On Mail, iSync, Address Book and iCal
One of the great benefits of having a .Mac account is iSync, which lets you easily back up all of your contacts, calendars, to-do items and bookmarks to your iDisk and download them to multiple machines, keeping all your information synchronized. This only works, though, if you’re using Apple’s address book, calendar, and browser applications; which until recently I was not (except Safari).
For the last five years I had been using Microsoft’s e-mail clients, starting with Outlook Express 4.5 for e-mail along with Palm Desktop to keep track of to-do items and appointments. Once Office 2001 arrived, I dropped Palm desktop and let Entourage, and later Entourage X, handle everything.
Entourage has served me well, but it is not without its issues. Contact and message databases become unstable once they get large, and its junk mail filtering capabilities are non-existent (though SpamSieve can help with that). Taking this into consideration, as well as the new computer that’s in my near future, I decided to make the switch to Apple’s applications: Mail, Address Book, iCal, and most importantly iSync.
Apple’s mail, address, calendar and syncing apps
Overall I am pretty pleased. All together they seem to take up less system resources than Entourage does all by itself, and although they are four separate applications they seem to integrate with one another very well. But, despite how easy they are to use and how well they integrate with the entire system (Address Book information being auto-complete info in Safari is a nice touch), they are also not without their own issues.
iCal
iCal is by far the least stable and poorest performer of the four applications, though I’m sure this comes as not real surprise to most people; since its release iCal has been a little unstable and slow. But in terms of overall functionality my complaints are not so much how iCal keeps track of things but rather how it communicates with my Handspring Visor Edge and how it publishes calendars to .Mac.
When I create appointments on my Visor and then sync them to my Mac they are all moved into one category. If I create an appointment in the “Personal” category, and another in the “Work” category on my Visor, they both end up in the same category in iCal, which, to say the least, is annoying. I am sure there is some technical limitation preventing Palm OS categories from becoming iCal calendars directly but it seems to me that this shouldn’t be that hard to get around.
I have a similar problem with iCal when it comes to .Mac. iCal can publish calendars to your iDisk, which is is a very handy tool if you have a lot of appointments you need to share, such as itinerary for a family trip or an appointment schedule for a group of salespeople. Where I have a problem, though, is that only one calendar can be published on a page at a time.
Why is it that I can’t publish my school schedule and my work schedule together on the same page? Or in other words, why can’t iCal generate a calendar web page that looks like the main interface of the iCal application? I could lump them into one calendar, but that seems to defeat the point of being able to have separate school and work calendars in the first place.
Address Book
Address Book is the one app that I have basically no complaints about. Information seems to sync to my Visor a little slower than the Entourage database, but other than that it works like a dream. The integration with the rest of the system adds all kinds of nice touches to applications (multiple addresses in Safari’s auto complete for example), and the fact that it can be accessed by any app makes the possibilities nearly limitless (as far as a contact database can go, anyway).
iSync
iSync is the main reason that I switched to Apple’s applications. There is a new computer in my future, and the ability to synchronize all of my information with just the push of a button is incredibly appealing, and having access to my entire Address Book database and all my Safari Bookmarks when away from my computer (via .Mac) is gravy.
The only problem I have with iSync is that if I don’t have my Visor around and attempt to sync my information by pressing the iSync button instead of the button on the Visor’s cradle, I get this warning:
Warning: Palm device wont sync
The warning itself isn’t the problem, though, the problem is that after I tell iSync to sync without the Visor it tries to anyway, and I get this error:
Error: Palm device not available
Didn’t I just tell it to disregard my Visor? Why has it tried to sync anyway? It just doesn’t make sense. I can tell the warning to not show up again, but the error persists. If I choose “Sync Now” from the iSync menu extra it seems to work fine so that’s what I am doing at the moment, but sometimes I need the application itself open (to change settings, for example) and this warning is annoying.
Out of all four apps, Mail is the one I use most, which is understandable since the Address Book database can be accessed from within Mail and e-mail arrives more frequently that new appointments need to be added to my calendars.
