diff --git a/src/main/ssh/connection/ssh-connection.ts b/src/main/ssh/connection/ssh-connection.ts
index 4b442390bdd..6f4e7920d87 100644
--- a/src/main/ssh/connection/ssh-connection.ts
+++ b/src/main/ssh/connection/ssh-connection.ts
@@ -27,6 +27,11 @@ import {
   type SystemSshBuildArgsOptions
 } from '../system-transport/system-ssh-args'
 import { spawnSystemSshCommand } from '../system-transport/system-ssh-command'
+import {
+  shouldUseSystemSshLoopbackRoute,
+  startSystemSshLoopbackRoute,
+  type SystemSshLoopbackRoute
+} from '../system-transport/system-ssh-loopback-route'
 import { removeControlSocketPath } from '../ssh-control-socket'
 import {
   INITIAL_RETRY_ATTEMPTS,
@@ -193,6 +198,8 @@ export class SshConnection {
   } | null = null
   private systemSshControlMasterDisabledForSession = false
   private systemSshGssapiOnlyForSession = false
+  private systemSshLoopbackRoute: SystemSshLoopbackRoute | null = null
+  private systemSshLoopbackRouteStarting = false
   private useSystemSshTransport = false
   private credentialAbortController = new AbortController()
   private readonly pendingSsh2Clients = new Set<SshClient>()
@@ -965,6 +972,7 @@ export class SshConnection {
               )
             ) {
               this.setState('connected')
+              this.startSystemSshLoopbackRoute(connectGeneration)
               resolve()
               return
             }
@@ -1088,9 +1096,44 @@ export class SshConnection {
     if (this.systemSshGssapiOnlyForSession) {
       options.gssapiOnly = true
     }
+    if (this.systemSshLoopbackRoute) {
+      options.loopbackRoute = this.systemSshLoopbackRoute.args
+    }
     return options
   }
 
+  /** Off the connect path: commands keep the direct proxy route until the forward is proven. */
+  private startSystemSshLoopbackRoute(connectGeneration: number): void {
+    const options = this.getSystemSshBuildArgsOptions()
+    if (
+      this.systemSshLoopbackRoute ||
+      this.systemSshLoopbackRouteStarting ||
+      !shouldUseSystemSshLoopbackRoute(this.target, this.systemSshResolvedConfig, options)
+    ) {
+      return
+    }
+    this.systemSshLoopbackRouteStarting = true
+    startSystemSshLoopbackRoute(this.target, this.systemSshResolvedConfig, options).then(
+      (route) => {
+        this.systemSshLoopbackRouteStarting = false
+        if (!this.isCurrentConnectAttempt(connectGeneration) || !this.useSystemSshTransport) {
+          route.dispose()
+          return
+        }
+        this.systemSshLoopbackRoute = route
+        route.onExit(() => {
+          if (this.systemSshLoopbackRoute === route) {
+            this.systemSshLoopbackRoute = null
+          }
+        })
+      },
+      () => {
+        // Why: per-command proxy logins still work; the route only makes them cheaper.
+        this.systemSshLoopbackRouteStarting = false
+      }
+    )
+  }
+
   // Why: ssh2 may destroy the proxy socket on auth failure, so credential retries need a fresh proxy process and Duplex stream.
   private respawnProxy(
     config: ConnectConfig,
@@ -1572,6 +1615,8 @@ export class SshConnection {
   }
 
   private resetSystemTransport(): void {
+    this.systemSshLoopbackRoute?.dispose()
+    this.systemSshLoopbackRoute = null
     this.systemSshResolvedConfig = null
     this.systemSshControlMasterDisabledForSession = false
     this.systemSshGssapiOnlyForSession = false
diff --git a/src/main/ssh/system-transport/system-ssh-args.ts b/src/main/ssh/system-transport/system-ssh-args.ts
index 3c72d3919a0..c2677cf44cf 100644
--- a/src/main/ssh/system-transport/system-ssh-args.ts
+++ b/src/main/ssh/system-transport/system-ssh-args.ts
@@ -18,6 +18,13 @@ export type SystemSshBuildArgsOptions = {
    * be read as having answered "nothing claims it". See `sshConfigMayClaimAlias`.
    */
   aliasClaimedByConfig?: boolean
+  /** Dial Orca's held `ssh -L` forward instead of the target's proxy. See `system-ssh-loopback-route`. */
+  loopbackRoute?: SystemSshLoopbackRouteArgs
+}
+
+export type SystemSshLoopbackRouteArgs = {
+  localPort: number
+  hostKeyAlias: string
 }
 
