Thanks for the pointers. I'll check with cpan-testers/rt. I think removing the fork is somewhat problematic, since you need both a client and a server for these tests, but perhaps a full "perl ... &" with a later kill will work. I'll describe the failed tests from SSLeay here, since one can hope that those cause the failed tests in IO::Socket::SSL.

Compilation environment: Visual C++ 7.1 (.NET 2003)
The Perl Core is 5.8.3 stable.tar.gz
Net_SSLeay.pm-1.25
IO-Socket-SSL-0.95
OpenSSL-0.9.7c
Net_SSLeay.pm crashes in test 5 and maybe 6; it's hard to tell because the minidumper dialog comes up twice (no, I haven't tried splitting the specific tests out). The minidumper dialog comes up with no information, since Perl's compiled using the defaults (optimized, etc). The transcript is (about 10 minutes into the test)...

ok 1
Testing pointer to int casting...
cc: cl
Microsoft (R) 32-bit C/C++ Optimizing Compiler Version 13.10.3077 for 
+80x86
Copyright (C) Microsoft Corporation 1984-2002. All rights reserved.

ptrcasttst.c
Microsoft (R) Incremental Linker Version 7.10.3077
Copyright (C) Microsoft Corporation.  All rights reserved.

/out:ptrcasttst.exe 
/out:ptrcasttst.exe 
ptrcasttst.obj 
ok
./ptrcasttst: 'void *' len: 4, 'unsigned long int' len: 4.
ptrcasttst: ok (00320F60 == 00320F60).
ok
ok
ok 2
ok 3
ok 4
        Spawning a TCP test server on port 1211, pid=-3920...
*** not ok 5tcp

        Spawning a SSL test server on port 1212, pid=-2720...
ok 5
ok 6
ok 7
ok 8
ok 9
        Sending 1 MB over localhost, may take a while (and some VM)...
                ...took 1 secs (1024 KB/s)
ok 10
3512: ssl read failed at examples/cli-cert.pl line 53.
[download]