Pretty much all of the things I dislike about Mail are nit picks, little details that most people can either ignore or work around. I can too, but in most cases I don’t think I should have to.
The toolbar for individual messages is customizable, but doesn’t contain some buttons I think it should. For example, there is no option to add “Next Message”/”Previous Message” buttons to the toolbar. It’s not the end of the world, but it is the difference between clicking once to view the message and clicking three times (once to close the current message, double click to open the next), which I would like to avoid.
I wish that I could add the “Junk/Not Junk” button to the individual message toolbar, too. As it stands right now, it can only be placed on the toolbar for the main window in Mail, which is a little frustrating. I still occasionally get spam messages that appears to be legitimate, and when I open them I’d like to be able to just junk them and be done with it as soon as possible.
On the subject of Mail’s junk filter, it takes a long time to train. Weeks after I started training it very obvious spam messages are still making it to my inbox; even ones that have spam headers from one provider (which Mail is set to trust) and “*SPAM DETECTED*” in the subject line from another provider. How many times does it have to be told that these messages are junk before it can figure it out on its own?
One last thing that I am somewhat disappointed with is the Trash and Junk mail boxes. The icons never change. The trash icon always appears empty and the junk icon always appears full.
The trash and junk icons whether there are messages in them or not.
I know that the text bolds and and the number of messages appears next to the icon, but I’ve been using Macs for a long time and the trash icon should have two states: empty and full. It’s easy to tell at a glance what is going on by the way the icon looks, and it makes sense that the junk mail box could behave similarly, too.
Conclusions
As mentioned above, I am pretty pleased with Apple’s e-mail, contact management and datebook applications overall. Most of the gripes I have are minor, some might even say single-minded, but all of them are downright annoying to me and none of the things that I’ve talked about seem like they’d be difficult to implement even as optional features.
I won’t be switching back to Entourage (or anything else) anytime soon, though. The benefits of using Apple’s applications far outweighs the added features in third party alternatives, despite annoyances.

I agree with your overall assement of the 4 apps. Howeber, I would like to add a couple of things. First, in Mail, we really need the ability to choose the period of time for Special Mailboxes to keep mail. Right now, there are 4 options (1 day/week/month or on quit). I prefer to use a 90 day period and have to hack the prefs file to make that happen. A fifth option that allows a user specifiable delay would be great!
My other gripe is with Addressbook. While does a great job of storing te data and being flexible for international data, the interface is abhorrent. More than anything, having to comb through every group to see if a card is a part of that group is ridiculous. I want to be able to look at a card and see what groups it is a member of. Keywords as a standard dataset would also be handy. Instead of freeform entry to the field, a pop-up of pre-defined keywords would allow one to standardize and avoid mispelling or mistyping that could cause you to miss a card on a search later.
i’m currently using apple’s iapps for my contacts/email/etc. and was acutually considering switching to the new entourage simply because it’s a single app with everything i need. guess i won’t be now?
In addition to your iCal comments I would like to have greater flexibility in the text windows: fonts, sizing and abbreviations (“P” rather than “PM”) etc.
Personal Organizer (Chronos) has greater flexibility, especially when it comes to printing a monthly view, but they seemed to have thrown in the towel and seem to be focused on producing new products.
iCal has some very nice features, and I hope that Apple continues to attack it’s short comings.
Althogh I like to use Mail it has lost emails from time to time, and that’s scary enough that I still use Entourage for my primary mail program.
So far it seems that my lost mail is all from my .mac account, but I’m not 100% sure of that.
Just a warning…
i use all of the apps too and would like to add a couple of gripes…
iSync
i had an issue too with iSync with the program popping up and saying it would do one thing and actually doing another when trying to sync with my bluetooth phone – it said it wouldn’t delete the numbers and in fact did, so i lost all of the numbers stored on my phone when i tried to sync. the only way i could get it to play ball was to start with a blank phone which is hopeless when you have a phone full of numbers and buy a new mac that you’d like to sync…
mail
when you try to create a list of, say, 100+ email addresses Mail tries to parse each address into a pretty blue tab. this was added in a recent version of the mail program and is utterly obnoxious – there’s no way of turning it off, annoyingly… just one of a few apple ‘downgrades’
I think the most significant of your comments relates to how to exchange field and category information between devices created by various manufacturers, in your case Apple and Palm. Hopefully they’re not using minor annoyances like that to get people to stick with Apple HW, like iPod.
