My mom (78) got a new kindle a couple years ago, after the previous one lasting over 10 years.

She’s not been using it now because “it’s not okay” anymore. After a lot of poking and prodding remotely (we live in different countries) to get to understand what the issue was for the kindle to “not be okay”, I managed to get her to tell me that “the screen is blank”. I said I’d check it soon after when I went to her place.

When I travelled there, not long after, I checked the kindle, turned on the screen, and it was blank. Because she’d finished a book and the last page was blank. All worked fine.

I have told her, but she refuses to use the kindle because “it’s not okay”.

In a separate conversation I offered to give my sister my really old kindle as hers is actually broken. My mom heard that and said she wanted it because hers is… Not okay.

The insistence and willful ignoring of what I said is the most infuriating part.

While helping my mother troubleshoot her phone:

I can’t do anything because the keyboard keeps going away

Everything I click on tries to take me to WalMart

It keeps saying the phone is overheating but it’s not overheating, should I download this program it’s recommending?

No! I didn’t download anything! I don’t download things! Wait… Is the app store considered “downloading”?

I can keep going lol

Fortunately my dad is a retired cybersecurity architect so they live as modern-day Luddites.

Don’t know about most painful, but it definitely sticks out.

My mother screamed for me at the top of her lungs on the other side of the apartment. I hurried into her office, where I see her pointing at the screen saying “FIX IT!” So I look at the screen and… it’s a save dialogue in Word, asking her if she wants to save her document.

Me: It’s asking you if you want to save the document.
Mother: Well how am I supposed to know that?
Me: Do you want to save the document?
M: I DON’T KNOW!!

It’s like she saw the dialogue and her brain crashed. She definitely could’ve read and understood it, but just chose not to. That sort of thing was a frequent occurrence sadly.

I set up my mom on Microsoft Outlook many years ago, back when you had to set the server and so on.

She called me a few days later and said her email wasn’t working, so I walked her through looking at the options, making sure the right addresses and preferences were checked, etc.

After about 45 minutes, I remembered that I already set everything up correctly and it was working. Then I decided to ask, “are you typing the @ symbol, or are you typing the word at in the email address?”

Yep.

My mom called me a few years ago, after she clicked the big red warning message in a pop up. After the nice tech support man got on her phone. After she let him install “some program”. Then she thought, maybe she should check with Perish. Yikes.

Friend of the family but still…

Had to travel by boat to an island with no road connection to turn on a printer, after having been promised that it was, in fact, on.

Once turned on it was working. Well as much as a printer can work.

Cave woman that I helped: “You’re not installing porn are you?”

Me: “Uhh, no?! Is that what you meant by helping you to setup the computer. Are you mistaking me for your husband?”

Painful would be the several (!) times I had to check the computer over after they fell for a tech help scam and lost money. The stupid thing was that if someone tried to sell them something on the street or phone they were smart enough to refuse, but for some reason a popup on the computer makes things legit. Even after it was a scam the last time it happened. Why?

There are many more lesser events that aren’t painful as much as just tedious, but I think having some patience and knowing what to tell them (vs. actually explaining it) helped. I tried to reduce the complexity and lock things down, but in the end it was just easier to come over and fix the problem every now and then.

Recently had to help my mom figure out her new internet setup. She wanted to keep her old phone number but it was not carried over to the new provider. My guess is she said that she wanted to keep it while ordering the new one but never followed any of the steps they gave her to make that work. So we called them and it was crazy how she was unable to explain to them what her current situation is and what needs to be fixed. Claiming that “nothing works” even though the internet works just fine and the only problem is the phone number. Also not really looking at the emails they send her and following the steps to activate the online service center where she could manage this stuff on her own.

Later I showed her that the laptop she got from work is able to connect to her new router wirelessly and does not have to be connected via cable. She already uses another laptop and her phone over wifi. Apparently she just has no interest in understanding how any of the internet systems work.

My father is an engineer, which has its ups and downs. He can definitely be trusted to read a dialog box and nearly 100% of the time even understand what it says. Abstract concepts, problems he’s never encountered before, all generally no issue.

My stepmother, however, once asked me if she needs to rewind a DVD before putting it away. We’ve been working on it with her over the years. She’s certainly better now, but she still has an acute case of just randomly clicking on things without reading them.

My Dad will ask me to help him with a tech issue then, because he spent 20-odd years doing spreadsheets and databases, he will decide that he knows more about the thing he’s just asked me for help with so I don’t help him anymore.

Most notably, when he was having issues with his video editing and I was doing a couple things with his export settings (we had a few classes about video editing in college- photography major) and half way through he decided I was wrong and the way he was doing it was best. The videos are now huge and unwieldy when they’re only going up on YouTube. 🙃

My late mother-in-law’s phone had so much malware running on it that it was completely inoperable. She had poor vision, so would just tap the screen at random to try to get dialog boxes to go away. She didn’t really use ut for anything but making and receiving calls. I booted the phone in safe mode and removed basically everything from it, but it would inevitably reinstall. Eventually, I just factory reset the phone to make it usable again. Then I went through the accessibility options and increased the font size to obnoxiously large so she could read it. She really just needed a dumb phone.

my parents are too tech savvy :/
But in school i removed a gum paper from the disk drive with a screw taped to the end of a brush if that counts

My father in law (age 78) just got a new phone. His last phone cost $100 new, was only a year old, and took actual seconds to respond to most things. It finally got stuck boot looping to recovery mode so I lent him my old OnePlus 7T to use because we were gonna get him a new one for his birthday, but he just went ahead and bought a new (used) Samsung for $200.

The Samsung is actually a pretty decent phone, but he refuses to learn how to use it. He badly wanted to use his old phone, but it won’t work anymore. He made me put the SIM card in his old phone. I told him he’s free to use that old thing, but I won’t be helping him with it anymore.

He is finally learning how to use his new phone a month after getting it. The man refuses to shell out for a half decent phone, despite having the money to. He’d rather spend $150 every 18 months buying a new crap phone than spend $400 on one that could easily last 5 years.

He doesn’t even need a smart phone. He doesn’t understand what a launcher is. So he downloads whatever crapware is advertised to him, then gets really confused why his home screen is all fucky. I’ve told him he should really consider getting a flip phone and using a laptop for anything else. He doesn’t want to. He wants a smart phone.

I can’t save this man. My parents are in their mid 50s and have finally caught up. 20 years ago, I was telling them they do not need the crapware DVD that came with the digital camera to import their pictures. All you need to do is put the SD card in the computer and copy the DCIM folder to the Pictures folder on the computer, then delete everything in the SD card’s DCIM folder to free up space.

Since I don’t use Windows anymore, I don’t answer Windows questions anymore lol If anyone calls with a Windows question these days, I just nope outta that.