What happens when you have an Apple ID without an email address and you change it? (And much more about Apple ID hell.)

I'll provide some back story below, but it's tedious and a bit ranty so I'll put the most useful stuff up front.

For *reasons* (see below) I have had an Apple ID associated with iTunes, App Store, physical Apple Store, hardware and other purchases for about 20 years. For other *reasons* almost lost to memory the username has not been a valid email address for most of those years. Until recently it had an associated email address it would forward to but Apple changed things sometime in the past two years and that stopped working.

I'm simplifying.

We will call this Apple ID username "bob@mac.com". I will use alice@icloud.com and dan@me.com for my new Store Apple ID ("Media & Purchases") and my longstanding iCloud Apple ID respectively.

Once bob@mac.com stopped forwarding I no longer received notifications related to Apple Discussions or emails related to charges. Since bob@mac.com was the store Apple ID for my family (this was the practice in early iTunes days) our children (now adult) used it for purchases. Simplifying a lot and omitting family details the lack of email meant no monthly statements -- so I didn't spot a scam subscription - among other things.

I knew I had to fix this but I dreaded the side-effects. I'd already tried undoing the shared store Apple ID and ran into disaster; I had to reverse that attempt. I had to fix the Apple ID invalid email problem first.

Before Apple broke forwarding for the Apple ID "bob@mac.com" I had used "alice@icloud.com" as a forwarding address. Although there was no clue in the Apple ID online configuration tool, I knew alice@icloud.com was still entangled with bob@mac.com (see below, this post goes on for a long time but still omits much).

Ok, so far? I gets a bit simpler then you can skip the back story.

Anyhow ... when Apple broke forwarding they seem to have introduced the ability to change an Apple ID userid - such as bob@mac.com. I believe, though I can't find any documentation, that the visible username with the form of an email address (ex: bob@mac.com) is an alias for an unchanging hidden identifier (maybe a GUID). 

After some thought I decided the cleanest approach would be to change my Store Apple ID visible username from bob@mac.com to alice@icloud.com (I knew the two were entangled, see below). It's easy to make this change from appleid.apple.com. When I did this I was not asked to confirm that alice@icloud.com was a valid email address I owned. All I got was an email sent to to alice@icloud.com saying the change had been made.

After I made the change I found the following. I expect other changes as Apple's different systems synchronize and update (I will update this as I learn more, I expect to learn of problems from family members later today):

1. I cannot login to the Apple ID or anywhere using bob@mac.com but the two factor notification dialog still says bob@mac.com (this may change).
2. I think I may have more control over Apple ID two-factor, I can add/remove trusted devices, remove from account, and I can add a second trusted phone number. I still can't add a backup email address; that is available on some other Apple IDs I have
3. Apple Discussions is intact. When I login with alice@icloud.com I show as "member since June 23, 2003".
4. Mail sent to bob@mac.com still fails, there's no redirect.
5.  iTunes on Mojave: asks me to sign in and displays new alice@icloud.com. Says session expired, asks again. Purchase history intact.
6. Media & Purchases on iPhone showed new iCloud address and I had no trouble with updating apps.

In addition, Messages in my personal dan@me.com iCloud stopped working! It turns out "Messages" has legacy associations with the old Apple Store ID used with iMessage before Apple implemented iCloud. I got this error message

Messages in iCloud not available as iCloud and iMessage accounts do not match. (Messages in iCloud is not available because iCloud and iMessage accounts are different.)

There's a fix here but it's not the one I needed. When I looked at Messages on my iPhone it showed only my Phone number, the Apple IDs were all absent. When I tried to enter an Apple ID it showed my store Apple ID; I chose "use other Apple ID" and entered my personal iCloud Apple ID. That worked and it immediately restored all my send/receive message list. I could then reenable messages in iCloud.

It didn't fully work on Mojave iMessages though. I reenabled using iCloud Messages in preferences there and about an hour or two later it seemed to start working (though uploading messages to iCloud is still ongoing.)

That concludes the current record of changes to date. So far it has been less of a problem than anticipated, but it's early days. I will add other issues as they emerge. Then I can return to the herculean tasks of moving family members off of a shared Media & Purchases account.

Below are details for the benefit of someone searching who finds this post. They are related older items that I will summarize in outline.

----------- additional details ---------------

As noted above years ago I had alice@icloud.com as forwarding email for the Apple ID bob@mac.com. The address bob@mac.com had no associated email because of complex changes Apple made in migrating from free iTools to not-free .Mac to MobileMe. [1][2]

When I finally realized I wasn't getting Apple media purchase statements for bob@mac.com I began investigating what had happened to the old alice@icloud.com iCloud account. I found it was deactivated. I was able to reenable it. That's when things got weird. Remember (if you read above) that there was no longer anything I the Apple ID settings for bob@mac.com that showed alice@icloud.com.

Once I reenabled alice@icloud.com with a new password I found that:

• Both alice@icloud.com and bob@mac.com worked as usernames for the same bob@mac.com Apple ID.
• The password for the bob@mac.com Apple ID had changed to match the alice@icloud.com password. [This actually took a day to propagate to iTunes purchases]
• Both alice@icloud.com and bob@mac.com showed the same iCloud services (mail, etc).
• bob@mac.com was still not a valid email address. 

fn -

[1] https://en.wikipedia.org/wiki/MobileMe#.Mac

Originally launched on January 5, 2000, as iTools, a free collection of Internet-based services for Mac OS 9 users, Apple relaunched it as .Mac on July 17, 2002, when it became a paid subscription service primarily designed for Mac OS X users. Apple relaunched the service again as MobileMe on July 9, 2008, now targeting Mac OS X, Microsoft Windows, iPhone, and iPod Touch users.

On February 24, 2011, Apple discontinued offering MobileMe at its retail stores, and later from resellers.[2] New subscriptions were also stopped. On October 12, 2011, Apple launched iCloud to replace MobileMe for new users, with current users having access until June 30, 2012, when the service was to cease.

... The original collection of Internet software and services now known as iCloud was first called iTools, released on January 5, 2000, and made available free of charge for Mac users.

Services offered by iTools included the first availability of @mac.com email addresses, which could only be accessed through an email client (e.g. the Mail app); iCards, a free greeting card service; iReview, a collection of reviews of popular web sites; HomePage, a free web page publishing service; the first version of iDisk, an online data storage system; and KidSafe, a directory of family-friendly web sites.

.Mac[edit]
As costs rose, most particularly due to iDisk storage space, the wide demand for @mac.com email accounts, and increasing support needs, iTools was renamed .Mac on July 17, 2002, as a subscription-based suite of services with a dedicated technical support team.[25]

... Existing iTools accounts were transitioned to .Mac accounts during a free trial period that ended on September 30, 2002. This move generated a mixed reaction among Mac users, some believing .Mac was overpriced...

[2] eWorld https://en.wikipedia.org/wiki/EWorld

. Yesterday the password for App Store was different from password for Apple ID but today they seem to be same. I think they are two different systems that update every few hours...

