Got a bit of a silly one here but I am thinking of doing a few SIN-DPS and DPS-SIN flights back to back. I understand there is a transit option at DPS that allows you to skip immigration but I was wondering if anyone had experience with this. Because of the short layover, KLM does not offer same day SIN-DPS-SIN round trips so my plan was to stack round trips together. As an example:

RT 1 SIN-DPS Aug 20th
RT 2 DPS-SIN Aug 20th
RT 2 SIN-DPS Aug 21st
RT 1 DPS-SIN Aug 21st

Since my "connecting" flight is the same aircraft and on a new PNR will I have any troubles with using the transit option? I *should* have a ground staff escort due to Ultimate status but I want to be positive before booking my silly trip. Thanks in advance!