1. Usually debts are paid off first, then preferred shareholders get their money back, before regular shareholders get a chance to sell. I got a 1099 for $0.00 one year thanks to this!

2. When new shares are issued, usually preferred shareholders get shares for free to maintain their percentage in the company. Other existing shareholders do not, of course.

Google "preferred participating". Not all preferred offerings are participating but some are.

Also, define "current". What matters the most is its valuation at exit relative to its valuation in the final few funding rounds.