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With “Bypass RD Gateway server for local addresses” enabled, Remote Desktop Connection does not simply classify an address as local because it falls within a private IP range. Windows uses a detect mode: it tries to connect directly to the Remote Desktop Session Host and uses the configured RD Gateway if a direct connection cannot be made. DNS, routing, firewall rules, VPN state and TCP 3389 reachability can all affect the result.
What the checkbox tells Remote Desktop Connection to do
The checkbox selects an RD Gateway usage mode called TSC_PROXY_MODE_DETECT. Microsoft describes that mode as: “Use an RD Gateway server if a direct connection cannot be made to the RD Session Host server.” The API documentation maps this mode to the checkbox in the Remote Desktop Connection client: Microsoft’s GatewayUsageMethod documentation.
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In practical terms, the client attempts a direct connection to the destination. If that path works, it bypasses the gateway; if it cannot establish the direct connection, it uses the configured gateway. The checkbox controls gateway use, rather than applying a universal test that labels certain IP addresses “local.”
Why “local” does not just mean a private IP address
Microsoft’s support documentation describes the option in terms of preventing traffic to and from local network addresses from being routed through the TS Gateway: Remote Desktop Connection client documentation. That user-facing description does not establish a universal RFC1918 or subnet rule for deciding when to bypass.
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The operational question is whether the client can reach the Session Host directly. A private IP might still need the gateway if direct access is blocked or unavailable. Conversely, a hostname’s DNS answer and the routes available to the client can make its direct path possible in one network context but not another.
How DNS and network conditions affect the decision
The RDP protocol specification says that the RD Gateway resolves the destination name to an IP address using DNS: MS-RDSOD protocol specification. DNS matters because the address returned for a hostname can vary between networks, including when split DNS is in use. A VPN can also change which routes are available.
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After name resolution, direct reachability is affected by routing, firewall and access-control rules, NAT, and whether TCP port 3389 is reachable. These conditions can change when a device joins or leaves a VPN or corporate network. Microsoft does not publish a universal description of the exact probe order, timeout or any additional hidden heuristic used by every Remote Desktop Connection build, so those implementation details should not be assumed.
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How to troubleshoot unexpected gateway use
- Resolve the destination name. Check which IP address the hostname returns in the network context where the connection behaves unexpectedly. If the name resolves differently on and off VPN, the client may be trying a different destination.
- Test direct TCP reachability. In PowerShell, run
Test-NetConnection -ComputerName <host> -port 3389 -InformationLevel Detailed, replacing<host>with the destination hostname or IP address. Microsoft recommends this test for direct RDP reachability: Microsoft’s Remote Desktop connection troubleshooting guidance. - Compare hostname and IP tests. If the hostname test fails but a test to the resolved IP succeeds, investigate name resolution. If both fail, check the route, VPN connection, firewall and access policy, and whether the Session Host accepts direct connections on TCP 3389.
- Compare behavior with bypass disabled. If the connection works only when the checkbox is cleared, the gateway path is succeeding where the direct path is not. Check the gateway configuration and its authentication or access requirements alongside direct network reachability.
Direct connection and gateway connection: practical differences
| Factor | Direct RDP path | RD Gateway path |
|---|---|---|
| Network reachability | The client must be able to reach the Session Host directly. | The client uses the configured gateway when a direct connection cannot be made in detect mode. |
| TCP 3389 exposure | Direct reachability to the Session Host on TCP 3389 is relevant. | The direct path may be unavailable; the gateway provides the alternate connection path. |
| DNS and destination | The address resolved for the destination name affects the direct connection attempt. | The protocol specification states that the RD Gateway resolves the name to an IP address using DNS. |
| Gateway authentication and policy | The connection does not traverse the RD Gateway when the direct path succeeds. | Gateway authentication and policy requirements apply to a connection that uses the gateway. |
| Latency | Depends on the direct route between client and Session Host. | Depends on the route through the gateway as well as the onward path to the Session Host. |
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