Failed to authenticate on SMTP server error using gmail

Email Problem Overview

I'm trying to set up email for my first laravel project, and was thrilled that there's a laracast for it: https://laracasts.com/lessons/mailers

I've followed the simple steps, chose gmail in mail.php (x's added for anonymity):

'driver' => env('MAIL_DRIVER', 'smtp'),
'host' => env('MAIL_HOST', 'smtp.gmail.com'),
'port' => env('MAIL_PORT', 587),
'from' => ['address' => '[email protected]', 'name' => 'Diane Kaplan'],
'encryption' => env('MAIL_ENCRYPTION', 'tls'),
'username' => '[email protected]',
'password' => 'xxxxx',
'sendmail' => '/usr/sbin/sendmail -bs',
'pretend' => false,

.env has (x's added for anonymity)- the laracast doesn't have us use MAIL_USERNAME and MAIL_PASSWORD, but they're updated for good measure assuming I'll pull from there later:

MAIL_DRIVER=smtp
MAIL_HOST=mailtrap.io
MAIL_PORT=2525
MAIL_USERNAME[email protected]
MAIL_PASSWORD=xxxxxx
MAIL_ENCRYPTION=null

But in the first little moment of truth trying to send a mail (3:30 mark), I get an authentication error: Swift_TransportException in AuthHandler.php line 181: Failed to authenticate on SMTP server with username "[email protected]" using 3 possible authenticators

Based on a little stackoverflow reading, I tried turning on 'access to less secure apps' in my gmail settings, but no change in the error. (And the other posts about this issue had other factors that made a fancier problem than mine).

Nothing jumps out at me from laravel.log (below)- any ideas?