 export function buildSshArgs(target: SshTarget, options?: SystemSshBuildArgsOptions): string[] {
@@ -64,6 +71,16 @@ export function buildSshArgs(target: SshTarget, options?: SystemSshBuildArgsOpti
   }
 
   const useConfigHost = shouldUseOpenSshConfigHost(target)
+  const loopbackRoute = options?.loopbackRoute
+  if (loopbackRoute) {
+    // Why: OpenSSH keeps the first value it sees per option, so these win over ssh_config's route
+    // while User, IdentityFile, certificates, and known_hosts files still come from the alias.
+    args.push('-o', 'HostName=127.0.0.1')
+    args.push('-o', `Port=${loopbackRoute.localPort}`)
+    args.push('-o', 'ProxyCommand=none')
+    args.push('-o', 'ProxyJump=none')
+    args.push('-o', `HostKeyAlias=${loopbackRoute.hostKeyAlias}`)
+  }
 
   // Why: a wildcard `Host *` block supplies ProxyCommand/ProxyJump for every alias, so an alias
   // whose own Host block was renamed or deleted still looks config-backed and gets dialled bare —
@@ -74,7 +91,7 @@ export function buildSshArgs(target: SshTarget, options?: SystemSshBuildArgsOpti
     appendUnclaimedAliasEndpoint(args, target)
   }
 
-  if (!useConfigHost && target.port !== 22) {
+  if (!useConfigHost && !loopbackRoute && target.port !== 22) {
     args.push('-p', String(target.port))
   }
 
@@ -96,11 +113,12 @@ export function buildSshArgs(target: SshTarget, options?: SystemSshBuildArgsOpti
     args.push('-o', 'GSSAPIAuthentication=yes')
   }
 
-  if (!useConfigHost && target.jumpHost) {
+  // Why: `-J` after `ProxyJump=none` is a fatal duplicate in OpenSSH, so the route skips both proxies.
+  if (!useConfigHost && !loopbackRoute && target.jumpHost) {
     args.push('-J', target.jumpHost)
   }
 
-  if (!useConfigHost && target.proxyCommand) {
+  if (!useConfigHost && !loopbackRoute && target.proxyCommand) {
     args.push('-o', `ProxyCommand=${target.proxyCommand}`)
   }
 
@@ -167,6 +185,9 @@ export function getSystemSshBuildArgsFromOperationOptions(
   if (options?.aliasClaimedByConfig === false) {
     buildArgsOptions.aliasClaimedByConfig = false
   }
+  if (options?.loopbackRoute !== undefined) {
+    buildArgsOptions.loopbackRoute = options.loopbackRoute
+  }
   return Object.keys(buildArgsOptions).length === 0 ? undefined : buildArgsOptions
 }
 
diff --git a/src/main/ssh/system-transport/system-ssh-forward-process.test.ts b/src/main/ssh/system-transport/system-ssh-forward-process.test.ts
index 8c45fb8ac60..695b9eacd76 100644
--- a/src/main/ssh/system-transport/system-ssh-forward-process.test.ts
+++ b/src/main/ssh/system-transport/system-ssh-forward-process.test.ts
@@ -442,6 +442,52 @@ describe('system SSH forward process', () => {
     await expect(pending).resolves.toBeUndefined()
   })
 
