More #TechFailures. I'm copying files from my Dropbox folder to an external drive, and when I go back to check, sometimes there are files on the external drive that have "zero bytes." Which is to say, THEY WEREN'T COPIED. What the hell. What the hell what the hell what the hell.
September 7, 2026 at 9:51 PM
More #TechFailures. I'm copying files from my Dropbox folder to an external drive, and when I go back to check, sometimes there are files on the external drive that have "zero bytes." Which is to say, THEY WEREN'T COPIED. What the hell. What the hell what the hell what the hell.
literally never seen this before. having to check every folder. this is bad. i don't know if it's a Mac thing or a Dropbox thing or a special horrible combo, but it's one of the worst things a computer system can do, imo. #TechFailures
September 7, 2026 at 10:12 PM
literally never seen this before. having to check every folder. this is bad. i don't know if it's a Mac thing or a Dropbox thing or a special horrible combo, but it's one of the worst things a computer system can do, imo. #TechFailures
Dropbox on the Mac continues to be #1 on my list of #TechFailures.
In July, Dropbox on the Mac decided to make all of my files online-only. I'm led to believe this is because File Provider on Mac dies this by default without asking when it decides you don't have enough room on your hard drive.
In July, Dropbox on the Mac decided to make all of my files online-only. I'm led to believe this is because File Provider on Mac dies this by default without asking when it decides you don't have enough room on your hard drive.
September 7, 2026 at 6:51 PM
Dropbox on the Mac continues to be #1 on my list of #TechFailures.
In July, Dropbox on the Mac decided to make all of my files online-only. I'm led to believe this is because File Provider on Mac dies this by default without asking when it decides you don't have enough room on your hard drive.
In July, Dropbox on the Mac decided to make all of my files online-only. I'm led to believe this is because File Provider on Mac dies this by default without asking when it decides you don't have enough room on your hard drive.
Shifting files on old drives to free up a drive for current use.
And it's objectively bad that Time Machine backups can't be moved from one disk to another. A few years ago, folks would just say archive it and get a new drive. But this is terrible in an era of expensive hard drives. #TechFailures
And it's objectively bad that Time Machine backups can't be moved from one disk to another. A few years ago, folks would just say archive it and get a new drive. But this is terrible in an era of expensive hard drives. #TechFailures
September 7, 2026 at 1:42 AM
Shifting files on old drives to free up a drive for current use.
And it's objectively bad that Time Machine backups can't be moved from one disk to another. A few years ago, folks would just say archive it and get a new drive. But this is terrible in an era of expensive hard drives. #TechFailures
And it's objectively bad that Time Machine backups can't be moved from one disk to another. A few years ago, folks would just say archive it and get a new drive. But this is terrible in an era of expensive hard drives. #TechFailures
#TechFailures
New one: Apple Mail and Google Groups aren't playing well together. Seeing a VERY weird quirk in which new messages in a thread appear in Apple Mail with the SAME CONTENT as the previous message - the PREVIOUS PERSON'S CONTENT instead of the new person's response. WHAT THE HELL?
New one: Apple Mail and Google Groups aren't playing well together. Seeing a VERY weird quirk in which new messages in a thread appear in Apple Mail with the SAME CONTENT as the previous message - the PREVIOUS PERSON'S CONTENT instead of the new person's response. WHAT THE HELL?
September 4, 2026 at 5:01 PM
#TechFailures
New one: Apple Mail and Google Groups aren't playing well together. Seeing a VERY weird quirk in which new messages in a thread appear in Apple Mail with the SAME CONTENT as the previous message - the PREVIOUS PERSON'S CONTENT instead of the new person's response. WHAT THE HELL?
New one: Apple Mail and Google Groups aren't playing well together. Seeing a VERY weird quirk in which new messages in a thread appear in Apple Mail with the SAME CONTENT as the previous message - the PREVIOUS PERSON'S CONTENT instead of the new person's response. WHAT THE HELL?
