Monday, July 14, 2008

iPhone vs. Entourage: The iPhone 2.0 Smackdown

September 2009 update:  Yeah yeah yeah I know that even iPhone 3.0 is already a fading memory for most of us and Apple is moving on to create better and more creative affronts to our unrealistic expectations of them.  Writings behind here are rather old, if you haven't noticed, so please take these elder brethern in the forgiving spirit you would extend to a 1958 issue of Popular Science or a printout of an old Gopher page.  They were created on punch cards, after all, so cut me some slack.

With the iPhone 2.0 release now in hand, it’s been time to discover new, and old, issues with synchronization. I’ve inadvertently wiped my Outlook calendar twice, and finally figured out why. There’s a bug in Apple’s iPhone–to–iCal software, and one in Microsoft’s Entourage–to-iCal, if I am getting this right.

First, let’s review how this has been working for the past year or so. Let’s start with the components.

Apple’s calendar program:
Apple has their own calendar program, iCal. It can maintain multiple calendars, which are keyed by color and name. Let’s say you’ve decided to make Private green, and business blue. There’s a list of calendars on the screen, and you can check which ones you want to display at any time. If you have a 9AM private appointment for “Dentist” and a 10AM business appointment for “Meeting”, then your calendar will show “Dentist” in a green box, and “Meeting” in a blue box.

In that list of calendars, you can also highlight a whole calendar, and delete it (it asks if you’re sure).

Apple’s iPhone program:
When you have an iPhone plugged in, you can specify what things should be synchronized: music, videos, contacts, calendar, and so on. You can also specify “copy computer to iPhone just this once” for each function.

What it does is sync iCal to the iPhone. It can also sync .Mac (dot mac), which is their web-based service, in the process so you can keep your calendar in the cloud, but I’ve not enabled that since simple earthbound reliability has been enough of a challenge.

Microsoft’s Office and Sync program:
Microsoft has an Office suite for Mac, and that’s what I’m using, the latest releast: 2008. Word, Excel, PowerPoint. They all look like their PC equivalents, mostly And, for some odd reason, they call the Office suite Entourage, which does email, calendar and contacts, and looks way different from Outlook. But it works, and connects to the corporate server, so I don’t complain. Entourage has a set of Preferences (like all mac apps), and among these are “synchronize events and tasks with iCal and .mac”.

Sync services between Microsoft Office and Mac programs are done by a separate program, "Sync", also written by Microsoft's Mac group.  It's always running, and for the calendar it coordinates Entourage’s database to iCal. You never know when it will do this; there’s an element of surprise involved. Sometimes it’s seconds, sometimes hours.

Office for Mac 2008
I changed from 2004 to 2008 (hesitant to call it “upgraded”) about four months ago. Things have been working fine.

The iPhone
The iPhone has a calendar program which looks a little like...well, like any calendar program. You can see your appointments, open them up to read them, make new appointments.

So those are the pieces. I never use iCal specifically, its blue “Entourage” calendar is just a transfer point for calendar information as it buzzes back and forth between Entourage and iPhone.

Iphone 2.0
This is where peaceful Mac – Windows coexistence starts to collapse. Two different chains of events occurred.

First problem: My Outlook calendar was flooded with newly-generated multiple entries for old events, mostly multiple-day events. So I would have eight entries for an all-day meeting called “Event,” on Wednesday, for example, and six entries for “Different Event” on Thursday, and so on. It pretty much filled the screen although I found that the previous entries were still in there, just covered over. I also found that there were now two “Outlook” calendars in iCal.

What I did:
> Deleted the spurious entries in Outlook by hand.
> Unchecked the “sync Entourage to iCal” preference
> Re-checked the “sync Entourage to iCal” preference. When you do this, it gives a new option to copy Entourage to iCal, copy iCal to Entourage, or merge. I chose “copy Entourage to iCal”.
> Found that iCal had a second Entourage calendar again, so I deleted this.

What happened:
> Entourage was zeroed out, all blank.

What I conclude:
> There’s a bug in the Microsoft sync code for this corner case: if you delete the iCal calendar it’s trying to copy Entourage to, it deletes the Entourage data too.

Second problem:
It turns out that those multiple entries were caused by syncing iCal to iPhone. I clicked the option to copy iCal to iPhone, and multiple entries were the result.


> Don’t delete a duplicate Entourage calendar in iCal until synchronization is complete. Even then, be scared.

> I am still thinking about how to get iPhone back into orderly synchronization. What should work is
> Copy Entourage to iCal unconditionally once, via Preferences
> Copy iCal to iPhone unconditionally once, via configuration option
> Turn on normal sync

But it’s not operating reliably.

I offer this for those who may encounter the problem. It’s not dissimilar to problems I had several years ago with Palm synchronization to Outlook, but those things appear to have been cleared up and our IT organization is pretty happy with Good (which accounts for their recent sneers at my problems).