Please file a bug in bugs.winehq.org, and attach the log from running the app in a clean .wine after doing e.g. export WINEDEBUG=+wininet wine foo.exe > log.txt 2>&1 Error 12055 is ERROR_INTERNET_SEC_CERT_ERRORS, so it may be some certificate-related problem. It'd be nice to see some more detailed openssl log info, maybe that message should at least show the output of pERR_get_error().