It began subtly, in the way that computer problems can often creep up on you. I was trying to erase and restore an iPad Pro, the memory of which had gotten full. Never buy a 64-gigabyte anything, it's a constant disappointment.
I've become practiced at this maneuver, having done it several times in the two-plus years of owning the iPad. And so the predictable set of steps was what I expected to encounter. Imagine my surprise, then, when I wasn't able to erase the iPad because my Apple I.D. password suddenly wasn't being accepted.
I went to Apple's iCloud site in the Safari browser on my MacBook to verify that I wasn't having a senior moment about my password, a distinct possibility. I was greeted with a message I'd never seen before: "iCloud encountered an error while trying to connect to the server."
I have a second Apple iCloud I.D. that I use. I tested that one. It worked just fine. Moreover, a check of the iCloud status page showed no general outages. I deduced there was an issue with that one iCloud account itself.
Friday March 12
It was early on the morning of March 12th. I reached out immediately to Apple support, via chat, and was told to await a call later on that morning, during normal support hours.
Thus began what I would come to think of as the '855 Debacle, the numbers being the last three digits of my Apple support ticket.
When I finally got someone on the phone, let's call him Tim, he said that it looked like it was an issue of "maintenance" on the account. Tim asked did I want to wait to see if it cleared up, or submit an engineering request. I said I wanted to submit an engineering request. I'd never heard of anything like this, and I was certainly curious to have an explanation.
Later in the day, a new advisor contacted me, let's call her Joanne. Joanne said that an engineering request had been submitted and that it was going to take some time. How much time? I asked. Well, it was a Friday and she was leaving for the weekend. I'd probably hear something by the following Tuesday. Did she know anything about this supposed maintenance, I asked. No, she said. What kind of maintenance was it, I wondered. Was it planned, or unplanned?
What I was driving at, was, if it was planned, shouldn't someone have notified me? If it was unplanned, shouldn't someone have alerted me? What kind of mega-corporation renders your service unavailable and has nothing to say about it?
Joanne said she knew nothing further at this time, but would endeavor to get an answer.
I waited. As Friday descended into darkness, it dawned on me that iCloud Drive, which I use to keep files synchronized across three iPads, an iPhone, and a MacBook, would be unavailable without this primary Apple I.D. It was dawning on me that with days of unavailability, I would have a real problem. (In fact, numerous Apple services across the devices, all tied to my Apple I.D., became partially or completely inoperable, as described in a companion article.)
I went to the Apple Discussion Forums. Nothing helpful came up when searching on the mysterious server error message. So I waited.
I improvised a form of sneaker-net to get around the lack of iCloud support, sending documents back and forth between my devices using AirDrop. Having to suddenly resort to this side channel began to drive me crazy. Would I really have to wait days, I wondered?
I tried to relax over the weekend. Frequently checking the iCloud site to see if things were back did not calm me down, and, of course, things were not back. By Monday, I had to take action. Early in the morning, I left a message in the Apple Discussion Forums asking if anyone had anything they could offer:
I have been shut out of my Apple ID -- a second ID, not the one I'm using for this forum -- for about three days now. I've spent hours in chat and on the phone, with the end result that I've been told that it's a matter of "maintenance" being done, with no further explanation. I've been given no time frame for resolution, just the assurance I would hear from another support engineer in another couple of days. I opened a second case today and am going to speak to someone on the phone in the morning. I probably will be told the same thing. Has anyone had this kind of experience lately? (Posted to the Forum at 2:45 am on 3/15/21).
Nothing. I waited. And then I decided I had to communicate my frustration. So, I started a new support case. I left the following message:
I have never been so disappointed and so frustrated with Apple. I have spent tens of thousands of dollars on Apple products over decades. My Apple ID is frozen now for three days, no one will tell me my, and it is destroying my business. And I'm told I just have to wait because of some vague engineering issue. This is the worst customer experience I've ever had with any product. Apple should be ashamed of themselves.
Later in the day, Monday, it was really beginning to steam me up that I had been waiting days. I decided to open a complaint with the Better Business Bureau in San Jose, California. I told the BBB,
I have been shut out of my Apple iCloud account for three days. I have had multiple discussions with the company to resolve the matter and I have been told I will have to wait until they resolve it, with no clear date as to when the matter will be resolved. I have been given no explanation as to why this service is unavailable.