My #TechFailures saga with Dropbox continues. Kept trying to re-download the files it had made online-only, and for a while they'd seem to be downloaded, but then they weren't! Finally had to go into the preferences and discovered my selective sync settings had been wiped...
September 4, 2026 at 1:42 AM
My #TechFailures saga with Dropbox continues. Kept trying to re-download the files it had made online-only, and for a while they'd seem to be downloaded, but then they weren't! Finally had to go into the preferences and discovered my selective sync settings had been wiped...
In the meantime, I decided I wanted to ditch DropBox, natch, because this behavior sucks. #TechFailures, baby! I've been trying out Proton's cloud service. But it does a weird thing that I don't understand and that makes me nervous: bsky.app/profile/greg...
Proton Drive is sometimes randomly replacing the first couple of letters of documents with "~$"
wtf
#TechFailures
wtf
#TechFailures
August 29, 2026 at 12:44 AM
In the meantime, I decided I wanted to ditch DropBox, natch, because this behavior sucks. #TechFailures, baby! I've been trying out Proton's cloud service. But it does a weird thing that I don't understand and that makes me nervous: bsky.app/profile/greg...
#TechFailures
Finally circling back around to try to get a real fix on my DropBox issues. Brief recap: My Mac suddenly decided to take all my DropBox files offline. Apparently a thing it just does sometimes! So they were only in the cloud, not on my computer. MANY GIGS OF FILES...
Finally circling back around to try to get a real fix on my DropBox issues. Brief recap: My Mac suddenly decided to take all my DropBox files offline. Apparently a thing it just does sometimes! So they were only in the cloud, not on my computer. MANY GIGS OF FILES...
August 29, 2026 at 12:41 AM
#TechFailures
Finally circling back around to try to get a real fix on my DropBox issues. Brief recap: My Mac suddenly decided to take all my DropBox files offline. Apparently a thing it just does sometimes! So they were only in the cloud, not on my computer. MANY GIGS OF FILES...
Finally circling back around to try to get a real fix on my DropBox issues. Brief recap: My Mac suddenly decided to take all my DropBox files offline. Apparently a thing it just does sometimes! So they were only in the cloud, not on my computer. MANY GIGS OF FILES...
lol i tried to make a threads account, closed the window when it asked me to upload a selfie, then checked back later, added the selfie, and now it gives me this info.
I'm banned from Threads after never succeeding in setting up the account and making zero (0) posts!
I'm banned from Threads after never succeeding in setting up the account and making zero (0) posts!
August 18, 2026 at 3:44 AM
#TechFailures Started a new TikTok account (I know, I know) and it won't let me follow people. Like it actually SUGGESTS people for me to follow, and then I click on them and it looks like I've followed them, but then I check my "Following" list and they're not there.
August 18, 2026 at 3:43 AM
#TechFailures Started a new TikTok account (I know, I know) and it won't let me follow people. Like it actually SUGGESTS people for me to follow, and then I click on them and it looks like I've followed them, but then I check my "Following" list and they're not there.
Amazon prime video premiered their new Spider Noir show with much publicity promoting that viewers can pick a black and white or psuedo technicolor version, but had no way to choose black and white on amazon fire tvs, luckily, reddit users found a workaround… which amazon shut down 2 weeks later.
July 8, 2026 at 5:48 AM
In a year full of highs and lows for AI, the failures serve as a stark reminder of the technology's unpredictability. Companies must learn from these mistakes to build safer, more reliable systems. #AI #TechFailures #Innovation
January 3, 2025 at 6:22 AM
In a year full of highs and lows for AI, the failures serve as a stark reminder of the technology's unpredictability. Companies must learn from these mistakes to build safer, more reliable systems. #AI #TechFailures #Innovation
Bionic eye startup fizzled out, leaving hope in the dust. 💔 Innovation needs backing, not just hype. Let's learn from this—solid funding is crucial! #InvestSmart #TechFailures
it's phrased poorly, i'm also bemoaning that i read a news article where they were helping someone specific, and then nothing ever since, vanishing into vapor
like this startup that made eye implants and then they went bankrupt and they were left with junk
spectrum.ieee.org/bionic-eye-o...
like this startup that made eye implants and then they went bankrupt and they were left with junk
spectrum.ieee.org/bionic-eye-o...
