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I had this working at one time, but it stopped a while ago. The password for the account is valid, and noting in my script has changed.

Send-MailMessage -From [email protected] -Subject "Server ESI-NIKE Has Rebooted" -To [email protected] -Attachments C:\1\Reboot\Previous5.txt -Body "ESI-NIKE has rebooted. Please check the Event Log if this reboot is unexpected" -SmtpServer smtp.gmail.com -Port 587 -usessl -Credential (New-Object -TypeName System.Management.Automation.PSCredential -ArgumentList "[email protected]",(Get-Content -Path [email protected] | ConvertTo-SecureString))
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    What error(s) do you get? Commented Jan 22, 2020 at 17:57
  • Send-MailMessage : The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.0 Authentication Required Commented Jan 22, 2020 at 19:07
  • Does this answer your question? Send-MailMessage on PowerShell does not work Look at my answer on that thread. It is specifically regarding how to make it work for gmail. Commented Jan 22, 2020 at 19:24
  • Unfortunately not. I already enabled less secure apps. Commented Jan 22, 2020 at 19:36
  • @GlenKrinsky Just a thought. In the From field, it should be your gmail address and not anything else. Some mail server support setting anything there. Not gmail. Commented Jan 23, 2020 at 1:45

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Stop working for me too. for severail years I have been using PowerShell script to send emails via Gmail, rather Google G Suite, it just stopped working recently. Error is, SMTP requires a secure connection, but I am already using port 587, changed to port 465, still not working

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