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I have urls that point to pages I don't know yet if exist. Whenever reaching those, I perform a not-so-quick external sources check, and if exists generate the page on the fly. In order to avoid this behavior for search engine crawlers, I'm showing them a 404 header code. When a user comes, I'm first loading a status bar with flush() and then if I didn't find just display an error message with a 200 header code, because the headers are already sent in the flush() status bar. Whenever the page ends up as empty with an error message and a 200 code, it's like a 404 soft error.

Although my reasons are legit, I'm a bit concerned if Google might misinterpret this behavior and consider it cloaking?

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Whenever I have seen cloaking detected by Google, the 'punishment' has been for the pages to be deindexed, but your pages would be returning a 404 anyway, so nothing will be indexed, and nor are you trying to trick Google into indexing a page with content not seen by a user. I also would speculate that the situation would likely be viewed as a misconfiguration if it was looked at closely.

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