Chronicles of a Windows user gone iPhone (2017)


If you’ve been following Pocketnow for almost 20 years, you may remember when we did numerous series of articles where one of us as an expert in one platform, would switch to a different platform that we had never used and chronicle our experiences. I haven’t used an iPhone as a daily driver ever, and haven’t really used iOS much since iOS 4, but I have had to help friends and colleagues set up our custom private security certificates for Exchange server sync and such. So I’m not completely unfamiliar with it. Anyway, this is part 1 in an attempt to give up my trusty Nokia Lumia 1020 Windows Phone 8.1 device to see how the iOS world lives. As a word of warning, this is written from the perspective of someone new to iOS and often it’s important to take a step back and look at things with fresh eyes to see if it really is well-designed or if that’s something we just believe because it’s what we’re told. iOS 11 is supposed to come out today, but I thought it’d be best to do the set up right away while this iPhone is still on iOS 10.

Setting up the iPhone 6s took a lot longer than expected. First of all, I couldn’t get past the language selection screen without a SIM card and then I couldn’t get past the activation screen without an AT&T SIM card as I wanted to use it with T-mobile. Unlocking the phone via ATT was denied after a couple days, so that didn’t work. Luckily I had an old inactive ATT nano SIM that at least let me continue with the rest of the setup… and there were a lot of other setup screens to go through! I skipped the iCloud restore options, since I hadn’t used my iCloud account since iOS 4 and I figured a new account would be better anyway.

First Impressions

When I finally got to the home screen, I thought to myself… “Well, this is the same that it’s been since 2007.”  It’s still just a grid of icons. Same as the Palm Pilots of the late 90’s. Same as Windows 3.1 in the early 90’s. Different background picture though. The way the background image on the lock screen subtly moves as you tilt the phone is a really nice touch that I loved when it was in the Zune HD.

The iPhone 6s itself feels pretty nice, except that the thin smooth edges seem like they’ll be very slippery and the rounded protruding glass screen seems very delicate, like it could break very easily. Maybe that’s why I see so many people with cracked iPhone screens.


Naturally the first thing I’m going to do is set up at least some of my email accounts. Adding my primary Microsoft Exchange account was very easy and the iPhone actually supports syncing mail, calendar, contacts, tasks (called reminders), and notes. That’s WAY more Exchange account support than Windows Phone 8 (which doesn’t sync notes) and Windows 10 Mobile (which doesn’t sync notes or tasks unless you install the To-Do app.)

Switching between mail accounts is awful on iOS 10 since you have to use the back button in the upper left (out of reach for one-handed use) until you get to the list of accounts. There’s no way to pin specific folders to the home screen which is much better for organizing priority accounts and ignoring low-priority accounts. Luckily, I was able to find the Mail notification settings where I could turn off sound effects for low-priority accounts, and customize sound effects for high-priority accounts. Thank goodness for that!  I can also turn off icon badge notification numbers for specific accounts, but again, I can’t separate those unread numbers by accounts or folders like I can on Windows Phone, which is much more useful.

Apple Mail is also terribly slow at receiving email!  It does support push receiving for Microsoft Exchange accounts (includes Office 365, via Exchange ActiveSync as well as Apple iCloud accounts, but it does not support push receiving for IMAP accounts. Personally I would call that a major deal breaker as the IMAP IDLE push email solution has been around for decades. You can only set IMAP accounts to sync periodically, and the lowest time option is 15 minutes. That’s crazy! No wonder people with iPhones are terrible at using email.  On Windows Phone, all of my emails arrive instantly and reliably on all accounts.

On the other hand, unlike Windows Phone, Apple’s Mail app does correctly flag IMAP server emails with their reply/forward status.

App Store

The next thing I need to do is install my apps. Unfortunately, that didn’t work right away. iOS gave me an error when trying to download one app, and on the second attempt told me that this Apple ID hasn’t been used in iTunes yet, so then I had to go through MORE SETUP SCREENS requiring more information and user agreements.

