Joe Flowers wrote:
[...]
I can decrypt the HTTPS traffic OK [...] where the HTTPS
traffic is initiated from a web browser (IE) on the client machine.

BUT, when I try my HTTPS client application (on the client machine,
talking to the server machine), the application seems to work correctly
other than I am not able to see the decrypted data in Wireshark. [...]

Is there a trick to getting Wireshark to work with OpenSSL applications
or is there something wrong with my application which prevents Wireshark
from decrypting the data?

This sounds more like a Wireshark than an openssl question.

I suspect, if your configuration of Wireshark is correct, that the negociated ciphersuite uses Diffie-Hellman, so can not be externally decrypted.

Two solutions :
- configure openssl on your server to disable the DH ciphersuites
- use Debian for the server so that's it possible to break the generated DH secret and decrypt the session ;-)
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