[2015-11-26 12:25:55] local.ERROR: exception 'Swift_TransportException' with message 'Failed to authenticate on SMTP server with username "[email protected]" using 3 possible authenticators' in /home/vagrant/Code/Family-laravel/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Transport/Esmtp/AuthHandler.php:181
Stack trace:
    #0 /home/vagrant/Code/Family-laravel/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Transport/EsmtpTransport.php(307): Swift_Transport_Esmtp_AuthHandler->afterEhlo(Object(Swift_SmtpTransport))
    #1 /home/vagrant/Code/Family-laravel/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Transport/AbstractSmtpTransport.php(118): Swift_Transport_EsmtpTransport->_doHeloCommand()
    #2 /home/vagrant/Code/Family-laravel/vendor/swiftmailer/swiftmailer/lib/classes/Swift/Mailer.php(79): Swift_Transport_AbstractSmtpTransport->start()
    #3 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Mail/Mailer.php(395): Swift_Mailer->send(Object(Swift_Message), Array)
    #4 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Mail/Mailer.php(181): Illuminate\Mail\Mailer->sendSwiftMessage(Object(Swift_Message))
    #5 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Support/Facades/Facade.php(220): Illuminate\Mail\Mailer->send('emails.welcome', Array, Object(Closure))
    #6 /home/vagrant/Code/Family-laravel/app/Http/routes.php(59): Illuminate\Support\Facades\Facade::__callStatic('send', Array)
    #7 /home/vagrant/Code/Family-laravel/app/Http/routes.php(59): Illuminate\Support\Facades\Mail::send('emails.welcome', Array, Object(Closure))
    #8 [internal function]: App\Providers\RouteServiceProvider->{closure}()
    #9 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Routing/Route.php(155): call_user_func_array(Object(Closure), Array)
    #10 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Routing/Route.php(130): Illuminate\Routing\Route->runCallable(Object(Illuminate\Http\Request))
    #11 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Routing/Router.php(704): Illuminate\Routing\Route->run(Object(Illuminate\Http\Request))
    #12 [internal function]: Illuminate\Routing\Router->Illuminate\Routing\{closure}(Object(Illuminate\Http\Request))
    #13 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(139): call_user_func(Object(Closure), Object(Illuminate\Http\Request))
    #14 [internal function]: Illuminate\Pipeline\Pipeline->Illuminate\Pipeline\{closure}(Object(Illuminate\Http\Request))
    #15 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(103): call_user_func(Object(Closure), Object(Illuminate\Http\Request))
    #16 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Routing/Router.php(706): Illuminate\Pipeline\Pipeline->then(Object(Closure))
    #17 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Routing/Router.php(671): Illuminate\Routing\Router->runRouteWithinStack(Object(Illuminate\Routing\Route), Object(Illuminate\Http\Request))
    #18 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Routing/Router.php(631): Illuminate\Routing\Router->dispatchToRoute(Object(Illuminate\Http\Request))
    #19 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Foundation/Http/Kernel.php(236): Illuminate\Routing\Router->dispatch(Object(Illuminate\Http\Request))
    #20 [internal function]: Illuminate\Foundation\Http\Kernel->Illuminate\Foundation\Http\{closure}(Object(Illuminate\Http\Request))
    #21 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(139): call_user_func(Object(Closure), Object(Illuminate\Http\Request))
    #22 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Foundation/Http/Middleware/VerifyCsrfToken.php(50): Illuminate\Pipeline\Pipeline->Illuminate\Pipeline\{closure}(Object(Illuminate\Http\Request))
    #23 [internal function]: Illuminate\Foundation\Http\Middleware\VerifyCsrfToken->handle(Object(Illuminate\Http\Request), Object(Closure))
    #24 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(124): call_user_func_array(Array, Array)
    #25 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/View/Middleware/ShareErrorsFromSession.php(49): Illuminate\Pipeline\Pipeline->Illuminate\Pipeline\{closure}(Object(Illuminate\Http\Request))
    #26 [internal function]: Illuminate\View\Middleware\ShareErrorsFromSession->handle(Object(Illuminate\Http\Request), Object(Closure))
    #27 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(124): call_user_func_array(Array, Array)
    #28 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Session/Middleware/StartSession.php(62): Illuminate\Pipeline\Pipeline->Illuminate\Pipeline\{closure}(Object(Illuminate\Http\Request))
    #29 [internal function]: Illuminate\Session\Middleware\StartSession->handle(Object(Illuminate\Http\Request), Object(Closure))
    #30 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(124): call_user_func_array(Array, Array)
    #31 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Cookie/Middleware/AddQueuedCookiesToResponse.php(37): Illuminate\Pipeline\Pipeline->Illuminate\Pipeline\{closure}(Object(Illuminate\Http\Request))
    #32 [internal function]: Illuminate\Cookie\Middleware\AddQueuedCookiesToResponse->handle(Object(Illuminate\Http\Request), Object(Closure))
    #33 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(124): call_user_func_array(Array, Array)
    #34 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Cookie/Middleware/EncryptCookies.php(59): Illuminate\Pipeline\Pipeline->Illuminate\Pipeline\{closure}(Object(Illuminate\Http\Request))
    #35 [internal function]: Illuminate\Cookie\Middleware\EncryptCookies->handle(Object(Illuminate\Http\Request), Object(Closure))
    #36 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(124): call_user_func_array(Array, Array)
    #37 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Foundation/Http/Middleware/CheckForMaintenanceMode.php(42): Illuminate\Pipeline\Pipeline->Illuminate\Pipeline\{closure}(Object(Illuminate\Http\Request))
    #38 [internal function]: Illuminate\Foundation\Http\Middleware\CheckForMaintenanceMode->handle(Object(Illuminate\Http\Request), Object(Closure))
    #39 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(124): call_user_func_array(Array, Array)
    #40 [internal function]: Illuminate\Pipeline\Pipeline->Illuminate\Pipeline\{closure}(Object(Illuminate\Http\Request))
    #41 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php(103): call_user_func(Object(Closure), Object(Illuminate\Http\Request))
    #42 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Foundation/Http/Kernel.php(122): Illuminate\Pipeline\Pipeline->then(Object(Closure))
    #43 /home/vagrant/Code/Family-laravel/vendor/laravel/framework/src/Illuminate/Foundation/Http/Kernel.php(87): Illuminate\Foundation\Http\Kernel->sendRequestThroughRouter(Object(Illuminate\Http\Request))
    #44 /home/vagrant/Code/Family-laravel/public/index.php(54): Illuminate\Foundation\Http\Kernel->handle(Object(Illuminate\Http\Request))
    #45 {main}

Email Solutions

Solution 1 - Email

This will not work as of May 30, 2022 checkout here https://support.google.com/accounts/answer/6010255?hl=en&authuser=6 Thanks @sarout for pointing this out.

