Using stunnel for NNTPS. Stunnel starts without any apparent problems (log looks normal), but simply doesn't intercept packets from my news reader. There is no activity in the log and sniffing the packets shows everything happening on 119. My understanding of the concept is that there are no configuration changes needed in the newsreader; IOW, I leave it pointing to the unsecured NNTP server with the port set to 119.  I fear I'm missing something very obvious.
 
BTW, I've confirmed the ability to use NNTPS with this particular server by using Outlook Express, which is compatible with NNTPS.
 
Version: 4.20; I used the Windows binary. Running XP.
 
Config:
 
; Some performance tunings
socket = l:TCP_NODELAY=1
socket = r:TCP_NODELAY=1
 
; Some debugging stuff useful for troubleshooting
debug = 7
output = stunnel.log
 
; Use it for client mode
client = yes
 
; Service-level configuration
[nntps]
accept = 192.168.1.101:119
connect = secure.news.easynews.com:563
 
 
Log:
2007.12.28 22:24:46 LOG5[6640:6644]: stunnel 4.20 on x86-pc-mingw32-gnu with OpenSSL 0.9.8d 28 Sep 2006
2007.12.28 22:24:46 LOG5[6640:6644]: Threading:WIN32 SSL:ENGINE Sockets:SELECT,IPv6
2007.12.28 22:24:46 LOG5[6640:5936]: No limit detected for the number of clients
2007.12.28 22:24:46 LOG7[6640:5936]: FD 196 in non-blocking mode
2007.12.28 22:24:46 LOG7[6640:5936]: SO_REUSEADDR option set on accept socket
2007.12.28 22:24:46 LOG7[6640:5936]: nntps bound to 192.168.1.101:119