That’s when I gave up.  Stay tuned for part 2 where maybe I’ll have more patience and hopefully we’ll successfully update to iOS 11.

Chronicles of a Windows user gone iPhone (part 2)

The new iOS 11 Mail app looks much better to me. It now has a big bold typographic heading at the top.  For example “Inbox” is shown in a big font above my email listing.  This is good because it brings the interactive email list components lower down towards the bottom of the screen where my fingers can reach them. It also reminds me a lot of the old Windows Phone 7 Metro design language which really made a lot of sense.  I notice Mail still does not support push IMAP IDLE mail receiving, so that still sucks for IMAP and Gmail users.

General UI observations

I really like having a real physical home button at the bottom of the iPhone. Being able to feel that click is really important for eyes-free operation. Unfortunately it only really has about 3 functions. At the turn of the century, Windows Mobile phones generally had at least 4 programmable hardware buttons and a 5-way directional hardware button that was also programmable. Those allowed for excellent efficiency and eyes-free functions that are important while mobile. Of course, nothing really has that level of usability or customization these days and if you’re going to buy the iPhone X, you’re going to lose that tactile feel completely.

Uh, the WiFi is on. How am I supposed to dismiss this dialog? Reboot the phone?

Something I continuously hate about the iPhone’s UI is that the back buttons are generally in the upper left corner of the screen. Since thumbs don’t reach that far across a 4.7″ screen, that means I have to change hand positions or use two hands whenever I want to navigate within an app.  I see people struggling with this on the NYC subway all the time. It’s extremely inefficient and frustrating especially compared to Android and Windows Phones which have their system navigational buttons at the bottom where they’re easy to reach. Yes, Windows Phone and Android also have terribly placed buttons at the top of the screen (such as the notifications tray), but I can ignore having to see notifications more easily than having to use the back button.

Finger contortions or two hands required for basic navigation!?

Okay, it looks like there is a “reachability” mode where I can lightly double touch the home button in order to make the top part of the iOS screen move towards the bottom so that poorly-placed buttons are easier to reach with my thumb, but still… requiring 3 taps to do something that should take 1 tap is a huge exercise in inefficiency. In all cases, requiring hand re-positioning, 2 hands, or activating a reachability mode are all involving far too many muscle contractions to accomplish.

Why not design the interface to be usable in the first place instead of implementing such an awkward work-around?

Actually, where did the back button go?

I noticed quite a few times that there was no back button at all!  In some apps and in some cases, there is no persistent back button in the upper left corner. How can this be? It took me quite some time’s worth of trial and error to figure out that I had to do some sort of swiping gesture to go back to where I was before, or tap some unintelligible nondescript arrow that collapsed something and brought other parts of the UI back to where they were before.

Left to right swipes = back button?

In the comments of part 1, a friend mentioned the left to right swipe gesture as being a good one-handed alternative to the back button.  The context of our conversation was the Apple Mail app, to which I responded that the left to right swipe gesture marks a single email as unread.  It turns out that the left to right swipe gesture can do TWO THINGS in the mail app depending on how close to the left edge of the screen I start the gesture!

This is supposed to be easy?  Well it isn’t!  Hiding two functions within a single control gesture is a usability and user experience sin.  Easy would be a single back button that was always in the same place and always did the same thing and always looked exactly the same.  Adding multiple interaction methods and controls that do the same thing is too confusing for normal people and degrades the consistency of the system’s user interface.

The left to right swipe gesture almost never does the same thing too.  Sometimes it flips back to the previous screen, sometimes it opens a hamburger menu, sometimes it launches some camera interface within the app, sometimes it does nothing at all.  There are huge consistency problems with this phone’s user interface.

Chronicles of a Windows user gone iPhone (part 3)


In part 3 of this “Chronicles of a Windows user gone iPhone” series we’ll dig into more of the iOS apps that I want to use. As a Windows user, obviously most of these are going to be apps made by Microsoft so it will be interesting to see how Microsoft contributes to its competitor’s ecosystem. Of course, I’ll also look at a few other of my favorite 3rd party apps and maybe explore some of Apple’s built in apps that I’ve never used before. If you missed part 1 or part 2, you can check those out as well.