+  // Why: a slow ProxyCommand outlasts the grace period, and a caller that dials the port next needs it listening.
+  it('waits past the grace period for a listener when a listener timeout is given', async () => {
+    vi.useFakeTimers()
+    const child = createFakeProcess()
+    let listening = false
+    connectMock.mockImplementation(() => {
+      const socket = createFakeSocket()
+      queueMicrotask(() =>
+        listening ? socket.emit('connect') : socket.emit('error', new Error('ECONNREFUSED'))
+      )
+      return socket
+    })
+
+    spawnMock.mockReturnValue(child)
+    const forward = await startSystemSshPortForwardProcess(createTarget(), 5173, '127.0.0.1', 3000)
+
+    let settled = false
+    const pending = waitForSystemSshForwardStartup(forward.process, 5173, 30_000).finally(() => {
+      settled = true
+    })
+    await vi.advanceTimersByTimeAsync(SYSTEM_SSH_FORWARD_STARTUP_GRACE_MS * 4)
+    expect(settled).toBe(false)
+
+    listening = true
+    await vi.advanceTimersByTimeAsync(SYSTEM_SSH_FORWARD_LISTENER_PROBE_INTERVAL_MS * 2)
+    await expect(pending).resolves.toBeUndefined()
+  })
+
+  it('rejects when no listener appears within the listener timeout', async () => {
+    vi.useFakeTimers()
+    const child = createFakeProcess()
+    connectMock.mockImplementation(() => {
+      const socket = createFakeSocket()
+      queueMicrotask(() => socket.emit('error', new Error('ECONNREFUSED')))
+      return socket
+    })
+
+    spawnMock.mockReturnValue(child)
+    const forward = await startSystemSshPortForwardProcess(createTarget(), 5173, '127.0.0.1', 3000)
+
+    const pending = waitForSystemSshForwardStartup(forward.process, 5173, 5_000)
+    const assertion = expect(pending).rejects.toThrow('did not listen on 127.0.0.1:5173')
+    await vi.advanceTimersByTimeAsync(5_000)
+    await assertion
+  })
+
   it('sends SIGTERM then SIGKILL when the process does not exit', async () => {
     vi.useFakeTimers()
     const child = createFakeProcess()
diff --git a/src/main/ssh/system-transport/system-ssh-forward-process.ts b/src/main/ssh/system-transport/system-ssh-forward-process.ts
index 699f441e769..7a4b59877b0 100644
--- a/src/main/ssh/system-transport/system-ssh-forward-process.ts
+++ b/src/main/ssh/system-transport/system-ssh-forward-process.ts
@@ -135,9 +135,11 @@ function stopOnOwnListenFailure(process: ChildProcess, localPort: number): void
   process.once('exit', stop)
 }
 
