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
addite per Dejo, 8 de martio 2013
ligate per Dejo, 8 de martio 2013
ligate per paul_lingvo, 2 de julio 2013
ligate per paul_lingvo, 2 de julio 2013
ligate per CK, 11 de februario 2016
ligate per Shishir, 12 de februario 2016
ligate per fekundulo, 18 de martio 2017
ligate per PaulP, 7 de octobre 2017