Smtp Relay

[David Eng]

Hi,

i have a set up a smtp relay on gsuite to allow nor...@domain.com to send scripting notification

Here what i have done : 

Authorized senders: Only my domain addresses

Accept only messages from specified IP addresses: Yes

Allowed IP addresses: IPs Test

SMTP authentication required: Yes

Require TLS encryption: Yes 

it doesn't seems to be working when i try to send an email 

command : 

Send-MailMessage -From nor...@domaintest.com-to "to...@domaintest.com" -SmtpServer "smtp.gmail.com" -Subject "test" -Body "Test" -port "587" -UseSsl -Credential 

Send-MailMessage : The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.0 Authentication Required. Learn more at

At line:1 char:1

any idea ? 

[Jay Lee]

Well this isn't quite GAM related but...

Doesn't look like your client is authenticating properly. The -Credential parameter seems to send your Windows admin credentials by default which is unlikely to work against the Google SMTP server. Seems like you need to specify credentials to use:

https://jaylee.us/3ja

Jay Lee

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[Gabriel Clifton]

With Powershell, I usually do

$smtp = "smtp.gmail.com" # This is your SMTP Server
$to1 = "1...@domain.com" # This is the recipient smtp address 1
$to2 = "2...@domain.com" # This is the recipient smtp address 2
$to3 = "3...@domain.com" # This is the recipient smtp address 3
$smtpUsername = "authent...@domain.com"  
$smtpPassword = "password"  
$credentials = new-object Management.Automation.PSCredential $smtpUsername, ($smtpPassword | ConvertTo-SecureString -AsPlainText -Force)
$from = "<fr...@domain.com>" # This will be the sender's address

$subject = "Subject of email"

$MsgBody = "Body of email"

send-MailMessage -SmtpServer $smtp -Port 587 -UseSsl -Credential $credentials -To $to1, $to2, $to3 -From $from -Subject $subject -Body $MsgBody -BodyAsHtml -Priority high

Always works.

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Gabriel Clifton | Network Administrator

Fort Stockton ISD | Technology Center
gabriel...@fsisd.net | http://www.fsisd.net
Office (432) 336-4055 ext 2

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[David Eng]

Gabriel, 

I have tried and this is what i get 

send-MailMessage : The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.0 Authentication Required. Learn more at
At line:14 char:1
+ send-MailMessage -SmtpServer $smtp -Port 587 -UseSsl -Credential $cre ...
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
    + CategoryInfo          : InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [Send-MailMessage], SmtpException
    + FullyQualifiedErrorId : SmtpException,Microsoft.PowerShell.Commands.SendMailMessage

by the way i want to send from a noreply@..com to a specific groups ou users

any idea? 

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[Gabriel Clifton]

OK, check your Admin Console and make sure that the user has rights to send mail by SMTP.

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[David Eng]

Done it was disabled 

I have allow it how long does it takes to replicate ? 

that is in : admin.google.com >>Apps > G Suite > Settings for Gmail > End user access > Allow per-user outbound gateways  right? 

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[Gabriel Clifton]

Google can take anywhere from a few minutes to 24 hours for some settings.

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[David Eng]

Got it 

I will try and let you know 

hopefully it will work 

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[David Eng]

Gabriel, 

I have tried but still not working... any thoughts?

Error : 

send-MailMessage : The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.0 Authentication Required. Learn more at
At line:14 char:1
+ send-MailMessage -SmtpServer $smtp -Port 587 -UseSsl -Credential $cre ...
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
    + CategoryInfo          : InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [Send-MailMessage], SmtpException
    + FullyQualifiedErrorId : SmtpException,Microsoft.PowerShell.Commands.SendMailMessage
 

[Gabriel Clifton]

Sorry, that is all I can think of right now. 

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[David Eng]

Yes, i figured it out 

thanks guys for the help.

Le mar. 3 nov. 2020 à 19:46, Brian Kim <the.br...@gmail.com> a écrit :

Have you enabled less secure app access on admin console and on the account?

https://gsuiteupdates.googleblog.com/2019/12/less-secure-apps-oauth-google-username-password-incorrect.html

It's not recommended. SMTP with OAuth would be a much better solution. 

Another solution is to enable 2FA on the account you are using and use app-specific passwords. But not sure about timeline of Google unsupporting legacy authentication methods (less secure access, i.e username/password combination that does not support modern authentication like SSO or 2FA). 

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[Ross Scroggs]

David,

Please share your solution.

Ross

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Ross Scroggs

ross.s...@gmail.com

[David Eng]

Guys, 

In my case 

I had MFA set up, so i have created a an app password 

If there no MFA you will need to enable less secure app to allow request to their smtp 

you might as well need to configure smtp relay and allow which desired ip's and domain. 

David,

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[Gabriel Clifton]

Or what I did for a smtp account is create an account completely segregated from all your others, remove permissions from everything like no Gmail no drive no youtube no 2fa, and use a password generator to create a password with the max characters allowed so that everything is completely random. If the account is never used for anything you will minimize it's exposure to the outside world and with a super long random password there is little chance of it being compromised. 

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