Apple Watch Series 5/6, iPhone X, 11 communications failure

This is long and involved. If you don’t want to see what I went through and how well Apple support did — or didn’t — do, just scroll down to the bottom of this page. I did manage to solve the problem, with no help from Apple support, although the hoops that they made me jump through gave me the idea for what was wrong.

Yesterday, 9/25/2020, I received my new Apple Watch Series 6. I’d been using a Series 5. My old Series 5 had been working fine until the update of my iPhone X to iOS 14.0, which broke communication with my watch. I got a message saying that I needed to update the watch OS in order to reestablish communication. I tried to do that, but the update kept hanging. I gave up, knowing that I’d get a new watch in a couple of days.

When the new watch came, I went to the watch app on my iPhone X, and tried to cancel out of it. The app said that I had two choices: a) I could keep on trying to update the watch, or  b) it would unpair the watch and reset it to factory settings. I chose the latter. I checked with iCloud, and the watch was no longer listed as one of my Apple devices.

Then I paired my new watch with the iPhone X and told it to restore from the backup. That appeared to go fine, but when I started to explore my new watch, I noticed sever interrelated things that were amiss.

• The ECG app complication was missing from the face of the watch
• The ECG app icon on the watch was partially obscured by a semi-transparent grey dot in the center, which made it look like a white doughnut with a dark gray hole in the middle and a red squiggle of icing running across it. It looked the same way in list view and in sea-of-icons view. I’m interpreting that to mean that the app is greyed out.
• When I pressed on the weird-looking ECG app icon, it wiggled, but the app didn’t open.
• On the iPhone X, the ECG app did not appear as a complication that I could add.
• I couldn’t find anyplace in the Heart app or the Watch app to install the ECG app.

This morning, my new watch wanted to be upgraded to OS 7.0.1. I upgraded it from the iPhone X. It now reads 7.0.1 (18R395). That didn’t change the situation with the ECG app.

I opened a phone support case. The tech asked me to upgrade my iPhone X from iOS 14.0 to iOS 14.0.1. I did so. No change.

I called back with my case number. The tech said the issue was beyond him, and asked to escalate my case. I asked if I should unpair and repair first, and he said no to do that. I held on hold for half an hour, and he said the anticipated wait time was 50 minutes. He said he was going to drop off the call, and that I should just be patient.

After an hour and a half on hold, I got to a tech. After checking on serial numbers and OS levels, he asked me to unpair and repair. After repairing, he suggested restoring from the latest backup of the Series 6. I did that, and things were much worse. Not only was the ECG app greyed out, so were many other apps.

We power cycled both the phone and the watch. No joy.

The tech sent me a link to a profile that I installed on the iPhone that will upload logs to Apple. We scheduled a call for Thursday at 11 o’clock, by which time the Apple folks should be able to review the logs and offer suggestions. Total time for the second phone call: two hours and 15 minutes.

I’m keeping the packing material, just in case.

At 11:30 on Thursday morning 10/1/2020 I had no call from Apple. I contacted tech support via chat. They said that the tech was too busy to call, and had sent an email. I checked my spam folder, but there was no email there, but I got a call at 11:40. I was immediately put on hold. After five or ten minutes, I got a new tech on the line. She verified that the watch was not working, and said that it had been uploading the logs every 24 hours since Saturday. Then she put me on hold again while she did some research. After a few minutes, the tech came back on the line, and said that she needed to transfer me Apple Watch support. She did so. The new tech asked what the problem was. I pointed her at this blog post, but she said her system wouldn’t let her access it. I gave her the reference number. She said that she needed to put me on hold while she did some research. So you see a pattern here?

I got the tech back after ten minutes or so. After another thirty minutes on the phone, the tech couldn’t think of anything more to try, and said she’d have to call me back. I suggested that I unpair and re-pair the watch while she was gone, and set it up as a new watch, since it seemed like the restore process might be the issue. Said said she’d call in about  45 minutes.

I rang off. Total time on the phone today: about an hour.

