The Story

Well in my previous post I discussed the issue I faced resolving an email problem with one of our development applications in which it was unable to send emails after a recent Exchange upgrade/migration. So initially we were going to simply rebuild our own workflow in-house using ASP .NET Core. Until we noticed that even our own workflows were failing… in this case the answer from the old post which was super vague “reconfigure the receive connector”. Then I somehow stumbled upon my answer through one of my hundreds of google searches… I founds this gem!

OK before I link the gem which will be the source to my answer. I also wanted to point something out real quick here in hopes maybe someone can comment below the answer to this one:

When using Exchange 2016 as an email SMTP relay, and you use a no-reply from address, with an external email address for the destination, how do you query to find out if its gone through, or stuck in que? All I could see in the ECP it always required me to select a mailbox… there’s no mailbox associated with these relayed email messages, so how does one check this?

OK, now for the gem. This guy “Paul Cunningham” He’s… uhhhhhh… He’s uhhhhh… he’s uhhhh a good guy. So I always knew you could use telnet to check certain ports and services… but this was so concise… it nailed the problem…

From my K2 Server or my in house workflow server:

1) Ensure Telnet Client feature is enabled

2) Open cmd prompt or PowerShell:

telnet exchangeServer 25
helo
mail from: user@corp.ca
rcpt to: ExternalUser@gmail.ca

220 EXSERVER.exchange2016demo.com Microsoft ESMTP MAIL Service ready at Thu, 22
Jun 2018 12:04:45 +1000
helo
250 EXSERVER.exchange2016demo.com Hello [192.168.0.30]
mail from: adam.wally@exchange2016demo.com
250 2.1.0 Sender OK
rcpt to: exchangeserverpro@gmail.com
550 5.7.54 SMTP; Unable to relay recipient in non-accepted domain

huh, just like the source blog, now why would I be getting that error… I allowed Anonymous users via the check box under the receive connectors security tab… yet Paul does a lil extra step that doesn’t seem to be mentioned elsewhere, and that check box I mentioned is his first line, but then look at the interesting second line….

[PS] C:\>Set-ReceiveConnector "EXSERVER\Anon Relay EXSERVER" -PermissionGroups AnonymousUsers

[PS] C:\>Get-ReceiveConnector "EXSERVER\Anon Relay EXSERVER" | Add-ADPermission -User 'NT AUTHORITY\Anonymous Logon' -ExtendedRights MS-Exch-SMTP-Accept-Any-Recipient

Since I was using anonymous settings on the Application server side (K2 in this case) I gave the second PowerShell cmdlet a run from my new exchange server.

Amazingly enough just like the source blog after running the second line (edited to fit my environment obviously) then the rcpt to succeeded!

20 EXSERVER.exchange2016demo.com Microsoft ESMTP MAIL Service ready at Thu, 22
Jun 2018 12:59:39 +1000
helo
250 EXSERVER.exchange2016demo.com Hello [192.168.0.30]
mail from: test@test.com
250 2.1.0 Sender OK
rcpt to: exchangeserverpro@gmail.com
250 2.1.5 Recipient OK

Part 2 – The Solution

If K2 is configured to use EWS, check that stuff out elsewhere, if you landed here from my previous post looking for the answer to the “There is no connection string for the destination email address ‘Email Address'” and wanted to know how that person altered his receive connector:

[PS] C:\>Get-ReceiveConnector "EXSERVER\Anon Relay EXSERVER" | Add-ADPermission -User 'NT AUTHORITY\Anonymous Logon' -ExtendedRights MS-Exch-SMTP-Accept-Any-Recipient