Is this an Asterisk problem or a phone problem?

Newbie here. I’ve just installed AsteriskNow and have hooked up a Snom 320 IP phone.

Question 1:
To dial out, it appears that I dial 9, the dial tone goes away, then I have to dial the rest of the numbers and hit the “checkmark” button to get it to accept the numbers and dial. This is unlike a more traditional system where you hit 9, get a different dial tone, and then just dial the number. Can I configure things so it works the old way? Is this a problem with my phone, or is this an Asterisk thing?

Question 2:
When I try to retrieve voice mail using the buttons on the phone, none of them work. So I dial x850 and get these horrible voice prompts: “mailbox”, “password”. No “please enter your extension” or “please enter your password”. Sorry, but my users just aren’t going understand the abbreviated prompts.

Is there any way to configure it so it automatically accesses the correct mailbox, and then politely asks for a password?

Q1: Pattern matching allows you to trigger dialing out “the old way”. Something like

; Local calls NANP exten => _9NXXXXXX,1,Dial(SIP/${EXTEN}@MYVOIPPROVIDER) for local calls and so on.

Q2: Asterisk offers various sounds and you can place your own recordings.

Generally speaking… I’d highly recommend the Asterisk book, “The Future of Telephony”.