I measure round trip with a bit of powershell, very straight forward.

We're an MSP so on an entirely separate mail domain, but you could replicate 
this from an internal account with a gmail account or similar.

I automatically send every half hour from our mailserver using the powershell 
'Send-Mailmessage' cmdlet, the subject contains a time stamp. The mailbox I 
send to at our client is set to auto reply and delete.

This powershell then runs a DO UNTIL loop using the script I lifted wholesale 
from here:

https://social.technet.microsoft.com/Forums/exchange/en-US/d5707d5b-e1ff-4811-a3d0-552bb0b00444/verify-receiving-emails-from-powershell
  I modified it slightly to only match the subject line of the sent mail.

The DO loop has an incremental number counter ($INT++) and a Start-Sleep 1, I 
then use 'IF Incremental number -GT than 60' as a rough measure of 1 minute 
which in turn fires an alert email to our helpdesk team if exceeded.

Honestly, its never caught anything prior to our other monitoring tools (Port 
25 check, Queue Lengths and Service Status) but it could easily run more 
regularly, or be used to trap an average round trip time for quality 
measurement. Or keep it in the toolbox and when someone asks if there is a 
delay you can use it as a quick check.

Patrick




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-----Original Message-----
From: [email protected] [mailto:[email protected]] On 
Behalf Of Dave Lum
Sent: 01 December 2014 19:52
To: [email protected]
Subject: Re: [Exchange] RE: Monitor Ex2010:

Looks compelling. What do others here use to monitor round trip time? I hate 
having my users tell me email doesn't work when all I can really do it look at 
Exchange queues and only hop to the SPAM filter when someone tells me they've 
been expecting something but haven't seen it...

Dave

> Ten bucks a month. Have not used them in a long time but they worked
> well back in the old days.
>
> https://www.site24x7.com/mail-server-monitoring.html
>
>
> From: [email protected]
> [mailto:[email protected]] On Behalf Of Orlebeck,
> Geoffrey
> Sent: Monday, December 1, 2014 2:15 PM
> To: '[email protected]'
> Subject: [Exchange] Monitor Ex2010:
>
> Just had an issue over the weekend where two separate environments
> running on top of our DMZ cluster stopped receiving external email
> after a networking change on the ESX hosts. Both environments are
> setup with one edge server and one HUB/CAS server (Ex2010 SP3 UR4
> across all VMs). Emails were timing out and senders were receiving 4.4.7 NDRs 
> from their servers.
> Restarting the Microsoft Exchange Transport service allowed mail to
> begin flowing again. We understand how/why the issue occurred,
> however, none of our regular SCOM alerts flagged any issues (no queue
> growth, ports are open, services were running, etc.). After the fact,
> we noticed our 3rd party spam filter was receiving "Message refused"
> errors. We are working with the vendor to see if we can setup a
> baseline alert if/when this issue comes up, but from a strictly
> Exchange perspective, we are lacking any alerting on an event such as this.
>
> I'm curious if anyone else has setup either a SCOM monitor or perhaps
> PowerShell script for testing external connectivity for something like
> this? I use the Exchange connectivity test a lot in troubleshooting,
> but that has to be performed manually. We'd like to setup an automated
> monitor confirming mail delivery and returning values based on
> outcome. The part I'm trying to figure out is the external portion,
> and how best to test against it, since all internal traffic was fine
> and nothing on the server itself showed any obvious problems. I have
> skimmed through a few of the logs on the Edge server but do not see
> any real differences from pre/post ESX host change that caused email to stop 
> flowing.
>
> Any insight or even general direction is greatly appreciated. Thank you!
>
> -Geoff
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