Lessons Learned from an Android to iPhone Convert. Part 1: Moving to iMessage

After 13 years of being a loyal Android user, I made the switch last month to iOS and bought the new iPhone 14 Pro. 

I loved my first Android phone — the iconic Motorola Droid back in 2009. Brief detour down memory lane: The Droid had a large gorgeous display, slider keyboard (for those of us who still liked Blackberry and not ready for the keyboardless iPhone), the powerful 5MP camera, and built-in “free” Google Maps/GPS navigation app. And backed by Verizon with a huge Star Wars R2-D2-themed marketing campaign. Sure those specs sound outdated now, but the Droid really put Android on the map, and since then I’ve been a loyal fan of Samsung Galaxy S smartphones.

Motorola Droid, 2009

So why the change after all these years? Mostly pressure from family and friends to get on iMessage and FaceTime (a.k.a. network effect), more parity between iOS and Android devices (i.e., less innovation these days, unless you want a foldable Z phone 😉), and increasing privacy and security protection concerns with Android/Google.

I do a LOT on my smartphone, including work and personal tasks. So I had a lot of concerns about my productivity on iOS and how smooth the migration would go. 

Migrating to iMessage

Most of the apps I use on Android exist on iOS. But iMessage is a walled garden, despite the recent advertising campaign by Google poking fun at Apple to get them to adopt RCS for cross-platform messaging interoperability.

The biggest unknown was transferring my 13 years of text messages to iMessage. I researched this for weeks and discovered there was no guaranteed 100% fool-proof way to do this. Verizon reps couldn’t make any promises. Even the geniuses at Apple who recommended their Move To iOS app conceded that it has failed at times.

I considered other options, including Verizon’s Content Transfer app and SMS Backup and Restore app. But ultimately I decided to try Move To iOS.

Surprisingly, Move To IOS worked…mostly. First, the app’s time estimate to complete migration is woefully inaccurate. It started with 6 hrs (!!!), then down to about 3 hrs in 15 mins. I had read reviews about it timing out and having to start over, so I sat there tapping both phones to wake them every few minutes. Then when it said 2 ½ hrs left, it finished unexpectedly. So in reality it was closer to 45 minutes.

Every text conversation appeared to have migrated over into iMessage! I was now part of the blue family. I can now get high-res videos and photos from other iPhone users, among other benefits.

With iOS 16 came new features that I love. Mark Unread is great. Now I wish there was a reminder option like Slack or snooze like Gmail. Also, the ability to delete or edit a text shortly after sending is great! And while not a new iOS 16 feature (but new to me), being able to reply in thread (like Slack) is awesome.

But there were a few wrinkles.

I did discover that my old “Android” phone number was treated as a different “person” than my new “iPhone” phone number in existing (I.e., pre-iPhone) group conversations with other iPhone users. See below example where my reply (in green even though it was sent from my new iPhone) showed me receiving a text from myself (in grey).

iMessage thought I was different person

Moreover, when someone else replied in an existing conversation, a NEW conversation was created with only my iPhone persona from that point forward. And this new conversation didn’t show past texts. However, at least I have my old conversations archived on my new iPhone in iMessage, even if it is a separate conversation now.

Another big problem was photos and videos that were in my texts didn’t port over. Instead I see alphanumeric jibberish like this. This led me to keep my old Samsung Galaxy phone indefinitely should I ever need to reference past photos or videos.

Missing images from old texts

I also had an issue where profile images for people had changed and in some cases reverted to photos that were several years old. Not even sure how iMessage even captured that meta data! So I had to update a bunch of profile pics.

Lastly, one feature I sorely miss from my Verizon Message+ app is the ability to send scheduled texts. Sure it could be used to send a late night text to a boss as if you were burning the midnight oil. But it is also useful to send a future reminder to someone (or yourself). Schedule a text saying “Remember to ask teacher about X” to your child, timed for after school gets out tomorrow. Maybe Apple will have this feature in 3 years.

Next time: Part 2: Working with Photos and Files 

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