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Alright so as the title says, I get this error when trying to send email via PowerShell:

Send-MailMessage : The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required.

I have looked at numerous questions related to the same issue. But I can't seem to make my script work:

    #Email alerts when a user gets locked out
##############################################################################
$pass = Get-Content .\securepass.txt | ConvertTo-SecureString -AsPlainText -Force
$name = "sender@gmail.com"
$cred = New-Object System.Management.Automation.PSCredential($name,$pass)
##############################################################################
$From = "sender@gmail.com"
$To = "recipient@domain.org"
$Subject = "User Locked Out"
$Body = "A user has been locked out of his/her account."
$SMTPServer = "smtp.gmail.com"
$SMTPPort = "587"

Send-MailMessage -From $From -to $To -Subject $Subject `
-Body $Body -SmtpServer $SMTPServer -port $SMTPPort `
-Credential $cred -UseSsl
##############################################################################

I have logged into the Gmail account from the machine that will be running the script. I have also enabled Access for less secure apps from the Google account manager. I do get this to work just fine if I prompt for the credentials using the -Credential (Get-Credential) instead of calling for the $cred variable.

Is there something I am missing?

Thanks, Dan

Daniel Dodds
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  • If you need to be authenticated with the SMTP server, do you need to send along SMTP user credentials? – Evan Frisch Jun 11 '15 at 19:11
  • @EvanFrisch He's doing that (`-Credential $cred`). – Ansgar Wiechers Jun 11 '15 at 19:27
  • @AnsgarWiechers I am definitely going blind, my bad. – Evan Frisch Jun 11 '15 at 19:30
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    If authentication works when supplying the password via `Get-Credential`, but not when reading the password from a file, the problem is most likely with the password file. Double-check the file's content (trailing whitespace, encoding, etc.). – Ansgar Wiechers Jun 11 '15 at 19:35
  • Thanks Ansgar, You got me to look at the right area. I figured it out. The password file contained the password already encrypted. I replaced it with the plaintext unencrypted password so it gets encrypted when setting my $pass variable. – Daniel Dodds Jun 11 '15 at 21:34
  • Possible duplicate of [Gmail Error :The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required](https://stackoverflow.com/questions/20906077/gmail-error-the-smtp-server-requires-a-secure-connection-or-the-client-was-not) – tripleee Jul 28 '18 at 09:33

3 Answers3

2

If the file contains the encrypted password it's better to read it like this (without the parameters -AsPlainText and -Force):

$pass = Get-Content .\securepass.txt | ConvertTo-SecureString

Demonstration:

PS C:\> $sec = 'foobar' | ConvertTo-SecureString -AsPlainText -Force
PS C:\> $sec
System.Security.SecureString
PS C:\> $txt = $sec | ConvertFrom-SecureString
PS C:\> $txt
01000000d08c9ddf0115d1118c7a00c04fc297eb01000000615ce070639b9647a5e05d42b41d373
0000000000200000000001066000000010000200000001614c19281e7c0b076cceb38e284b0f18b
c0d813ea40ed055dde96fd9ccb6977000000000e8000000002000020000000a10c7019eb224c3c6
387ba03bcd94993a50e0c468248284bbce4d235b11f1b94100000002421a5d7102de13c46ccc1db
c4921287400000000412332ecb500828f4403f3e225089c629369744bad62609b528ed0a7318abf
512c9b6a8884c43b3adc8a13d5d21a9ed27e56702bcc7db094da9d9d4c02dfa74
PS C:\> $sec2 = $txt | ConvertTo-SecureString
PS C:\> $sec2
System.Security.SecureString
PS C:\> $cred = New-Object Management.Automation.PSCredential 'foo', $sec2
PS C:\> $cred.GetNetworkCredential().Password
foobar

Beware though that encryption of secure strings is tied to the user and host encrypting them, meaning you can't decrypt a secure string on another host or as another user.

Ansgar Wiechers
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1

I found my answer after looking at my passwords file content, thanks to Angsgar. The securepass.txt had the encrypted contents inside, not plaintext. What I did was replace it with the actual password that will then be encrypted when setting my $pass variable. All is good now!

Daniel Dodds
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0

Ansgar's answer is a good generic answer, but for Google, they have multiple SMTP servers that you can use. smtp.google.com requires authentication, but not all of them do.

From Google's doc, if your site is a G Suite site and you will always be sending from a specific IP address, you can specify the address in G Suite configuration and then use the G Suite SMTP relay at smtp-relay.gmail.com. This is only available to G Suite users, and requires either authentication or a static IP. At our site, we have an internal SMTP server that we use for these sorts of emails which relays to Google's G Suite SMTP relay server.

If you are sending email only to Google or G Suite addresses, you can specify aspmx.l.google.com as your SMTP address. This is known as the restricted Gmail SMTP server.

Bacon Bits
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