SBS2011 Remote Desktop Gateway

Kijkziewo 1 Reputation point
2020-11-14T10:30:21.183+00:00

For years we're using our SBS2011 server as a Remote Desktop Gateway (with SSL certificate) to sign into a Windows 7 machine with RDP from the internet. Users don't have to establish a VPN connection first in order to reach this machine (all handled by the RD Gateway).

Question is if the security is at a acceptable level this way (except for the fact that SBS2011 is EOL; we are working on this, so please approach this case as if it's not EOL, thank you).

Windows Small Business Server
Windows Small Business Server
A family of Microsoft server products with messaging and collaboration, security-enhanced internet access, protected data storage, reliable printing, faxing, and the ability to run line-of-business applications. Replaced by Windows Server Essentials.
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  1. Karlie Weng 16,076 Reputation points Microsoft Vendor
    2020-11-16T02:57:37.113+00:00

    Hello @Kijkziewo

    RD Gateway allows TS clients to establish secure connections over SSL (443) using RPC Proxy, also known as RDP over HTTPS. To learn more about Remote Desktop Gateway see the following TechNet link:
    http://technet.microsoft.com/en-us/library/dd560672(WS.10).aspx

    SBS 2011 Standard Remote Web Access (RWA)
    https://techcommunity.microsoft.com/t5/windows-server-essentials-and/introduction-to-sbs-2011-standard-remote-web-access-rwa/ba-p/397960

    Another thread for your reference:
    https://social.technet.microsoft.com/Forums/ie/en-US/90f484ac-5a46-4689-af04-7fc2551c53a5/sbs-2011-standard-secure-rdp-?forum=smallbusinessserver

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    Best Regards
    Karlie