When does one make a Leshev again if they already made one that day?

If one is returning to the same Sukkah that he made the Bracha in that day, then he would only make another Bracha in one of 2 cases:

1. If he left the Sukkah for 1-2 hours. Practically, one shouldn’t make a Bracha unless 2 full hours elapsed, due to doubt.

2. Even if he left for less than the above time, but when he left the Sukkah he planned not to return till after 1-2 hours, then a Bracha is also made.

If, though, you are entering a different Sukkah, then you make the Bracha either way – this is even if you had in mind when making the Bracha in the first Sukkah that you will continue on the second Sukkah.

 

Sources:

.ראה שו”ע אדה”ז סי’ תרל”ט סי”א ואילך