 · Feb 19

Today it appears there is a single Apple ID with two usernames and one password. One username has iCloud services but is nowhere displayed in Apple ID information. twitter.com/jgordonshare/s…

... If you change a phone's Store ID to match the phone's iCloud ID  you cannot update all their apps with their iCloud ID password. You need to use the old Store ID password. Even when family sharing is in play...

... I have a hunch that Apple has an internal ID for users separate from the username (email form) displayed with their Apple IDs and Store IDs and iCloud IDs and that is what they use in FairPlay. 

ToDo apps: Microsoft's solution

I've used Appigo's ToDo app for about 12 years (with Toodledo at first). It's had problems over the years, but in general it's been a good subscription choice. There's a fairly hard data lock (maybe SQLite?) but manual reentry is feasible albeit annoying.

Lately, however, ToDo has been more ragged. A recent server side change induced a date bug (time zone?) that in turn showed me I was using a macOS app last updated in 2016. It appears to have been abandoned on the Mac App Store. When I went to Twitter I found Appigo's account was closed years ago for violating TOS. Eventually I found I could download a current version of their other App Store app from their web site.

At the moment the app is more or less working again, though parts of the macOS app UI are kind of weird. I figure there was some violent ownership transition with lost dev passwords in Appigo's history (maybe they got ransomwared?).

I decided to go shopping again. I'm looking at:

• Apple Reminders: hard data lock and I have to upgrade from Mojave to get to latest version (not happening).
• Google Todo: this is one hell of a weird product. WTF is their web strategy? Tied to Gmail? Tied to Calendar? At least there's data export.
• Things
• OmniFocus: poor Omni is in some disarray ...
• Microsoft To Do

Today I dug into Microsoft To Do. Of course it's a mess, but this is 2020 so we expect that. The mess starts with Microsoft reusing product names. To simplify a bit:

• There are classic Outlook Tasks. I'll call these TasksClassic. TasksClassic was excellent in many ways, including, once upon a time, great import/export options and lots of view flexibility (I like to sort by last modified!). Unfortunately it's dead, just barely hanging on in the current desktop app with some degree of synchronization with the new product.
• There's the new Wanderlist-based product variable called Microsoft To Do and ... Outlook Tasks (name reuse!). I'll call these TasksW for Wanderlist.

If you open the Help screen page for macOS TasksW (To Do) it takes one to a page on Outlook synchronization that's obsolete -- because the Outlook.com version of Tasks has switched from TasksClassic to TasksW. On the other hand the version of Office 365 on my Mac still has TasksClassic, and it does synchronize with TasksW as displayed on macOS and iOS Microsoft To Do.app.

Are you still with me?

This gave me a brief moment of hope that there was some data freedom here. I remember the import/export options of old Windows Outlook. Alas, the only import/export from macOS Outlook is Microsoft's PST format. There might be some way to do things with Outlook Windows or with 3rd party tools but I don't have the energy for that.

At this time I think TasksW is probably a decent enough product, but this has reminded me how screwed up Microsoft is. So I'm setting this one aside for the moment.

See also:

• There are no great task managers for the iPhone - but there's hope for 2011: My current task list started out on the Palm III and has migrated many times. I probably have uncompleted tasks from the 1990s. I think we're coming to the end of that data migration though. Note from 2010: "Google might finally provide an API for Google Tasks, allowing iOS client development."
• My ancient spreadsheet on migrating from Palm to iPhone - I think I used Outlook Tasks as part of the migration process, or maybe even Microsoft Access. Alas, too long ago. Painful though.

Appigo Todo Cloud.app - don't forget to unsubscribe when you leave

Even since iOS 11 editing in Appigo’s Todo Cloud.app has been buggy for me on iPad and iPhone alike. Just aggravating. Feels like they failed to revamp something. I wasn’t delighted with their sync technology, but I could live with that. The editing bugs finally broke me.

So I decided to exit. Somehow I remembered Todo Cloud is a subscription service. I found my way to the somewhat hidden account settings and disabled premium. Turns out that turns off auto-renewal. 

Hope it really works.

Appigo is a textbook example of how subscription solutions can disappoint. They never provided a good export strategy, so there’s a strong data lock. Then they failed to do minimal maintenance but continued to collect subscription revenue and sell the app.

So what will the replacement be? I’d like a product that

1. Did what Appigo ToDo Cloud did but actually worked
2. Had a web client as well as Mac, iPad and iPhone client
3. Supported family sharing
4. Had good data export (exit strategy).

I evaluated Things.app and OmniFocus. Things got #1 and 3. OmniFocus got #1 and 4. Neither got #2.

Hmm.

On the other hand, Reminders.app for iOS got #2 and #3 and it’s free. So it’s weirdly in contention.

For now I’m using Reminders.app for tasks and Trello for projects. I manually copying over tasks that had dates, it’s not too bad. The backlog of ‘someday’ tasks I’ll gradually slog away at.

If Things gets some data export I’ll probably buy it, but it’s expensive since it’s not a universal app. If OmniFocus gets family sharing I might buy it. Meanwhile I’ll see what I can make Reminders do.

I think this is my first significant iOS functional regression.

Update 5/22/2018

I just discovered I wrote about this in 2011 …

There are no great task managers for the iPhone - but there's hope for 2011

… Neither Things, nor Appigo’s ToDo.app (which I have used incessantly since 2008), nor OmniFocus, nor Remember the Milk.app nor Toodledo.app are a great solution. They all fall short…

Seven years later and ToDo.app is moribund (I’ve been using it for 10 years!) and both OmniFocus and Things are still flawed.

Since I first wrote this I’ve run into issues with Reminders.app — including sync bugs and even text editor bugs. On the other hand, OmniFocus is promising a web client. I’m going to transiently switch back to ToDo.app and see if WWDC providers some kind of family sharing for subscriptions. That would make OmniFocus pricing less extreme.

Scrivener - the book compiler. Review.

I'm using Scrivener to write Smartphones for All - Using iPhone and Android to build independence for atypical minds.

It’s brilliant software. On my Mac it uses the same text editing engine as TextEdit, including the same RTF format. So, like the Nisus Writer I once used, my writing is indexable by Spotlight and almost as future-proof as plaintext. (I thought RTF was dead. Guess not.)

Apple’s text engine has its share of bugs and limitations, but for basic text work it’s good enough. The primary weakness is table layout, but so far I’ve worked around that.  Scrivener manages the tasks TextEdit can’t do, like page references, footnotes, internal links, document structure and the like.

The real brilliance though is how Scrivener merges concepts of software code management with the traditional word processor. It treats text blocks as though they were blocks of code, including simple version management and “compiling” to multiple output formats (PDF, EPUB, etc). Rather than use some horrid database store, Scrivener leverages native Mac file structures to manage its data. Extra brilliance points for that.

On this compile framework Scrivener layers a rich set of power user features. The latter, I admit, can be overwhelming. I recommend learning the basics from the initial tutorial, then start writing and learn additional features over time.

