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With “Bypass RD Gateway server for local addresses” selected, Remote Desktop Connection uses a direct-connect detection mode: it tries to connect to the Remote Desktop Session Host directly and uses the configured RD Gateway if that direct connection cannot be made. “Local” is therefore not documented as a simple test for whether an address falls within a private IP range.
What the checkbox changes
The setting controls how the client uses an RD Gateway. Microsoft’s GatewayUsageMethod documentation maps the checkbox to TSC_PROXY_MODE_DETECT, which means: “Use an RD Gateway server if a direct connection cannot be made to the RD Session Host server.” Microsoft’s deployment command describes Set-RDDeploymentGatewayConfiguration -BypassLocal $True as bypassing the gateway for local connections (Microsoft documentation).
Microsoft support documentation describes the checkbox in terms of traffic to and from local network addresses not being routed through the gateway (Microsoft support). The API description clarifies the operational test: direct connection first, gateway if direct connection cannot be made. The public documentation does not define a universal private-subnet rule for deciding what counts as local.
How the client determines whether direct connection works
- It resolves the destination name. The address the client attempts to reach depends on DNS in the current network context. The RDP protocol specification says that the RD Gateway resolves the name to an IP address using DNS (MS-RDSOD specification).
- It attempts the direct path to the Session Host. If that path can be established, the client can bypass the gateway for the connection.
- If direct connection cannot be made, it uses the configured gateway. This is the documented detect-mode behavior; it does not mean that a private IP address is guaranteed to connect directly.
DNS answers, routing, VPN configuration, firewalls, access-control lists, NAT, and whether TCP port 3389 is reachable can all affect the direct attempt. A hostname may resolve to different addresses on a corporate network and away from it, so the same saved RDP destination can take different paths in different network contexts.
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Why “local” does not simply mean a private IP address
A private address can still require an RD Gateway when the client cannot reach the Session Host directly or policy requires gateway use. Conversely, the documented behavior is based on whether a direct connection can be made, not on a published universal list of local subnets. Microsoft does not specify the exact probe order, timeout, or any additional hidden heuristic for every Remote Desktop Connection build, so those details should not be assumed.
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How to troubleshoot an unexpected gateway connection
- Check name resolution. Determine which IP address the destination hostname resolves to on the affected network. Compare the result on VPN and off VPN if behavior differs.
- Test direct TCP reachability. In PowerShell, run
Test-NetConnection -ComputerName <host> -Port 3389 -InformationLevel Detailed. Microsoft recommends this test for checking direct RDP reachability (Microsoft troubleshooting guidance). - Interpret the result. A successful TCP test indicates that a direct connection is reachable at the tested address and port. If the hostname test fails but a test to the intended IP succeeds, investigate name resolution.
- Review the network path and policy. Check VPN routes, firewall rules, ACLs, NAT, and any policy that may require use of the RD Gateway.
- Compare with bypass disabled. If direct access is unavailable or gateway use is required by configuration, disable the bypass option and confirm whether the connection works through the gateway.
Direct RDP and RD Gateway: practical differences
| Factor | Direct connection | Connection through RD Gateway |
|---|---|---|
| Network reachability | The client must be able to reach the Session Host directly. | The client connects through the configured gateway when direct connection cannot be made in detect mode. |
| TCP 3389 exposure | The direct route must permit TCP 3389 from the client network. | The gateway provides the alternate route; its configuration and reachability matter. |
| Authentication and policy | Gateway-specific authentication and policy are not on the direct path. | Gateway authentication and policy requirements apply. |
| Latency | Depends on the direct network route. | Depends on the route through the gateway; no universal latency difference is established. |
| DNS | The client’s resolved destination must lead to a reachable Session Host address. | The gateway resolves the destination name to an IP address, according to the MS-RDSOD specification. |
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