I also agree with the iCal thing: 1 cal per page… then you have to switch back and forth between calnedars to find out where your free time block is.
But for me, the most important thing is full-bore multilingual capabilities, and this kind of relates to the post above about categories.
I have a lot of contacts stored with Chinese, Japanese, and Korean names. I keep the pronunctiation in the pronunciation fields.
Unfortunately, whenever I sync with something .Mac or my S/E T610, then I lose this multilingual information, and it’s replaced with ”?” or blank spaces. (Recently, Apple has improved this with the .Mac Address Book—now I can actually see and edit CJK names on .Mac… That’s worth an upgrade!)
However… The way Address Book ‘breaks’ when syncing to non-Apple devices (like Palm, Mobile phones, etc.) needs a lot of work. Using the information Address Book has at it’s disposal, it should be able to determine how to provide the optimal output to the device.
So, for example, format awareness/compatibility should be part of a device’s iSync profile. If a device will not support extended character sets, iSync should be able to switch from the actual name to the “Pronunctiation Name” for syncing.
I read somewhere about the best test of security is how well security fails. I think the same statement should be applied to synchronization software: it should fail gracefully, not corrupting and existing data (as .Mac AddressBook used to do) and as current synching with my T610 currently does (moving first and last names together, and shifting that back to the .Mac Adddress book’s firstname field!)
Frederick,
just a nice info for you:
when a contact is selected, pressing [ALT] (option key) highlights which groups this contact is part of!
Enjoy
Mail doesn’t have to be taught over a length of time to properly recognize junk/not junk – at least I’ve figured a workaround for it’s lack of ability to learn on it’s own. I use Yahoo! e-mail, which manages to filter out about 90% of the garbage that barages my e-mail account (and sends it to the bulk folder, where it is deleted after a day). I also use Spamfire – it runs on startup, keeps running, and checks every 15 minutes for spam. It generally gets about (I guess) 8% or so of the remaining junk. Thius leaves me with a couple of mails a week that are simple enough to teach Mail to recognize (usually through keywords in the header) and treat as junk.
I hate it when I add a new person in iChat and it shows up in the Address Book…rrrrr
Please Apple take that away.
Thats pretty much my gripe.
quote: “I hate it when I add a new person in iChat and it shows up in the Address Book…rrrrr”
Agreed. That feature is the most pointless feature when iChat and Address Book are combined. What’s the point of that, anyway?
A previous comment was complaining that in Address Book you can not see which categories a contact is in without going into each category. This is NOT correct. If you highlight a contact and then press the “option” key on your keyboard you will find that Address Book will highlight the categories that contact can be found in.
I don’t have any problem syncing first and last names with a Sony Ericsson T610. I just checked the contacts that I have entered on my phone, and they were all parsed correctly into separate first and last names in Address Book. In the phone menu, there’s a choice to synchronize by first name or last name. I have first name chosen. I wonder if that might influence whether the parsing works correctly.
I may be misreading something in your complaint about iSync, there are so many troubles I have had trying to get my SE P800 phone/pda to sync consistantly that I can understand your frustration, but I think the redundant alert messages you get if your Visor is not present can be avoided by temporarily turning off the ‘sync Visor’ radio-button in iSync – when you open the app instead of using the ‘sync now’ menu command, you can click on the graphic of your sync-able items, which you add yourself (in my case, the P800, my iPod, and my .Mac account, in your case, the Visor and .Mac, maybe more). If I only want to update my .Mac info, like bookmarks, etc, I click on the P800 icon and a list of options appears, one of them being a button saying ‘Synchronize P800’… I turn it off. Then I turn off iPod sync-ing the same way, and iSync ignores my P800 and iPod and goes directly to sync-ing the .Mac account, saving the time of a PDA sync. Of course , in your case, you can click the option back on to ‘sync Visor’ when you have it connected in the cradle…
Anyway, I find it hard to believe that a guy running a site called ‘GeekPatrol’ has not stumbled on this himself, so if you have, and this post’s “hint” is painfully obvious, forgive me! You may have done this already and it may be a unique error to the visor or something…
WOW! I didn’t know about that in Address Book! Highlighting a contact and pressing the OPTION key highlights the groups that contact belongs too…That’s great! All Apple has to do now is to make that a user preference (I would leave it on all the time…this is useful information). Thanks for the tip!
