Gmail SMTP not working

Installation Issues
1

Checklist
I have read intro post: About the Installation Issues category
I have read the tutorials, help and searched for similar issues
I provide relevant information about my server (component names and versions, etc.)
I provide a copy of my logs and healthcheck
I describe the steps I have taken to trouble shoot the problem
I describe the steps on how to reproduce the issue

Running: sudo /usr/share/php/passbolt/bin/status-report I get:

     ____                  __          ____  
    / __ \____  _____ ____/ /_  ____  / / /_ 
   / /_/ / __ `/ ___/ ___/ __ \/ __ \/ / __/ 
  / ____/ /_/ (__  |__  ) /_/ / /_/ / / /    
 /_/    \__,_/____/____/_.___/\____/_/\__/   

 Open source password manager for teams
-------------------------------------------------------------------------------
Passbolt CE 4.1.0
Cakephp 4.4.14
Linux virtual-machine2 5.15.0-1038-oracle #44-Ubuntu SMP Thu Jun 22 03:34:10 UTC 2023 aarch64 aarch64 aarch64 GNU/Linux
PHP 8.1.2-1ubuntu2.13 (cli) (built: Jun 28 2023 14:01:49) (NTS)
mysql  Ver 8.0.33-0ubuntu0.22.04.2 for Linux on aarch64 ((Ubuntu))
gpg (GnuPG) 2.2.27
libgcrypt 1.9.4
 ERROR: /usr/share/php/passbolt/bin/utils.sh: line 64: composer: command not found

     ____                  __          ____  
    / __ \____  _____ ____/ /_  ____  / / /_ 
   / /_/ / __ `/ ___/ ___/ __ \/ __ \/ / __/ 
  / ____/ /_/ (__  |__  ) /_/ / /_/ / / /    
 /_/    \__,_/____/____/_.___/\____/_/\__/   

 Open source password manager for teams
-------------------------------------------------------------------------------
 Healthcheck shell         
-------------------------------------------------------------------------------

 Environment

 [PASS] PHP version 8.1.2-1ubuntu2.13.
 [PASS] PCRE compiled with unicode support.
 [PASS] The temporary directory and its content are writable and not executable.
 [PASS] The logs directory and its content are writable.
 [PASS] GD or Imagick extension is installed.
 [PASS] Intl extension is installed.
 [PASS] Mbstring extension is installed.

 Config files

 [PASS] The application config file is present
 [PASS] The passbolt config file is present

 Core config

 [PASS] Debug mode is off.
 [PASS] Cache is working.
 [PASS] Unique value set for security.salt
 [PASS] Full base url is set to https://141.147.104.169/
 [PASS] App.fullBaseUrl validation OK.
 [PASS] /healthcheck/status is reachable.

 SSL Certificate

 [FAIL] SSL peer certificate does not validate
 [FAIL] Hostname does not match when validating certificates.
 [WARN] Using a self-signed certificate
 [HELP] Check https://help.passbolt.com/faq/hosting/troubleshoot-ssl
 [HELP] cURL Error (60) SSL certificate problem: self-signed certificate

 Database

 [PASS] The application is able to connect to the database
 [PASS] 32 tables found
 [FAIL] No default content found
 [HELP] Run the install script to set the default content such as roles and permission types
 [HELP] sudo su -s /bin/bash -c "/usr/share/php/passbolt/bin/cake passbolt install" www-data
 [PASS] The database schema up to date.

 GPG Configuration

 [PASS] PHP GPG Module is installed and loaded.
 [PASS] The environment variable GNUPGHOME is set to /var/lib/passbolt/.gnupg.
 [PASS] The directory /var/lib/passbolt/.gnupg containing the keyring is writable by the webserver user.
 [PASS] The server OpenPGP key is not the default one
 [PASS] The public key file is defined in /etc/passbolt/passbolt.php and readable.
 [PASS] The private key file is defined in /etc/passbolt/passbolt.php and readable.
 [PASS] The server key fingerprint matches the one defined in /etc/passbolt/passbolt.php.
 [PASS] The server public key defined in the /etc/passbolt/passbolt.php (or environment variables) is in the keyring.
 [PASS] There is a valid email id defined for the server key.
 [PASS] The public key can be used to encrypt a message.
 [PASS] The private key can be used to sign a message.
 [PASS] The public and private keys can be used to encrypt and sign a message.
 [PASS] The private key can be used to decrypt a message.
 [PASS] The private key can be used to decrypt and verify a message.
 [PASS] The public key can be used to verify a signature.
 [PASS] The server public key format is Gopengpg compatible.
 [PASS] The server private key format is Gopengpg compatible.

