"Failed to authenticate on SMTP server" after more than 100 emails - laravel

I'm trying to send about 500 emails with Laravel, my provider is Gmail.
The first 150 emails (more or less) are sent correctly, but after I receive this error:
"Failed to authenticate on SMTP server with username "XXXXXXX" using 3 possible authenticators. Authenticator LOGIN returned Expected response code 250 but got an empty response. Authenticator PLAIN returned Expected response code 250 but got an empty response. Authenticator XOAUTH2 returned Expected response code 250 but got an empty response."
My .env is
MAIL_MAILER=smtp
MAIL_HOST=smtp.gmail.com
MAIL_PORT=587
MAIL_ENCRYPTION=ssl
MAIL_USERNAME=...
MAIL_PASSWORD=...
I also tried to wait for about 5 seconds between each email, but it doesn't work.
Anyone knows how I can handle this?
Thank you

Try to use the next settings:
MAIL_PORT=465
MAIL_ENCRYPTION=ssl
Enable 2FA in your Google account and create an app password.
Use it in MAIL_PASSWORD

I had a similar problem, and here is how I solved it.
the Google mail service may have blocked emails from being sent from your app. Google surely viewed this as a security threat. you should definitely receive a security alert in your mailbox.
You just have to admit that it was you who tried to access the account or just change your gmail password. after that please change the info in the .env file and i think it will work.
try to change your password on gmail
and also in your .env file

Related

Gmail smtp not working with only one email

I am using gmail smtp in my laravel, It was working fine till yesterday but it suddenly stopped, I am getting this error
Failed to authenticate on SMTP server with username "email#gmail.com" using 3 possible authenticators. Authenticator LOGIN returned Expected response code 235 but got code "535", with message "535-5.7.8 Username and Password not accepted
Less secure apps was already on so i added 2 factor auth and created an app password but still not working, I created a test email and it worked fine, why is not working with my first email
This is my setting in env
MAIL_DRIVER=smtp
MAIL_HOST=smtp.gmail.com
MAIL_PORT=587
MAIL_USERNAME=email#gmail.com
MAIL_PASSWORD=password
MAIL_ENCRYPTION=tls
MAIL_EMAIL_ADDRESS=email#gmail.com
I also tried by adding double quotes, but still not wokring,
Can anyone please help
After the removal of less secure apps. You can no longer connect to googles smtp server using the actual password of the users gmail account.
YOu have two options.
enable 2fa on the google account and create an apps password. The apps password can then be used in place of the password in your code.
Switch to using Xoauth2.

Error On Setting Up SMTP On Ofiice365 On Laravel

When I am trying to set up SMTP mail account which my client gave there is an error where i could resolve ,
Can someone help
MAIL_DRIVER=smtp
MAIL_HOST=smtp.office365.com
MAIL_PORT=587
MAIL_USERNAME=xxxxxx
MAIL_PASSWORD=xxxx
MAIL_ENCRYPTION=tls used STARTTLS & ssl
This is the error that i get
Swift_TransportException
Failed to authenticate on SMTP server with username "appointments#test.org" using 2 possible authenticators. Authenticator LOGIN returned Expected response code 235 but got code "535", with message "535 5.7.139 Authentication unsuccessful, SmtpClientAuthentication is disabled for the Tenant. Visit aka.ms/smtp_auth_disabled for more info. [SG2PR04CA0177.apcprd04.prod.outlook.com] ". Authenticator XOAUTH2 returned Expected response code 235 but got code "451", with message "451 4.7.0 Temporary server error. Please try again later. PRX4 [SG2PR04CA0177.apcprd04.prod.outlook.com] ".
Can someone help
Thank you
https://wordpress.org/support/topic/5-7-139-authentication-unsuccessful-error-suddenly/
Someone disabled SMTP for the box you have a link with an explanation
in the error you posted.
One way to try:
Use the Microsoft 365 admin center to enable or disable SMTP AUTH on
specific mailboxes Open the Microsoft 365 admin center and go to Users
Active users.
Select the user, and in the flyout that appears, click Mail.
In the Email apps section, click Manage email apps.
Verify the Authenticated SMTP setting: unchecked = disabled, checked =
enabled.
When you're finished, click Save changes.