Mail
My only complaint is the search filter seems to stay the same across different mailboxes. I often go to my Sent box and search on the ‘To’ property but in my In box I usually want to search using the ‘From’ field. Why would I ever want to search against ‘From’ in my Sent box?
You can’t turn off a Palm device like the Visor when syncing through iSync. The box for turning it off is grayed out. This is due to the requirement that Hot Sync be started from the Palm device to sync to your other devices and .Mac
I migrated to the iApps about three months ago so I could synch up contacts and appointments on my moto 343 phone. the ability to ditch my Palm more than makes up for the lack of integration/centralized control.
My issue with the not-quite-yet-a-suite is the lack of a dashboard to pull all four together. Entourage did only-passable job of this. Entourage 2004’s Project Center is a great idea, but isn’t there yet. Same with CRM4Mac. It functions more as a contact tracker than anything.
I have to believe that Apple’s working this angle, and may use it as a point of differentiation with Appleworks. Think about it … complete transerency with the Word platform and pulls together the iApps like Office for Windows does AND allow you to run a “Project Center” using all of them linked together? Fready-deaky.
Ahhh… Eph, thanks for the clarification, I (obviously) didn’t know that. Sorry ‘bout that long useless post!
This brings me to the next issue I have with iSync, which is – Do they even test this stuff for more than a minue or two? In their lab, did anybody even try to sync without the palm or visor hooked up? I can see myself getting excited and forgetting to check, then moving on, but I’m not Apple. My p800 sync-ing works better now, but on the first version it was really a crap shoot. Sometimes it would work, other times, wouldn’t find the device. This was sometimes thought to be the Sony/Ericsson bluetooth implementation, however.
I can only attribute this to the sheer number of devices they are trying to support… incomplete testing to be finished by the end user.
Any idea on how to sync todo items on iCal with todos on the palm? i looked hard but i couldn’t find a way to address the issue.
I am also unable to get rid of all double emails that Mail from time to time downloads. the applescript that comes with phanter seems not working
Regarding next/previous browsing in Mail.app:
When you’re in the browser view, just press the space bar. It’ll page through the current message if it’s too big for the message pane, then go on to the next message.
To go to the previous message, press shift-space bar.
For those that would prefer to use the built-in databases that Apple provides (iCal, Address Book, and Mail) but would rather a more integrated approach, take a look at a product called Crm4Mac (strange name). It has a ways to go, in my opinion, but does a great job today and is getting better.
Apple definately has a ways to go to make iCal and Address Book “Prime Time”. When syncing a Palm with Address Book, only the Home addresses are synced. Not just annoying, but unacceptable! How about adding “double-click to edit” on an address card…seems like that should be a given. I’d also like to see compatibility for sending/receiving individual iCalendar events not just to other iCal users, but Outlook users as well. Banners in iCal month view, ability to attach vCards, files, etc. to iCal events, logging/journaling between Address Book and iCal, the list just goes on and on and on…
All that being said, the iApps are still the best thats available! Some of the other options that have been mentioned may fix one or two problems, but none of them comes close to perfect either, and none of them integrates quite as well as the iApps.
I’m curious about how to get over the device not available error. It get it on every device when I try to sync iCal. Funny, but Address book syncs OK. I can’t even sync my iPod anymore. Your comments about iCal instability are right on. I’ve come to realize this is probably an iCal issue rather than an ISync issue, because Isync seems able to perform other tasks.