 Application configuration

 [FAIL] This installation is not up to date. Currently using 4.1.0 and it should be v4.1.1.
 [HELP] See. https://www.passbolt.com/help/tech/update
 [FAIL] Passbolt is not configured to force SSL use.
 [HELP] Set passbolt.ssl.force to true in /etc/passbolt/passbolt.php.
 [PASS] App.fullBaseUrl is set to HTTPS.
 [PASS] Selenium API endpoints are disabled.
 [PASS] Search engine robots are told not to index content.
 [INFO] The Self Registration plugin is enabled.
 [INFO] Registration is closed, only administrators can add users.
 [PASS] The deprecated self registration public setting was not found in /etc/passbolt/passbolt.php.
 [WARN] Host availability checking is disabled.
 [HELP] Make sure this instance is not publicly available on the internet.
 [HELP] Or set the PASSBOLT_EMAIL_VALIDATE_MX environment variable to true.
 [HELP] Or set passbolt.email.validate.mx to true in /etc/passbolt/passbolt.php.
 [PASS] Serving the compiled version of the javascript app.
 [WARN] Some email notifications are disabled by the administrator.

 JWT Authentication

 [PASS] The JWT Authentication plugin is enabled
 [PASS] The /etc/passbolt/jwt/ directory is not writable.
 [PASS] A valid JWT key pair was found

 SMTP Settings

 [PASS] The SMTP Settings plugin is enabled.
 [PASS] SMTP Settings coherent. You may send a test email to validate them.
 [PASS] The SMTP Settings source is: database.
 [WARN] The SMTP Settings plugin endpoints are enabled.
 [HELP] It is recommended to disable the plugin endpoints.
 [HELP] Set the PASSBOLT_SECURITY_SMTP_SETTINGS_ENDPOINTS_DISABLED environment variable to true.
 [HELP] Or set passbolt.security.smtpSettings.endpointsDisabled to true in /etc/passbolt/passbolt.php.

 [FAIL] 5 error(s) found. Hang in there!


     ____                  __          ____  
    / __ \____  _____ ____/ /_  ____  / / /_ 
   / /_/ / __ `/ ___/ ___/ __ \/ __ \/ / __/ 
  / ____/ /_/ (__  |__  ) /_/ / /_/ / / /    
 /_/    \__,_/____/____/_.___/\____/_/\__/   

 Open source password manager for teams
-------------------------------------------------------------------------------
 Cleanup shell (dry-run)
-------------------------------------------------------------------------------
No issue found, data looks squeaky clean!

     ____                  __          ____  
    / __ \____  _____ ____/ /_  ____  / / /_ 
   / /_/ / __ `/ ___/ ___/ __ \/ __ \/ / __/ 
  / ____/ /_/ (__  |__  ) /_/ / /_/ / / /    
 /_/    \__,_/____/____/_.___/\____/_/\__/   

