How does the Update user trophies cron work?

Can someone explain the "Update user trophies" cron entry to me? I recently processed about 200 trophies manually using username criteria, but only a few were awarded, and all to the same user. Why didn't it process the rest? I tried manually running the update user trophies and even the hourly and daily cleanup jobs to try and force the rest but they did not process any further.

EDIT: Is it only done when a user logs in? I think that's what is happening, as the 2 people that have it now...

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