I have this problem too and it is very annoying.... In some situations I have found that if I mute my microphone before the call is answered then open the keypad it works. A sometimes workaround to somethign that should have been fixed a long time ago...... Please MS fix this problem.....
This is ridiculous. Being able to use the dial pad is essential for any phone service - apparently except for the largest VoIP operator in the world. They introduced the problem in 2011, and 2 years later it still hasn't been fixed.
Add to that the brain-dead move to disable shutting down Skype except by Task Manager. It's time to find a different service.
I just chatted with Skype support about a number for which the keypad wasn't working (couldn't enter the conference code). They had me log out of Skype and log back in. Then it worked.
This is terrible!
It worked perfectly for years, bet when I updates all my devices to Skype 184.108.40.206 it simply stopped working. Please fix ASAP, it disables 90% of usage and will make me look for other IP phone solution.
I use it to connect to job call bridges (approved use) and can't join any session any more. I am also a signed and paynug user of Skype. I could make it work just by random 2 times out of 30 but there is no repeatable process. I am also an IT person and believe it is a bug on latest version. There are probably milions of people with same problem around.
This is red flag issue, we all need a fix to this otherwise outstanding service!
Found the log, reset skype and try again sugestion and it worked. If trouble does not come back at each system reboot, looks fixes. Thanks to this forum!