The 2nd most-used app/service for me besides email, is probably Facebook.  Facebook apps on Windows Phone, and Android, and any web browser have all felt pretty similar to me.  Facebook on iOS feels totally different though.  It’s got a big row of unintelligible icons at the bottom of the screen and they don’t match the icons on the website! Yes, having these buttons at the bottom of the screen is much better than having them at the top where fingers can’t reach them, but unlike other iOS apps, this bottom bar of icons have no text labels and therefore I have no way of translating them into something understandable without tapping them and wasting my cognitive/muscle energy.  The triangle button on a squircle looks like a “play” button, but Facebook isn’t a media player so that doesn’t make sense. It turns out that just loads random videos… so I can completely avoid that. Not sure what the dog house icon is supposed to be. Marketplace? Forget that. And why is there a bell here instead of the globe icon Facebook has always had for notifications? Now that everyone has learned what the old icons meant, it’s time to change them, huh? That’s not smart.

I’m kind of surprised at how bloated the Facebook app on iPhone is compared to other versions.  I might just use the mobile website instead since that has much less extraneous junk, although it still has the poorly-placed icons at the top of the screen.

If you see a file manager, they blew it.

Okay, actually Steve Jobs said that if you see a task manager, they blew it. The reasoning behind that quote was because having to manage tasks and close applications was thought to be too complicated for normal users. People shouldn’t have to think about that kind of thing. That was in 2010 with the iOS 4 launch, but holding down the home button certainly does show a task manager now. Anyway, the same type of thought process normally has always applied to a file manager in Apple’s view.  Being able to access, organize, and arrange files on your smartphone shouldn’t be necessary. Although, now with iOS 11 we certainly do have a new “Files” app.


I was expecting this to be some sort of file manager like the name implies, but really it seems to only support iCloud file storage management, and even then it’s pretty weak in terms of features. OneDrive also integrates with the Files app, but there really isn’t anything you can do with it. I found no way to add OneDrive folders as favorites or tag them or move them or anything.  All I could do was browse and preview some files. The iCloud storage section does have a few basic features, but you really can’t do much here.


I’ve managed to almost completely stop using Skype on Windows due to its continued decline in reliability. On Windows, Skype is terrible at matching user-names with actual contact names, thus making a mess of conversation threads on all of my devices.  It’s not essential at all, but I thought I’d install the iOS version of Skype just to see what it was like.

It turns out Skype on iOS is even worse than the Windows UWP versions. The whole point of Skype was always to see which contacts are online/available and easily be able to video call, voice call, or instant message them.  Most of that is gone or obscured on the iOS app. It only has a “Chats” listing of threads with no way to see who’s online.  There’s a “Highlights” section with buttons for “following” friends as if it’s supposed to be some kind of social network now.  There’s also a “Capture” tab which looks like some Snapchat nonsense, so I’m sure I’m never going to use that.

Like a bad joke, if you have to explain your interface design, it’s not a good interface design.

I kind of wish Skype on iOS was more like Skype UWP on Windows 10 and allowed syncing text messages between iOS and Windows 10 devices. Unfortunately, that’s not the case as Skype on iOS seems to be having an identity crisis.

Tons of app tutorials

I also installed Cortana, OneNote, OneDrive, Groove Music, Xbox, and Microsoft Word.  Most of these required a re-login of my Microsoft ID, which is understandable since this isn’t Microsoft’s ecosystem, but it’s still annoying.  Another annoying thing is how many apps show introductory tutorials.  If your app needs a tutorial, that means you didn’t design its interface very well.  Apps like Cortana had tutorials about how to add the Cortana widgets to the iOS today screen or whatever it’s called.  Sure, I didn’t know how to do it, but requiring me to read through all these instructions, memorize them, and then navigate out of the app in order to perform the procedure is really tedious and certainly not intuitive or simple.

What if there is no “apps button”?

