Email Connector test fails with Gmail

[danhen310]

No problems signing-in directly to gmail.com, however with the same credentials:

Connecting...
Host: smtp.gmail.com
Port: 465
Encrypted connection: SSL
Auth: Y,[email@address],(Password)
Connecting...
Connecting...
Connecting...
Connecting...
Error Connect
SMTP Exception: Login failed, please make sure you are using the correct username and password. More details below:
e3: Login using LOGIN password failed: 535-5.7.8 Username and Password not accepted. Learn more at
535 5.7.8 https://support.google.com/mail/?p=BadCredentials u20sm19785281pgm.4 - gsmtp
g3: Login using PLAIN failed: 501 5.5.2 Cannot Decode response u20sm19785281pgm.4 - gsmtp
08/23/2021 18:03:08: Queued
08/23/2021 18:03:09: Connecting
08/23/2021 18:03:09: Connecting - SMTP Exception: Login failed, please make sure you are using the correct username and password. More details below:
e3: Login using LOGIN password failed: 535-5.7.8 Username and Password not accepted. Learn more at
535 5.7.8 https://support.google.com/mail/?p=BadCredentials d20sm16971952pfu.36 - gsmtp
g3: Login using PLAIN failed: 501 5.5.2 Cannot Decode response d20sm16971952pfu.36 - gsmtp
08/23/2021 18:03:10: Connecting
08/23/2021 18:03:11: Connecting - SMTP Exception: Login failed, please make sure you are using the correct username and password. More details below:
e3: Login using LOGIN password failed: 535-5.7.8 Username and Password not accepted. Learn more at
535 5.7.8 https://support.google.com/mail/?p=BadCredentials d22sm19232464pgi.73 - gsmtp
g3: Login using PLAIN failed: 501 5.5.2 Cannot Decode response d22sm19232464pgi.73 - gsmtp
08/23/2021 18:03:12: Connecting
08/23/2021 18:03:12: ErrorConnect - SMTP Exception: Login failed, please make sure you are using the correct username and password. More details below:
e3: Login using LOGIN password failed: 535-5.7.8 Username and Password not accepted. Learn more at
535 5.7.8 https://support.google.com/mail/?p=BadCredentials u20sm19785281pgm.4 - gsmtp
g3: Login using PLAIN failed: 501 5.5.2 Cannot Decode response u20sm19785281pgm.4 - gsmtp
(Internal: 20,1050)

Different response after changing only the port to 587:

Connecting...
Host: smtp.gmail.com
Port: 587
Encrypted connection: SSL
Auth: Y,[email@address],(Password)
Connecting...
Connecting...
Error Connect
SSL Exception: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol
08/23/2021 18:04:02: Queued
08/23/2021 18:04:03: Connecting
08/23/2021 18:04:03: Connecting - SSL Exception: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol
08/23/2021 18:04:04: Connecting
08/23/2021 18:04:04: Connecting - SSL Exception: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol
08/23/2021 18:04:05: Connecting
08/23/2021 18:04:05: ErrorConnect - SSL Exception: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol
(Internal: 20,1050)

Any suggestions would be greatly appreciated.
Thanks!

[Support Team]

Re: Email Connector test fails with Gmail

Thank you for posting this.

It seems that this error is related to Google's "Less secure app access". Please review the solution suggested in the following Gmail support forum thread:

https://support.google.com/mail/thread/5621336?hl=en

Here the steps you should to perform (copied from Google's forum thread linked above):

1. Login to Gmail account.
2. Go to account
3. Turn ON Less secure app access
4. After this when you try to send mail from your app you will get error .
5. Than go to Security issues found ( it's first option in security tab of Google account ) here you need to verify that last activity is verified and it's you .

Please give it a try and see how it works for you.

Hope this helps.

[danhen310]

Re: Email Connector test fails with Gmail

Thanks for your recommendation, however it appears that Google has changed GMail security. Although I previously turned on Less secure app access for all accounts over a year ago, that is now denied to accounts that have not used it recently.
Google now recommends enabling 2-step authentication and then signing-in with app passwords.
Please let me know if RangerMSP supports Google's recommendation, or
have another suggestion, or
I have to switch to an email address in another domain that is not hosted by Gmail.

[Support Team]

Re: Email Connector test fails with Gmail

That's interesting as we definitely do have Gmail/Google Account with that configured. In any case, if you have any other provider to configure SMTP with it may offer an immediate solution.

Hope this helps!

[danhen310]

Re: Email Connector test fails with Gmail

How recently have you added Less secure app access to a Gmail/Google Account?
This is a new change by Google.
If I use another domain at another provider, the email address will not be my business email.

[Support Team]

Re: Email Connector test fails with Gmail

From our testing - we see that when the 2-step authentication for Google account is turned on, then indeed the option to allow access for Less secure apps is not shown.

With 2-step authentication turned on, you can configure the password for a 3rd party application.

Google will generate a 16-character password that you should then use in the ServerConfig utility instead of your Google account password.

Please give it a try and keep us posted on this.





--

Besides the above, that should work, we'd add that even if you use Google Apps for your domain (or 365 or anything else), you should still be able to safely and reliably send emails out from your domain using other SMTP servers (e.g. not Google's).
You should use any other SMTP server service (i.e. a hosted service or a server you host yourself) and ideally configure SPF and DKIM records at your domain's DNS table to teach the world that this mail server is a legit mail server for messages sent From your domain. So regardless of anything else, this should still be an option.

Hope this helps!