All software dies. One day Scrivener will die too. But with the ability to complete to multiple formats, and the use of native file system semantics and RTF data, Scrivener is as future proof as any power tool can be [1].

[1] Scrivener’s design is a guide to how photo management software should be built. Please, someone do this.

Calendars 5.app for iOS - don't break my heart.

I've only been using Calendars 5 for a few hours and I'm in love.

I'm sure I'll hate it eventually, but I usually do my hating faster than this. Calendars 5 is the best calendar app I've used since DateBk 5; it gives me hope I can survive Johnny ("The Designer") Ive's kneecapping of iOS 7 Calendar.app.

This is what we've needed. No #$@$@ wasted white space. This is a Calendar app that lets us actually, you know, see the friggin' appointments.

It synchronizes with any one or more of Google Calendars, Google Tasks, and the "native" iOS Calendar apps. I think the Google Calendar sync is using Google's native APIs; I didn't have to use Google's odd web page to setup CalDAV sync for multiple Google Calendars. i had only to enter my Google credentials and all my 15 or so Google personal, family, and subscribed calendars were immediately available.

But what about my Corporate Exchange Calendar? I figured that wouldn't work - but I was wrong! I enabled 'Native'/'Local' Calendars as well as Google (when I first connected it seemed I could do only one or the other, that's wrong) and I picked up my corporate calendar that way [1]. (Calendar.app on my phone also has my Google Calendars, but native support is much nicer than CalDAV support so I disabled those.)

I don't use Google Tasks, but Emily has been reluctant to add the complexity of a separate task manager to her Calendaring. With Calendar 5 there's only one place to look.

List, Day, Week and Month view in vertical and horizontal layout are all effective on my iPhone 5. Did I mention Search in List view? Fast!

This is the Calendar app I've been waiting for. Not Cue, not Fantastical, not Agenda -- this one.

[1] I didn't try to edit that Exchange Calendar, that barely works at the best of times on Calendar.app.

Tip: Use contexts in Toodledo, Appigo Todo.app and others to identify quick tasks

For historic reasons, and because between the two of them I have a unique set of features I can't find elsewhere, I use Toodledo online and Appigo's Todo.app on my iPhone (they sync). The combination is a bit of a kludge, but by now they are burned into my brain. It would take real improvements for me to switch, and I haven't seen them [1]. For example, Appigo's online task app is missing Toodledo's essential mailto feature.

Despite years of use however, I've not done much with Contexts in either Toodledo or Todo [2]. I understand the theory, but in practice it's been too much bother -- until today.

Today I realized what I needed was an easy way to tag small tasks that I can easily knock off when I have a free minute or less -- and I realized a single letter context was a convenient way to do that. So I deleted all the unused Contexts I'd created, and added a new one called 'q' (for quick!). Now, when I'm bored, I filter on q and knock off a bunch of little tasks.

[1] I could build such a great task app if I had another life or two ...
[2] Todo syncs contexts with toodledo. 

Pre-Lion Macs: Go iCloud or Google?

It's been a while since I reviewed the PIM world [1], but a post on CardDav sync between MacOS Mountain Lion (10.8) and Google Contacts brought me up to speed. In particular, I thought about the special case of a pre-Lion Mac user (Snow Leopard and Leopard especially - 10.6 and 10.5). I'll assume for the purposes of this post that every Mac users also has an iOS device.[2]

Every Mac/iOS user has to choose between Google and Apple for Calendar and Contacts (and thus Email). On Mountain Lion (or Lion) the choice is more difficult; those operating systems can work directly with Apple's iCloud. So it's not a slam dunk decision [3].

On pre-Lion Macs however, the choice is fairly easy. Older Macs can't use iCloud sync or data services at all; they can only access the web interface to iCloud Contacts and Calendars. On the other hand, even old Mail.app can use Google's (troublesome) IMAP services, and old versions of iCal can more or less interoperate with Google Calendar. Google's web interface to Contacts is crude, but their Calendar web services are much more robust than iCloud calendar. If there were any doubt, Gmail and Google Docs would seal the deal [7].

So, if you're an iOS/Snow Leopard user you can (mercifully) forget about iCloud. You need to use Google; for maximal Google compatibility SL users can even install Chrome [5].

You still have one choice though. You can:

• pay for Google Apps ($50/year) and use ActiveSync [4] on your iPhone and web UI on your Mac with optional user of iCal (CalDAV) and Mail (IMAP) on the desktop [6]
• use ad-supported Google Services and use web UI on Mac and the standard sync services for iPhone or Mac: CalDAV (calendar), IMAP (Mail), CardDAV (iPhone, not Desktop alas).

I don't think ActiveSync is necessarily superior to CalDAV/IMAP/CardDAV any longer -- but it is simpler to setup on the iPhone. Still, that's not enough to choose between paid and ad-supported. The main thing you get for your $50/year is freedom from ads and phone support. The last isn't a small thing.

Snow Leopard users used to feel abandoned and left out. No longer! Sometimes lack of choice is a feature. Apple has spurned you, Google awaits with open arms. What are you waiting for?

--

[1] PIM: Personal Information Management. Always includes Calendar and Contacts; since PalmOS usually tasks and notes (or equivalents). In the 90s it was mostly PalmOS and Palm Desktop for me, in 2013 it's a bit more complex:

• Contacts: iOS/iCloud/MacOS/Win7OutlookExchange via ActiveSync + Google/MacOS via CardDAV
• Tasks: Todo.app/Toodledo via proprietary + iOS/Win7OutlookExchange via ActiveSync
• Notes; Simplenote/Notational Velocity
• Calendar: iOS/Google via ActiveSync + iOS/Win7OutlookExchange via ActiveSync

I've simplified a few of those connections. I think we're starting to hit the boundaries of human cognition.

[2] If you're Mac/Android you have to Go Google. Mac/RIM or Mac/Microsoft -- you're on your own and you're used to being hard core.

[3] I've largely gone Google myself.

[4] I don't think Google offers free versions of Google Apps any longer. I'm from the early generation when it wasn't hard to end up with a half-dozen App/Domain combinations all of which were grandfathered in to ActiveSync support.

[5] Real old Mac users may want to try Camino.

[6] It's not clear to me that Google Apps users can use CardDAV services.

[7] iCloud can still be used for iDevice backup and media services, but trusted friends tell me the backup is unreliable.

iCloud: how is it going?

Apple, for about the fourth or fifth time, is trying to deliver network based services (their early attempts predate the internet).

This time it's iCloud.

I don't have any personal experience with iCloud. My family is still on MobileMe; at the moment I use it only to sync Contacts between iPhone, multiple OS X machines, and even an instance of Outlook running in an XP VM [1]. To Apple's credit, they extended our service period after introducing iCloud [2].

I haven't moved to iCloud because, although Apple 3.0 did well with iTunes, it has an abysmal track record with things like Calendars, Contacts, and Tasks. I don't know why. I assume it's because those were career killers at Steve Jobs' Apple. Maybe he wasn't interested, maybe he assumed the considerable problems were trivial compared to the things he cared about.