OneDrive had a first run tutorial that didn’t even make sense. It told me to go to iMessages and open the waffle menu. There is no iMessages on this iPhone. There is a “Messages” app, but it doesn’t have a waffle menu. So there’s another user experience failure. It turns out I have to “activate” iMessages with my Apple ID in the settings somewhere (which isn’t clear at all), and even after I did that the “apps” button looks completely different from what is illustrated in the OneDrive tutorial.

FaceTime just hangs on the activation screen for some reason. There’s no error message or anything indicating why it doesn’t work.  (It turns out I have to go to the settings to “use Apple ID” for this too.)


One app that I used to use all the time on Windows Phone was MyFitnessPal. They stopped supporting it a while back and the social news feed aspect has stopped working, so I thought I’d install it on the iPhone. Turns out the iPhone version of the app is pretty terrible, although it does work.  On Windows Phone, the MyFitnessPal app had voice commands, so I could actually record weight measurements using Cortana.  It also had pinnable live tiles for direct shortcuts to entering data or displaying data.  With one tap on the start screen I could launch the bar-code scanner and record all the nutritional information for something I was going to eat.  The iOS version of the app takes 5 taps to launch the bar-code scanner! It’s a much less efficient design.

What’s with the ads all over these apps?

Outlook for iOS

In part 1, I went on about how terrible it is that Apple’s Mail app doesn’t support push syncing for IMAP accounts and one of our readers mentioned how Outlook for iOS is a really good email app for iPhones. So today I totally shut off the Mail app’s notifications and installed Microsoft’s Outlook for iOS mail app.  This is basically a re-branding of Acompli’s mail app after Microsoft bought out that company and it is widely considered to be the best email app for iOS.

Of course, I’m familiar with Outlook on Windows and macOS. I’ve been using Outlook for Windows since it was first released in the 90’s. The desktop Windows version is by far the most powerful communications and personal information management tool around (followed closely by eM Client)… But Microsoft’s mobile versions of Outlook have always been stripped down and not quite good enough.  Outlook for iOS is also a stripped-down personal information management app, and still not quite good enough.

I’m also familiar with Acompli’s Android version of the email client, which was also renamed to Outlook for Android, and I have to say the iOS version is much nicer than the Android version.  Thank goodness there are no distracting bright-colored circles in the email listing!

Switching between email accounts is still a total pain though. Outlook for iOS lists them hidden behind a hard-to-reach hamburger button and then only identifies the accounts with a colored circle and the letter of the first part of the email address.  For me, all of them are the letter A, so that’s ridiculously painful to use.

A hack to get messages organized.

I did however find a way to get my emails segregated so that I can prioritize their placement on the iPhone’s home screen.  I actually ended up installing multiple email apps and set up different accounts in each one so that I could have different icons showing different email unread counts.  It’s still a total pain compared to what I can do in Windows, but it kind of works.  Now I can keep the spam email accounts separate from my level 1 and level 2 priority accounts. Unfortunately, the iOS icon badges all constantly show the unread number of messages even after I’ve scrolled through the listings. I much prefer Windows Phone’s method where the live tile only shows the new messages that have arrived since the last time I looked at the email app. The Windows method means I can quickly see what’s new and easily ignore the unread messages I don’t need to open without having to do anything to them.

Chronicles of a Windows user gone iPhone (part 4)


I’ve been using the iPhone 6s with Apple’s new iOS 11 for a while now. I’ve criticized the intrusive set up process, the poor inconsistent one-handed usability issues, and a few app annoyances.  In part 4 I’ve discovered even more awkward interface issues and but maybe I’ll come to terms with them after all. If you missed part 1part 2, or part 3, you can check those out as well.


