Monitor mail flow between two sites no in same domain or forest

I have a question which I could not find anywhere on the net.  It is not a "how to" question that you hear everyday.  What I am looking for is a procedure to monitor mail flow.  This monitor is not internal between servers within a domain or forest, but between two separate domains via the internet.  To understand better, here is my situation:
 
We are company A, we have a parent company, B.  There are times when company B's email system does not send us mail in a timely fashion (via the internet, no special WAN setup).  There are times when we do not get mail for over three hours, but this is not the issue - we need to know when this is happing so we can notify them.  I am the Exchange Admin at company A where I was asked to monitor the mail flow between the two companies.  It is not enough to ping the server to check if it is online, they want me to have system or third party program that automatically sends an email from a test mail box on company A to a test mailbox on company B.  Then a confirmation or reply from B to A.  This test will run every hour, if mail is not sent within and hour or two, automatic notifications are send via email, pager, snmp, etc.

Have you ever heard of anything like this?  Right now to satisfy the VP of IT, I have a small program that sends a test email to a non-existent account to company B every hour.  The system administrator returns an undeliverable message in return so I know that they are at least sending mail back from their SMTP servers on time, but this does not verify that mail originating from their system is sending out in a timely fashion.  Our 24 Ops center is making sure they receive a message every hour.  It would be best if we had an automated system running in place.
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xxgeniusAsked:
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David WilhoitSenior Consultant, ExchangeCommented:
Well, I have suggestion, but I'm not sure it's what you're looking. In every email header from the internet, there's a path description from point A to point B for each hop. there's a time stamp as well. I bet if you take the header of a message that has been delayed, and look at the timestamps, you'll see the hop where the email was delayed. I did this a couple of weeks ago, and pinned down the culprit pretty easy.

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xxgeniusAuthor Commented:
True, however I am not worried about troubleshooting time delay since the issue is caused by company B.  What we need is an alert system that lets us know that the delay is happining.  Sometimes this delay goes unrecognized and no one notices that mail from our parent company is delayed coming in.
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David WilhoitSenior Consultant, ExchangeCommented:
How can you monitor what you don't know about? there's no traffic to monitor, if the mail isn't getting there. the only place to see the delay, is from the source of the traffic. Destination doesn't know about it until it gets there.

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VahikCommented:
This a very unusuall request.let's assume u could monitor their queue
and determin there is a delay.U still need their exchange to send u an alert.If it is not able then how would u know there is a delay?Even if i were able to give u some kind of solution mail maybe stuck in ur queue and delay maybe caused by ur exchange.Have u thought about that?I have a simple but crude solution which will cost u no more that
buying a simple program and monitoring ur computer every hour.
Would this be acceptable?Call back if intrested.
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VahikCommented:
Oh bytheway genius this question is worth atleast 10000 points.
What do u think kidego?If u say yes i will split it with u.
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xxgeniusAuthor Commented:
I am not trying to troubleshoot the issue, what I need is to know that the issue exists in the first place. What I am looking for IS that program that lets me know mail flow has stopped.  Here's an example: there is a program called TOPPER (http://www.re-soft.com/product/topper1.htm), but this program does not work that well.  I  need a program that this describes.
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xxgeniusAuthor Commented:
Hey, if you can find this solution, I'll dish out all my available points on this one question!!!!
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David WilhoitSenior Consultant, ExchangeCommented:
Well, appreciate the offer, but my current objection stands: you can only track this from the SOURCE. Does this delay happen on your side, if sending to them? If not, what is the configuration differences between the 2 servers? My feeling is that you should be troubleshooting the issue and resolving, not trying to figure out how to monitor something that's broken.

Does the source server run GFI mailEssentials?

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VahikCommented:
Genuis i just wanted to see if u are still here.
U need two outlook clients(or any client)that are on all the times.
U need a program( On the other side that u want to moinitor)send out
an email on regular interval(every hour should do the job).Now u go
on outlook client on ur side and using rule wizard(for rule wizard to work u must be logged on to the client)create a rule that everytime an
email arrives from certain user from other side to run an application.
One of the application that u can run is a .bat file containing a
NET SEND MESSAGE (or maybe an application that will send u a pager message)that an email has arrived.U should get this messages every hour on the hour and if u dont then u will know there is a problem either on ur side or the other side.Is this good enough for u?
I have seen a program on outlook section that will archive ur emails and send on specific time that u like.I will try to find it and post it for u.
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VahikCommented:
Genius i forgot to mention that u can keep the points.This an intresting question so i will give u some of my points for just posting it.How about that.
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VahikCommented:
One more thing.Net sent messages are logged in event viewer and u
can catalog it
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xxgeniusAuthor Commented:
Good point Vahik.  however, currently I am using a solution just like this.  I found a small program called MailRules (www.mailrules.com).  This can send out mail on a time interval.  I am sending out mail every hour to the remote mailbox as explained above.  What I had my parent company do was make a contact on their GAL so I can have the remote mailbox use the Out of Office assistant rules, this way no Outllok client needs to be running on their end.  The problem with this is that we do not wna to have sucessful mail monitored, rather have a program is automatically trigged when it doesn't arrive.  This way our 24/7 Ops group can have one less thing to worry about.  One thing I like to mention is that this is right now one of the highest priorites in my company.  Our parent company has had problems with mail flow to our company, but that is not our issue, we are only concerned about noticing when it the mail flow from them is back logged longer then 2 hours.  

Perhaps this is a program idea some might be interested in developing for profit :)
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VahikCommented:
Well genuis i gave u my two cents on this problem.sorry that was not what u were looking for.good luck.
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BrentDevOpsCommented:
Actually is you know how to run linux there is some really good tools to do this.

The program you are looking for is a NOC type app.... which most are *nix based.

One is called nagios(its free).  Though you may want to wait for 2.0 to come out.  one called Cacti can generate graphs from the logs.  NICE SETUP!  All free, but you have to know linux/unix and have some brains to set it up.



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xxgeniusAuthor Commented:
I used Topper from Bright Mountain Software -- this works great
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