I unpaired the watch and re-paired it as a new watch. No joy. Lots of grayed-out apps.

After an hour and a half, I got an email from Apple saying they were trying to reach me but were encountering a busy signal. They said they’d keep trying. I checked and made sure the line was working and clear, and waited. After another half hour, I got a call saying there was no answer, and they were giving up, and I should call back if I wished to pursue it. I called back. The tech wanted me to start all over explaining the problem, but I insisted that he read the record of the incident. He did, and asked me if re-pairing as a new watch fixed the problem. I said it did not. He said he’d transfer me to a “senior advisor”, and he put me on hold.

After five or ten minutes, the new Apple tech came on the line. I show him how to access this blog, and he familized himself with the case. I installed a support app that let him see the display, and show me a red arrow that told me where he wanted me to press, and we walked through some things. He ran some diagnostics, which the watch passed.After a while, we agreed that we’d done all we could, and that they’d send me a box, so that I could return the watch for a replacement.

But I was getting suspicious of the phone. Remember at the top of this post when I'[d have trouble updating my old Series 5 Apple Watch? What if the problem wasn’t the watch, but the phone? I said I’d unpair the Series 6 watch, pair the phone to the Series 5 watch, and see if that worked.

I upgraded the OS on the Series 5 watch using the iPhone, paired the two, with the watch set up as a new watch. Same grayed-out apps.

I sent an email to Apple informing them of those results. It seems to me that the problem must be with the phone. I await instructions from Apple.

Friday, 10/2/2020, a week after I received the watch, I got an email from Apple asking for the iPhone serial number. I responded with the number.

Saturday, 10/3,2020, I got a message from the tech saying my iPhone was out of warranty, and that I should try resetting it to factory settings and setting it up as new. That’s going to take hours, and if it’s a hardware problem it’s not going to fix the issue, and at the end of that time, I’ll have an old phone. Much as it pains me to solve this problem by throwing more money Apple’s way, I’m ordering a new phone.

10/6/2020

The new iPhone 11 Pro arrived from Verizon. I turned it on, and brought it close to the old phone. I told both phones I wanted to transfer my information to the new phone, and it set about doing that via Bluetooth. The old phone had a spinning icon in a window labeled Finish on New iPhone. The new phone went back to the Hello screen. I swiped up, and attempted to activate the new phone. No luck. Then I got a message to call Verizon at 877 807 4646. I did.

The tech tried a few things, but couldn’t get any of them to work. He had me turn off both phones, turn the new on back on, and set it up manually. However, because of two-factor authentication, it sent a message with a code to the old phone. I turned it back on, got the code, entered it in the new phone, and turned the old phone off again. I went through the setup, and somehow — from the failed synch over Bluetooth? — it knew my WiFi password. It asked me to update the OS to 14.0.1. I did. That took a while. Actually, the download only took a couple of minutes, but the rest  of the update took 20. When it finished, it turned the power off. It did not. After a while, I pressed the power button. It showed the the apple, and started what looked like a normal boot. But about 20% of the way into the boot, the screen went blank, the apple game up again, and the progress bar went back to 0%. Finally, it finished  the boot. It downloaded some information from iCloud. Then it did another reboot. it said Hello, and then the screen went blank. I waited, and power it up again. The phone didn’t pass the Verizon test-call exercise. The tech had me reset the network settings. Then it did pass. I made some test calls, and received a test message.

Everything appeared to finally be copacetic. Then I got a popup message from the new phone (the old one was powered off at this point) saying the phone was not activated. That gave me pause, but the tech said there was nothing to worry about.

Total time spent on the phone: about anr hour and twenty minutes.

The next step was getting an Apple watch paired. I powered up the old iPhone, and unpaired the Apple Watch Series 5. Then I shut off that phone. On the new phone, I paired the watch. Everything seemed to go normally, except at one point after I entered my Apple ID, the phone said it couldn’t contact the server. It want OK the second time, though. I said to set the Series 5 up as a new watch. The download to the watch went faster than it had with the old iPhone. Then, when the progress bar got to about 7:30, it stopped moving for several minutes. It jumped to 11:30, hung there for a few more minutes, and finaly completed.

