EHLO Exchange community,
It seems that PelNet has been well received and I’ve been receiving requests to add much wanted functionality to PelNet. So this article is a quick update on some of the cool new features that administrators can use to help troubleshoot and validate mail flow.
The new features added in this release:
The above features gave birth to two new parameters validateTLS and CertThumbPrintOverride.
Let’s recap the parameters with the new ones introduced.
This can also be used to test TLS to a specific host before assigning the certificate to the SMTP service in Exchange, i.e. pre-validations prior to production change. The certificate needs to be in the local machine certificate store.
It’s important to note that the code logic uses best effort to determine the SMTP certificate assigned. Using the CertThumbPrintOverride parameter allows you to override this easily.
Show the full help with examples
Get-help .\pelnet.ps1 -full
To test mail flow and validate TLS to a smarthost against all the transport servers on port 25 to multiple recipients. (Will not submit the message for delivery)
.\PelNet.ps1 -From firstname.lastname@example.org -Rcpt email@example.com,firstname.lastname@example.org,email@example.com -smarthost webmail.contoso.com -validateTLS
To test mail flow and validate TLS to a smarthost against all the transport servers on port 25 to multiple recipients. (Submits the message for delivery and override the certificate to use)
.\PelNet.ps1 -From firstname.lastname@example.org -Rcpt email@example.com,firstname.lastname@example.org,email@example.com -smarthost webmail.contoso.com –validateTLS –mailsubmissiontest –certThumbprintOverride 1A13124HJG1234K12JHG312J123D
To test mail flow and validate TLS to EOP from your hybrid servers on port 25 to multiple recipients (also submit the mail to EOP).
.\PelNet.ps1 -From firstname.lastname@example.org -Rcpt email@example.com,firstname.lastname@example.org,email@example.com -smarthost adatum-mail-onmicrosoft-com.mail.protection.outlook.com –validateTLS –sourceTransportServers E15HYBRID01,E15HYBRID02 -mailsubmissiontest
The TLS validation logic will authenticate against the remote server with the certificate assigned to SMTP or the certificate that matches the thumbprint used in the override parameter. If the remote host is configured with Opportunistic TLS and the handshake fails the session will fall back to unencrypted SMTP.
The console output won’t show the verb’s being sent as the code is invoking on multiple servers concurrently, but the final output table and output file will be exactly as previously described in PelNet 1.0.
From the below output:
STARTTLS verb being sent with server responding with 2.0.0 SMTP Server Ready and subsequent SSL Stream is established by authenticating against target host using certificate that matches thumbprint provided (or dynamically found using best effort).
Verbs being sent over SSL stream and successful recipient lookup.
The following is an example of a certificate validation issue on one server:
Some of the most common certificate validation errors are:
The above validation error was quickly fixed by installing the root certificate from the Contoso environment on the EX14- 02 server.
Until next time,
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