I'd suggest inserting a comma in the same way you did for the other two related English sentences.
FROM:
When you start looking like your passport photo you should go on vacation.
TO:
When you start looking like your passport photo, you should go on vacation.
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This sentence was initially added as a translation of sentence #355
added by Dejo, March 8, 2013
linked by Dejo, March 8, 2013
linked by paul_lingvo, July 2, 2013
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