I'm hoping Apple 4.0 will do better, but iCloud is a Jobs-era project. So I don't expect it to start well.

So far there haven't been many iCloud reviews I trust. I suspect the people I do trust don't trust Apple -- so they're hanging back. Tidbit's Rich Mogull posted on his experience. It was miserable...

... within minutes I realized the enormity of my error as all my calendars, on all devices, simultaneously disappeared. Lacking a corporate calendar server, this meant years of old appointments, and months of upcoming appointments, were all gone...

... Since I’m good about backups, I figured I could restore from Time Machine. In a few minutes my calendars were back to normal... and a few seconds later they were all gone again. “This,” I thought to myself, “is bad.”...

... but as anyone who experienced a sync conflict could tell you (which was pretty much everyone) each device maintained its own data and made its own decisions...

Yep, that's what I expected. It's not that Mobile is any good -- Rich isn't joking when he wrote that every MobileMe user has had sync problems. Synchronization is Hell, after all. Rather that there's been no reason to expect Apple 3.0 to do better with iCloud than they did with MobileMe.

Elsewhere Calendar Swamp has given up on iCloud. That's two.

On the other hand, nobody has anything good to say about iCloud support for Contact, Task and Calendar synchronization.

So my best guess is, iCloud is doing as expected. That is, badly.

Now we get to see what Tom Cook cares about. Will he invest resources to make iCloud work? Heaven knows, these days I really want an alternative to Google.

I'll check back in about 2-3 months.

[1] Where one can use Access 2003 to manipulate calendar data. I use Google Calendar for our family's 15 (total) calendar subscriptions. It works pretty well, though I fear for its future.
[2] That's the way to sunset a service. Google hasn't done nearly as well with its recent service terminations.

Toodledo: How you can give me the search I need with your current architecture

I've been a Toodledo web app customer for years. I use their web task management service with Appigo's ToDo.app.

It's an old relationship born of historic necessity. Toodledo and Todo don't approach tasks and projects the same way, there's the usual awkwardness of dueling data structures. These days most people would want to use Toodledo's cloud service with Toodledo's iPhone app or Appigo's Todo.app with their Todo online.

I've lived with the two for a while though. I appreciate Appigo's elegant iOS client, and it rarely fails me. That reliability means a lot. I know what works with Toodledo and what doesn't; I only use what works. On the other hand, I admire Toodledo's wide range of task integration and data liberation policies, especially the ability to mail myself a task. That's huge.

On the other hand, I need Todo's full text search. I've been pestering Toodledo to provide full text search of my tasks for (literally) years. They won't do it. So I have full text search of tasks on my iPhone but not on the web. On the web I can only search within a field (default is the task title).

Frustrating. I'm ready to leave both of them for something better. Still, I'll make one last try to persuade Toodledo that they can give me 80% of what I want without abandoning their current infrastructure.

Toodledo, here's the search I want built using your save search function, where "term" is the string I want to search on.

See, it's not so hard. You can do this with your current infrastructure by

1. Let me save this search with a name.

2. Let me make the named search my default search.

3. Provide a checkbox that means "search all fields with this string". Check it and gray out two of the fields leaving me one to type in (there are more elegant UIs obviously, this one has the fewest changes).

Thanks for considering this!

Update: Even simpler. Just let us save this as the standard search.

Update 9/12/11: This time Toodledo had a different response to my inquiry: "This is on our to-do list, but it is our policy to not comment on our roadmap or delivery dates for future feature improvements or bug fixes.". Joy!

Lessons from sharing our team videos

In a burst of foolish optimism, I volunteered to do some videos of our team pitchers and share them.

This turned out to be much harder than I imagined. It's one of those tasks where each step has multiple options, but only a few choices really work.

Along the way I tested and abandoned MobileMe's video gallery [1] and Karelia Sandvox [2]. I briefly considered then discarded Picasa Web album video sharing.

I did figure out a path that works. Two of 'em actually. I'll share the easy one first.

The easy option

Use an iPhone. Take short clips. Don't edit. Upload. Share links.

The much more painful deluxe option

The deluxe option assembling multiple video fragments from a Canon dLSR HD video camera into a one video for each pitcher, then embedding them in a web page.

If I ever do this again, this is what I'll do for the deluxe option.

I. Getting the video

1. Bring a tripod (!) and an external microphone.
2. Have the coach use the external microphone to narrate comments.

II. Use iMovie and share via YouTube hidden links

This was the first time I used the new iMovie. I read a few pages in the surprisingly well done Portable Genius Guide to iLife (see [3]).

1. Each player gets one Project/Movie.
2. Edit in 3:4 ratio -- this is the pitcher we're working on.
3. From iMovie share to YouTube as "private" at the highest available resolution.
4. In YouTube change these to "hidden".

This is time consuming. It took about 10 minutes for each clip to create a movie and upload. An alternative would be to export as .mp4 (NOT default .m4v) then bulk upload overnight [4]

III. Share images using Blogger and MarsEdit or HTML markup

1. I tried a few web page editors, but, as noted above, I didn't have much luck.
2. Instead I used YouTube's embed code (iframe markup) and pasted the embed text into the MarsEdit HTML view for each video. It was tedious but gave good results.

- fn -

[1] I'd not tried it before. Now I see why Apple gave up on the Galleries.
[2] Crashed on me during my video uploading attempts. Could be just bad luck -- pretty much every OS X app I use crashes sooner or later. Almost like 10.6.7 is an unhappy host OS. Still, bad timing.
[3] iMovie notes

• Clip Library is a pool of shared clips that can be included by reference in multiple Projects (movies). Clips can be stored in iPhoto, Aperture 3+ or iMovie. I think Clip processing is smoothest if they live in iMovie. Clips can be split, reorganized, rated, merged. Even deleted, though that's not obvious.
• A "project" is a movie.
• In a clip or a project/movie click to set start point, space to play
• click then drag to create a frame within a single clip (can't span clip): Click into  this frame and drag and drop to the Project area. It took me forever to understand this. I kept thinking I had to edit the clip first.
• Native export is .m4v -> evil, vile, worthless, foul spawn of satan. Want .mp4

[4] The settings to make this work are not obvious. I got decent results when I used Export to Quicktime, MP4, then set data rate to 4096, image size 768x576, Fit within size for crop, and "best quality" encoding mode in video options.

There are no great task managers for the iPhone - but there's hope for 2011

I'm surprised by the conclusion of my recent survey [3] of iPhone/OS X/Web task management solutions. There are still no great task managers for the iPhone.

Neither Things, nor Appigo's ToDo.app (which I have used incessantly since 2008), nor OmniFocus, nor Remember the Milk.app nor Toodledo.app are a great solution. They all fall short. None of them are the equal of the venerable, simple minded, task manager that came with the PalmOS in 1994 and was improved with integration into DateBk in the late 1990s.

You may wonder why I condemn all of our current options. I'll start by listing the base requirements.

