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If you include a copile log (if it works) next time, we can maybe figure it out better without pure speculation. Like an entity leaking of somesort. Or share your .vmf so we can take a look at what is wrong. But if you are 100% sure it goes trough a brush its probably grouped to or is a brush entity like func_detail or func_brush. These don't seal maps if i recal.
If its going trough your skybox, if you have one, i recommend rebuilding it.
Or click on "To world" on the top right (next to "to entity").
there is probably some informations about the leak
As for what happens when your map runs out of leaks, when you are going to attempt to open the pointfile, instead of having a "Load pointfile -Yes No" dialog box, you are going to get a window's browser. If it happens, then you don't have any leaks. The compiler will also tell you if there are errors, so always check it and if you don't have a clue on what to do, then interlopers.net/errors (check my FAQ for that).