David J. Danto


Business travel thoughts in my own, personal opinion




eMail: ddanto@IMCCA.org      Follow Industry News: @NJDavidD


“Are You Watching? – The (Very Long) Saga Of Apple Support”

Thanks very much for all the emails about my blog last week – the one on how Apple and their apps are “complicit.  (I love hearing from people who actually read my stuff.  It doesn’t matter if you agree or disagree, give me tips on what I can include and/or correct something I’ve written.  Keep emailing.)  Many of you were as fed up with Apple as I was.  Others suggested I should have leapt to a newer version of iPhone, and a couple suggested I’m making something out of a nothing-burger.  This week I’ll finish the story of my Apple complaint with the sad saga of my Apple Watch and Apple Support. 

Let me start by explaining that on my fortieth birthday, my late mother in law (who was one of the nicest and loveliest souls I’ve ever had the privilege of knowing) gave me a gift of a watch.  It was a beautiful (and expensive) Rado timepiece that managed to bridge the gap between me – the techie nerd that always wore calculator watches and me – the business professional I was supposed to be, who should be wearing a timepiece with class and style.   It has a classic look, but also has hidden, embedded digital features (digital time, second time zone, stopwatch, etc.) Costing over $1k at the time, I wore it proudly for many years – until a couple of years ago when my wife decided I had suffered without wrist-toys for long enough and bought me an Apple Series 1 Watch as a holiday present (while it was on a black Friday sale at Macys.)

I was never really a fan of Apple watches – nor other similar things like Google Glass – which I felt honestly said more about the ego than the class of the wearer, but I tried it and found it useful in a very limited capacity.  I didn’t want or need the health tracker, the severely limited apps, the useless messaging capabilities, or the annoying sounds that interfered with the way I wanted my phone to alert me, but I did like a screen that at a single glance could tell me the date, temperature, the time in two time zones, the latest news headline – and as a plus let me know when I was getting an incoming call.  I started wearing it and it stuck.  I put my Rado in my dresser drawer.

Now with the saga of my replacement phone, and the required upgrade to a new iOS complete (again, both of which I detailed last week) I needed to un-pair my watch from the old phone and re-pair it to the new one.  That was apparently going to be a problem.  I followed all the instructions to un-pair and reset the watch, then attempted to pair it to the new phone.  The phone recognized it, paired it, said it needed an upgrade to a new Watch OS, said it was going to perform the upgrade, and then immediately said the watch was on the correct, current Watch OS.  Nothing happened.  The watch had the Spirograph like image, and said it was waiting for the phone.  The phone said the watch had the latest OS (when it didn’t) and froze there.  If I tried to exit the screen, the phone would caution me about stopping the upgrade (that wasn’t happening) and un-pairing the watch.  Checkmate. 

Thus begins the new saga of Apple Support. 

I searched Google for a similar complaint and found dozens of them.  OK, so it was good to know I wasn’t in the Twilight Zone or doing anything wrong.  I then clicked over to Apple Support, and asked to be contacted over the phone (a pretty painless process with a minimal wait.)  When the agent and I spoke he walked me through some basic steps I hadn’t checked (reboot both devices in a specific order, put the watch on a charger, ensure that I have a strong WiFi signal, keep the two devices very close, etc.)  No dice – same problem.  After about an hour of trying, he said that – despite what the phone and watch both were indicating – it may in fact be performing an upgrade and may just take an hour or so to complete.  He suggested to just let the two of them be and he’d enter a ticket to call me back 90 minutes later to ensure it worked.  (It didn’t.)

Ninety minutes later I received an email that Apple tried to call me and couldn’t get through.  I was home, and gave them my landline number to dial, so that excuse didn’t bear-up to scrutiny, but whatever.  I clicked through the support website, asked for another call, got one, and referenced the case number.  This next agent said he was “sorry I was having trouble as these Apple Watches are always rock-solid.”  I reminded him of the Google search I did that turned-up dozens of cases of the same issue, and the agent said, ‘well, yes – rock-solid except for this issue.’  He agreed that the watch had a software problem and said I’d have to take it to be repaired.  I explained that the watch was a holiday purchase by my wife – at a bargain price – and I wasn’t willing to pay to have it fixed.  He explained that he thought the watch worked just fine, and if that were true – and this was just a software issue – there’d be no charge to fix it.  He said I should drop it off.  I told him I had an Apple Store a 20 minute drive from my house, and he replied “oh, don’t take it there.”  He explained that the Apple Stores were jammed-up with people buying the new iPhone 11 and new watch, and since there was a Best Buy five minutes from my house I should take it there.  He made an appointment for me in two days (this was Saturday and the appointment was Monday) and told me it’d just be a quick drop-off.  I thanked him and we ended the call.

