View Full Version : Entourage blocking out-of-country emails... Help please! :)

07-29-2008, 01:02 PM
Hey there, I need some help with an annoying problem if anyone can spare a moment. We have an Exchange server with PCs and Macs on the network. I'm trying to figure out why the Mac systems running Entourage 2004 can't receive emails from other countries (namely, Brazil) yet all the PCs running Outlook 2003 and 2007 can receive out-of-country emails.

I have searched all of the Entourage 2004 settings and can't figure out where these are going, or how to stop this out-of-country blocking. They aren't winding up in the trash, nor are they winding up in junk. They just *disappear*, yet the same senders show up just fine in my Outlook.

Can anyone help with this? Thanks a ton!

07-29-2008, 02:06 PM
If the e-mails are disappearing, (rather than ending up in the Junk folder), this sounds like a server issue. Perhaps talk to your Exchange server system administrator.


07-29-2008, 02:11 PM
I do the Exchange administration, for the most part. There is nothing on the Exchange server that is set to block foreign IPs, and if someone from Brazil emails an Outlook user and an Entourage user, only the Outlook user receives it. The address and domain are on our whitelist for spam, btw. But Entourage users could never get these Brazilian emails ever after we changed spam filters... only Outlook users... it's plaguing me...

07-29-2008, 02:19 PM
In fact, if it makes any difference, a Mac user said this morning that their computer at home could see an email from Brazil in their inbox, but as soon as they got to work, the said email was gone, nowhere to be found in their trash can, or junk filter. We've been battling this whole Brazilian email thing for a year now and so far, have only been able to tell Mac users to just use webmail for receiving out-of-country email, which totally blows... The only thing I can deduce the problem to is specifically with Entourage...

07-29-2008, 03:02 PM
Although I still doubt that the problem is client-side, especially since you say it only started after you changed spam filters, try this test:

In Entourage > Account Settings... > select the Exchange account > click Edit > Account Settings tab > Exchange Server > instead of entering your Exchange server's IP address or domain name, enter the webmail address for this Exchange account. Now, ask someone from Brazil to send an e-mail to this test account. Does it show up in Entourage normally?


07-29-2008, 03:07 PM
Sorry, my comment about the spam filter must be confusing. I had said that it's blocking Brazilian mail even after changing spam filters. I'm saying that with two totally different spam filtration systems (both with the Brazilian addresses whitelisted), it's still not coming through to the users on Entourage. I know for certain it's not the spam filter, especially since it's not showing up in the spam quarantine either. As for the Exchange server, the Intelligent Message Filter is turned off and spam is only handled by a third party, so I know Exchange isn't doing it.

I will try what you mentioned and see if that does the trick, as far as entering the external webmail address instead of the internal server address.

You also asked if it shows up in Entourage normally... I'm not sure what you mean by that...

Thanks for your help. :)

07-29-2008, 03:12 PM
Was the Mac user at home using Entourage or Mail? Did the message remain after returning from work? Have you tried using Mail on a Mac at work?

07-29-2008, 03:18 PM
You also asked if it shows up in Entourage normally... I'm not sure what you mean by that...

I mean that after you've entered the webmail address into Entourage in place of the Exchange server address, do Brazilian e-mails then show up in Entourage for that Mac user?


07-29-2008, 06:50 PM
Do you have any logs for your exchange server? I am not an exchange admin, but I do my fair share of mail admin work. All my mailservers have detailed logs, or I can turn on detailed logging. If they saw it at home, what were they using? OWA? Entourage? Outlook?
I am pretty sure you can turn on some logging on the Exchange server, maybe even to the point of showing each step of the connection per email. See if you can do that, and see what you see from them seeing the email at home, then them opening the email at work. Can you look at their emails via the filesystem? (again not an exchange admin, but it seems like it should be possible) Could this be something being corrupted by Entourage because of something in their email?
I know if you properly craft an email, you could make Courier-IMAP to puke, and corrupt the email making it not show. Though that has been fixed for awhile if I remember correctly.