Gregory Wege wrote:
* stunnel version 4.25

That's probably not the case here, but it usually a good idea to upgrade before sending an email to ~500 subscribers of this mailing list.  8-)

2009.12.16 06:56:19 LOG5[2336:4016]: hobbit_ssl accepted connection from 127.0.0.1:1725
2009.12.16 06:56:19 LOG7[2336:4016]: FD 396 in non-blocking mode
2009.12.16 06:56:19 LOG6[2336:4016]: connect_blocking: connecting 10.132.55.24:1982
2009.12.16 06:56:19 LOG3[2336:4016]: connect_blocking: connect 10.132.55.24:1982: No buffer space available (WSAENOBUFS) (10055)

I asked Google a question about WSAENOBUFS and it replied with:
http://support.microsoft.com/kb/q196271/

For some reason your server opened more connections than Windows could handle in its default configuration.  Execute cmd.exe and type:
netstat -bn
to see the list of your connections with program names involved in creating each connection.

Mike