I pressed the crown to get started, and again to bring up the menu. Half the icons were grayed out. I guess it wasn’t the phone.

10/6/2020

I sent a message off to Apple telling them what had happened, and giving them a link to this page. I received a response that asked me to send in the Series 6 watch. Obviously, they don’t understand what’s going on. I have a brand-new iPhone 11 that can’t set up the old watch. I haven’t even tried the new phone with the new watch. I pointed those facts out in an email, and haven’t heard back yet.

10/7/2020

I went to town today and my new iPhone 11 couldn’t contact the Internet. I reset the network settings. That didn’t work immediately, but after about five minutes, I got a notice that my phone had been successfully activated, and I could go on-line.

It’s now Thursday, 10/8/2020, almost two weeks after the issue first surfaced. I received this email today from Apple:

You can try to reset/wipe the watch again, then reset it up as new.  Choose to not restore anything from iCloud.  Just completely set it up as new.  This will not allow it to sync anything from iCloud.  If your theory is correct, (which is makes alot of sense), it should solve  your icon issue.

I didn’t have high hopes, because that was what I had been doing all along, but I gave it a try, this time with the iPhone 11 and the Apple Watch Series 6, which was the only combination I hadn’t tried. No joy.

I followed the instructions, using the iPhone 11 I just bought, and the Apple Watch Series 6. But there’s a memory process in play here. There is a timer icon in the lower left of my Infograph face, where it was when everything was working. But in the Watch app on the iPhone, that position is listed as off. If I tap it, the watch asks if I want to restore “Timer”. If I say yes, it takes me to the app store. Then I can tap on the download from cloud icon. But when I go back to the watch face, tapping on that icon brings up the same message about restoring “Timer” so the restoration didn’t take place. This is also no change from before.

The phone has some memory of the way a previous watch has been set up, even if you tell the watch app in the phone to set the watch up as new. Could this be the source of the grayed-out icons?

It’s Friday, 10/9/2020, and I got this email from Apple: “I am going to have to consult engineerings again for this, along with your screenshots of the watch showing the exact issue.  I have sent you a link you can log into with your apple id with & upload the screenshots to me.  They will help the cause immensely.”

I sent them the screen shots.

10/12/2020. I sent Apple an email asking for a progress report.

10/13/2020. No response to yesterday’s email. I sent another.

10/14/2020. I got a call from Apple support. The tech had me download some more monitoring software power-cycle both the watch and the phone, and sent the logs to engineering for evaluation. They couldn’t find anything wrong. They said they’d keep looking. After the call was over I got a request to update the watch OS to 7.0.2. I did so.

10/15/2020. I got an email from the tech saying the watch still looked like it was on 7.0.1, and asking me to double check. I did so. The watch thinks it’s on 7.0.2.

10/16/2020. Nothing from Apple.

10/19/2020 Sent the follow message to Apple Support:

It’s now been more than three weeks that I’ve been working with Apple support on this issue. Have you made any progress? From my end, it appears there has been none.  Have you eliminated any possibilities? What are the possibilities that remain? What will happen next?

10/20/2020 Received the following from Apple Support:

I will be call you shortly.  Can you send me the serial number to the iPhone that will pair with your watch?  I have to run the diagnostics from that.

I responded:

I’m not sure what you mean by the iPhone that will pair with my watch? Neither iPhone pairs properly with the watch.

The tech called, and said that he meant the watch that was currently paired with the watch. That’s the iPhone 11, which I bought because Apple refused to troubleshoot the problem with my out-of-warranty iPhone X. I gave him the serial number, and he downloaded a diagnostic app that ran on both the watch and the phone and sent the logs to Apple. He said that he’d send the logs to engineering, and call me tomorrow. I pointed out that we had done the exact same thing on 10/14, and asked what happened with those logs. The tech didn’t know.

