctp, line 22]
www-data@passbolt:~/passbolt/logs$ cat error.log
2018-07-02 13:34:36 Error: [Cake\Network\Exception\BadRequestException] The OpenPGP key data is not valid.
Request URL: /users/validateAccount/4a48f59d-5c93-4463-9a95-0baa7847cb45.json?api-version=v1
2018-07-02 13:41:40 Error: [Cake\Network\Exception\BadRequestException] The OpenPGP key data is not valid.
Request URL: /users/validateAccount/4a48f59d-5c93-4463-9a95-0baa7847cb45.json?api-version=v1
2018-07-02 13:49:45 Error: [Cake\Network\Exception\BadRequestException] The OpenPGP key data is not valid.
Request URL: /users/validateAccount/0413951d-59f1-4f47-b767-f95725a8e120.json?api-version=v1
2018-07-04 06:52:00 Error: [Cake\Routing\Exception\MissingRouteException] A route matching “/account/settings.json” could not be found.
Request URL: /account/settings.json?api-version=v2
2018-07-04 06:57:50 Error: [Cake\Routing\Exception\MissingRouteException] A route matching “/account/settings.json” could not be found.
Request URL: /account/settings.json?api-version=v2
Thanks for your time.