An Odyssey from Mac to iPad

Earlier this fall, I decided it was time for a change. My iPad Mini 5 was getting long in the tooth, and I wasn’t all that happy with my 2019 MacBook Pro — I don’t care for the Touch Bar or the chicklet keyboard. I’ve also been getting the feeling that development on the Mac, for a number of applications, is beginning to lag behind equivalent features in iOS and iPadOS.

So I’m in the middle of a move to an iPad Pro 11 (M1) with the Magic Keyboard and the Apple Pencil v2.

Just to make life interesting, I also decided to move off of 1Password for a few reasons:

• V8 will be using the Electron platform, one of those develop-once-port-to-all-architectures plays that reminds me of the initial promise of Java, a promise that ended up with shorter development times but the UI and performance suffering from a decline to the lowest common denominator. V8 has been described as “a web app in a frame” and I agree. Ech. I suspect AgileBits will be losing a fair number of loyal customers over this.
• Over the last few years, 1Password has begun to feel a bit bloated, possibly trying to do too much.
• Strange inconsistencies in app behavior like not supporting text substitution (they do in iOS, but not in macOS), a rigid view on how the apps should be used, and a fairly insular vibe from the development team about feedback.
• Every time there was an update I had to go through the “quit everything completely and start fresh” dance. I haven’t ever seen that with another extension.

And to top it off, I decided at the same time to migrate off of OmniFocus, deciding it was simply a more complex tool than I needed.

In summary, my migration plate is fricking full.

Migrating from macOS to iPadOS

One of the main factors that makes this move even worth considering is that I’ve long-since moved all of my documents into iCloud.

Considerations:

• Audio Hijack — I’ve used it twice in the last five years. Not needed.
• BBEdit — I’m not coding anymore. Not needed.
• Handbrake, MDRP — haven’t used these in years as I’ve gone all in on streaming media. Not needed.
• TextEdit (sadly missing in iPadOS) — convert everything to Pages. A compromise.
• Photoshop — I’ve found OmniGraffle a more flexible and fun tool for my uses, and the vector graphics are more pleasing. This takes more work, but I thnk I’ll be okay with it.
• Signing documents. I usually did this in Preview (not available in iPadOS) but found that Files and Safari support this capability via Markup — And my signatures carried over from Preview, a bonus.
• Mail. iPadOS allows you to use all the same flag colors as macOS (something of which I wasn’t aware), but the implementation of smart folders is sorely lacking, so if you use flags a lot, you’ll find this constraining as you cannot, for example, filter for messages with a green flag. My solution was to simply reduce how much I use flags — which struck me as a good simplication anyway.

Migrating from 1Password to Keychain and Notes

Keychain won’t accomodate all the different data types I have stored in 1Password. In a way, that makes my point about 1Password doing too much. So I’ve distributed 1Password data types to other apps:

• Login credentials (about 350 of them!) are migrated to Keychain. The new 2-factor cabability in Keychain was one of the things that convinced to jump. And while looking up passwords in the Keychain app on macOS is painful, on iOS the Settings/Password interface is better.
• Using secure notes in Keychain is a pain in the ass. Installing secure notes as password-protected notes in the Notes app works really well.
• Credit cards get stored in Keychain and are accesssed via Safari’s autofill. It’s odd that Keychain doesn’t store the 3-digit security code for credit cards, but can be accomplished by the next bullet:
• Bank account and credit card info in 1Password gets moved into password-protected notes in Notes.
• There are times when one wishes to generate a complex password directly. I found a Shortcut that does just that and integrates nicely into the iPadOS share sheet.

Limitations:

• You cannot secure a note with a password if it contains a PDF. Weird.
• You cannot secure a note with a password if it contains a tag. Also weird.
• Keychain doesn’t handle multiple domains for a single login gracefully — for example, Conde Nast and the NewYorker are effectively the same account reached via two different URLs. In Keychain, you need separate entries — and then Keychain complains about using the same password for different sites. On the other hand, the model employed by companies like Conde Nast makes the security road warrior in me wonder whether that model might actually be less secure in the long run anyway. Note: turns out there are entries with multiple URLs for a given set of credentials — but as of now it’s unclear how to explicitly make that happen.

Migrating from OmniFocus to Notes and Reminders

I’ve been using OmniFocus pretty extensively for years. I confess I’ll miss the ability to set an item to repeat a specified period after completion rather than the more rigid calendar method. But I’ll get over it. All in all, I moved about 300 items out of OmniFocus:

• “Checklists” (lists of items where you want to check them off but not have them disappear) were moved into Notes’ native checklist format.
• Items with due dates were moved into Reminders.

Somewhat surprisingly, this went more smoothly than expected.

Caveats

While I feel I’ve managed to deal with most of the issues in this migration, there are a few things that remain problematic:

• OmniGroup, in their infinite wisdom, decided at some point that OmniGraffle for iPadOS would no longer support custom fonts, for example fonts installed from Adobe via Creative Cloud. When I called this out, their first response was “that’s just the way it is”, but when I argued that (a) this was supposed to be their “Premier Design Application” and fonts aren’t exactly a trivial aspect of design, and (b) that files created on the Mac would no longer necessarily be compatible with the iPad version, which is screwed up, their answer became “oh — our developers found the switch to make this work; we’ll be including it in a maintenance release real soon now.” I get the security concerns about bad actors using fonts for tracking, but this really should’ve been addressed long before now. I await the change before I pony up the subscription fee.
• While Lightroom Mobile handles about 90% of the things I want to do in photography (my needs are far less than they used to be — partly because my mantra, in many cases, has become “oh, just get over it”), the Mac version and in particular the Classic version (and, let’s be honest, the Mac version of Photoshop) still have features I may continue to need, like modifying metadata.
• Autopopulation of SMS 2-factor codes doesn’t work with the Magic Keyboard. You have to launch the virtual keyboard, which is somewhat awkward.

The first two of these caveats may mean keeping a Mac around for the time being. Don’t get me started about multiple Apple IDs and the limited utility of Family Sharing versus Apple simply getting real and allowing people to merge their IDs. I mean, we’ve only been asking for this for what, 12 years?

Epilogue

Overall, I’m pretty happy with this move:

• The Magic Keyboard has the old action I’ve missed, and I’m finding the narrow keyboard and smaller touch pad aren’t turning out to be a problem.
• The larger iPad is welcome, and surprisingly doesn’t feel much heavier than my Mini (sans keyboard, of course).
• The combination of the M1 iPad Pro, Magic Keyboard and Pencil v2 is really quite an elegant, compact solution for home and for travel.
• Being able to keep the Pencil v2 charged by magnetically sticking it to the edge of the iPad is awesome, as opposed to all the machinations required to keep the v1 pencil charged (wihout losing that damned cap.)
• Being closer to using the same OS across all devices (iPhone, iPad, Apple Watch, Apple TV) is a definite plus.

Finally, this project required me to take a hard look at the way I was using a number of tools and assess their need. I feel like my overall work process has become leaner and more, dare I say, agile as a result.

From Jean Paul Sartre on Le Dodge Dartre: “as interior parts fall off I am struck by the realization of their pointlessness. I might not know if the window is up or down. It is of no consequence.”