> From: openssl-users <openssl-users-boun...@openssl.org> On Behalf Of David
> Harris
> Sent: Wednesday, 19 October, 2022 18:54
> 
> Do recent versions of OpenSSL 1.1.1 have dependencies on some Windows
> facility (winsock and wincrypt seem likely candidates) that might work on
> Server 2019 but fail on Server 2012?

OpenSSL on Windows has always had a dependency on Winsock/Winsock2 (see 
b_sock.c, e_os.h, sockets.h) for supporting socket BIOs. Obviously OpenSSL used 
for TLS is going to be interacting with Winsock. I can't think of any 
difference between Server 2012 and Server 2019 that would be relevant to the 
issue you describe.

OpenSSL 1.1.1 uses Windows cryptographic routines in two areas I'm aware of: 
rand_win.c and the CAPI engine. I don't offhand see a way that a problem with 
the calls in rand_win.c would cause the particular symptom you described. My 
guess is that you're not using the CAPI engine, but you might check your 
OpenSSL configuration on the failing system.

I think more plausible causes of this failure are things like OpenSSL 
configuration and interference from other software such as an endpoint 
firewall. Getting SYSCALL from SSL_accept *really* looks like 
network-stack-level interference, from a firewall or similar mechanism.

Personally, if I ran into this, I'd just build OpenSSL for debug and debug into 
it. But I know that's not everyone's cup of tea.

-- 
Michael Wojcik

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