I once had a boss (he was MD of an ~40 person web company) who did the following to send me a digital photo. I was in the room when this happened; I came close to a hernia from supressed laughter:
1) Connect digital camera cable.
2) Click the ‘browse these photos as a slideshow’ button on the autorun popup.
3) Clicked the next button about 100 times (past about three years of holiday photos, it seems)
4) Clicked ‘Save’, which put the photo in the ‘My Pictures’ folder.
5) “Okay, now I need to get that out of the My Pictures folder and into my My Documents”
6) Open Outlook.
7) Click the ‘Attach Picture’ button (which opens the My Pictures folder).
8) Attached correct picture, then addressed the email to himself.
12) Email finally arrived. I’m pretty sure this email travelled about 400 miles, via the datacentre in London)
13) Saved all the attachments (including his own email signature).
14) Open ‘My Documents’.
15) Dragged it to the shared drive.
16) “There you go, it’s on the shared drive for you!”
I quit that job not soon after.