Review: Entourage 2008 vs Apple Mail

I used Entourage 2004 on my MacBook for about a year and then, in January, I upgraded to Entourage 2008. There were a couple of things I found frustrating about Entourage (especially compared with Outlook 2000 on the PC) such as the inability to easily put tables into HTML emails. But I persevered until last week when I finally upgraded to Mac OS 10.5 Leopard. The following article is a review of the pluses and minuses for Entourage 2008 versus the free Apple Mail 3.3 that comes with Leopard.

I was quite disappointed by the new look for Entourage 2008. It seemed that the fonts were harder to read and in particular the difference between bold and normal fonts (which show new unread mails) was difficult to make out. But gradually as I used it, I came to like many of the features (apart from, as I said above, the inability to add tables easily).

Things I like about Entourage 2008

In no particular order, here are the things that I’ve liked about Entourage.

• The notification window-let that appears so you can quickly see who the mail is from without having to switch to Entourage to see it. There is a GrowlMail plugin, but at the moment it doesn’t work with the latest version of Mail. If it worked, it would do exactly what I want.
• The ability to assign colours to categories of contacts and then emails from people in the groups are shown in the group colour. I’ve now worked out that I can achieve the same thing using Rules in Mail, but it’s more complicated to do than just assigning a colour to a group.
• Autocompleting addresses, this works very intuitively and even suggests addresses from recently received emails even if they aren’t in your address book. I can’t exactly tell if this works the same way in Mail yet, but it doesn’t seem to work quite as well. Also in Entourage you can just tab through once you’ve entered the To field through the CC and you’re in the Subject field, one more tab gets you into the body and then you can start typing. In Mail there are a few more extra tabs you have to press to get over the various other fields (depending on how you’ve set up your mail window). It’s a shame really, if they weren’t in the tab order, or if the tab order put them before the addresses, it would be much more streamlined for keyboard use.
• Being able to create accounts for sending only. I have one account which just forwards emails to my main accounts, but sometimes I want to be able to appear to have sent from it, so that replies are addressed correctly. In fact I’ve (eventually) found that there’s a really neat way to do this in Mail: what you do is in the preferences for one of your accounts, in the “Email Address” box, you add multiple email addresses as a comma-separated list. Then when you create a new email, all the email addresses appear as a drop down and you can choose the one you want to use.
• The junk mail filter. With Outlook I used to use SpamBayes. This is a pretty good plug-in and seemed to work really well with the sort of spam that SpamAssassin didn’t pick up. However with Entourage 2004 and 2008 I didn’t bother with an external tool, I found that the junk mail filter did a pretty decent job. I’m finding that Mac mail doesn’t (yet) seem to do as good a job, maybe it will improve, I certainly hope so!
• The richness of information you can put about a contact. Contacts can have all sorts of useful fields and adding them to groups is really easy and straight forward. It’s a great shame that this richness doesn’t quite get synchronised with the Apple Address Book. Some things like photos, you can add to both Entourage and the Address Book, but they don’t get synchronised (and they don’t get synchronised with my Windows Mobile phone either).
• Mail merging, for example to print labels for everyone categories as in my Christmas Card list. This just worked as expected. I haven’t tried Mail merging from Mail and Address Book, but I’ve read that it isn’t quite so easy (in fact a quick look suggests that it’s going to be anything but easy!).
• Auto-correction. I really like the auto-correction when I spell words incorrectly and it fixes common mistakes. I also really like the fact that if I type word1–word2 it replaces it with word1—word2. Though there’s spelling checking in Mail, there’s no equivalent to this as far as I can tell. That’s something I’m really going to miss!

Things I like about Mail 3.3

I’ve only been using this for a few days, so there may be all sorts of neat tricks that I don’t know yet. Again these are in no particular order.

