How can I extend my stay in Thailand from April 16th to May 16th after already extending for 30 days?

How about stating where you are in thailand

@Colton ******

so people can recommend the closest border for you to bounce out and back at?

No. You can only extend it one time. A border bounce is possible. Leave Thailand and come back in and get 30 days exempt.

short answer, you can't 😮

That 30 day extension on a free entry stamp is a "one and done" type of thing

you need to exit/re-enter the country to get a NEW free entry stamp and you can extend that for 30 days once like you did on this entry.

You could get a 60 day extension IF you were married to a thai, or had half thai children, but other than that, you need to border bounce for a new free entry stamp