Thanks ! I understand that the problem is mainly because the FTP server's TLS parameters aren't secure enough.
But for your information, FileZilla has no problem connecting this server.
I was curious and with Wireshark, I found that the TLS handshake uses cipher
TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA with FileZilla, whereas it uses
TLS_DHE_RSA_WITH_AES_256_CBC_SHA with WinSCP.
And indeed, TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA needs a smaller DH key and seems a bit better than TLS_DHE_RSA_WITH_AES_256_CBC_SHA. For example in Microsoft documentation about TLS ciphers in Windows (cf.
https://learn.microsoft.com/en-us/windows/win32/secauthn/tls-cipher-suites-in-windows-11-v22h2), where TLS_DHE_RSA_WITH_AES_256_CBC_SHA is now even disabled by default.
I can see that you are using OpenSSL DEFAULT ordered ciphers list (where TLS_DHE_RSA_WITH_AES_256_CBC_SHA is before TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA), whereas FileZilla's supported ciphers list explicitely gives priority to TLSv1.3, then ECDHE, then the rest.
I don't know if you care to have the same level of compatibility for old servers than FileZilla, without changing the minimum TLS version in WinSCP. If so, maybe you can call OpenSSL with a param
cipher TLSv1.2:ECDHE:ALL:!COMPLEMENTOFDEFAULT ? It will use the same list of DEFAULT ciphers, with a priority for TLSv1.3 ciphers (always) then TLSv1.2, and for older TLS versions, there is a priority on ECDHE ciphers.
Demo:
openssl.exe s_client -cipher TLSv1.2:ECDHE:ALL:!COMPLEMENTOFDEFAULT -connect ftp.dlptest.com:21 -starttls ftp