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In Oranje's FAQ I read that if their stability is high or yours is low the chance of success is slim. If they were to declare war on another country or some other stability altering effect were to befall them I believe you would succeed. Otherwise it's a hit or miss proposition as far as I can tell.

Traveler :)
 
You must have a common border.
Originally posted by Kagetora
I have 2 vassals I have had over 10 years and +200 relations and the annex never lights up. Any ideas?
 
You must be in the same military alliance, have more provinces than them, have more troops than them, a royal marriage may be required too. There are other threads that define the full criteria.
 
No common border needed

As Spain I have annexed Naples 3 times. Here are the criteria that I observed.

1) +190 relations for 10 full years
2) Military alliance
3) Already a vassal, vassalized for 10 years in my game

I did not have a royal marriage.
My armies were much stronger than theirs.

You probably need to vassalize them before getting the annexation to light up.

--Avenger