Evidently transliterating Hebrew is a good way to get into trouble at a spelling bee. At the recent 2006 National Spelling Bee, 12 year-old Saryn Hooks found that out the hard way. The Costa Mesa Daily Pilot reports,

Saryn was cruising along quite nicely until she was asked to spell “hechsher” …. Saryn got it wrong, heard the dreaded bell toll and dutifully took her seat. But a young man from Poway, Lucas Brown, sitting in the audience with a laptop computer, couldn’t believe what his laptop was telling him. Lucas Brown’s sister, Julia, was also a contestant and Lucas, like many family members, was there to keep an eye out for any variable spellings that might influence a judge’s ruling. The moderator had told Saryn the correct spelling was “hechscher,” but the cyber-dictionary on Lucas’ laptop spelled Saryn’s word exactly as she had — hechsher — and there was no variable spelling. If Lucas and his laptop were right, the judges were wrong! Lucas told his father, David Brown, who raced to the back of the room to tell the officials, who dropped their jaws when they determined that Lucas and his darned laptop were absolutely correct.

Oh, that darned laptop! Saryn’s just lucky they didn’t ask her to spell “mashgiach.” Anyway, the rest of the (sadly overwritten) story is here.
(Thanks to Rabbi Uri Cohen for the link.)