• The fact that it tells you how many unread emails there are in the Dock icon. This seems a neat feature—though the Growl preview as mail came in would be even nicer.
• The feature that allows you to store phone numbers against contacts or create to-do items and appointments from snippets of text. I’ve already found this pretty useful.
• Searching is so much faster! The search for mail from a person in the current folder in Entourage worked pretty well and I used this feature most of the time, but it was quite limited. It only seemed to work on their name rather than the email address, so you couldn’t type in “isocra” and get the emails from everyone at isocra.com. Searching for text in the content of a mail in multiple mailboxes seemed really quite slow. Just the reorganisation of the screen (adding the toolbar and the results panel) seemed pretty slow—so much so that I always thought twice before using it, preferring to use Spotlight instead. Searching in Mail seems to work really well. Typing “isocra” gives all the emails from anyone at isocra.com.
• Archiving folders to mbox format. This seems like a good idea for old projects. It means that you haven’t lost the emails, but they aren’t cluttering up the Mail application all the time. On the other hand, I feel more confident having them in the standard mbox format than some proprietary format that can’t be read by anything other than the original application.
• Migrating from Entourage to Mail. OK, so this isn’t something you do more than once, but it was unbelievably easy. I just asked it to import from Entourage and it imported several thousands of emails. It didn’t import the account information, I had to set that up by hand, but that didn’t take long.
• I actually like having separate applications for Calendar, Mail and Address Book. Since they all work well together, it’s useful having them separate, not least because you can look at your calendar while composing an email. (I know you can have multiple windows in Entourage, but it never seems to work as well for me.)
• Even in the latest Mail 3.3, you still don’t have a lot of control over the format of an email. However what you can do is to create a table in, say, TextEdit, and then paste it in. You can then still edit it (to an extent—you can’t add columns or rows or change the size). Ironically you can also take cells from Excel and paste them in and it maintains quite a bit of the formatting too. In Entourage, if you do the same you get some of the formatting, but you don’t get the table—even if you paste from Excel.
• Time Machine integration. I feel much more secure using Time Machine for backup. In fact it’s one of the main reasons why I upgraded to Leopard. Mail (not surprisingly) integrates well with Time Machine and you can go back and look at how your mailboxes looked on any day for which there is a backup. Entourage doesn’t play well with Time Machine apparently, since the “main” identify gets backed up each time it is modified, which is every time you send or receive a mail. If you are using this combination, read this article about Entourage and Time Machine.

Synchronisation

I am asking rather a lot from the Apple Sync Services. I have a Windows Mobile 5 phone and I use Missing Synch for Windows Mobile. I also want to synchronise my calendar with other family members so that we each know what other appointments we have. For this I use Busy Sync. Finally I have a .Mac account and I use the built-in synchronisation to keep some of the information backed up remotely.

Getting all this working with Entourage as well was not easy. Entourage does work with Sync services, but only grudgingly. It will expose a calendar (called “Entourage” whether you like it or not) and this can be synced with the other tools, but pretty frequently they’d all get mixed up and then you’d get 250+ conflicts that you had to step through choosing one seemingly identical event over another as the one to use.

Taking Entourage out of the equation does seem to have simplified things and now I don’t seem to get quadruple events for the dentist and so on.

Conclusion

Both applications do all the basic stuff well and have lots of good features in common, for example the Smart Folders and Smart Mailboxes each allow you to see all the emails that conform to the constraints that you specify regardless or where they are actually stored. Both applications have rules that can move emails into folders or delete them or whatever. Each app supports some sort of To Do items and allow you to create and accept invitations to appointments. Mail provides “stationery” to jazz up your emails, but though that might be nice for home use, I can’t see a real application for it. It would have been more useful to make it easy to add in rich home-made HTML.

If you have Exchange Server, then probably Entourage is the way to go. Especially since with Sync Services you can almost have the best of both worlds. Also if you are going to do lots of mail merging, then Entourage will make life easier for you. However, if HTML emails are what you need and/or more complex syncing, then Mail seems to have the edge. I’m going to stick with Mail for the time being and see how it goes. I’ve now got some rules set up to highlight different incoming mails and I have my list of “from” email addresses, so I’ve got very much the same set up that I had with Entourage. I’m still not convinced by the Junk Mail filter though and I’m missing the auto-correction. But for a built-in (essentially free) program, it really does give Entourage a run for its money.

Of course if you use IMAP to access your mailboxes, you can potentially use both, especially if you get the synchronisation of contacts and calendars working!