+/** `listenerTimeoutMs` requires a listener by then instead of accepting a still-silent forward. */
 export function waitForSystemSshForwardStartup(
   process: ChildProcess,
-  localPort: number
+  localPort: number,
+  listenerTimeoutMs?: number
 ): Promise<void> {
   return new Promise((resolve, reject) => {
     let stderr = ''
@@ -189,8 +191,18 @@ export function waitForSystemSshForwardStartup(
     process.once('error', onError)
     process.once('exit', onExit)
     graceTimer = setTimeout(() => {
-      finish(resolve)
-    }, SYSTEM_SSH_FORWARD_STARTUP_GRACE_MS)
+      if (listenerTimeoutMs === undefined) {
+        finish(resolve)
+        return
+      }
+      finish(() =>
+        reject(
+          new Error(
+            `System SSH port forward did not listen on 127.0.0.1:${localPort} within ${listenerTimeoutMs}ms`
+          )
+        )
+      )
+    }, listenerTimeoutMs ?? SYSTEM_SSH_FORWARD_STARTUP_GRACE_MS)
     scheduleProbe()
   })
 }
diff --git a/src/main/ssh/system-transport/system-ssh-loopback-route.test.ts b/src/main/ssh/system-transport/system-ssh-loopback-route.test.ts
new file mode 100644
index 00000000000..86e42c87747
--- /dev/null
+++ b/src/main/ssh/system-transport/system-ssh-loopback-route.test.ts
@@ -0,0 +1,340 @@
+import { EventEmitter } from 'node:events'
+import { PassThrough } from 'node:stream'
+import { beforeEach, describe, expect, it, vi } from 'vitest'
+
+const { existsSyncMock, spawnMock, connectMock, createServerMock, treeKillMock } = vi.hoisted(
+  () => ({
+    existsSyncMock: vi.fn(),
+    spawnMock: vi.fn(),
+    connectMock: vi.fn(),
+    createServerMock: vi.fn(),
+    treeKillMock: vi.fn()
+  })
+)
+
+vi.mock('../../windows-process-tree-kill', () => ({
+  terminateWindowsProcessTree: treeKillMock
+}))
+
+vi.mock('./system-ssh-orphaned-forward', () => ({
+  stopOrphanedOrcaSshForward: vi.fn().mockResolvedValue(false)
+}))
+
+vi.mock('fs', async (importOriginal) => {
+  const actual = (await importOriginal()) as Record<string, unknown>
+  return { ...actual, existsSync: existsSyncMock }
+})
+
+vi.mock('child_process', () => ({ spawn: spawnMock }))
+
+vi.mock('net', () => ({ connect: connectMock, createServer: createServerMock }))
+
+import type { SshTarget } from '../../../shared/ssh-types'
+import type { SshResolvedConfig } from '../config/ssh-g-config-resolution'
+import { buildSshArgs, getSystemSshBuildArgsFromOperationOptions } from './system-ssh-args'
+import {
+  getLoopbackRouteHostKeyAlias,
+  shouldUseSystemSshLoopbackRoute,
+  startSystemSshLoopbackRoute
+} from './system-ssh-loopback-route'
+
+const SYSTEM_SSH_PATH =
+  process.platform === 'win32' ? 'C:\\Windows\\System32\\OpenSSH\\ssh.exe' : '/usr/bin/ssh'
+const FREE_PORT = 49811
+const ROUTE = { localPort: FREE_PORT, hostKeyAlias: 'devbox' }
+
+function createTarget(overrides?: Partial<SshTarget>): SshTarget {
+  return {
+    id: 'target-1',
+    label: 'Dev box',
+    host: 'devbox',
+    configHost: 'devbox',
+    port: 22,
+    username: '',
+    source: 'ssh-config',
+    ...overrides
+  }
+}
+
+function createResolved(overrides?: Partial<SshResolvedConfig>): SshResolvedConfig {
+  return {
+    hostname: 'devbox',
+    port: 22,
+    identityFile: [],
+    identitiesOnly: false,
+    forwardAgent: false,
+    proxyCommand: 'aws ssm start-session --target %h',
+    proxyUseFdpass: false,
+    controlMaster: 'no',
+    controlPersist: 'no',
+    userKnownHostsFiles: [],
+    globalKnownHostsFiles: [],
+    strictHostKeyChecking: 'ask',
+    hashKnownHosts: false,
+    updateHostKeys: 'no',
+    ...overrides
+  }
+}
+
+type FakeProcess = EventEmitter & {
+  pid: number
+  stdin: PassThrough
+  stdout: PassThrough
+  stderr: PassThrough
+  kill: ReturnType<typeof vi.fn>
+  exitCode: number | null
+  signalCode: NodeJS.Signals | null
+}
+
+function createFakeProcess(): FakeProcess {
+  // oxlint-disable-next-line typescript/consistent-type-assertions -- SAFETY: the fields are assigned on the next lines, before the process is returned.
+  const proc = new EventEmitter() as FakeProcess
+  proc.pid = 4242
+  proc.stdin = new PassThrough()
+  proc.stdout = new PassThrough()
+  proc.stderr = new PassThrough()
+  proc.kill = vi.fn().mockReturnValue(true)
+  proc.exitCode = null
+  proc.signalCode = null
+  return proc
+}
+
+function createFakeServer(): EventEmitter {
+  // oxlint-disable-next-line typescript/consistent-type-assertions -- SAFETY: the fields are assigned on the next lines, before the server is returned.
+  const server = new EventEmitter() as EventEmitter & {
+    listen: ReturnType<typeof vi.fn>
+    close: ReturnType<typeof vi.fn>
+    address: ReturnType<typeof vi.fn>