 Open source password manager for teams
-------------------------------------------------------------------------------
Data check shell
[PASS] Data integrity for AuthenticationTokens.
  [PASS] Can validate: 24/24
[PASS] Data integrity for Comments.
  [PASS] Can validate: 0/0
[PASS] Data integrity for Favorites.
  [PASS] Can validate: 0/0
[PASS] Data integrity for Gpgkeys.
  [PASS] Can encrypt: 1/1
  [PASS] Pass validation service checks: 1/1
  [PASS] Entity data and armored key data matches: 1/1
  [PASS] Is not expired: 1/1
  [PASS] Is armored key format valid: 1/1
[PASS] Data integrity for Groups.
  [PASS] Can validate: 0/0
[PASS] Data integrity for Profiles.
  [PASS] Can validate: 1/1
[PASS] Data integrity for Resources.
  [PASS] Can validate: 124/124
[PASS] Data integrity for Secrets.
  [PASS] Can validate: 118/118
[PASS] Data integrity for Users.
  [PASS] Can validate: 1/1
2023-07-14 02:38:30 error: [Cake\Routing\Exception\MissingRouteException] A route matching "/ab2h" could not be found. in /usr/share/php/passbolt/vendor/cakephp/cakephp/src/Routing/RouteCollection.php on line 197
Request URL: /ab2h
Client IP: 46.101.210.113
2023-07-14 04:00:42 error: [Cake\Routing\Exception\MissingRouteException] A route matching "/geoserver/web/" could not be found. in /usr/share/php/passbolt/vendor/cakephp/cakephp/src/Routing/RouteCollection.php on line 197
Request URL: /geoserver/web/
Client IP: 64.62.197.118
2023-07-14 04:03:48 error: [Cake\Routing\Exception\MissingRouteException] A route matching "/.git/config" could not be found. in /usr/share/php/passbolt/vendor/cakephp/cakephp/src/Routing/RouteCollection.php on line 197
Request URL: /.git/config
Client IP: 64.62.197.114
2023-07-14 04:55:42 error: [Cake\Routing\Exception\MissingRouteException] A route matching "/ab2g" could not be found. in /usr/share/php/passbolt/vendor/cakephp/cakephp/src/Routing/RouteCollection.php on line 197
Request URL: /ab2g
Client IP: 134.122.103.1
2023-07-14 04:55:42 error: [Cake\Routing\Exception\MissingRouteException] A route matching "/ab2h" could not be found. in /usr/share/php/passbolt/vendor/cakephp/cakephp/src/Routing/RouteCollection.php on line 197
Request URL: /ab2h
Client IP: 134.122.103.1
2023-07-14 04:55:43 error: [Cake\Routing\Exception\MissingRouteException] A route matching "/t4" could not be found. in /usr/share/php/passbolt/vendor/cakephp/cakephp/src/Routing/RouteCollection.php on line 197
Request URL: /t4
Client IP: 134.122.103.1
2023-07-14 07:38:21 error: [Cake\Routing\Exception\MissingRouteException] A route matching "/Public/home/js/check.js" could not be found. in /usr/share/php/passbolt/vendor/cakephp/cakephp/src/Routing/RouteCollection.php on line 197
Request URL: /Public/home/js/check.js
Client IP: 47.251.14.232
2023-07-14 07:38:22 error: [Cake\Routing\Exception\MissingRouteException] A route matching "/static/admin/javascript/hetong.js" could not be found. in /usr/share/php/passbolt/vendor/cakephp/cakephp/src/Routing/RouteCollection.php on line 197
Request URL: /static/admin/javascript/hetong.js
Client IP: 47.88.90.156

Trying to run sudo -H -u www-data bash -c "/usr/share/php/passbolt/bin/cake passbolt send_test_email --verbose --recipient=my_email@gmail.com" returns:


     ____                  __          ____  
    / __ \____  _____ ____/ /_  ____  / / /_ 
   / /_/ / __ `/ ___/ ___/ __ \/ __ \/ / __/ 
  / ____/ /_/ (__  |__  ) /_/ / /_/ / / /    
 /_/    \__,_/____/____/_.___/\____/_/\__/   

 Open source password manager for teams
-------------------------------------------------------------------------------
 Debug email shell
-------------------------------------------------------------------------------
Email configuration
-------------------------------------------------------------------------------
Host: smtp.gmail.com
Port: 587
Username: my_email@gmail.com
Password: *********
TLS: true
Sending email from: <name> <my_email@gmail.com>
Sending email to: my_email@gmail.com
-------------------------------------------------------------------------------
Trace
[220] smtp.gmail.com ESMTP u11-20020a05600c00cb00b003fbb346279dsm1311619wmm.38 - gsmtp
 EHLO localhost
[250] smtp.gmail.com at your service, [<my IP>]
[250] SIZE 35882577
[250] 8BITMIME
[250] STARTTLS
[250] ENHANCEDSTATUSCODES
[250] PIPELINING
[250] CHUNKING
[250] SMTPUTF8
 STARTTLS
[220] 2.0.0 Ready to start TLS
 EHLO localhost
[250] smtp.gmail.com at your service, [<my IP>]
[250] SIZE 35882577
[250] 8BITMIME
[250] AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
[250] ENHANCEDSTATUSCODES
[250] PIPELINING
[250] CHUNKING
[250] SMTPUTF8
 AUTH PLAIN *****
[535] 5.7.8 Username and Password not accepted. Learn more at
[535] 5.7.8  https://support.google.com/mail/?p=BadCredentials u11-20020a05600c00cb00b003fbb346279dsm1311619wmm.38 - gsmtp
Could not send the test email.
Error: SMTP Error: 530 5.7.0  https://support.google.com/mail/?p=WantAuthError u11-20020a05600c00cb00b003fbb346279dsm1311619wmm.38 - gsmtp

