It seems to me like "Ask Different" is against these rules.
Its not for three reasons:
- Apple doesn’t hold the trademark on the slogan/phrase “Ask Different.” Their phrase, as you have noted is “Think Different.”
Apple only limits the use where disparaging
Disparaging Manner: You may not use an Apple trademark or any other Apple-owned graphic symbol, logo, or icon in a disparaging manner
Fair Use doctrine allows use of trademarked items (regardless of their T&Cs) to criticize, comment, or parody. This site is filled with criticisms and comments about Apple Products.
If you want an excellent example of this, look at the “Hackintosh” community. Per Apple’s own guidelines, you are prevented from using “Variations, takeoffs or abbrieviations of their name, products, slogans, etc”
Variations, Takeoffs or Abbreviations: You may not use an image of a real apple or other variation of the Apple logo for any purpose. Third parties cannot use a variation, phonetic equivalent, foreign language equivalent, takeoff, or abbreviation of an Apple trademark for any purpose. For example:
Not acceptable: Appletree Jackintosh Apple Cart iPodMart
If that were truly the case and enforceable, the Hackintosh community would have been gone a long, long, time ago.
Disclaimer: I’m not a lawyer. I don’t play one on TV or any streaming service. Nothing here should be construed as legal advise. It is only my opinion on this matter.