How to Make One Exception to a Windows Firewall Outbound Rule
According to the Windows Firewall documentation, block rules always take precedence over allow rules, therefore even if your allow rule looks more specific than a block rule, the allow rule will not work, and the traffic matching both allow and block rules will be blocked. The option “Allow this firewall rule to override block rules” is available only for rules which require IPSec, and is not available for outbound rules.
The only thing you could do with Windows Firewall to achieve something close to what you need is to switch the default behavior for outbound connections to “Block”, then add explicit allow rules for all outbound connections that you need (not just for that single program). Alternatively, you can look for third-party firewall software with more features.
If you want to allow only one address for any program, e.g. 10.10.10.10, you can make 2 rules: One for block addresses 1.1.1.1 - 10.10.10.9 and an another for block 10.10.10.11 - 255.255.255.255. For me this works.