I went to my dresser and found my wonderful Rado – dead.  I hadn’t used it in two years and it obviously needed a new battery.  I went to Amazon and bought twenty batteries for $5.99 to be delivered the next day (Sunday.)  While I was there, I checked the prices of refurbished Series 1 Apple Watches.  They’re going for about $150.

On Monday – with my Rado and its new battery on my wrist – I went to the Best Buy to drop off my watch.  Guess what.  The Best Buy – while having the record of ‘someone’ having a Geek Squad appointment from Apple at my timeslot – receive no data from Apple.  They don’t have my name or my case number, and have no way of looking anything up based upon that case Image-1number.  Really?  Apple Support sends unsuspecting people to Best Buy on a regular basis, but doesn’t communicate the case number to the Geek Squad and doesn’t give them any way of finding the case number?  That seemed beyond ridiculous to me, but that’s where we were.  Apparently the only way they can act on the Apple product is by its serial number – a difficult thing to do when one has a watch that is not paired (with no digital readout on the watch-face nor phone.)  Apple’s serial number is etched into the crease where the band attaches.  It is barely visible when new, and absolutely unreadable when aged.  After using lights, zoomed cameras, and everything else we could think of, the clerk asks me to log into my iTunes account on his open PC.  What?  He wants my Apple password on a shared machine?  I very reluctantly did it to move this along – and found out that the serial number isn’t listed on my account (of course not – the watch is no longer paired to my phone.)  After about an hour of this nonsense I told the clerk to get Apple on the phone – NOW.

After about twenty minutes on the call, with the clerk having handed the phone to me, the Apple Support tech came back on and wouldn’t read me the serial number (I suppose for security reasons) but mercifully did let me read her the portion I could see and then corrected the three digits I guessed at incorrectly.  Bingo!  We now have the serial number – only an hour and a half after I arrived to “just drop it off.”  The Geek Squad geek that was helping me then went to work, entering the serial number, and taking the next step – which was apparently doing all of the tests I already did all over again to see what was wrong.  I told him we did this already, but of course we learned that he can’t access Apple’s records, and he clearly doesn’t trust me, so he attempts to try to do all the diagnostics all over again.  Also of course, he can’t, because he can’t pair the watch to anything with the current OS, WHICH IS THE ACTUAL FREAKING PROBLEM!  Convinced that he now has a handle on the situation, he asks me to type my personal information into his form so he can process the repair.  “Oh, by the way” he tells me, “no one is going to fix this – they’re just going to swap it out.”  Since it’s out of warranty that was going to have a $200 charge.  It took all my energy to not have a cow at that point.  I told him to give the watch back to me and I walked out of the store.  A complete waste of two hours.  (Just in case anyone doesn’t believe the story at this point, please do check out the TweetStorm I was sending in real time while there.  Neither Apple Support nor Best Buy Support ever answered any of the tweets.)  I take back my earlier comment – I am completely in the Twilight Zone.

Upon arriving home I clicked-through to Apple Support again, and again asked to be called.  When the agent got on the phone I said I was furious, and asked how this could have gone so wrong. “How can you send someone to a repair agency that has no record of the case number?  How can you charge me for a repair you told me wasn’t my fault if it was due to your software?”  The agent asked me to hold for an ‘escalation supervisor’ who would help me resolve all of this.  When this person came on the phone, she was very understanding and apologetic, and said she’d help me resolve the situation.  She said I never should have been sent to the Best Buy.  I told her no one should ever be sent for a repair case where the location can’t reference the repair case.  She agreed and suggested I put that into my comments (if this ever gets resolved) and she would as well.  She walked me through the pairing process one more time, it failed again, and she asked me for screen shots (which I’ve shared above.)  She told me she’d make an appointment for me at the nearby Apple Store Genius Bar to just drop it off and get it resolved.  She said “if they find something wrong with the hardware of the watch then there would be either a charge or an offer to upgrade the watch to a newer one, but from what I was explaining and sharing, it was 99% probably just a software issue and there’d be no charge.  I thanked her and ended the call.  (I then had to change my iTunes password on all my devices of course, since it was in the cache of an open PC at a local store with dangerous “geeks” – what fun!)

