If you feel the need to cloak, just do it within reason. Don’t cloak because you can, but because it’s technically the most elegant procedure to accomplish a Web development task. Bing and Google can’t detect your (in no way deceptive) intend algorithmically. Don’t spam away, though, because you might leave trails besides cloaking alone, if you aren’t good enough at spamming search engines. Keep your users interests in mind. Don’t comply to search engine guidelines as set in stone, but to a reasonable level, for example when those force you to comply to Web standards that make more sense than the fancy idea you’ve developed on internationalization, based on detecting browser languages settings or so.
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Related link: Google deindexes their very own help files for whitehat cloaking.
Add'l related story: Why Google Should Ban Its Own Help Pages — But Also Shouldn’t