I was asking for restitution in the form of a refund. I pay $9.99 a month for the maximum two-terabyte version of iCloud Drive, the Apple storage function. So, I figured I was due some pro-rated amount for the downtime. All I really wanted was an explanation, and perhaps an apology.
It was now getting close to Tuesday. My frustration had turned to mild exhaustion. I resolved to simply sulk and see what engineering might reveal when I finally heard back.
Tuesday March 16
Tuesday rolled along with not a peep from Apple. In the meantime, I received word from the BBB that my complaint had received a response from Apple. It contained a reference to the EULA, the end-user license agreement, for MacOS High Sierra. It was pointed out that by using the software, I had decided to abide by the terms limiting what I could expect:
USE OF THE APPLE SOFTWARE AND ANY SERVICES PERFORMED BY OR ACCESSED THROUGH THE APPLE SOFTWARE IS AT YOUR SOLE RISK AND THAT THE ENTIRE RISK AS TO SATISFACTORY QUALITY, PERFORMANCE, ACCURACY AND EFFORT IS WITH YOU.
I didn't respond immediately, even though I was amused that the company was referencing High Sierra, since my issue was not with the MacBook, and anyway, I was using MacOS Big Sur, not High Sierra.
Later that evening, I opened another support case to tell Apple I hadn't heard from Joanne, or anyone, all day. A new advisor came on the line, let's call him Greg.
Greg said, looking at the notes, he could see "they are aware of the issue with iCloud" and they "don't have an ETA." This time, Greg informed me that there was "something happening to multiple people that they need to fix." He informed me I might have to wait more than a week. "It's something internal," Greg continued. "It is something internal on our side." Greg told me he'd ping Joanne and I should wait to hear from her.
"They're going to reach back out to Joanne," he said. "You'll notice when there's a resolution because it will automatically sign you in" to iCloud, he assured me, "when they fix it…" I asked again if he knew anything more. Not much, Greg said, other than "chances are, it's not very many people" who were affected. Well, being in this select group didn't make me feel any better.
I might have gone through the roof after getting off the call, except that suddenly, my iCloud account started working again. My iOS devices, like a chorus from a Greek drama, produced alerts all at once asking me to sign in to iCloud: "Update Apple ID Settings" "Some account services will not be available until you sign in again." In the depths of my frustration, it was a moment of clouds parting, sun shining in.
So, now services were back, and I felt some relief, but I still wanted answers. I set up a new call for Thursday, March 18th.
Thursday March 18
When Thursday rolled around, a senior advisor called, let's call him David.
David said they had been "having issues with some services." I brought up the fact that there had been some talk of a "maintenance issue." Did he know anything about that? He didn't, but he said he was taking over ownership of the case from Joanne, and would reach out to engineering to find out what the maintenance had been. He said he would follow up with an email to me once he heard from engineering.
Apple sent a survey following the call, for me to fill out, to which I replied with this comment:
I still have no idea why my Apple ID became inoperable. I was not given any explanation, nor any warning of the interruption of service. Apple displayed no urgency in resolving the matter, instead telling me to wait days and days for a resolution.
I waited almost a week, and when I didn't hear back from David, I sent a message to him, via the link in the follow-up email, asking if he'd heard anything. David wrote back saying the engineering department was still researching the matter. He also left me a voicemail.
A pattern during all of this was that the Apple Support people seemed genuinely caring, concerned, and willing, if ineffectual. In my brain, David was becoming a brother in arms, trying to get answers, and engineering was becoming my tormenter.
Despite all that, I still wasn't getting answers as to what had happened. I left more messages for David.
Tuesday March 23
Just when you think it's safe to go back in the water, as they say, something happens again. March 23, after suddenly not being able to load anything in Finder on the MacBook from iCloud Drive, nor on iPad from iCloud Drive, I once again went to iCloud dot com in Safari on the desktop, with something of a lump in my throat.
Once again, it gave a cryptic error message, "There was a problem loading the content of this folder."
