When I used the command originate to call a skype user, say "bob",

originate skypiax/skypiax2/bob 1001

I could receive the DTMF digits that bob clicked through Skype dialpad.

However, when I use the same command to call a PSTN number,

originate skypiax/skypiax2/+19991234567 1001

I did not receive any DTMF digits that the callee pressed on his/her
telephone key pad.

Why?

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