Exchange Server Delivery Issue

[allanc]

One of my clients is having an issue where one of their client states that email is being delivered about 12 hours after it is being sent.
Please see attached snapshot for a specific example where the Email header is being analyzed.

My client is running Exchange Server 2007.
Their domain name is 'sender.com' in this example.
They are sending Email through their ISP ('isp') in this example who is delivering to the recipients ('rece.com') Exchange Server in this example.

What I am trying to determine is whether or not the ISP is holding onto the Email for about 12 hours before it is being delivered to 'rece.com'. Or, whether the ISP delivered the Email efficiently to the recipient's server.

This has been escalated to level-3 support at the ISP who is stating that the Email was delivered quickly.
However, I have my doubts.

 

[YeOldeStonecat]

If you look it up with message tracking on the server? Same exepected time?
Any middle-man SMTP mail bastion services in the mix sniffing SMTP traffic?

Just looking at that converted header....(dunno who did it)...looks like it was not delivered quickly. Which is why I'd want to compare that time versus message tracking.

 

[allanc]

If you look it up with message tracking on the server? Same exepected time?
Any middle-man SMTP mail bastion services in the mix sniffing SMTP traffic?

Just looking at that converted header....(dunno who did it)...looks like it was not delivered quickly. Which is why I'd want to compare that time versus message tracking.

Yes, the same data is displayed (in terms of it getting to the ISP) on the senders Exchange Server.
I do not have direct access to the recipient's Exchange Server but the IT there says there are no irregularities.

 

[ShinyTech]

Maybe try setting up a third party smarthost on the exchange server and see if it goes any faster. You can use most any email as a smtp smarthost just to test the theory and find out. If this is the ISP that is delaying the message the smarthost would resolve the issue and let you know it is the ISP for sure.

 

[allanc]

Maybe try setting up a third party smarthost on the exchange server and see if it goes any faster. You can use most any email as a smtp smarthost just to test the theory and find out. If this is the ISP that is delaying the message the smarthost would resolve the issue and let you know it is the ISP for sure.

To clarify:
The physical server that Exchange Server is installed on would connect directly to the recipient's Email server?
That would involve modifications to the MX and an additional NIC, correct?
If so, why temporarily?

 

[allanc]

If you look it up with message tracking on the server? Same exepected time?
Any middle-man SMTP mail bastion services in the mix sniffing SMTP traffic?

Just looking at that converted header....(dunno who did it)...looks like it was not delivered quickly. Which is why I'd want to compare that time versus message tracking.

The ISP said that the attachment clearly indicates that it is the recipient's issue.
I asked him specifically what the log would look like if it was the ISPs problem and he could not answer that question.

 

[ShinyTech]

I said temperary because you could use an email address that you have through your personal ISP to test. To give an example we had a client that was using a centurylink smarthost and it had black listed the aol servers so that people couldnt send to people with aol emails addresses. We switched them to an Ipower smarthost and the issue was resolved.

The steps are easy to setup a smarthost on the exchange server. All you need is an email address through a different ISP. It makes it so all outgoing email goes through that email address (invisible to the end user). This way if the ISP is having issues delivering to a certain other ISP, more times then not another ISP can send to them fine.

http://support.prolateral.com/index.php?/Knowledgebase/Article/View/117

this is for exchange 2007 / 2010 to set up a smarthost. No need to change MX records or anything, its a simple setup in exchnage on the server. If you need a different or better explain of setting up a smarthost just reply and I will look for it.

 

[allanc]

I said temperary because you could use an email address that you have through your personal ISP to test. To give an example we had a client that was using a centurylink smarthost and it had black listed the aol servers so that people couldnt send to people with aol emails addresses. We switched them to an Ipower smarthost and the issue was resolved.

The steps are easy to setup a smarthost on the exchange server. All you need is an email address through a different ISP. It makes it so all outgoing email goes through that email address (invisible to the end user). This way if the ISP is having issues delivering to a certain other ISP, more times then not another ISP can send to them fine.

http://support.prolateral.com/index.php?/Knowledgebase/Article/View/117

this is for exchange 2007 / 2010 to set up a smarthost. No need to change MX records or anything, its a simple setup in exchnage on the server. If you need a different or better explain of setting up a smarthost just reply and I will look for it.

I have not read your link but I get the concept .
Verrry interesting.
One question though:
Does it have to be an Email address that belongs to an ISP?
For example, my ISP is Rogers. So does it have to be something@rogers.com or can/should it be an Email address that belongs to my company such as me@mycompany.com (mycompany is not an ISP)?

 

[allanc]

Maybe try setting up a third party smarthost on the exchange server and see if it goes any faster. You can use most any email as a smtp smarthost just to test the theory and find out. If this is the ISP that is delaying the message the smarthost would resolve the issue and let you know it is the ISP for sure.

Could it not be either that the ISP is holding onto the Email for 11 hours or that the recipient's Exchange Server is 'not letting in' for 11 hours?
Can you determine that from the initial post with the attachment?

 

[OfficeTechs]

as already mentioned i think setting a smart host will show you quickly where the problem lies. Its literally 10 minute job to add a smart host and its easy to roll back.

In a previous position our exchange server would not deliver to any hotmail address. I literally created a new hotmail account, used those details as the smart host and routed any hotmail,msn,live domains through that smart host. Problem solved.

 

[allanc]

as already mentioned i think setting a smart host will show you quickly where the problem lies. Its literally 10 minute job to add a smart host and its easy to roll back.

In a previous position our exchange server would not deliver to any hotmail address. I literally created a new hotmail account, used those details as the smart host and routed any hotmail,msn,live domains through that smart host. Problem solved.

I think that I may be able to test it today.

 

[ShinyTech]

I would use an email address that is associated with a large group. I dont know what you have down there but in florida we have centurylink, roadrunner, att, etc. If its a bigger name the chances the smarthost will be blacklisted will be less and the chances the email will be considered as a safe sender is greater.