Should one laugh or cry?
These are real, observed messages from software:
Excel sometimes can't paste, but it can detect the problem and warn you:

What about fixing the bug instead? And who can have written such a strange bug...
David Pogue is right when he says: "I want to sense that an English major lost sleep over the wording of the dialogue boxes". Cinema 4D, an excellent 3D modelling program, had this to say to me:

Hmmm… which button do I press now?
One I have not yet caught in the act (because it only asks me when I install it) presents me with an awkward choice:
| Are you in the US or in Canada? |
| [Yes] [No] |
What it presumably wants to ask is:
Choose in which region you are: [US and Canada] [rest of the world]
Adobe's updater works behind the scenes, seldom letting you catch an update file. It is also prone to this:

On 27 October 2002 I saw this in the window of a major bank in central New York:

All the nice advertising screens in all of the bank's windows had stopped.
Windows95 on Virtual PC, a long time ago, suggested:

Wow. Actually I can even do it between Mac OS X and Virtual PC Windows applications.
Very useful explanations are to be found in the Applescript dictionaries:
icon family : A family of icons
icon view options : the icon view options
column view options : the column view options
list view options : the list view options