1. Simple enough for a non-geek to use with at least basic task attributes (due date, priority, task name, description, category [1]) and views (filters, sorts).
2. Data freedom: import/export capabilities for all tasks.
3. Synchronization to a desktop or web version that matches the "data model" of the iPhone version and has the same usability standards. [2]
4. Affordable (total solution costs < $50)
5. Calendar integration, even if that's only an "agenda" type view of tasks and dates.
6. Search across all "fields" (attributes).
7. Utter, absolute reliability.
8. Instant on, no delays in task entry.
9. Archiving of completed tasks.
10. Local iPhone app with synchronizatio -- not dependent on a data connection to work.

Sounds easy, doesn't it?  Palm did most of this fifteen years ago, and Pimlico's DateBk delivered the complete package (and more) over ten years ago. Must be easy [4]...

Evidently not. Nobody does it for the iPhone today. Let me name the failures ...

1. OmniFocus is too expensive ($100 for iPhone/desktop pair) and is too complex. At a lower price point though I'd seriously consider them despite the complex. I'm an Omni Group fan.
2. Things has reliability issues, is too expensive and doesn't support data freedom. Their iTunes ratings continue to decline.
3. Appigo's ToDo.app doesn't have a robust and reliable web or desktop solution and lacks data freedom. The best option is to sync with Toodledo's web app, but that app has a different data model than ToDo.app. This is what I use every day however.
4. Toodledo's own iPhone/web solution is limited by their complex (and, sadly, ugly) web app. The web app search is field specific and so almost useless.
5. Remember the Milk has a bad reputation as a business partner, their iTunes ratings are poor (?reliability), they are relatively costly at $25/year, and there's no data freedom. (Corrected from original - see comments.)

It's a sad situation. The best option is still the combination of Appigo's ToDo.app and Toodledo's web service; I pay for both. I do, however, grit my teeth every time I use Toodledo's web client, especially if I need to search for something.

I'm hopeful we'll see a fix in 2011. There are at least three ways the logjam could break.

Apple's OS X app store could reenergize the flagging OS X desktop, and new desktop products might appear at better price points. If Apple were to provide OS X App Store developers with a standard way to synchronize to iOS devices I'd expect a great solution. Alternatively,  Apple could forget it hates its customers, and finally put a bullet through iCal (sadly, will require 10.7). Lastly, and least likely, Jobs might decide he doesn't totally hate task managers after all.

Google might finally provide an API for Google Tasks, allowing iOS client development. Or they might provide HTML 5 (Gears-like) offline Google Tasks web app with synchronization support for Safari. [6]

Lastly, the Omni Group could create a "lite" version of OmniFocus for the App Store and sell both an iPhone and desktop OmniFocus Lite for under $50.  Or some other current vendor will fill out an existing solution.

If we assume an average probability of each of these outcomes of 50%, there's an almost 90% probability [5] we'll get finally get a great iPhone task management solution next year.

I'll raise a beer when it happens.

See also (mostly not about tasks, but all about PIM functions and the amazingly hard Palm to iPhone migration)

• Why the iPhone doesn't do tasks: a theory (2007 - how sad. I thought we'd see a fix in 2008! Later I decided that Jobs hates task managers.)
• Gordon's Notes: Cloud data: Should I trust (Simplenote) Simperium? (2010 - No. But do trust in data freedom.)
• Migrating Notes from ToodleDo to ResophNotes and the Simplenote ecosystem (2010, notes were hard too.)
• Nerdvana now: Our family calendar is working – and how Gmail parses Outlook invites (2008. Things got better. Calendars are still not perfect (CalDAV vs. ActiveSync vs. iPhone data models esp with invitations) but this is one PIM functionality that's substatially improved over the past twenty years.)
• Gordon's Notes: The descent of the PDA: Newton, Palm, Blackberry and iPhone (2008)
• My Palm to iPhone migration challenge -- summarized (I've updated the spreadsheet describing the nasty Palm to iOS migration.)
• iPhone ToDo app and why my reviews are better than the rest (2008)
• Palm to iPhone migration - address book and notes (2008 - mostly historic, Simplenotes.app was the real fix)
• Palm to iPhone - only the notes remain (2008 - Evernote then, but I gave it up. Then Notebook.app, finally Simplenote)
• Gordon's Notes: What the iPhone needs is Gorilla Haven’s DateBk6 (2009 - it did show up on Android as Pimlical this year)
• Palm to iPhone - the summary and Palm to iPhone - the update (2008 - I like the pictures)
• Palm/Palm Pilot: Personal Experiences and Tips (My 1990s era PalmPilot page - just for the nostalgia. Things got ugly there too.)
• Synchronizing iPhone to Google - a review

- fn -

[1] The big "breakthrough" change to the Palm ToDo (task) list was the radical addition of up to 16 categories. For quite some time Palm tasks lacked "categories" (single tag). The original Palm design team were even more radical minimalists than Apple's modern iPhone OS team.
[2] This is huge. If data models don't match perfectly non-geeks, and even geeks, will eventually be frustrated -- even if they don't understand why they are frustrated.
[3] Looking for a good solution for Emily, and deciding none existed.
[4] I'm being sarcastic of course. One of the hardest things in software development is deciding what to omit. It's the old line about sculpture - great art consists of removing the inessential.
[5] 1 - (1/2*1/2*/2) = 7/8
[6] More likely now that the Google/Apple war is over.

After the hack: A disposable Google Identity

Aside from the tedious task of reviewing and upgrading a large number of passwords, the biggest change I've made after my Google account was hacked is that I no longer enter my important credentials on untrusted devices. That includes any machine that lives in the virus and Trojan infested world of the XP based American corporation.

This is a bit of a pain. It would be less of a pain if my iPhone had a keyboard [1] and could drive an external display, but that's a few years away.

For now I'm taking a two step approach when I work with devices I don't control (non-OS X/iOS).

1. Using email as a transaction source.
2. Creating a disposable alter ego - a full gmail identity with limited privileges.

There's a lot of typing work I can do using email to "secret" addresses. I can mail tasks to Toodledo which in turn sync to Appigo's ToDo.app on my iPhone. I can mail drafts or posts to Blogger. I can mail invitations to my Gmail address that will turn into Calendar invites. I can't (yet) mail to Reader Shared Notes, but there are workarounds [2].

Of course a keystroke logger will capture these addresses, but there's no money in abusing these and the damage potential is pretty small.

The second task will be much easier when Google finishes the big project of integrating Google App identities with the Gmail/Google Account infrastructure. When that's done it will be easy to create disposable identities with shared access to calendar and contacts. That's many months away however, and based on some early testing a standard Google App account isn't quite good enough.

So for now I created a full Gmail account to serve as a disposable identity. It will have access to our family calendars and will have read/write (but not admin) access to my blogs but minimal access to Contacts. If I lose control of that account, I'll remove its privileges and walk away.

Annoying new world!

[1] I'm hoping to buy a kb like the one I used to use with my Palm Vx ten years ago, but I get the sense manufacturers are waiting for iOS 4.2.
[2] I mail to buzz.kateva.org which I follow in Reader. I Google Reader share from their.

