#18925
For fun, Asterisks.com shares some amusing blunders collected by editors.
Asterisks.com (1999). Humor>Language>Writing>Localization
#19529
The Benefits of a Job Well Done 
A parable about the lives of a high-tech technical writing team. Ken puts his twenty-five years as a technical writer to good use in this fictional work about four people hired to write manuals for Xoom-tek. In the chapter excerpted, Ken takes a humorous look at RIFs and downsizings.
Wisman, Ken. TECHWR-L (2003). Humor>Documentation>Software
#20776
The Biggest Lies Heard by Technical Writers 
This list is the result of a thread started on the Techwr-l listserver group about the biggest lies we, as technical writers, hear on an almost weekly basis.
Documentia (2003). Humor>Writing>Technical Writing
#24016
#21664
Boredom: The Secret of Tech Writing
Of course, it's not 100% all of the time boring. Just some of it, on a fairly regular but not intolerable basis. But boring all the same.
Higgins, Lisa. TECHWR-L (2000). Humor>Writing>Technical Writing
#23219
The Bumper Book of Technical Boobs
Humorous examples of accidental (and humorous) errors in technical descriptions. Most of the gems on the following pages were, thankfully, picked up at the editing stage. One or two slipped through into printed books; some didnÕt even get as far as first draft stage. We have wondered for a long time about the mentality of the people who write this sort of thing; now you, too, can sit at your desk and try to figure out what these technical authors (yes, they actually get paid for this!) and engineers are on, where they got it from and whether they will give you some.
Watson, Sophie. ISTC (2004). Humor>Writing>Technical Writing
#28305
HCI Vistas presents cartoons that illustrate the interesting relationship between the human and computer.
Katre, Dinesh S. HCeye (2006). Humor>Computing>Human Computer Interaction
#24008
Technical writing sounds like the ideal job.
Dyen, Natalie Zellat. NatalieWritings. Humor>Writing>Documentation
#13941
If it's a good day, you arrive at work around seven o'clock, grateful for having missed the morning rush hour. Today's not a good day, so instead you crawl out from under the shakey shelf in your cubicle, glad that neither your cranky, obsolete computer nor the stale glass of Jolt cola fell on you during the night. Don't laugh; it's happened before, and putting yourself back together again cost you an hour of sleep you desperately needed. You smell the stench of cold pizza, and what's really appalling is that you're not sure whether it's coming from your shirt, your breath, or a hidden cache somewhere in the cubicle under piles of documentation someone left you to review. That's not your problem right now.
#10847
Dilbert, sometimes referred to as a 'patron saint of technical communicators,' represents a sort of workplace humor that often illuminates TC experiences. This website shows the past month's worth of episodes from the daily syndicated cartoon.
Adams, Scott. United Feature Syndicate. Humor>Workplace>Engineering
#13066
A web-based game, in which you master the usability issues of driving a Mack truck over well-known usability experts.
Urbanev.com (2000). Humor>Usability>Traveler Information>Games
#25807
Some people ask me about the frustrations and difficulties involved in the business of technical documentation. As a reply, I tell them this joke.
Documentia (2003). Humor>Documentation>Writing>Technical Writing
#19766
E-Mail, Acronyms, and Alphabet Soup
Emoticons have become pretty complex, now including ones like :-# [lips are sealed], :-& [tongue tied], or :-'' [pursing lips].
Ray, Deborah S. TECHWR-L (1998). Humor>Writing>Correspondence>Email
#29416
Conveying the emotional tone of a Web page has, up until now, been impossible with HTML, and the XML standard fails to address this issue. As an interim solution, developers have proposed several new tags to the World Wide Web Consortium (W3C).
Hart, Geoffrey J.S. Geoff-Hart.com (1998). Humor>Computing>XML>Emotions
#10796
This morning I woke up in a cold sweat -- which was odd, because I usually wake up in bed. In my dream, or rather nightmare, I was reviewing a manuscript that was due to be returned to a client that very morning. As I recalled the dream, I realized why I was sweating -- the manuscript had been edited by someone who combined the worst characteristics of every copy editor I'd ever known.
Mickle, Lee. Editorial Eye, The (1997). Humor>Writing>Editing
#25999
Engineering Terms in Plain English
Twenty terms from engineering writiting translated into the vernacular.
PlainLanguage.gov (2004). Humor>Writing>Engineering>Minimalism
#31881
Some people are really creative and can take everyday ordinary things and turn them into something extraordinary. This is certainly the case with Streeter Seidell and Dan Gurewitch, the creators of Font Conference.
Seidell, Streeter and Dan Gurewitch. College Humor (2008). Humor>Typography
#27489
Hall of Technical Documentation Weirdness
Lists wacky, bizarre, surreal and otherwise strange examples of technical documentation, particularly illustration.
Barefoot, Darren K. Hall of Technical Documentation Weirdness (2005). Humor>Writing>Technical Illustration>Technical Writing
#20778
Hall of Technical Documentation Weirdness
Welcome to my Hall of Technical Documentation Weirdness. On this page, I list wacky, bizarre, surreal and otherwise strange examples of technical documentation, particularly illustration.
DarrenBarefoot (2003). Humor>TC>Technical Illustration>Localization
#26030
Hexadecimal Color Codes in HTML That Look or Sound Dirty, But Are in Fact Merely Colorful
It's just like how you can make your calculator spell BOOBS, although people inexperienced with HTML probably won't appreciate it.
Genusa, Angela. McSweeney's Internet Tendency (2004). Humor>Web Design>HTML>Color
#10794
How come...everyone still says there is 'an error in the docs!'
Gooch, Chris. TECHWR-L (1999). Humor>Writing
#10799
A dog-ate-my-homework computer failure from the Ray computer logs.
Ray, Deborah S. TECHWR-L (1998). Humor>Computing
#11754
I open my usability presentations with this true story: I was given a large, frozen turkey a few years ago. When it came time to prepare the turkey, I placed it on a kitchen counter to let the turkey thaw.
Thomas, Joyce. Usability Interface (2001). Humor>Documentation
#26000
Fifty-two humorous rules about how to write well (each of which is broken).
PlainLanguage.gov (2004). Humor>Writing>Grammar
#24178
For this year's humor contest, Intercomasked readers to write instructions for imaginary devices. The contest was inspired by Stanislaw Lem, a writer of science fiction who also published collections of reviews and introductions to books that don't exist.