I opened a new support ticket. A senior advisor came on, let's call her Phyllis. Phyllis took a look at the notes of the '855 case and mumbled something about engineering doing maintenance on the account. To her credit, Phyllis seemed just as interested as I was. "Partitions…" she noted. There was something about partitions. Phyllis excused herself to check the non-public discussion board.
She came back after a little while, saying, "Interesting: When your other advisor contacted engineers," I assume, referring to David, "the response came back that there had been a migration in progress, but that the migration had been generating errors, according to the notes in the internal system." My mind raced. New questions. What the heck kind of migration?
Phyllis noted that the last note that had been left internally was the day before, March 22. It said something about "nested folders on iCloud Drive…" Something from engineering about if there are too many nested folders in a customer's iCloud Drive account.
Again, engineering seemed to be a shadowy presence, holding lots of cryptic information, revealing nothing but throwing out insidious little breadcrumbs.
How many folders might be too many nested folders? It wasn't clear. Phyllis noted that I had 48 gigabytes of data just within the Documents folder alone. Was that unusual? I asked, rather limply. Phyllis went through the sizes of other data, such as the Books files — I have a lot of ebooks in the books program, all sync'd to the cloud. Preview — also, a lot of PDFs. I couldn't deny it, I am a digital pack rat.
But then, that's why I was paying Apple $9.99 a month.
Phyllis noted that the '855 case was already in "escalation mode," and repeated that it was "due to maintenance." After again reflecting out loud on how long things had been going on for, Phyllis remarked, with some wonderment, "I've never seen it where it doesn't perform when it's in escalation mode."
She said she was going to take ownership of the case. Phyllis had me go through the remote diagnostics process, whereby a system log is packaged into a large file and sent to Apple via file transfer. "Gathering System Diagnostic..."
Again, her manner very sweet, very concerned. "I'm going to mark this as business critical," she said, "because I feel you need those documents for your job." My heart swelled with affection for this Phyllis. We uploaded the diagnostics so she could use them, and wished each other a good night.
A day later, Phyllis emailed me that she was waiting to hear from engineering. I proceeded to email and leave messages for another week or so, while also trying to get some information from David. The problem of iCloud Drive persisted on and off during the week.
Friday April 2
Around April 2, after several days of things being relatively okay, I again had an iCloud-related issue. I couldn't download a file that was stored on iCloud. I opened a new support ticket. I got passed to a few people, and then to a new senior advisor, let's call him Justice.
Justice looked at the notes from the '855 ticket. "Okay so it's been going on for almost a month now," he observed. Well, I appreciated his seeming incredulity. Again, a comrade in arms.
"I know you've been working with them for quite some time now," said Justice. Justice had me take screen recordings on the MacBook and the iPad of the problem. It was a Friday. Justice said he would be off until Monday, but he would plan to contact me then.
After getting off the phone, I received the support survey link in a text message. I filled out the survey, declaring myself "somewhat dissatisfied" because the issue was not revolved. I also left the following feedback:
This same issue has been going on for three weeks. It is very frustrating and is impacting my productivity. Despite the professionalism of Apple Support personnel, I still have no idea why my services have been affected for three weeks. I'm very disappointed with this quality of service from Apple.
Still fuming, I remembered Apple's unanswered reply on the Better Business Bureau Web site. I went and fired off my rebuttal to Apple's legalese: "This response from the vendor did not address the concern," I wrote.
There are two reasons the response is erroneous. 1) The response from Apple Inc. describes a software license for macOS High Sierra. None of my devices from Apple use macOS High Sierra. My Apple MacBook Pro uses macOS Big Sur. The iPads and iPhone involved in the incident use iOS, not macOS. Therefore, the reference is erroneous. 2) The response does not address the product impacted, Apple iCloud Drive. That is the service for which I pay $9.99 per month. That is the service that is impacted and for which I was seeking a refund. The response by Apple does not address Apple iCloud Drive at all, therefore it doesn't address the complaint.
Friday April 9
A week later, I was notified of a new response from Apple. This time, they offered me the iCloud Drive legalese.
