Serge Hallyn, thank you for responding to this bug.

> Do you know exactly how wine goes about executing the .exe file?

No, but if you have a more specific question, a better answer may be
produced.

> Could you provide the output of starting the program through strace?

See attached strace.log.bz2 performed at the Terminal:

sudo setcap cap_net_bind_service=+ep /usr/bin/wine && strace -o
/tmp/strace.log -f -tt -s 256 wine /home/rusivi/.wine/drive_c/Program\
Files/Hotspot\ Shield/bin/openvpntray.exe

lsb_release -rd
Description:    Ubuntu 10.10
Release:        10.10

apt-cache policy wine1.3
wine1.3:
 Installed: 1.3.13-0ubuntu1~maverickppa2
 Candidate: 1.3.13-0ubuntu1~maverickppa2
 Version table:
 *** 1.3.13-0ubuntu1~maverickppa2 0
       500 http://ppa.launchpad.net/ubuntu-wine/ppa/ubuntu/ maverick/main
i386 Packages
       100 /var/lib/dpkg/status

** Attachment added: "strace.log.bz2"
   
https://bugs.launchpad.net/ubuntu/+source/libcap2/+bug/695581/+attachment/1855568/+files/strace.log.bz2

** Changed in: libcap2 (Ubuntu)
       Status: Incomplete => New

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https://bugs.launchpad.net/bugs/695581

Title:
  setcap does not provide WINE access to port < 1024 for Hotspot Shield

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