Do your letters of recommendation have to be sent out to colleges at the same time as your transcript?

Not necessarily but if everything arrives in a single mailing or faxing, there is less likelihood of the parts not being kept together and perhaps being lost when other mailings or faxings come in. At the schools in which I worked as a teacher, we handed in our reccomendations to the guidance counselor who sent them along with the transcripts to avoid such problems.