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Entourage 2008: The Worst Piece of Junk, Ever!

Written by on January 16, 2009

You know, Outlook 2007 is by far the best email application I know. So when I bought its Mac equivalent, Entourage 2008, I expected everything to work as smooth as silk. I was wrong... Entourage 2008 is the worst piece of crap I have ever had the displeasure of using.

[Note: This article is one big rant]

I have seen my share of annoying email applications. Most noticeably is Lotus Notes, which I have to use at work. But Entourage has won the winning price for being the most useless email system I have ever seen. It is so bad, that I had to stop using it altogether.

You would think...

The first problem I encountered when switching from Outlook 2007 (Windows), to Entourage 2008 (Mac), was that the two "Outlooks" are completely incompatible. You cannot transfer your contacts, you cannot transfer you calendars, you cannot transfer your to-do's, nor can you open up any of your old mail files - nothing works.

It took me several hours just to find some work around, which allowed me to manually transfer my contacts, by first having to export them to a text file. Then, by manually assigning the fields, importing it into Entourage, only to find that everything ended up as one big mess.

At this point I gave up trying to move my appointments and to-do's, resorting instead to add them manually.

It is all junk...

Setting up the damn thing actually turned out to be the easy part, because the real problems were only just beginning. And the junk mail filter causes it all.

The first email I got was promptly marked as junk, so was the second, and the third, and everyone after that. It seemed that Entourage wanted to get rid of every email as fast as humanly (or inhumanly) possible.

This came as a bit of a surprise to me, because the junk filter in Outlook works like a charm, and have always done so.

But that was not all, far from it.

When I told it that an email was "not junk", it promptly removed the junk status (as it is supposed to), but also deleted the file altogether. Yes, it deleted it - permanently.

I don't know about you, but one would think that email marked, as "not junk" are the very ones you want to keep. I lost a lot of emails today.

I then decided to turn off the junk mail filter, and instead create a custom rule. It is a very simple one, one that I have been using in Outlook for several years. It simply states that unless an email has "tbvalid" in the subject, or is from one of the people in my contact list, then it should move it to the junk mail folder.

That rule actually worked. It handled the mails as was supposed to. Except that a number of emails was still sent to the junk mail folder because they wasn't in my contact list.

Entourage then has a little "usability" feature. It automatically marks every single email as junk, if it is move to the junk mail folder. So all the email move by my rule was also marked as junk. But that meant that the original problem returned, that every email marked, as "not junk", would be permanently deleted.

Then I had an idea. What if I simply moved the email out of the junk mail folder? Surely that would "un-mark" it as well? But no, because that would mean that Entourage actually worked, and we have already established that it doesn't.

Because when you move a junk mail out of the junk mail folder, Entourage automatically detects that it is flagged as junk, and promptly moves it back into the junk mail folder... or deletes it, depending on what mood it is in.

There was no way to move en email out of the junk mail folder. If I moved it manually, it was promptly returned or simply deleted. And, if I marked it as "not junk" it was promptly deleted.

I checked, double-checked, and checked everything again. I check the rules, the junk mail filter settings (which was off) and checked the mailing list rules (there are none). I turned off everything, and I even tried to setup my account from scratch - but to no avail.

Let's delete everything...

Later yesterday Entourage suddenly decided to do a little filtering of its own. I had to check an invoice, so I went into my invoice folder, only to find that every email was very quickly being removed from view.

After about a minute of frantically looking for my lost invoices, I finally found them... in my junk mail folder. I tried to move them back out into the invoice folder, but that was impossible. I then went into another folder, only to see the same thing happening again... and again in another folder. Apparently Entourage had decided to run the junk mail filter on all my emails every time the folder was synched with the server. Even on the old emails, already stored in sub folders.

At this point, I opened up Apple Mail, and got everything back where it was supposed to be.

I have now spent more than 3 hours trying to do every trick I can think of, and my only conclusion is that the junk mail system simply doesn't work. It constantly takes over the systems for no apparent reason, and when it does - you have no way to solve it.

Mails are being deleted from folders simply by going into them. At other times they are simply marked as junk (which has the same effect as deleting them). And this happens even when all the rules are off.

...and to put the final nail in the coffin, Entourage have an absolutely annoying notification system. It notifies you that a new mail has arrived, even if it is a junk email (and it has identified it as such). This means that my inbox notifies me every 4 minutes that I have received yet another spam email.

Oh, and did I mention that when I wanted to send an email, Entourage automatically suggested an address from the emails within my junk mail folder?

I wanted to send an email to my work account (something I had to remember today), and when I started typing my email address, it suggested a "Thomson", who had sent me a spam email earlier that day. Why it picks up addresses from my junk mail folder is simply beyond my comprehension.

I have had it with Entourage... What a load of junk (literally). I am going back to Apple Mail. It is not as powerful, but it works flawlessly.

(for the technical inclined, I am using an IMAP account)

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Thomas Baekdal

Thomas Baekdal

Founder of Baekdal, author, writer, strategic consultant, and new media advocate.

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