+  }
+  server.listen = vi.fn().mockImplementation(() => {
+    queueMicrotask(() => server.emit('listening'))
+    return server
+  })
+  server.address = vi.fn(() => ({ address: '127.0.0.1', port: FREE_PORT }))
+  server.close = vi.fn().mockImplementation((cb?: () => void) => cb?.())
+  return server
+}
+
+function createListeningSocket(): EventEmitter {
+  const socket = Object.assign(new EventEmitter(), { setTimeout: vi.fn(), destroy: vi.fn() })
+  queueMicrotask(() => socket.emit('connect'))
+  return socket
+}
+
+/** The probe command over the route answers like a remote shell with this exit code. */
+function answerProbe(proc: FakeProcess, code: number): void {
+  setImmediate(() => {
+    if (code === 0) {
+      proc.stdout.write('ORCA-SYSTEM-SSH-LOOPBACK-OK\n')
+    }
+    proc.stdout.end()
+    proc.emit('exit', code, null)
+    proc.emit('close', code, null)
+  })
+}
+
+function spawnedArgs(call: number): string[] {
+  return spawnMock.mock.calls[call]?.[1] ?? []
+}
+
+describe('buildSshArgs with a loopback route', () => {
+  it('dials the held forward ahead of the alias so OpenSSH keeps these over ssh_config', () => {
+    const args = buildSshArgs(createTarget(), { loopbackRoute: ROUTE })
+    const routeStart = args.indexOf('HostName=127.0.0.1')
+
+    expect(routeStart).toBeGreaterThan(-1)
+    expect(args.slice(routeStart - 1, routeStart + 9)).toEqual([
+      '-o',
+      'HostName=127.0.0.1',
+      '-o',
+      `Port=${FREE_PORT}`,
+      '-o',
+      'ProxyCommand=none',
+      '-o',
+      'ProxyJump=none',
+      '-o',
+      'HostKeyAlias=devbox'
+    ])
+    expect(args.slice(-2)).toEqual(['--', 'devbox'])
+  })
+
+  it("drops a manual target's own port and proxies, which would fight the route", () => {
+    const args = buildSshArgs(
+      createTarget({
+        source: 'manual',
+        configHost: undefined,
+        host: 'devbox.internal',
+        port: 2200,
+        username: 'dev',
+        jumpHost: 'bastion',
+        proxyCommand: 'cloudflared access ssh --hostname %h'
+      }),
+      { loopbackRoute: ROUTE }
+    )
+
+    expect(args).not.toContain('-J')
+    expect(args).not.toContain('-p')
+    expect(args.filter((arg) => arg.startsWith('ProxyCommand='))).toEqual(['ProxyCommand=none'])
+    expect(args.slice(-2)).toEqual(['--', 'dev@devbox.internal'])
+  })
+
+  it('carries the route into file-transfer operations', () => {
+    expect(getSystemSshBuildArgsFromOperationOptions({ loopbackRoute: ROUTE })).toEqual({
+      loopbackRoute: ROUTE
+    })
+  })
+})
+
+describe('shouldUseSystemSshLoopbackRoute', () => {
+  it.each([
+    ['a ProxyCommand host on Windows', createTarget(), createResolved(), {}, 'win32', true],
+    [
+      'a ProxyJump host on Windows',
+      createTarget(),
+      createResolved({ proxyCommand: undefined, proxyJump: 'bastion' }),
+      {},
+      'win32',
+      true
+    ],
+    [
+      'a direct host on Windows',
+      createTarget(),
+      createResolved({ proxyCommand: undefined }),
+      {},
+      'win32',
+      false
+    ],
+    ['macOS, which multiplexes instead', createTarget(), createResolved(), {}, 'darwin', false],
+    ['Linux, which multiplexes instead', createTarget(), createResolved(), {}, 'linux', false],
+    [
+      'a host that opted out of connection reuse',
+      createTarget({ systemSshConnectionReuse: false }),
+      createResolved(),
+      {},
+      'win32',
+      false
+    ],
+    [
+      'a Kerberos host',
+      createTarget(),
+      createResolved({ gssapiAuthentication: true }),
+      {},
+      'win32',
+      false
+    ],
+    [
+      'an alias no Host block claims',
+      createTarget(),
+      createResolved(),
+      { aliasClaimedByConfig: false },
+      'win32',
+      false
+    ]
+  ] as const)('%s → %s', (_name, target, resolved, options, platform, expected) => {
+    expect(shouldUseSystemSshLoopbackRoute(target, resolved, options, platform)).toBe(expected)
+  })
+})
+
+describe('getLoopbackRouteHostKeyAlias', () => {
+  it("keeps the known_hosts name OpenSSH used for the proxied route's host and port", () => {
+    expect(
+      getLoopbackRouteHostKeyAlias(createTarget(), createResolved({ hostname: 'i-0abc' }))
+    ).toBe('i-0abc')
+    expect(
+      getLoopbackRouteHostKeyAlias(
+        createTarget(),
+        createResolved({ hostname: 'i-0abc', port: 2222 })
+      )
+    ).toBe('[i-0abc]:2222')
+  })
+
+  it("prefers the user's own HostKeyAlias", () => {
+    expect(
+      getLoopbackRouteHostKeyAlias(createTarget(), createResolved({ hostKeyAlias: 'pinned' }))
+    ).toBe('pinned')
+  })
+})
+
+describe('startSystemSshLoopbackRoute', () => {
