Wait Time Option not responding to DTMF

I've setup an ingroup and we wanted to use the Wait time option Press_CID_callback. When i test the ingroup and make a call the prompt plays OK but whenever i press 1 on my phone it doesn't respond, nothing happens. When i make a callmenu with options 1 and 2 those work fine when i dial with the same phone (skypeout), so it does not seem like a general DTMF problem.
My settings:
Any suggestions?
This is what i see in the CLI, it starts playing the wait time prompt and then just continues with music on hold:
My settings:
Wait Time Option: PRESS_CID_CALLBK
Wait Time Second Option: NONE
Wait Time Third Option: NONE
Wait Time Option Seconds: 30
Wait Time Option Extension: NONE
Wait Time Option Callmenu: NONE
Wait Time Option Voicemail: NONE
Wait Time Option Transfer In-Group: NONE
Wait Time Option Press Filename: to-be-called-back|digits/1
Wait Time Option Press No Block: N
Wait Time Option Press Filename Seconds: 20
Wait Time Option After Press Filename: vm-hangup
Wait Time Option Callback List ID: 105
Any suggestions?
This is what i see in the CLI, it starts playing the wait time prompt and then just continues with music on hold:
[Mar 6 17:48:35] -- Stopped music on hold on SIP/TRUNK_9_SIP-000005da
[Mar 6 17:48:35] -- Playing 'sip-silence' (escape_digits=) (sample_offset 0)
[Mar 6 17:48:35] -- Playing 'sip-silence' (escape_digits=) (sample_offset 0)
[Mar 6 17:48:35] -- Playing 'sip-silence' (escape_digits=) (sample_offset 0)
[Mar 6 17:48:35] -- Playing 'sip-silence' (escape_digits=) (sample_offset 0)
[Mar 6 17:48:35] -- Playing 'sip-silence' (escape_digits=) (sample_offset 0)
[Mar 6 17:48:35] -- Playing 'sip-silence' (escape_digits=12) (sample_offset 0)
[Mar 6 17:48:35] -- Playing 'to-be-called-back' (escape_digits=12) (sample_offset 0)
[Mar 6 17:48:37] -- Playing 'digits/1' (escape_digits=12) (sample_offset 0)
[Mar 6 17:48:39] -- Started music on hold, class 'ERSmusic', on SIP/TRUNK_9_SIP-000005da
[Mar 6 17:48:41] -- Stopped music on hold on SIP/TRUNK_9_SIP-000005da
[Mar 6 17:48:41] == Spawn extension (default, 99909*3***DID, 2) exited non-zero on 'SIP/TRUNK_9_SIP-000005da'