Migrating Notes from ToodleDo to ResophNotes and the Simplenote ecosystem

[Shortly after I first wrote this, C.Y. released ResophNotes 1.0.5. Among other things, such as the ability to store notes as indexable .txt files, it has direct support for importing ToodleDo’s CSV file. He’d told me the release was coming soon, I did it my way just for geek fun. I’ve therefore moved the details of what I did to a footnote. BTW, turns out C.Y., like me, migrated to Simplenote from Toodledo/Appigo!]

Once I'd rescued my memory fragments from Outlook 2007 my next goal was to unify them from the former Palm Memos I'd (painfully) migrated to ToodleDo and thus Appigo's Notebook.app.

I've been reasonably happy with the combination of ToodleDo and Appigo, but notes are very much a 2nd class citizen on ToodleDo (they're all about tasks) and their search tools are pretty weak. I also wanted to be able to access and work with my notes from my desktop on Windows and the Mac, to be able to back them up, to have them be exposed to Spotlight search on OS X, to integrate my old corporate Outlook Notes with my old personal former Palm Memos and to have at least one open source repository in the mix. I needed the notes to live in a standard file format (UTF-8 text or RTF) free of all data lock.

Sounds like a lot, but the combination of ResophNotes (XP and higher - free but do donate), Simplenote (Cloud, ad-supported or $9/year - I paid - see documentation), Simplenote.app (iPhone and iPad app, free) and Notational Velocity (open source, OS X - documentation) gave me everything I wanted -- plus Chrome extensions for editing.

There was only one thing standing in my way. How could I get my ToodleDo notes into Simplenote?

I knew that ResophNotes (Win) would import Outlook's peculiar CSV files (embedded paragraphs!), but the developer, C.Y. I still days away from releasing a more general CSV import feature. I was impatient, so this is what I did. (see footnote [1])

During my early import experiments, because I used a Mac for part of the process, I ran into character encoding problems. Since ResophNotes doesn't yet have note multiselect and delete [2] I had to find its database and delete it.

ResophNotes exports and imports .RSN files (yay! backup!), but that's not how it works with notes. I found them in "C:\Documents and Settings\jfaughnan" in a .ResophNotes folder (hidden). To delete them and start over you have to quit ResophNotes, then find the instance in Task Manager Processes and kill it, then you can delete the files.

That let me start over again.

BTW, here's how the notes look in Notational Velocity's "Notational Notes" store:

Yes, each note a separate Rich Text file (I may convert to safer plain text) -- all Spotlight indexed.

Just in time for my birthday.

Nerdvana.

[1] Now that ResophNotes has direct ToodleDo import, I’ll include this as a reference for how one might support CSV variants other than ToodleDo or Outlook. My procedure was especially weird because I happened to have a Mac at hand…

1. Use ToodleDo's Notes CSV export to my Mac.
2. Import into FileMaker and use Calculation field to merge the ToodleDo Title and Notes into an Outlook style "Note Body". I next renamed the ToodleDo "Folder" column to Category.
3. Created FileMaker columns to match Outlook's names, and exported as CSV. I had to paste this string in as the first row: "Note Body","Categories","Note Color","Priority","Sensitivity". I left all values except Note Body and Category null. In retrospect I should have appended "Categories" as a string to the end of "Note Body" to facilitate search.
4. I used TextWrangler to clean up some character encoding CR/LF issues. This was only necessary because I got a Mac in the mix. Curse that ancient CR/LF screwup. It seems to have survived into the world of UTF-8 encoding.
5. I fired up my Fusion VM (way better than it first was on 10.6) and my old XP image and moved the file over. I opened it in Word and saved as UTF-8 to remove any residual character encoding issues.
6. I imported into ResophNotes. When I was sure all was well, I synchronized ResophNotes with Simplenotes and all my notes merged into one lovely repository. I fired up Notational Velocity in another window and confirmed all was fine there as well.

[2] Since the latest version can store as .txt files, I assume one could just delete all the .txt files! I haven’t tried this tough.

Escape from Outlook Notes - ResophNotes, SimpleNote for iPhone and Notational Velocity

I had despaired of rescuing my notes from Outlook 2007.

I'd written hundreds over time. In the old days I used Palm products that would sync with Outlook, so I could carry them with me. Now my iPhone, after years of struggle, gives me good Outlook sync with Contacts and Calendars. Notes and Tasks, however, have been orphaned. There's no real hope of an Outlook Notes to iPhone sync solution; although a few people use Outlook Tasks almost nobody uses Outlook Notes.

I've learned to live without corporate Outlook Tasks (I schedule my time on a 3 week plan basis), but I wanted those notes. I decided they needed to live within either ToodleDo Notes/Appigo Notebook, iPhone Notes (unlikely), or the Simplenote / NotationalVelocity universe (for various reasons I've given up on Evernote).

Today I discovered ResophNotes, a Windows app that syncs with the Simplenote cloud data store. The Simplenote cloud data store, of course, also syncs with Notational velocity (open source, OS X Spotlight indexed), OS X Tinderbox, OS X Yojimbe (3rd party sync), and there's a Chrome extension for editing notes.

I exported my Outlook 2007 notes to Outlook's odd CSV format (includes line feeds!), then I imported into ResophNotes and synchronized with Simplenote's cloud store. Then on my iPhone I viewed them in the Simplenote iPhone client.

It worked better than I'd expected.

Now I can move my old (originally Palm III Notes, now ToodleDo/Appigo Notebook) personal notes to the same cloud store. I'll sign up for the $10/year premium Simplenote service. (Currently I have free version.) If Simplenote belly up the rich ecosystem and open source Notational Velocity desktop solution provides the insurance I need.

A good day.

See also:

• Gordon's Notes: The rise of software rental (aka software as service)
• Moving Palm notes to Toodledo via CSV file - what worked. (Hard!)
• Appigo Notebook is coming to the iPhone
• Kiss your Google Notebook good-bye
• Palm to iPhone migration - address book and notes (Aug 2008 - dated)
• Toodledo gets it
• Appigo and Toodledo – nasty emergent design flaw makes a mess of my iPhone Notes and Tasks
• Evernote's import/export test (updated)

Update 7/31/10: The author of ResophNotes tells me he's preparing a new version that will import CSV files -- like the ones ToodleDo Notes export creates. Incidentally, I discovered that FileMaker Pro 8 does a great job opening Outlook's CSV files with embedded line feeds. I never imagined ...

Appigo ToDo.app has lost RTM sync services

Appigo has a very fine task management application called "ToDo.app". I've used it for about two years. It allowed me to synchronize tasks to one of two cloud services: Toodledo and Remember the Milk.

About a year ago Toodledo introduced their own task management application, but Appigo's sync still worked on both RTM and Toodledo. Appigo also added a desktop sync app, though it's remained in 'beta'.

More recently RTM introduced their own iPhone app. On May 12th they turned off sync support for all their customers who used Appigo ToDo.app.

