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.

Conclusions:

> 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).

Entourage Not Connecting via VPN: A hint

There are other sources on the web regarding this problem: Entourage 2004 shows  "(Not Connected)" next to the account name, but gives no clue as to why.  This occurs even when the VPN connection exists and is solid, and occurs without warning on an otherwise functional computer.  Most recently, I closed the laptop at one location and opened it at another, re-entering VPN.  Restarting the machine didn't fix it, nor did any of the online advice.

I wandered over to the IP guys, and one of those tolerant gentlepersons suggested that I try using the numeric URL for the Outlook server, rather than its name.   This eliminates the step of going to the DNS. 

Tried that, and it works great.  Thanks, guys!  

Groundswell

I'm at a company conference.  One guy in a large meeting room came over to talk when he saw my laptop - turns out he had been elected by his whole group to ask me how I got the Mac!  

Two weeks ago our desktop computer support person from IT mentioned that he thought we should change all the PC's to Macs.  

Cisco VPN with Mac

Guess what?  Cisco has a Mac version of their VPN!  It works under 10.4 versions, and under 10.5 and 10.5.1 as well!

If your IT department doesn't support Mac (as I've said, they're invariably overloaded so that's not an unreasonable initial stance), you can either pull in a favor from a friend in IT (she just has to go to the protected part of the Cisco site, which she can do if she's in your IT group, and get the Mac client for VPN and email it to you), or google the web for a copy.  I found a current copy on some European site, perhaps a university. (Suppose I could have shmoozed one of our IT guys, but I got into the challenge.)  The newer version I now have, 4.9.01 from about 2006, is much more forgiving of the vagaries of hotel networks and such, so I am no longer having any problems (well, no more than my PC friends) with consistency as long as the actual connection is good. 

In a hotel, the sequence is: pick a network, clear a path to the internet, then clear a path through VPN.  Hotels are the most challenging, so if you can do a hotel, you're a pro.  Home DSL is easy in comparison.

Pick a network.

1.  Plug in the network cable, or click on the wireless antenna icon.

2. If you clicked wireless, it will show you a list of possible networks.  Pick the one you want and click on that.

3.  The antenna symbol will now show you some bars, which says you have a physical connection.  Or it won't, in which case you are missing a password, or something's changed.  

What you have now is a path to the hotel's network.  From here, you need to get to the real internet; the hotel may give you some ads or limited Yahoo access, but they'll usually charge for full access.

Clear a path to the internet.

1.  Click Safari, or your chosen browser.  Do you get your home page?  I bet you don't.  I bet you get the hotel's page, you've been redirected to it, because they want to ensure your satisfaction (charge you money) and deliver optimal performance (charge you money) before they let you get to the network, a grace for which they're likely to want to charge you money.  Heck, they're charging you $10.95 for bad porn on the TV with all the interesting bits edited out, why would they let you have internet porn, with those bits still retained, for free?  And the details of surfing aren't reported on your hotel bill, so you can go ahead and prepare your expense report with a clear conscience.  I'm sure you've done at least one work-related email, right?  

Incidentally, I know this because I talked with a guy who did this.  He was an odd one; he didn't seem to think that we were given sex so we'd be easier to damn.   

2.  OK, you've got the hotel's page, so you agree to the charges, or you click to say that although they're not charging you, you're willing to take responsibility for your own actions.  One way or another, you get a few last frantic popups asking for spare change or to meet their sister who is lonely, and it says "you're now on the web."  Type www.google.com or something you know what it looks like.  If it looks like that, you're done.  

Click the Cisco VPN button

If there's a path to the internet, it will show you a small introductory window, looks like a skinny lady on the beach (properly attired, which is Cisco porn I suppose), and then ask for account and name.  You type that in, it consults its inner child, and then comes back with a new popup that says that your company owns your computer, your soul, and your sense of self.  You agree to that, as I always do, and the window goes away.  

Then there you're left with this this Cisco window, just hanging around on an otherwise clean screen.  Hit Command-h (it's the "hide" shortcut; "Command" is the "Apple" button, or the "four-leaf clover" button; there's not a clear Windows analog to it and it took me a while to figure out when I first started using the Mac).  The Cisco window will now tuck itself into the toolbar, wherever you've put it on your screen.  If you want to see the Cisco window again, such as to log out of VPN, you can either click that thing at the bottom right or Command-Tab your way through the currently operating programs (do you know that Command-Tab shortcut?  it's really handy) to get to it. 

You're now on your corporate network, courtesy of Wozniak, Jobs, Chambers, Morgridge, and probably 10,000 talented Silicon Valleyers who actually did the work.  Welcome!

Leaving Cisco VPN

When you shut down your computer or disconnect from the web, it's cleanest if you bring the VPN window back up and click "disconnect."  Otherwise a complaint pops up and you have to close that too.  I had some problems with laptop restart in the past, under earlier versions of VPN, but that doesn't seem to be an issue anymore.  

MacWorld, and Mr. Jobs' "failure"

A very brief note for today.  Seeing the responses to Mr. Jobs' keynote, in which viewers are disappointed that they were not "wowed" more, I can't help thinking that the word "spoiled" has unfairly fallen into disuse.  The resurgence of Apple is an accomplishment of almost mythical proportions in modern times, and any judging must be done on its average performance, not its instantaneous.  If this trend of "he wowed us last year, but didn't wow us as much this year so I'm disappointed" continues, I will expect to see this continue into increasingly fractalized microclimates: "but then he wowed me from 1:18 until 1:22 when he hit a lull and then I was really disappointed, but then at 1.24 he seemed to turn into a tailwind and wowed me again for seven minutes until..."

At some point, this kind of evaluation ceases to serve and commences to strut, hollow-eyed and pointless.  We read for understanding and perspective.  Please give us that.