Sending Email using Outlook / Office365 with Laravel - Failed to authenticate on SMTP server

I'm trying to send an email with our Laravel app using Office365/Outlook. It has worked well with gmail but when I switched over to Office365, the following error appears:
Failed to authenticate on SMTP server with username
"xxxxxx#companyname.co" using 2 possible authenticators. Authenticator
LOGIN returned Expected response code 235 but got code "535", with
message "535 5.7.3 Authentication unsuccessful
[HKAPR03CA0035.apcprd03.prod.outlook.com]
". Authenticator XOAUTH2 returned Expected response code 235 but got code "535", with message "535 5.7.3 Authentication unsuccessful
[HKAPR03CA0035.apcprd03.prod.outlook.com]
".
This is what I have in my .env file:
MAIL_DRIVER=smtp
MAIL_HOST=smtp.office365.com
MAIL_PORT=587
MAIL_USERNAME=xxxxxx#companyname.co
MAIL_PASSWORD=emailPassword
MAIL_ENCRYPTION=tls
MAIL_SMTPAuth=true
MAIL_FROM_NAME=CompanyName
MAIL_FROM_ADDRESS=xxxxxx#companyname.co
*note: this is not the real username, password and from address.
I also tried changing the port to 25 but I get the same error
I'm using a dedicated support email from my company. And from what I confirmed with our IT, the support email does not have 2 factor authentication and the "Authenticated SMTP" setting is also enabled via the admin panel of Office365 so I don't know what seems to be the problem.
Keep in mind that for the new tenants, Microsoft turns SMTP authentication off, and it needs to be explicitly enabled. Please see
Enable or disable authenticated client SMTP submission (SMTP AUTH) in Exchange Online
as well as
What are security defaults?
I had the same issue and I called Microsoft support. They instructed me to change some security properties in Microsoft Azure. Here is my answer.
You have to enable the 2 factor authentication, the go to your account settings and create an application password. Then you have to use the new application password in your code. Check this link

How to solve the Sendgrid STMP Error 250 response in Laravel

I am using Sendgrid for the mail service.
My Account is two factor authentication is enabled.
My .env
MAIL_DRIVER=smtp
MAIL_HOST=smtp.sendgrid.net
MAIL_PORT=587
MAIL_USERNAME=S4gYKuoPRBaOAy7qT__J8w
MAIL_PASSWORD=SG.APIKEYPASSWORD
MAIL_ENCRYPTION=tls
MAIL_FROM_NAME="Xyz Name"
MAIL_FROM_ADDRESS=xyz#xyz.com
If I execute the mail then I am getting below error.
Swift_TransportException : Failed to authenticate on SMTP server with username "S4gYKuoPRBaOAy7qT__J8w" using 2 possible authenticators. Authenticator LOGIN returned Expected response code 250 but got an empty response. Authenticator PLAIN returned Expected response code 250 but got an empty response.
And If I disable the two-factor authentication then it works with the UserName and Password of the account but sendgrid will suspend my account if I do it like this.
Can anyone faced this issue. if yes then please let me know how you solved the problem.
Try using the literal value 'apikey' as the MAIL_USERNAME, and the key from an API Key that you create in Settings >> API Keys as the MAIL_PASSWORD.
They are now enforcing 2FA, and auth with keys instead of a user/password when using 2FA, starting Nov 18, 2020. I just changed over and this worked for me.
For example,
MAIL_DRIVER=smtp
MAIL_HOST=smtp.sendgrid.net
MAIL_PORT=587
MAIL_USERNAME=apikey
MAIL_PASSWORD=SG.xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx
We should highlight this one
MAIL_USERNAME=apikey
The string "apikey" is literally the MAIL_USERNAME` for all

Failed to authenticate on SMTP server with username "apikey" using 2 possible authenticators in SendGrid

I got the following error when trying to send an Email via SendGrid SMTP.
Failed to authenticate on SMTP server with username "apikey" using 2 possible authenticators. Authenticator LOGIN returned the Expected response code 250 but got an empty response. Authenticator PLAIN returned Expected response code 250 but got an empty response.
MAIL_DRIVER=smtp
MAIL_HOST=smtp.sendgrid.net
MAIL_PORT=587
MAIL_USERNAME=apikey
MAIL_PASSWORD=mysecretkey
MAIL_ENCRYPTION=tls
MAIL_FROM_NAME="RPLS"
MAIL_FROM_ADDRESS=info#rtsss.com
check your IP to be whitelisted in Sendgrid dashboard
https://app.sendgrid.com/settings/access

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