Did you turn on the "Allow less secure apps" on? go to this link

https://myaccount.google.com/security#connectedapps

Take a look at the Sign-in & security -> Apps with account access menu.

You must turn the option "Allow less secure apps" ON.

If is still doesn't work try one of these:

Go to https://accounts.google.com/UnlockCaptcha , and click continue and unlock your account for access through other media/sites.
Use double quote in your password: "your password"

And change your .env file

MAIL_DRIVER=smtp
MAIL_HOST=smtp.gmail.com
MAIL_PORT=587
MAIL_USERNAME[email protected]
MAIL_PASSWORD=xxxxxx
MAIL_ENCRYPTION=tls

because the one's you have specified in the mail.php will only be used if the value is not available in the .env file.

Solution 2 - Email

Nothing wrong with your method, it's a G-mail security issue.

Login g-mail account settings.
Enable 2-step verification.
Generate app-password.
Use new-generated password in place of your real g-mail password.

Don't forget to clear cache.

php artisan config:cache.
php artisan config:clear.

MAIL_DRIVER=smtp
MAIL_HOST=mailtrap.io
MAIL_PORT=587
MAIL_USERNAME[email protected]
MAIL_PASSWORD=generatedAppPassword
MAIL_ENCRYPTION=tls

Solution 3 - Email

If you still get this error when sending email: "Failed to authenticate on SMTP server with username "[email protected]" using 3 possible authenticators"

You may try one of these methods:

Go to https://accounts.google.com/UnlockCaptcha, click continue and unlock your account for access through other media/sites.
Using a double quote password: "your password" <-- this one also solved my problem.

Solution 4 - Email

I had the same issue, but when I ran the following command, it was ok:

php artisan config:cache

Solution 5 - Email

Change the .env file as follow

MAIL_DRIVER=smtp
MAIL_HOST=smtp.googlemail.com
MAIL_PORT=587
MAIL_USERNAME[email protected]
MAIL_PASSWORD=password
MAIL_ENCRYPTION=tls

And the go to the gmail security section ->Allow Less secure app access

Then run

php artisan config:clear

Refresh the site

Solution 6 - Email

If you still get this error when sending email: "Failed to authenticate on SMTP server with username "[email protected]" using 3 possible authenticators"

You may try one of these methods:

Go to https://accounts.google.com/UnlockCaptcha, click continue and unlock your account for access through other media/sites.

Use double quote for your password: like - "Abc@%$67eSDu"

Solution 7 - Email

This is how I solved this issue:

Change the .env file as follow

Screenshot Reference

2. Never forget to restart the server after you change the .env file

Solution 8 - Email

I had the same problem and I've already tried everything and nothing seemed to work until I just changed the 'host' value in config.php to:

 'host' => env('smtp.mailtrap.io'),

When I changed that it worked nicely, somehow it was using the default host " smtp.mailtrap.org" and ignoring the .env variable I was setting.

After making some test I realize that if I placed the env variable in this order it would worked as it shoulded:

MAIL_HOST=smtp.mailtrap.io

 MAIL_DRIVER=smtp

 MAIL_PORT=2525 

MAIL_USERNAME=xxxx

 MAIL_PASSWORD=xxx

 MAIL_ENCRYPTION=null

Solution 9 - Email

I also got the same error-

Make sure less secure app access is enabled in your gmail account https://myaccount.google.com/security#connectedapps
Put double quotes to the password "password" in .env file

These solutions worked for me.

Content Type	Original Author	Original Content on Stackoverflow
Question	Diane Kaplan	View Question on Stackoverflow
Solution 1 - Email	Milan Maharjan	View Answer on Stackoverflow
Solution 2 - Email	benjolly1989	View Answer on Stackoverflow
Solution 3 - Email	H45H	View Answer on Stackoverflow
Solution 4 - Email	Lộc Đặng Hữu	View Answer on Stackoverflow
Solution 5 - Email	Shasika Madhushan	View Answer on Stackoverflow
Solution 6 - Email	Shilwant Gupta	View Answer on Stackoverflow
Solution 7 - Email	Sushil Timilsina	View Answer on Stackoverflow
Solution 8 - Email	Luis Mata B.	View Answer on Stackoverflow
Solution 9 - Email	Raj	View Answer on Stackoverflow