More secret gestures

In part 2 I learned about the secret left-edge screen gesture that sometimes acts as a back button, sometimes opens hidden menus, sometimes does other things, and sometimes does nothing. Swiping horizontally is a pretty good navigation method for handheld smartphones. It reminds me of the old panoramic hubs in Windows Phone 7, except those were much better in a few key ways. In Windows Phone 7, when you activated a hub, its full length 2D panorama graphic flew into view like a sheet of paper and then settled on one specific section. This animation was a brilliant way of indicating to the user that there was more content to the left and right. If that wasn’t enough, the hub designs landed in a way that cropped a bit of text on the edges. Again, this was a very smart way of showing the user that there’s more stuff beyond the edges. Anyone who understands our language can recognize those letters and instantly see that some part of the word is missing on the edge. Tapping and dragging the rest of the word into view was totally intuitive for being able to see the hidden content. There are no such visual indicators at all for teaching users about the left-edge swipe gesture in iOS. It’s completely non-discoverable and I never would have found it if someone didn’t tell me about it.

The fly-in hub designs were great for showing side scrolling capabilities.

But wait, there are more hidden gesture controls! I already knew about the top-edge screen gesture since Android and Windows Phone 8 both implemented that long ago. It’s still a bad design decision, but at least I knew about it. On iOS, there’s also a bottom edge swipe gesture.  Swiping up from the bottom edge shows a pile of ambiguous icons that turn out to be toggle switches. The bottom row can be customized in the settings to launch a handful of different things without having to go back to the home screen, and that’s a really great option. The mess of unlabeled icons can be really hard to understand though. I customized my bottom row to show some options that I thought would be useful, but I’ve already forgotten what the icons actually do so I’ll probably have to go back into the settings to read the labels there. Having this kind of thing in the bottom edge screen gesture is great because the bottom edge of the screen is very easy to reach while holding the phone. It’s not great that the discover-ability is really low and it’s not great that the icons are unclear. There are also some issues with the radio toggle buttons not actually functioning as radio power toggles.

Now here’s an even crazier hidden gesture control.  If I swipe down on the home screen, the system search appears along with the keyboard right away!  This was a totally accidental find. I was probably trying to access the notifications drop down with a top-edge screen swipe.  If you miss the top edge, then you get the search. Yep, that’s 2 top-down swipe gestures that do completely different things. Simple and easy? Not really! These complicated gestures certainly do add efficiency for power-users to navigate the operating system, but simple and intuitive they are not.

Arranging icons

As I found in part 3, having different icons for different email accounts is an improvement, but trying to arrange them is awful. In iOS 4, it used to be that I could tap and hold on an icon on the home screen, then all of them would start wiggling and that would mean I could rearrange them… or uninstall them by tapping the little X in the corner of each icon.  Nowadays, tap & hold brings up a context sensitive menu related to the app I tapped & held my finger on. But wait!! Sometimes tap & hold DOES go to icon rearrangement mode.

It turns out the tap & hold action has two different functions depending on the radius of your finger’s contact area or something.  How is that intuitive or simple?  Sorry, it isn’t. Apple calls this awkward mash up of a single control method for two functions “force touch 3D touch” because generally you have to press harder to get a larger touch radius. In practice it’s very difficult to figure out the difference between activating 3D touch and activating tap & hold. Usually when I want one function to activate, the other one does. I’m sure this takes some “getting used to” and eventually I’ll adapt to this convoluted user-interaction method.  Actually, it looks like if I adapt to the phone and touch really really lightly I can enable the icon arrangement mode… while if I press really really hard I can activate the context sensitive menu. Seriously unintuitive!

Maybe all of these hidden controls are good

For beginning users, hidden controls like all of these screen gestures and variable pressure controls and double taps and double presses are clearly a bad thing. They increase complexity and are impossible to quickly learn without being taught (or by accident). In observing or talking to my friends who have always used iPhones, many of them don’t even know about some of these gestures. Many of these gestures don’t actually work on their iPhones because they have cases that cover the edges of the bezel.

On the other hand, these hidden commands actually make using iOS much more efficient for people who know about them.  If I can remember which secret gesture does what or build some motor memory for them, it actually makes getting things done much faster than simply poking about at buttons on the screen.

Originally Published: The Chronicles of a Windows user gone iPhone part 1, part 2, part 3, and part 4.

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