I have checked openssl sources, look as BIO_printf and BIO_write function to not use lock mechanism.

The solution would be to either have a lock around and do every time: lock, open file, write, close, unlock;

Why we cannot open the file once and use logic inside childrens

lock, write, unlock

You can read more on the net about opening a file before fork() and what happens after forking, etc ... In short, if you do not want to complicate the life a lot, it is not a good idea at all. Each process will have a clone of the file descriptor, with managing own states after fork ...

I also noticed that the file name is reallocated in pkg using a local variable in a function and not freed.

is memory allocated here and not freed?

@@ -636,6 +710,7 @@ int tls_h_mod_pre_init_f(void)
 #endif
        SSL_load_error_strings();
        tls_mod_preinitialized=1;
+       prepare_keylog_file(cfg_get(tls, tls_cfg, session_keylog_filename));
        return 0;
 }

I meant the keylog_file variable which is local to the function and then lost:

+int prepare_keylog_file(str session_keylog_filename)
+{
+	char *keylog_file = NULL;

I couldn't spot where is freed.

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