Using encrypted password to send mail is failing - powershell

Question

I'm trying to use a stored encrypted password in a script that sends an email but I keed getting the error:
send-mailmessage : The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM
[DM6PR66666019.namprd456.prod.outlook.com]
I used the following code to create the text file:
$passwordtostore = 'NotTheRealPassword$9gv8z6VHnPfDd8zc'
$secureStringPWD = $passwordtostore | ConvertTo-SecureString -AsPlainText -Force
$secureStringText = $secureStringPWD | ConvertFrom-SecureString
Set-Content "c:\temp\scriptsencrypted_password1.txt" $secureStringText
I use the following to import the password:
$passwordFile = "c:\temp\scriptsencrypted_password1.txt"
$password = Get-Content $passwordFile | ConvertTo-SecureString
Here's the sendmail function I am using:
function SendMail($ToEmails,$FromEmail,$Subj,$Body,$UserName,$Password){
$cred = New-Object System.Management.Automation.PSCredential $UserName,$Password
$MailParams=#{"from"=$FromEmail; "to"=$ToEmails;"body"=$Body;"subject"=$Subj;"smtpserver"="smtp.office365.com"}
send-mailmessage #MailParams -Credential $cred -UseSsl $true -port 587
}
Here's the code which calls the function:
$alertEmail = "me.stillme#mydomain.com"
$username="psemail#mydomain.com"
$passwordFile = "c:\temp\scriptsencrypted_password1.txt"
$password = Get-Content $passwordFile | ConvertTo-SecureString
$credential = New-Object System.Management.Automation.PsCredential($username, $password)
Import-Module -Name "..\SendMail.psm1"
... Doing some stuff
SendMail $alertEmail $username "This is the subject" "this is the body" $credential.UserName $credential.Password

Answer 1

Personally, I fail to see why you would make a function in a module you need to import for the Send-MailMessage cmdlet..
This makes things a lot harder to use.
Also, it kind of looks like you are switching the emailaddresses To and From inside the function.
Anyway, things go wrong when you are creating the credentials, split it into username and (secure) password to send as parameters to the function and recombine them into a credentials object in there.
Why not skip that module function and simply do:
$password = Get-Content 'c:\temp\scriptsencrypted_password1.txt' -Raw | ConvertTo-SecureString -AsPlainText -Force
$credential = New-Object System.Management.Automation.PsCredential('YourLoginName', $password)
$MailParams=#{
From = 'me.stillme#mydomain.com'
To = 'psemail#mydomain.com'
Body = "this is the body"
Subject = "This is the subject"
SmtpServer = 'smtp.office365.com'
Port = 587
UseSsl = $true
Credential = $credential
}
Send-MailMessage #MailParams
This will make your script far more readable/maintainable

Answer 2

I found two issues with my code above:
An unescaped $ in the password.
Once I added " -NoNewline" to the set-content, it began to work.
So, to create the encrypted file:
$passwordtostore = "7K9CBgvc4rttvfctrsef6PVHqnP6fDdwhatevervtfdscttzSc"
$secureStringPWD = $passwordtostore | ConvertTo-SecureString -AsPlainText -Force
$secureStringText = $secureStringPWD | ConvertFrom-SecureString
Set-Content "D:\Powershell Scripts\encrypted.hash" $secureStringText -NoNewline
Then to retrieve the password and use it in a credential:
$password = Get-Content $passwordFile -Raw | ConvertTo-SecureString
$credential = New-Object System.Management.Automation.PsCredential($username, $password)
It wasn't the source of the issue, but I did implement #Theo's suggestion re: using send-mailmessage.