Hello Adam,
you did not mention which Skype version, screen reader, and operating system are you running... We assume that you use Windows with JAWS and scripts, I hope this procedure works for you since I nid to test it a little bit with recent Skype versions, and since it's much time that I don't make Skype out calls. Inside the conversation, go to Call menu, look for the voice saying, "Show dialpad" and check it with enter. You can now try using normal keyboard to use tones, if they don't work try pressing ctrl+shift+d.
Bye!
Barbuz
Thanks for posting to the skype english list.

to contact skype support with any questions regarding your account email 
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To  access scripts for the latest version of skype go to
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