It seems like we’re going around in circles on this.

10/21/2020 No call from Apple.

10/22/2020. The Timer app, which had been grayed out, came back to life, and works. Apps still grayed out:

1. Alarms
2. Audiobooks
3. Blood Oxygen
4. Breathe
5. Calculator
6. Calendar
7. Camera Remote
8. Compass
9. Cycle Tracking
10. ECG
11. Find People
12. Home
13. Mail
14. Maps
15. Memoji
16. Music
17. News
18. Noise
19. Podcasts
20. Radio
21. Reminders
22. Remote
23. Shortcuts
24. Sleep
25. Stock
26. Stopwatch
27. Voice Memos
28. Walkie Talkie
29. Wallet
30. Weather

I received an email from Apple support:

Just heard from Engineering.  Please update to 14.1 on your iPhone.  It just came  out today

I upgraded the OS. No change. I asked if I should unpair and re-pair.

Received the following message from Apple Support:

OK, here are a few other steps they would like you to go over.  Just let me know if you have any positive results with your apps afterwards – -thanks:

– Be sure Apple ID signed in on iPhone
– Sign out and back in to their Apple ID.   Does the same issue occur?
– Try deleting  and redownload the affected app on their iPhone.  Does it then load properly onto the watch?
– Are you installing the apps from the Apple Watch app on their iPhone or from the App Store directly on the watch?

– If they’ve only tried one of the methods above (Apple Watch app or watch App Store on the Watch), have them try the other to see if the same issue occurs

I signed out and back in to Apple ID. Some old situation, except that my phone wouldn’t let me look at Apple News+.  I could see it on all my other devices, though.

Went  to the top of my grayed-out app list. Looked for “Alarms” on the iPhone. Can’t find that app. Next is “Audiobooks”. Could only find third-party apps. Skipped to “ECG”. Got message saying that “This app can be downloaded only on Apple Watch.”

I can’t figure out how to install apps from the watch. On the phone, in the Watch app, none of the grayed-out apps appear. When I go to the App Store on the watch and search, none of the apps above come up in the search results, just third-party apps.

I emailed all of the above results to Apple.

10/24/2020. I sent the following email to Apple:

I didn’t hear from you yesterday. That’s a disappointment.

Let’s review the situation. It has been four weeks since I first reported a single grayed-out app on my new Apple Watch. Since then, I have been performing the steps you have suggested, which first resulted in the graying-out of many more watch apps, and on Thursday caused me to loose access to News+ on my iPhone. You have run diagnostics on the watch twice, and uploaded the logs. You have never told me  what, if anything, has been found in those logs that is useful. The last set of instructions you sent me looked like they applied to someone with a different problem.

I have no sense that we’re making any progress at all.

Please tell me what you think the path to success in troubleshooting this issue is, and how long it should take.

I received this:

Sorry Jim, I am just waiting to hear back from Engineering, as we haven’t received anything new from them yet.  I am out of office now until Tuesday, when I return I hope to have word from them.  I know it’s been 4 weeks also.

I am sorry this is taking longer than expected too.  I am beginning to think it’s going to be a replacement?  We will see early next week.

I sent this:

What would you replace? I’ve got two phones. I’ve got two watches. Neither phone works right with either watch.

10/27/2020 I received this from Apple Support:

Receiving word back from the Engineer handling this issue:  Apple has received reports of this behavior. Those reports are under investigation by Apple.

Your feedback on the issue will help isolate what is happening here.  It is very much appreciated.

A solution may come in the form of an update, in which we will let you know, and are encouraged to keep all devices up to date, as I know you are.  Thank You,

They are looking into the situation diligently, and I will let you know the second that I hear back from them.

Again, thank you for your patience on this matter.

11/6/2020 A new iOS update for the phone became available yesterday, 14.2. I installed it on the iPhone 11. No change. Watch apps still grayed out. The phone still thinks I haven’t subscribed to News+.