Their Bionic Eyes Are Now Obsolete and Unsupported
These early adopters found out what happened when a cutting-edge marvel became an obsolete gadget... inside their bodies.
spectrum.ieee.org
June 2, 2025 at 8:01 PM
Bionic eye startup fizzled out, leaving hope in the dust. 💔 Innovation needs backing, not just hype. Let's learn from this—solid funding is crucial! #InvestSmart #TechFailures
Yesterday, after struggling for over an hour with Jira trying to figure out how to set up a small project, I decided to go with Azure DevOps instead. So I signed up with my personal account and it linked to my academic account and now won't work. So now just using a spreadsheet for task tracking.
July 9, 2026 at 4:40 PM
Your Biggest Clients Can Become Your Biggest Critics
❌ Major hospitals like CommonSpirit Health dropped Olive AI due to failed implementations. Execution matters!
🔗 startupobituary.com/p/olive
#CustomerSuccess #ExecutionMatters #TechFailures
❌ Major hospitals like CommonSpirit Health dropped Olive AI due to failed implementations. Execution matters!
🔗 startupobituary.com/p/olive
#CustomerSuccess #ExecutionMatters #TechFailures
Startup Obituary : Olive
The AI Healthcare Dream That Flatlined. From a $4 Billion Vision to a 2023 Shutdown—Unraveling the Rise and Fall of a Digital Health Unicorn.
startupobituary.com
March 11, 2025 at 8:14 PM
Your Biggest Clients Can Become Your Biggest Critics
❌ Major hospitals like CommonSpirit Health dropped Olive AI due to failed implementations. Execution matters!
🔗 startupobituary.com/p/olive
#CustomerSuccess #ExecutionMatters #TechFailures
❌ Major hospitals like CommonSpirit Health dropped Olive AI due to failed implementations. Execution matters!
🔗 startupobituary.com/p/olive
#CustomerSuccess #ExecutionMatters #TechFailures
There is a special place in hell for the person who assembled my Roomba! #roomba #robotsriseup #techfailures
July 16, 2025 at 1:37 PM
There is a special place in hell for the person who assembled my Roomba! #roomba #robotsriseup #techfailures
Apple’s 3 biggest wins and 3 greatest failures of 2025 #Technology #Business #Other #AppleWins #TechFailures #2025TechTrends
Apple’s 3 biggest wins and 3 greatest failures of 2025
The tech industry has endured another turbulent year, buffeted by the continued rise of artificial intelligence and the economic threats posed by President Donald Trump’s tariffs. Even the most prominent...
puretech.news
December 20, 2025 at 12:45 PM
Apple’s 3 biggest wins and 3 greatest failures of 2025 #Technology #Business #Other #AppleWins #TechFailures #2025TechTrends
Microsoft Made Another Copilot Ad Where Nothing Actually Works #Technology #SoftwareandApps #Other #Microsoft #Copilot #TechFailures
Microsoft Made Another Copilot Ad Where Nothing Actually Works
Microsoft's latest holiday ad for its Copilot AI assistant features a 30-second montage of users seamlessly syncing smart home lights to music, scaling recipes for large gatherings, and parsing HOA guidelines...
puretech.news
December 19, 2025 at 9:32 PM
Microsoft Made Another Copilot Ad Where Nothing Actually Works #Technology #SoftwareandApps #Other #Microsoft #Copilot #TechFailures
When AI reasoning goes wrong: Microsoft Research shows more tokens can mean more problems #Technology #SoftwareEngineering #ArtificialIntelligence #AIResearch #MachineLearning #TechFailures
puretech.news/article?id=4...
puretech.news/article?id=4...
