Running asterisk 1.8.2 but encountering quite of such messages:
WARNING[4593] chan_sip.c: Retransmission timeout reached on transmission 00235eb7-b6450006-e398ebf1-c50390e8@192.168.1.215 for seqno 102 (Critical Response) – See doc/sip-retransmit.txt.
Packet timed out after 28544ms with no response
I had a similar problem to yours, where that my newly installed Asterisk 1.8.2.3 kept retransmitting packets and the call to anything only lasted a short time (way less than 1 min).
Anyway… i realised that in my SIP debug (on thr CLI) that i was running my Asterisk locally, but, my Asterisk was re-writing the packets to go out to my External IP instead of my local address!! Definately wrong, so knowing this, i checked my NAT settings (in my SIP.conf) and sure enough i had the wrong “externip” and wrong “localnet” values (I configured the Asterisk at home and then brought it to work which is on different subnet, oops ). So the ACKs were not getting sent to the correct route because of this.
So, i suggest trying you system again and testing it within your same network (without internet for now) becuase you can make SIP calls internally. Which will remove the NAT out of your variables. So in your SIP debug you can look for local IPs in all your SIP messaging except for 127.0.0.1, because this is the loop-back and not a true NIC address.