The text below the password strength meter says "Use upper and lower case characters, numbers and symbols like !"?$%&( in your password." But the passwords returned by wp_generate_password() don't do that - in fact they aren't measured as "strong" by the meter, just "good".
The enclosed patch increases the length of generated passwords, and includes symbols in the character set. It also allows the length to be specified with a parameter. Passwords generated after the patch are almost always considered strong by the strength meter.
Regardless of whether or not the increased length is accepted, I think it'd be a good idea for wp_generate_password() to accept a length parameter.