When AI reasoning goes wrong: Microsoft Research shows more tokens can mean more problems
Not all AI scaling strategies are equal. Longer reasoning chains are not sign of higher intelligence. More compute isn't always the answer.Read More
puretech.news
April 16, 2025 at 1:30 AM
When AI reasoning goes wrong: Microsoft Research shows more tokens can mean more problems #Technology #SoftwareEngineering #ArtificialIntelligence #AIResearch #MachineLearning #TechFailures
puretech.news/article?id=4...
puretech.news/article?id=4...
The two key iPhone 16 features I wanted are massive flops #Technology #ConsumerTechnology #Smartphones #iPhone16 #TechFailures #SmartphoneNews
The two key iPhone 16 features I wanted are massive flops
I repeatedly told you during the iPhone 16 rumors season that I wanted two things from the model I'd get and two things along. These were the phone's rumored signature features: Camera Control and Apple...
puretech.news
March 13, 2025 at 8:45 PM
The two key iPhone 16 features I wanted are massive flops #Technology #ConsumerTechnology #Smartphones #iPhone16 #TechFailures #SmartphoneNews
What other apps, tech, businesses, or cultural phenomena from the last decade do you remember saying goodbye to?
Share your "in memoriam" additions! 👇
#InMemoriam #TechFailures #BusinessFailures #SportsRelocation #ForbesCurse #GoneButNotForgotten
Share your "in memoriam" additions! 👇
#InMemoriam #TechFailures #BusinessFailures #SportsRelocation #ForbesCurse #GoneButNotForgotten
July 7, 2025 at 10:27 AM
What other apps, tech, businesses, or cultural phenomena from the last decade do you remember saying goodbye to?
Share your "in memoriam" additions! 👇
#InMemoriam #TechFailures #BusinessFailures #SportsRelocation #ForbesCurse #GoneButNotForgotten
Share your "in memoriam" additions! 👇
#InMemoriam #TechFailures #BusinessFailures #SportsRelocation #ForbesCurse #GoneButNotForgotten
What can businesses learn from #BlackBerry's fall? 🤔
Once the undisputed leader, their story is a powerful reminder about complacency, innovation, and adapting to change. Don't miss this crucial #BusinessLesson. #TechFailures #StartupLessons
Once the undisputed leader, their story is a powerful reminder about complacency, innovation, and adapting to change. Don't miss this crucial #BusinessLesson. #TechFailures #StartupLessons
The Rise and Fall of BlackBerry: A Cautionary Tale
BlackBerry. The name itself conjures images of a bygone era, one dominated by physical keyboards, secure communication, and a sense of corporate indispensability. Once the undisputed king of the smartphone market, BlackBerry's meteoric rise was matched only by its precipitous decline, leaving behind a cautionary tale of innovation, complacency, and the brutal pace of technological evolution. For many, the story of BlackBerry begins with its iconic devices – the 850, the Curve, the Bold – but its roots lie deeper, in the innovative spirit of Research In Motion (RIM), founded in 1984 by Mike Lazaridis and Douglas Fregin.
www.lessworth.com
May 30, 2025 at 2:51 PM
What can businesses learn from #BlackBerry's fall? 🤔
Once the undisputed leader, their story is a powerful reminder about complacency, innovation, and adapting to change. Don't miss this crucial #BusinessLesson. #TechFailures #StartupLessons
Once the undisputed leader, their story is a powerful reminder about complacency, innovation, and adapting to change. Don't miss this crucial #BusinessLesson. #TechFailures #StartupLessons
I predict this thread will consume Bluesky! #TechFailures are a daily menace with most of my software these days. (Off to check my Dropbox, sigh).
Just making a thread of #TechFailures, because I'm seeing a lot of them these days. Not the big obvious stuff, but the everyday garbage I have to deal with, ranging from annoying to incredibly disruptive.
Yesterday and today: Dropbox on my Mac changed all my files to online-only. Without my asking.
Yesterday and today: Dropbox on my Mac changed all my files to online-only. Without my asking.
July 8, 2026 at 7:59 AM
I predict this thread will consume Bluesky! #TechFailures are a daily menace with most of my software these days. (Off to check my Dropbox, sigh).