Never a problem. There is usually quite a bit of bags there in front of the counter.

Since I fly DL to SIN I am too frugal(cheap) to pay for a hotel for 2-8am. I always PREBOOK T1 ambassador hotel for 6 hour. Sleep and then head into town. I had friends who did not prebook and end up sleeping on the loungers.

Check in at 2am, get up at about 7:30, wash up, check out at 8am. Grab breakfast at the terminal.

Head down to entry immigration about 9:15, you should have your bags past customs at the taxi stand at 9:30 which is the end of the morning taxi surcharge periodor SMRT station at the end of the morning rush hour.

Never a problem with missing bag or query by immigration officer.