It’s now been seven weeks since I got the Apple Watch 6 that didn’t work right. I have now spent about $1600 for Apple products that don’t work: the first $400 for the watch, and then $1200 for the iPhone 11 that I got when Apple said my iPhone X was out of warranty and that they would no longer support me on trying to get it connected to the Watch series 6. About 30 watch apps are grayed out. And, in trying to fix all of the above, following the instructions of Apple support broke News+ on the iPhone.

Assuming that there is just one thing that’s causing all this, it’s got to be the backed up data in my Apple account, or in the process of restoring that data. But I know of no way to selectively restore some data from the Apple account. Setting up the phone as a new phone doesn’t keep data from being loaded. The minute I sign into my Apple account, a bunch of data downloads, and I have no control over what data is downloaded. If I set up another Apple account, that might fix things, but than I wouldn’t have any synchronization across my Apple devices, and I’d have to pay for new subscriptions and apps.

11/7/2020 I updated the watch OS to 7.1 (18R590). No change in symptoms.

11/10/2020 I received the following from Apple Support:

If you would create a brand new Apple ID to sign your phone into, and then repair your watch to it.  (Unpair the current setup before trying any of this).   This would prove your point & solve this mystery of these icons.  Your other account will still be there to sign back into when & if needed.

If this would resolve things, I can work with iTunes regarding apps & other subscriptions.

Regarding your News app on the iPhone, delete it & then re-download and install it again from the App Store

11/11/2020 I deleted the News app, and tried to download a new copy from the Apple store. The download hung. The News app icon is grayed out on the iPhone. When I tap it, nothing happens. Cancelling the download and trying again produces the same result. There’s a pattern here. It seems the more I try what Apple support suggests, the more things break. Remember, this all started out with a single Apple Watch app not working.

I unpaired the watch, logged out of my Apple account, logged in to a different one, and re-paired the watch. No change. Most apps grayed out. Note that if what’s wrong is what I think is wrong — that it’s a problem with backed up data — changing Apple accounts wouldn’t fix it.

11/12/2020 I downloaded the CNN news app from the Apple store to make sure that I could download apps in general. That worked fine.

I had a thought. What if the failure to load the News app on the iPhone and the other apps on the watch had a common cause, such as being blocked by a firewall. Surely Apple wouldn’t let those downloads fail silently. But what if they are doing exactly that? And what if they are using different servers for different aps? I took my phone to a place with no WiFi service, canceled the News app download, and reinstalled it from the app store. It worked. Not only that, but News+ worked, too.

I checked my Sophos firewall exceptions. I had one for Apple:

• Apple uses protocols and payloads in its downloading that the Sophos firewall in its default settings recognizes as malware.
• The Sophos firewall blocks those downloads. The firewall may or may not do this silently, but it doesn’t matter, since there appears to be no user interface to the app download process on either the iPhone or the Apple Watch.
• Thus, the downloads fail.
• The watch and the phone recognize that the downloads have failed. Evidence for this is that simply removing the firewall blocking (see below) doesn’t fix things. To fix things, you have to cancel the earlier downloads and restart them after the block has been removed.
• However — and this is the part that really should be fixed — the watch and the phone give no warning to the user that the downloads have failed, and just keep the icons grayed out as if a normal download, so the user has no idea that the download has been blocked.
• Apple used to use a set of servers for downloading apps and backups that could be encompassed in the following Sophos scanning exclusion: ^([A-Za-z0-9.-]*\.)?apple\.com\.?/ That was the exception that I had used previously, and it has worked just fine.
• Apple has added some servers for some apps that can’t be used with the above exception, although that exception works fine for many apps. This explains why the missing apps on the watch were the same apps every time.
• Adding the following exceptions makes all the app downloads work:
  ^([A-Za-z0-9.-]*\.)?cdn-apple\.com\.?/
  ^([A-Za-z0-9.-]*\.)?cdn\-apple\.com
  ^([A-Za-z0-9.-]*\.)?icloud\.com\.?/
  ^([A-Za-z0-9.-]*\.)?mzstatic\.com\.?/