Then, just to make sure I wasn’t going crazy, I re-paired the watch to my old iPhone.  Not only did it work, it restored it from the back-up and everything worked perfectly again.  Clearly there was NOTHING wrong with the watch.  There was a problem with Apple’s software not being able to update the watch’s old OS to the current one.

Two days later (Wednesday) I dropped off the watch at the Genius Bar.  The agent started to try to test it – but then at my urging – read the notes of the case and realized that it wasn’t necessary.  He said he’d send it out and then have it shipped right back to me at home – I wouldn’t even have to stop there to pick it up.  The whole process took ten minutes.

Then, when I arrived back home, I saw this in my email”

You could have fried an egg on my head at that point.  Hours and hours of effort later, promises that there’d be no charge, a Genius Bar conversation that agreed that this was a software issue, no mention of a charge, then this email, informing me that I was going to be charged $50 more than we paid for the watch years earlier, and $50 more than I could get a replacement for on Amazon today – for a watch that WORKED JUST FINE!

Here we go again.  I tried to call the store, learning that that was totally impossible as all calls go to a central Apple support desk.  After 15 minutes on hold, I hung-up and clicked through to the Apple Support website again and asked that an agent call me (again.)  When one did I asked for the escalation supervisor, explained the story (again) and said I didn’t want to pay to repair a perfectly working Apple Watch just because they can’t perform an upgrade on the new software they’ve forced upon me.  This escalation supervisor wasn’t as nice as the last one.  She said “no one should have told [me] there’d be no cost for an out of warranty repair.”  “Fine” I said, “get a hold of the store, stop the process, and send the watch back to me.”  I’d just use it stand alone without pairing it to my new phone.  After ten more minutes on hold, she said she reached the store who “admitted they entered the repair incorrectly.”  They’d pull and change the paperwork and there wouldn’t be a charge, and they’d reach out to me if there were any issues.  I said “OK, thank you” and hung up.  Two hours later I received another email from Apple, essentially identical to the one above, and also listing a $199 charge. 

Yesterday I received this email:

Rather than fix the software issue that they caused in a perfectly working watch, they’ve gone ahead and replaced it despite my multiple requests not to do so.  Rather than send it to me, they’re asking me to “pick it up.”  I should not (over) pay for this service that I didn’t request.  I’ll just demand the watch be returned to me in the condition that they received it.


At that point I sent the portion of this blog above this line to @AppleSupport on Twitter.  There was no response (again.)  I called the store with the new phone number provided in the ‘arrange your pick-up time’ email, and this time – after holding for ~ 10 minutes – actually reached someone in the store!  They were apologetic and put me on hold to get a “manager.”  Five minutes later I asked the manager (Chris) to give me an email address that I could use to send him these details of my saga, and he gave me a general email that the store could access.  I included a link to this blog and my mobile phone number.  He promised he’d read it and get back to me by the end of the day. 

Chris called me back – in five minutes – and said come pick up the watch, he was personally waiving all fees.  Astounding – finally an actual human with a conscience at Apple!  I just about fell off my chair.

I’d like to say that was the end of the saga, but of course it wasn’t.  The replacement watch wouldn’t pair with my phone because the very latest Watch OS pre-installed on it required my phone to be on the very latest version of iOS.  I was of course planning to stay on 12.1.4 until all the bugs were shaken-out of 13, but to make the watch work I was going to have to abandon that smart strategy.  (This was just one last facepalm moment to end the story.)

The dot-one version of iOS 13 was out – with at least some bug-fixes – so I took the plunge earlier than I wanted to, if for no other reason than because I had already invested so much time in the process that I needed to know if it would work.  After upgrading the iPhone 7 to iOS 13.1, the watch paired, actually restored from the original backup that transferred when I upgraded from the iPhone 6s, and everything now works.

My cost – in dollars, nothing.  In time, eight hours in the course of one week, one trip to Best Buy, two trips to the Apple store, seven support calls.

What are my conclusions?  I’m just about giving up on this big Apple circus.  There is clearly no coordination between groups, no care about the customer experience, and – with just one single exception so far – everyone just says whatever they feel like to make sure the customer doesn’t get upset while in front of them / speaking with them. 

My Rado is continually looking better and better on my wrist.


This article was written by David Danto and contains solely his own, personal opinions.

All image and links provided above as reference under prevailing fair use statutes.