I leave Jesse to grizzle. If he's still grizzling after about 10 minutes I go in.
If he starts to get upset I go in.
When I go in, I re wrap him give him a cuddle & the dummy if just the dummy doesn't work, then put him back down & do it again.
Right now he's been in there not making a sound for about 10 minutes - refuses to go to sleep tonight. He's just started talking/winging. I'll give it til he's just winging, not breaking it up with talking to go in.
There he goes. Off to try & sleep.