I compiled this list from HN news article titles that claimed something was broken.
Everything
TV
Java and Python sorting algorithm
OSX memory management
Hiring
HTTP
The internet
Email
Math.random in V8
Some links
The string type
Google's hiring process
Web development workflow
EC2 firewall
RNG
SSL
The ocean
Email forwarding
Sleep
WhatsApp
Bookmarks
Bitcrypt
The patent system
Breaking news
POSIX close(2)
Scientific peer review
Your Tumblr
systemd
Your wireless router
Nearly all binary search and merge sorts
OpenGL
Bread
Maven
HN submissions system
Your Docker image
iOS 8.0.1
VirtualBox
OpenSSL's implementation of DSA
Airport security
Facebook
The War on Drugs
Diablo III economy
All the crypto code you've ever written
Web development
Unicode in Python
Go packaging
DNS in OSX 10.10
Agile
Interviews
Security of USB
Mac App Store DRM
HTML <a> element
Your business
The venture capital model
CMS
RC4 in TLS (kind of)
GSM encryption
Visa and MasterCard security
Google's design process
Silicon Valley
java.nio.file.WatchService, on Linux
Employee equity
East New York
Language learning
DCI in Ruby
Logout in Ruby on Rails
Performance tools
India's higher education system
Copyright
Algorithm development
GitHub's language detection
Shopping
HN flagging system
Google App Engine
Photo uploading
US justice system
Outlook
Our pricing model
RC4 in TLS
The calorie
Online dating
Bitcoin
Tech journalism
Firebug
California's jaywalking law
Wireless
Browsers
Your online WYSIWYG editor
Skype for Windows
NBC's Olympics coverage
The payments industry
Someone's iPad
The App Store business model
Hollywood
The 30-day free trial
America's meritocracy
Continental Airlines funnel
Advertising in mobile games
Flash ads
PayPal