I am using an app password given as such “xxxxxxxxxxxxxxxx” - 16 characters no spaces and yet it still fails. After some googling, the error code 530, 5.7.0 means 530, "5.7.0", Must issue a STARTTLS command first. How would I configure passbolt to do this?

2

Since you are connecting to google it might be an issue with MFA. For the sending from email address do you have MFA configured for this?

If so you will need to set up an app password and use that instead of the default password on the account

3

As already mentioned, I am using an app password.

4

Apologies, went a bit too quickly and missed that line in there.

Did you also allow the less secure apps option in your gmail account?

The reason I am a bit more focused on the app password side of this is that there is a STARTTLS already in that output

5

With 2FA you can’t allow less secure apps, that’s why you use app passwords.

6

It also looks like the Less Secure Apps option was completely disabled as of last year(full disclosure I don’t use gmail for anything like this), and yet they still mention checking it on their suggested support link

A couple other google support pages(1,2) point to the need to log in with that account on a browser(or if logged in to log out and back in). Have you tried that?

7

I have not, as I only connect to the server via SSH, as it is a cloud machine. How would I sign into google using terminal?

8

I could be reading it wrong but I believe you can just log in to the account from any browser and not specifically from the passbolt server

9

Oh, then I have done that after resigning in to my account locally.

10

did this work eventually? im having the same issue.

 ____                  __          ____  
/ __ \____  _____ ____/ /_  ____  / / /_

/ // / __ `/ / / __ / __ / / _/
/ / // ( | ) // / // / / /
// _,///./_//__/

Open source password manager for teams

Debug email shell

Email configuration

Host: smtp.gmail.com
Port: 587
Username: ccc@gmail.com"
Password: *********
TLS: true
Sending email from: Passbolt ccc@gmail.com
Sending email to: youremail@domain.com

Trace
[220] smtp.gmail.com ESMTP v5-20020a17090a778500b0028098225450sm6535382pjk.1 - gsmtp
EHLO localhost
[250] smtp.gmail.com at your service, [202.83.109.8]
[250] SIZE 35882577
[250] 8BITMIME
[250] STARTTLS
[250] ENHANCEDSTATUSCODES
[250] PIPELINING
[250] CHUNKING
[250] SMTPUTF8
STARTTLS
[220] 2.0.0 Ready to start TLS
EHLO localhost
[250] smtp.gmail.com at your service, [202.83.109.8]
[250] SIZE 35882577
[250] 8BITMIME
[250] AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
[250] ENHANCEDSTATUSCODES
[250] PIPELINING
[250] CHUNKING
[250] SMTPUTF8
AUTH PLAIN AHNoYXduLmRhbW9uQGdtYWlsLmNvbSIA*****
[535] 5.7.8 Username and Password not accepted. For more information, go to
[535] 5.7.8 Can't sign in to your Google Account - Gmail Help v5-20020a17090a778500b0028098225450sm6535382pjk.1 - gsmtp
Could not send the test email.
Error: SMTP Error: 530 5.7.0 Can't sign in to your Google Account - Gmail Help v5-20020a17090a778500b0028098225450sm6535382pjk.1 - gsmtp
<t$ ./bin/cake passbolt send_test_email --recipient=youremail@domain.com

11

I also setup a new GMAIL account just to test…in case my settings are preventing the app from signing. the same error as above.

12

Just to be sure, which of the google/gmail methods are you using?

13

i am using Google Email …

14

Alright, and just to be sure you set up an App Password and are using that here, correct?

15

roger that i am certainly using an app password and also ensured that 2Fa is enabled on my gmail