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If anyone can shed light or point me to a tutorial, I'd appreciate it. We are a tiny company and have experienced occasional delays in receiving email sent between staff members. We are in separate cities but all in the same state; our webhost/email ISP is across the country from us. If it matters, we're on Macs and most of use Entourage. Our email configurations are POP server: and SMTP: (When we used our DSL providers for SMTP we had unreliable service) Our ISP says they're not seeing delays related to their equipment and the problem is elsewhere in the network. A co-worker believes that the delays are with the ISP. Is there a good way to figure this out?

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Take a look at the headers of the email. You'll see lines that start with Received: which indicate the path the e-mail took (read them from bottom to top). They should also have a time stamp which will let you know if there's any delay in the mail server system(s).

For example, you might find lines like:

Received: from ([])
    by (Postfix) with ESMTP id 93F1F5001BE
    for <>; Fri, 19 Mar 2010 02:05:07 +0000 (UTC)

Received: from ([])
    by (Courier) with ESMTP id 9AF35001BDF
    for <>; Fri, 19 Mar 2010 02:04:52 +0000 (UTC)

Notice in my example that the timestamps are only 15 seconds apart, this would be fairly normal (though times up to a couple minutes would also be normal).
Also note, there may be other stuff in between some of the Received lines, they don't have to be grouped together.

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The nature of the internet means that messages are not instant. @Chris S describes how you can interpret the path that describes the delay. – Xavierjazz Mar 20 '10 at 2:47
@Xavierjazz, I'm doing a lot of assuming here, assuming that all of the e-mail servers belong to the ISP, that they have Entourage set to send immediately (there's a option to wait until the next send/receive cycle), that the send/receive cycle is a decently short amount of time. It was also not specified how long the delays are, minutes, hours, days, more(?!). Just looking at all the timestamps on the receive headers will give you an idea of how long it took to get from the first mail server to the last mail server, nothing else. – Chris S Mar 20 '10 at 14:46

@Chris S has it right for troubleshooting, but what sort of delays are you experiencing? SMTP/POP is not a "push" email service like Microsoft Exchange is.

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The delays have been 15 minutes to several hours to some that have simply vanished. I've asked my co-worker to forward the most recent one that was delayed so I can look at the headers. – user31716 Mar 20 '10 at 15:59
@Kiki, when you forward an e-mail it get's an all new set of headers (somethings stay the same, but not the Received lines). – Chris S Mar 23 '10 at 1:16

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