Apple: "DOES NOT GUARANTEE, REPRESENT, OR WARRANT THAT YOUR USE OF THE SERVICE WILL BE UNINTERRUPTED OR ERROR-FREE, AND YOU AGREE THAT FROM TIME TO TIME APPLE MAY REMOVE THE SERVICE FOR INDEFINITE PERIODS OF TIME, OR CANCEL THE SERVICE IN ACCORDANCE WITH THE TERMS OF THIS AGREEMENT."
Well, sure, I thought. But I also thought to myself that interestingly, such a disclaimer makes no mention of any obligation to disclose or make clear when the service is unavailable. Again, the issue was not even so much the failure of a paid service, but rather the complete lack of disclosure of any kind before, during or after the incident.
Weeks went by, I emailed and left messages for David, Phyllis, and Justice. Nothing. I still had a warm good feeling about Apple Support, knowing that somewhere, David, Phyllis and Justice probably really would like to be able to get an answer from engineering, just as I did.
Monday May 10
We were now into May, with no answer and increasingly little response from my messages to David, Phyllis, and Justice. On May 10th, I called the main Support number, and was passed to a new senior advisor, let's call her Dianne.
Dianne looked at the case notes. She noted there were no replies from engineering of late. Dianne remarked that there can sometimes be a matter of data corruption. It seemed to her, she said, that the matter was connected to trying to recover data or data loss in some form. She offered that she could try to send in another request. "I see multiple requests," she noted. "David made a lot of requests. They — meaning, engineering — would come back with replies like 'it's fixed'."
When pressed for an answer as to what happened, said Dianne, engineering would reply by apologizing for any inconvenience. "It seems to me like we will not get an answer," Dianne told me, and I had to agree with her. I thanked her for trying and we wished each other a good night.
The next day, I sent in a request for comment to Apple's public relations line. A PR rep, let's call him Carson, wrote back sounding most interested, and asking for the details. I shared the case numbers, and a summary of what had transpired, somewhat shorter than this article.
Carson apologized for the inconvenience, and said he would look into the matter. He asked about my deadline for publication, and I said I was flexible; I was most concerned to learn something that might be of use to readers if they ever found themselves in this situation. He promised to follow up once he found out more.
Monday May 24
I followed up on May 24, and Carson said he was still checking.
I haven't heard back from anyone since. I still have no explanation what went wrong. Happily, iCloud Drive has not lapsed back into craziness, so that the frustration of March and April is starting to seem a distant memory.
Lacking any feedback from Apple, I'll offer what takeaways I can piece together from all of this.
Failures can happen, but Apple apparently considers days worth of failures no big deal, even though in any sane operational environment, such an extended period of downtime would be deemed a serious matter, even if it only affects a minority of users, or even just one user.
It appears Apple is relatively unconcerned that some individuals who depend on iCloud to get work done may be hampered. That's particularly interesting in a world of increasingly remote work, where iCloud could be a real resource for those working from a home office.
Another observation I'll offer is that when Apple systems experience failures, it appears that systems staff are not prepared with engineered solutions to ameliorate the matter for customers.
I'll add that Apple operations engineering appears to function in a way that is more or less divorced from Apple support staff. Support staff appear to have to go begging for a coherent answer from systems engineers, who appear to treat such requests as unimportant.
Finally, the most interesting aspect of all this is that an instance of "maintenance" is not regarded as something that the customer needs to be alerted to. There appears to be no mandate for maintenance notification or maintenance explanation.
Unlike the real world, where planned maintenance comes with warnings, and unplanned maintenance comes with explanations, apologies, etc., for Apple systems engineering, it seems the customer end of the bargain, the customer experience, is basically irrelevant.
The subtext is that Apple's iCloud is lacking in some very basic principles of operations discipline that pertain to customer experience. That's a disturbing phenomenon given that Apple is releasing more and more devices into the wild that are strictly appendages to a cloud service, such as AirTags.
The prospect is there for a world filled with black-box devices running on an unstable cloud service, which could bring a new level of headache for users.
Be that as it may, since Apple's best practices are unlikely to get better anytime soon, the best customers can do is drive defensively.
Apple's iCloud, as with all consumer digital services, is a best-effort facility. You should expect it may well fail, and fail hard, at some point in your use of the service. You should be prepared with alternatives.