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Entourage 2008 and Exchange 2007 pains

September 4, 2008

I set up an Exchange 2007 server this week and had several Mac clients that needed to connect. We got Entourage 2008 and had a few problems getting it to talk.  Several “Login Failed” messages prompting for your username and password again, but clearly that wasn’t the problem since we could login to web access with the same credentials.  The correct settings in Entourage are:

Under Authentication, the Account ID is just your username (no DOMAIN\ or and the domain is the NETBIOS domain name (not FQDN).

Under Server Information, the Exchange server should be in the format:

Of course, if using SSL then make sure it’s https and check This DAV requires a secure connection.

But wait! The above settings were not working for me! Finally I figured out that if I could browse to then it should work, but that URL was not working. I was getting a Can’t Display This Page or 500 error. I tried removing and recreating the Exchange virtual directory using remove-owavirtualdirectory and new-owavirtualdirectory on the Exchange server, but still wouldn’t work.  I must have screwed something up in IIS or something along the way, but couldn’t get it working. So finally, I created a new website in IIS, created a new Exchange virtual directory and called it “mac”, and it worked perfectly. So my URL became and it worked. I could have called it exchange instead of mac, but either way, it worked using a different website thant the Default Web Site.

Next problem was moving the data from Mac Mail into Exchange. Drag and drop worked fine except the dates all changed to today’s date!  Supposedly some people out there fixed this by exporting Mail into some other format, then into Outlook Express on a Windows computer, then into Exchange, but that was too much work. I figured out if you just change the view to Sent instead of Received, the dates were correct. Apparently it only jacked the Received date and not the Sent date. And in almost all cases the sent and received dates should be the same. Annoying, but a reasonable workaround.

Third problem was moving Calendar entries into Exchange. Importing them from another app always seemed to put them in “On My Computer” instead of in my Exchange account.  Should then be easy to drag and drop to Exchange, right? Well, not so much. I needed to select all calendar items at once, but this was proving difficult. Finally figured out I could do a search for all calendar items, which would then let me select all in the search results window, then I could drag to Exchange. Sheesh.

The Public Folder URL worked fine. I used:

The Directory also worked OK, even over SSL. Just put the server name in there, like this:

Be sure and open up port 636 (LDAP SSL) and 3269 (MS GC SSL) if you want your mac laptops accessing it from outside the office.

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