Appigo Todo and RTM

... Late Tuesday night, May 11, 2010, we (Appigo) were contacted by the folks at Remember The Milk via email in which they informed us they had disabled sync access for both Todo for iPad and Todo for iPhone. This service has been available in two of our apps previously (Todo and Todo Lite for iPhone). Todo for iPad was a natural extension and no sync code was changed to support Todo for iPad. We don't agree with their assessment, but including this service in Todo for iPad violated their developer agreement, which was only valid for Todo for iPhone...

A recent ToDo.app update disables RTM support -- since it's no longer available.

There's nothing about this on the RTM web site. For that matter, it's very hard to find anything about this on Appigo's web site either! The release history page, for example, says nothing about this update.

I doubt RTM will be in business in six months.

As for Appigo, they're not handling this very well. They need a lot more material on their main web site pages about what's going on.

Toodledo, where I'm a paying customer, is the only party that's coming out of this looking good. I like their "data freedom" approach to managing customer information.

Why Apple's Notes.app and Voice Memos.app are newly on my home screen

One of the design principles of the original PalmPilot was "no delays". In the time it took to get to the Newton's note pad, the PalmPilot and Palm III user would have entered their task item and put the device away.

I miss that philosophy. It takes about 30 seconds for may of my 3G iPhone 3rd party apps to accomplish simple tasks.

Apple's apps are much faster - though still not as fast as the Palm III native apps. So even though I like the 3rd party alternatives much better, Apple's Notes.app and "Voice Memos.app" are back on my home screen. The better apps are just too slow.

My standard iPhone configuration

I've recently configured 3 iPhones - one for Emily, two for friends. So the configuration routine is fresh in my mind and ready to share.

I'll hopefully update this with some reference links, but here's the quick summary. The phones are configured around Google Services, except for Contacts which are a festering sore in Google-Land.

Basic setup

1. Check version (lately has been 3.1)
2. Turn off auto-ask WiFi
3. Picture of business card as wallpaper (so phone can be returned if found)
4. Google-phone configuration
5. Auto-lock to 2 minutes, show passcode lock
6. Mail: Show To/CC label, Signature, Default account (if needed),
7. Contacts: Sort and display order, Default account (if needed)
8. Calendars: Time Zone support Off, Default Calendar (if needed)
9. Demonstrate use of the Search screen

Google-phone configuration (calendar sharing)

1. Mail: Default iPhone Gmail setup (IMAP)
2. Google Calendar Configuration including Calendar subscription and sharing
3. Calendar and Google Contacts: Exchange Server ActiveSync then Google Sync so phone can display multiple Google Calendars selected from the primary Google Calendar collection (m.google.com and tap on "Sync") [1][2]. Warning: This setup tries HARD to get you to wipe out all other iPhone accounts. Be careful not to do so. In the setups I do people sometimes need to sync with an Outlook desktop calendar, and they almost always need to sync to a desktop Contacts collection. [2]
4. Desktop Contact synchronization (this is controlled by iTunes) [2]

Third party apps (install and configure)

1. Google Mobile (m.google.com)
2. Facebook
3. Optional: Appigo Tasks.app sync to Toodledo

Problems

1. No Google task sync solution
2. Google Contacts smell of squashed skunk
3. Only one Exchange Server account per phone (CalDAV?)

See also: My iPhone Home Screen

Footnotes

[1] For Google Apps setup see a recent Google Sync post of mine.

[2] The one substantial advantage of MobileMe for Mac users is the Contacts integration. If the Calendar sharing were not so pathetic and the data lock not stronger than Sauron's Ring it would be interesting.

Tasks from Palm to iPhone via Toodledo

I don't think this was available when I moved my PalmOS tasks to my iPhone.

Toodledo will import PalmOS Task archives: Toodledo : Palm PDA Import/Export.

So you can import your tasks to Toodledo, then sync them to your iPhone using either the Toodledo iPhone app or Appigo's Todo.app.

I've used Toodledo and Appigo Todo.app for over a year. Neither is perfect, but they're both a solid B+. I really don't know a better solution.

PS. How could they be better? Well, if Appigo doesn't make any more bone-headed changes to the Todo.app (they've mercifully reversed some past mistakes), and if Toodledo stopped deleting tasks > 1 yo and changed quick search to scan all task fields, then they'd be a solid A.

Update: Incidentally, I'm experimenting with the RSS feed view of my tasks in Google Reader. I think I'll figure out a good use for this feature.

Buying my Chrome OS (XP) Netbook

Apple saved me some money the other day.

Apple persuaded me that I should forego a MacBook Air or new MacBook in favor of a netbook running Google Chrome atop creaky old Windows XP.

Thanks Apple.

I thought of waiting for Windows 7, but then reality spoke up. Regardless of what anyone might say, I know that Windows 7 won’t really work on a paltry Netbook. In any case Microsoft will pull XP from the market, jack up the price of the OS, and try to push everyone to high end machines (Ballmer has said as much publicly).

Makes more sense for me to buy an XP Netbook before Win 7 comes out, and just run Chrome and Windows Live Writer. It will be my preview version of Chromestellation.

I’m going to need a companion data service, but I’ll add that as a dongle or use the Verizon MiFi (No love for AT&T here) …

… the Novatel MiFi 2200, available from Verizon starting in mid-May ($100 with two-year contract, after rebate). It’s a little wisp of a thing, like a triple-thick credit card. It has one power button, one status light and a swappable battery that looks like the one in a cellphone. When you turn on your MiFi and wait 30 seconds, it provides a personal, portable, powerful, password-protected wireless hot spot…

…The MiFi gets its Internet signal the same way those cellular modems do — in this case, from Verizon’s excellent 3G (high-speed) cellular data network. If you just want to do e-mail and the Web, you pay $40 a month for the service (250 megabytes of data transfer, 10 cents a megabyte above that). If you watch videos and shuttle a lot of big files, opt for the $60 plan (5 gigabytes)…

…If you type 192.168.1.1 into your Web browser’s address bar … the MiFi’s settings pages magically appear. Now you can do geeky, tweaky tasks like changing the password or the wireless network name, limiting access to specific computers, turning on port forwarding …

…The MiFi recharges from a wall outlet; it still works as a hot spot while it’s plugged in…

With the MiFi you can get your App Store-plagued iPhone off AT&T’s dying data network.

So, which Netbook to buy? Here Amazon, as usual, is my friend. The #1 seller in Amazon’s netbook category is the $380 ASUS Eee PC 1005HA-PU1X-BK 10.1-Inch Black Netbook (with $20 for an upgrade to 2GB)

Display: 10.1-inch 1024x600 LED-Backlit Widescreen LCD (Color-Shine/Glossy Screen Technology)

Intel CPU: Intel Atom N280

Wireless Data Network: WLAN: 802.11b/g/n (draft 2.4GHz n) & Bluetooth V2.1 + EDR

Camera: 1.3M Pixels

Audio: Stereo Speakers, High-Definition Audio CODEC, Digital Array Microphones

Storage Cards: 2-in-1 MMC, SD(SDHC) flash card slot

Input/Output: 1 x VGA connector, 3 x USB 2.0 ports, 1 x LAN RJ-45, 2 x audio jacks: Headphone & Mic-in

Dimensions: 10.31 (W) x 7.01 (D) x 1.02~1.44 (H) inches

Weight: 2.81 lbs (with battery)

Or what about the Acer Aspire One for $300? That one also comes with an evil AT&T service plan option (integrated 3G dongle) …

To be updated with my purchase decision …

Update 7/31/2009: In response to a provocative comment, I clarify my perspective on the logic of AT&T/Apple's actions.

