Oops! I ruined your life. :)

It was one of those, “please, please, let this send,” kind of moments when you hope a weak airport WiFi connection doesn’t disconnect, a low-battery indicator doesn’t shut down your laptop — who knows where there’s an outlet in this airport — and your email actually sends to your million dollar client when the message popped up and your stomach drops: “Oops!”


Like some kind of creepy, American Psycho moment, a hardly-discernible, non-apologetic message from Gmail put this exact dagger into my heart and sent me wondering what went wrong.

Sure, of course, just lemme look up error #001. What?

Google’s Chrome browser gives off an even worse error message that doesn’t make things better, just a wanna-be-hipster-piece-of-software knocking off a Susan Kare classic laughing in your face when you’re frustrated:

aw, snap!

Maybe this is part of some awful brand initiative. After all, Google is a place of smiles. An every-color-of-the-rainbow logo, and three square meals place to work with unbelievable benefits. But, then again, Google is hardly alone in this kind of “smile when you’ve fallen” approach to error messages.

Microsoft is sadly considering implementing the same, cutesy thinking in a revamp of their blue screen of death as a part of their otherwise exciting, new Windows 8 operating system:

Windows 8 blue screen of death

Oh, great. My 14 year-old cousin is writing error messages in Redmond.

Fortunately, Microsoft offers some advice. Just search for the error message, “HAL_INITIALIZATION_FAILED”…oh wait, this is the blue screen of death. My computer is totally effed.

Not to be oops-outdone by Google, Microsoft’s XBox website includes the word, “Oops!” twice in an error message, first in the header and then as the first word to explain the header. Obviously, after frustrating someone, the best thing to do is say “Oops!” over and over again.


Oops! Oops


Sure, I’ll “like” that page.


And if you thought the non-profit Mozilla Foundation avoided this kind of creepy, cutesy error messaging in their Firefox browser, you thought wrong.


The legoman is sorry that you can’t load your favorite TV show.

In times like this, there’s always YouTube, right? Millions of fun videos to help us laugh at times of stress.

Youtube is sorry


(Downtime Blog)

Grab some music off my Apple iCloud?

iCloud cute

Check my Twitter feed?

Fail Whale

Is there no escape from this cute hell‽

The hip company Plaxo — your address book for life — has not only embraced the “oops” but entered another level of creepy. Shhh…this error is just “our little secret.”

Plaxo creepy oops

What’s happening?

You know, not too long ago, whenever something in software was confusing to users, software-makers had a brilliant, can’t fail, simple solution: add a how-to in the help section. Instead of spending hours making strange features straightforward, software companies passed the buck to the user: “Um, we can’t figure out how to make it easy to do, so just read the manual.”

Now it seems like there is another, new kind of awful simple solution for glitches and errors that infuriate people: a cutesy smiley face. After all, no one cares if you ruin their life as long as you do it with a smile, right?

American Pyscho


The root of Oops!


In 1925, a New Yorker cartoon caption is credited with being the first published instance of “Whoopsie Daisy!” But the real root of the “oops” phenomenon in software might be pointed to the Linux operating system.

Linux pengiun

This is your fault, Penguin. Please stop looking at me like that.

Upon “a bug in the kernel” Linux kicks back an OOPS error message. First developed in 1991, Linux’s code for error messages may have crept into the developer’s subconscious eventually leading to today’s proliferation of “oops.” Here’s an example:


  Unable to handle kernel paging request at virtual address 211e2018
  *pde = 00000000
  Oops: 0000
  CPU:    0
  EIP:    0010:[<c0129577>]    Not tainted
  Using defaults from ksymoops -t elf32-i386 -a i386
  EFLAGS: 00010083
  eax: d7ee5000   ebx: b420e080   ecx: c164e000   edx: c1615d04
  esi: c16073d0   edi: 00000246   ebp: 000001f0   esp: d7c5de84
  ds: 0018   es: 0018   ss: 0018
  Process mount (pid: 25, stackpage=d7c5d000)
  Stack: 00000000 c0309c00 000001f0 00000000 c01fadb7 c16073d0 000001f0 c1615a40
        c1615700 c1615a40 c01fa126 00000001 000001f0 00000000 c022f793 c1615a40
        00000001 00000000 000001f0 d7b6fde0 d7c5df14 0000006e bfffec0c 00000018
  Call Trace: [<c01fadb7>] [<c01fa126>] [<c022f793>] [<c01f8acb>] [<c01f8720>]
    [<c01f9450>] [<c0106d40>] [<c0106c4f>]
  Code: 8b 44 81 18 89 41 14 83 f8 ff 75 1d 8b 41 04 8b 11 89 42 04


(If you’re curious about all the hex, an explanation is available from madwifi.)


When cute works


Don’t get me wrong, there’s nothing wrong with cute.

(Cute overload)

Cute works well when you expect nothing from something. Like, babies.

LOL, he pooped his pants!
Awww, he farted!
Haha, he just puked on me!

But cute doesn’t work when you have expectations. Like, with adults.

Please, use the toilet…and the toilet paper.
Ohmygawd, that smells awful!
Do you need to go home?

So when a company like Google was still young, hip and start-upy, their error messages were indeed cute. Those silly Nooglers!

Google Reader OoopS!

How fresh!

But now that they are a publicly traded, 186 billion dollar company that we rely on for important business communications, which could make or break jobs, their cute error messages are about as cute as a Bill Gates tossing floppy disks. In other words, just plain creepy.

Turn it down from 11


The language of error messages in old software like MS-DOS were notoriously unfriendly.



Oh yeah, duh, ff0a8e6c shouldn’t have been pointing to HAL.DLL!


So, people who care about user experience have provided guidance. So, so many articles about writing good error messaging have been written over the past three decades. Here’s one. Here’s another. And another. And another. And another. And another from Yahoo! writers. Another, equating error messages to lost revenue. Another, on 404s

But today’s insulting cutesy error message writers have swung the pendulum too far. A common recommendation to use natural language to turn an incomprehensible “Error: Stack Overflow” has not turned into something polite and understandable, but instead an insulting “Oops! Aw, snap!”

What we need to do is dial it down from 11 on the friendly meter…11 is just too creepy. There is a happy middle ground where developers can apologize and software can provide the user polite guidance about what to do next. Website, app, software, you screwed up; help the user get their desired task completed ASAP.

To paraphrase Jon Stewart, oops is not the four letter word I would have chosen.

(The Daily Show) For the impatient, start at 6:52



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