Skip to main content

Doing a SMTP telnet test with a Powershell script

One of the array of diagnostic tests you may find yourself doing when you’re trying to fix a problem sending and receiving messages to a domain is to do a telnet on Port 25 to a mail server you maybe having a problem with and then trying to run though manually issuing the SMTP commands to send a message to this server so you can see what the responses are. A description of this process can be found in this KB there is also a great tool called SMTPDiag which will run this type of test and more. If you want to do the same thing from a Powershell script well your in luck because the .Net framework makes this process pretty easy. Lee Holmes posted this great script for replacing the missing Telnet on Vista. What I’ve done is rework this script so instead of being an interactive telnet script it’s a script that connects to port 25 on a mail server and then runs through issuing Mail FROM and RCPT TO commands and shows the responses back to the command-line. The script itself takes three command line parameters which are the DNS or IP of the server you want to test and a domainname for the domain you want to test to see if the server will receive email for and a domainname to test a send from( The script doesn’t actually send a message as it quits after the RCPT TO command). To run the script you need to use something like

C:\tnetsmtp.ps1 server.com.au recipeintdomain.com sendingdomain.com

(9/10/2006 Updated input parameters thanks to Hector)

I’ve put a downloadable copy of the code here the script itself looks like.

#param([String] $remoteHost =$(throw "Please specify the Target Server"),[String] $domain = $(throw "Please specify the #recipient Domain"),[String] $sendingdomain = $(throw "Please specify the Sending Domain"))

param([String] $remoteHost,[String] $domain, [String] $sendingdomain)


if ($remotehost -eq "" -or $domain -eq "" -or $sendingdomain -eq "") {"Please specify the Target Server, recipient domain and sending domain"
return; }


function readResponse {

while($stream.DataAvailable)
{
$read = $stream.Read($buffer, 0, 1024)
write-host -n -foregroundcolor cyan ($encoding.GetString($buffer, 0, $read))
""
}
}

$port = 25
$socket = new-object System.Net.Sockets.TcpClient($remoteHost, $port)
if($socket -eq $null) { return; }

$stream = $socket.GetStream()
$writer = new-object System.IO.StreamWriter($stream)
$buffer = new-object System.Byte[] 1024
$encoding = new-object System.Text.AsciiEncoding
readResponse($stream)
$command = "HELO "+ $domain
write-host -foregroundcolor DarkGreen $command
""
$writer.WriteLine($command)
$writer.Flush()
start-sleep -m 500
readResponse($stream)
$command = "MAIL FROM: "
write-host -foregroundcolor DarkGreen $command
""
$writer.WriteLine($command)
$writer.Flush()
start-sleep -m 500
readResponse($stream)
$command = "RCPT TO: "
write-host -foregroundcolor DarkGreen $command
""
$writer.WriteLine($command)
$writer.Flush()
start-sleep -m 500
readResponse($stream)
$command = "QUIT"
write-host -foregroundcolor DarkGreen $command
""
$writer.WriteLine($command)
$writer.Flush()
start-sleep -m 500
readResponse($stream)
## Close the streams
$writer.Close()
$stream.Close()

Popular posts from this blog

The MailboxConcurrency limit and using Batching in the Microsoft Graph API

If your getting an error such as Application is over its MailboxConcurrency limit while using the Microsoft Graph API this post may help you understand why. Background   The Mailbox  concurrency limit when your using the Graph API is 4 as per https://docs.microsoft.com/en-us/graph/throttling#outlook-service-limits . This is evaluated for each app ID and mailbox combination so this means you can have different apps running under the same credentials and the poor behavior of one won't cause the other to be throttled. If you compared that to EWS you could have up to 27 concurrent connections but they are shared across all apps on a first come first served basis. Batching Batching in the Graph API is a way of combining multiple requests into a single HTTP request. Batching in the Exchange Mail API's EWS and MAPI has been around for a long time and its common, for email Apps to process large numbers of smaller items for a variety of reasons.  Batching in the Gr...

Sending a Message in Exchange Online via REST from an Arduino MKR1000

This is part 2 of my MKR1000 article, in this previous post  I looked at sending a Message via EWS using Basic Authentication.  In this Post I'll look at using the new Outlook REST API  which requires using OAuth authentication to get an Access Token. The prerequisites for this sketch are the same as in the other post with the addition of the ArduinoJson library  https://github.com/bblanchon/ArduinoJson  which is used to parse the Authentication Results to extract the Access Token. Also the SSL certificates for the login.windows.net  and outlook.office365.com need to be uploaded to the devices using the wifi101 Firmware updater. To use Token Authentication you need to register an Application in Azure https://msdn.microsoft.com/en-us/office/office365/howto/add-common-consent-manually  with the Mail.Send permission. The application should be a Native Client app that use the Out of Band Callback urn:ietf:wg:oauth:2.0:oob. You ...

How to test SMTP using Opportunistic TLS with Powershell and grab the public certificate a SMTP server is using

Most email services these day employ Opportunistic TLS when trying to send Messages which means that wherever possible the Messages will be encrypted rather then the plain text legacy of SMTP.  This method was defined in RFC 3207 "SMTP Service Extension for Secure SMTP over Transport Layer Security" and  there's a quite a good explanation of Opportunistic TLS on Wikipedia  https://en.wikipedia.org/wiki/Opportunistic_TLS .  This is used for both Server to Server (eg MTA to MTA) and Client to server (Eg a Message client like Outlook which acts as a MSA) the later being generally Authenticated. Basically it allows you to have a normal plain text SMTP conversation that is then upgraded to TLS using the STARTTLS verb. Not all servers will support this verb so if its not supported then a message is just sent as Plain text. TLS relies on PKI certificates and the administrative issue s that come around certificate management like expired certificates which is why ...
All sample scripts and source code is provided by for illustrative purposes only. All examples are untested in different environments and therefore, I cannot guarantee or imply reliability, serviceability, or function of these programs.

All code contained herein is provided to you "AS IS" without any warranties of any kind. The implied warranties of non-infringement, merchantability and fitness for a particular purpose are expressly disclaimed.