Project Contacts: Now mixing Outlook/Exchange, PST file, Outlook/Home, MobileMe Sync, OS X Address Book and the iPhone.

A recent Apple Discussion Thread led me to take a new direction with Project Contacts.

To put it mildly, there’s a lot of complexity in this post. However initial results are very positive. This method will require me to purchase a MobileMe account, something I was hoping to avoid. (See below for a partial index to past efforts.)

The end result is that I have a single collection of work/home contacts across iPhone and OS X Address book at home. The work contacts portion of this collection is updated weekly. At this time the update is one way, from Work to Home.

For anyone who may be facing these challenges, I have provided a skeletal outline here of what I did and what I would do if starting from scratch. You will see how insanely complex this is. Note that as of this writing the care PIM data that was once in Palm/Desktop is now scattered across Google (Calendar and a detached set of Contacts), Outlook/corporate, Toodledo and MobileMe. Everything does come together in my iPhone. The current solution involves a wide variety of vendors. For example, Apple's MobileMe calendaring is pathetic; far weaker than Google Calendar and a joke compared to Outlook (which makes Apple's no-show on tasks even more crazy). On the other hand Apple's Contact framework is very robust, much stronger than Google and a rival to Outlook.

This ruddy mess is a real indictment of Apple and a fat opportunity for the PalmPre.

So much for prelude. Here’s the outline, strictly for the uber-geek:

Here’s what I actually did:

• Copying contacts from Outlook/Exchange root to Outlook PST caused the EX (Exchange server x.500) email addresses to be updated to SMTP (standard internet) email addresses.
• PST on thumb drive to home (simple)
• Copy into Home Contacts
• Sync to MobileMe
• In MobileMe web assign all to a Group
• Sync to OS X Address Book (small conflicts)
• Sync to iPhone (ok)
• Sync to Outlook Home: Each Group in OS X Address Book became a Contacts Subfolder in Office 2003. This means the cardinality relationship to Address to Group may have to be One to One.

Expected problem:

• Contact belongs to two Groups in OS X Address Book (multiple inheritance)
• Contact assigned to ONE Subfolder in Office 2003.
• In OS X change Group assignments.
• What happens in Outlook?

Here’s what I suggest doing (LOTS of backups of OS X Address Book as go along)

1. Outlook/Corporate create PST file, copy work contacts. Do not copy lists or groups of contacts, only contacts.
   
2. PST file to thumb drive
3. Home Outlook mount PST data file. Make sure Contacts folder is empty
4. Sync iPhone to OS X Address Book
5. Create new group in OS X Address Book that will hold corporate contacts
6. Sync to fresh MobileMe Account
7. Sync fresh MobileMe account to home Outlook
8. Now Outlook will have an empty subfolder. Dump the Contacts transported into the PST file into that empty folder.
9. Sync from Outlook to MobileMe
10. Sync from MobileMe to OS X Address Book
11. Sync to iPhone

A partial index to past and related efforts at work/home Contact integration:

• Synchronization (all)
• MobileMe (all)
• Outlook (all)
• Contacts (all)
• Synchronization is Hell.
• Root causes: Why you can't sync your work and home calendars to your phone
• Project Contacts: Integration across iPhone, Google and whatever
• Work home contact integration: Outlook to Google to OS X Address Book (X.500 EX email problem)
• Synchronization case study: Address Book, the iPhone, and Google Contacts
• iPhone sync to Google contacts - 3 methods and work/home implications
• Outlook contacts to OS X Address Book - 3 techniques
• Google saves my iPhone (Google Exchange Server emulation for iPhone)
• Googaby: Novel approach to Google Contacts and OS X Address Book integration
• OS X Address Book to Google Apps Contacs using Google ActiveSync
• Work home contact integration: Outlook to Google to OS X Address Book
• Access OS X Address Book records using OpenOffice database?
• Synchronizing iPhone and Gmail contacts: getting OS X Address Book into Gmail
• gSyncit vs Google Calendar Sync with Outlook 2007
• gSyncit for Outlook 2007 to Google Calendar and Contacts Sync
• Prediction: We won’t see a fixed MobileMe until 10.6 is out
• MobileMe alternatives – including for iPhone Sync (MacWorld)
• Palm Pre is Exchange sync based
• iPhone: MobileMe vs. Google services
• MobileMe, Microsoft Outlook, Exchange, iTunes and yes, sync Hell
• Is it too late to go back to Palm 1994?
• Palm to iPhone - the update
• Synchronization is hard - more evidence
• Palm to iPhone migration - address book and notes
• Spanning Sync tells us what's wrong with Google's free CalDAV sync
• Apple can't do synchronization - again
• MobileMe syncs with Outlook (but then Apple turned it off for Exchange clients)
• Interoperability and my Contact information: Microsoft Outlook and Access, FileMaker Pro and Palm Contacts

Update 5/15/09: Now that I've got this working I'm trying various optimizations. For example, my contacts don't change that often. It's easy to create a view in Outlook that sorts by modified date. It's fairly trivial to send out a few changed .msg in an email and let Outlook at home merge them in. I still have to think about how to work with Google's Contacts, but I'm seeing a few interesting options.

It's weird how powerful MobileMe contacts are, yet how feeble MobileMe calendaring is. We're due for a MobileMe relauch, so I expect some developments before September.

Lastly, I should probably mention why I took this route. The more I looked at the workarounds for getting Outlook/Exchange corporate contact data to Google or the OS X Address Book the worse they looked. Their are problems with data models, problems with the intractable horror of the Outlook Add-In architecture, problems with Exchange server and problems with corporate access. This approach is crude, but for me, once I figure it out, fairly painless. I think it will fly until we get something better.

In the meantime, I'm rooting for the PalmPre to humiliate Apple and make them reconsider the direction they're taking.

Update 5/15/09b: Now that I've got this setup working I can see weird new affordances. For example, one of my top 10 OS X frustrations is the inability of FileMaker to work with the Address Book SQLite data stores. Ahh, but now my address data is synchronized between Outlook/Home and Address Book, and I can use Microsoft Access with Outlook/Home. So I can clean things up there, and MobileMe sync will propagate my fixes. I think I'll find a way now to get my Google Contacts into the battlefront.

Update 5/16/09: Great comment by Faheem, who's achieved a similar outcome using Plaxo without paying for MobileMe. I took a look, but Plaxo didn't feel right for me.