+  beforeEach(() => {
+    existsSyncMock.mockReset().mockImplementation((p: string) => p === SYSTEM_SSH_PATH)
+    spawnMock.mockReset()
+    connectMock.mockReset().mockImplementation(createListeningSocket)
+    createServerMock.mockReset().mockImplementation(createFakeServer)
+    treeKillMock.mockReset().mockResolvedValue(true)
+  })
+
+  it('opens the forward over the real proxy, then proves a login over the route', async () => {
+    const forward = createFakeProcess()
+    const probe = createFakeProcess()
+    spawnMock.mockReturnValueOnce(forward).mockImplementationOnce(() => {
+      answerProbe(probe, 0)
+      return probe
+    })
+
+    const route = await startSystemSshLoopbackRoute(
+      createTarget(),
+      createResolved(),
+      { loopbackRoute: { localPort: 1, hostKeyAlias: 'stale' } },
+      'linux'
+    )
+
+    expect(route.args).toEqual(ROUTE)
+    expect(spawnedArgs(0)).toContain(`127.0.0.1:${FREE_PORT}:localhost:22`)
+    expect(spawnedArgs(0)).not.toContain('ProxyCommand=none')
+    expect(spawnedArgs(1)).toContain(`Port=${FREE_PORT}`)
+    expect(spawnedArgs(1)).toContain('ProxyCommand=none')
+    expect(spawnedArgs(1)).toContain('BatchMode=yes')
+    expect(forward.kill).not.toHaveBeenCalled()
+  })
+
+  it('stops the forward when sshd refuses logins over it', async () => {
+    const forward = createFakeProcess()
+    const probe = createFakeProcess()
+    spawnMock.mockReturnValueOnce(forward).mockImplementationOnce(() => {
+      answerProbe(probe, 255)
+      return probe
+    })
+
+    await expect(
+      startSystemSshLoopbackRoute(createTarget(), createResolved(), {}, 'linux')
+    ).rejects.toThrow('loopback route probe failed (exit 255)')
+    expect(forward.kill).toHaveBeenCalledWith('SIGTERM')
+  })
+
+  it('gives up without a probe when the forward exits before listening', async () => {
+    const forward = createFakeProcess()
+    spawnMock.mockReturnValueOnce(forward)
+    connectMock.mockImplementation(() => {
+      const socket = Object.assign(new EventEmitter(), { setTimeout: vi.fn(), destroy: vi.fn() })
+      queueMicrotask(() => socket.emit('error', new Error('ECONNREFUSED')))
+      return socket
+    })
+
+    const pending = startSystemSshLoopbackRoute(createTarget(), createResolved(), {}, 'linux')
+    setImmediate(() => {
+      forward.stderr.write('kex_exchange_identification: Connection closed by remote host\n')
+      forward.emit('exit', 255)
+    })
+
+    await expect(pending).rejects.toThrow('Connection closed by remote host')
+    expect(spawnMock).toHaveBeenCalledTimes(1)
+  })
+
+  // Why: killing ssh.exe leaves its ProxyCommand child running, still holding the proxy tunnel open.
+  it('stops the whole forward process tree on Windows, falling back to the direct kill', async () => {
+    const forward = createFakeProcess()
+    const probe = createFakeProcess()
+    spawnMock.mockReturnValueOnce(forward).mockImplementationOnce(() => {
+      answerProbe(probe, 0)
+      return probe
+    })
+    const route = await startSystemSshLoopbackRoute(createTarget(), createResolved(), {}, 'win32')
+
+    treeKillMock.mockResolvedValueOnce(false)
+    route.dispose()
+
+    expect(treeKillMock).toHaveBeenCalledWith(4242, { site: 'system-ssh-loopback-route' })
+    await vi.waitFor(() => expect(forward.kill).toHaveBeenCalledWith('SIGTERM'))
+  })
+})
diff --git a/src/main/ssh/system-transport/system-ssh-loopback-route.ts b/src/main/ssh/system-transport/system-ssh-loopback-route.ts
new file mode 100644
index 00000000000..013f35690bd
--- /dev/null
+++ b/src/main/ssh/system-transport/system-ssh-loopback-route.ts
@@ -0,0 +1,148 @@
+/**
+ * Connection reuse for proxied targets where OpenSSH cannot multiplex (Windows has no ControlMaster).
+ * One held `ssh -N -L` pays the ProxyCommand/ProxyJump handshake once; later commands log in over
+ * 127.0.0.1 through it instead of re-running the proxy for every exec.
+ */
+import type { ChildProcess } from 'node:child_process'
+import type { SshTarget } from '../../../shared/ssh-types'
+import { terminateWindowsProcessTree } from '../../windows-process-tree-kill'
+import type { SshResolvedConfig } from '../config/ssh-g-config-resolution'
+import type { SystemSshBuildArgsOptions, SystemSshLoopbackRouteArgs } from './system-ssh-args'
+import { spawnSystemSshCommand } from './system-ssh-command'
+import {
+  startSystemSshPortForwardProcess,
+  waitForSystemSshForwardStartup
+} from './system-ssh-forward-process'
+
+// Why long: the forward pays the full proxy handshake, which is the slow part this route exists for.
+export const SYSTEM_SSH_LOOPBACK_ROUTE_LISTEN_TIMEOUT_MS = 60_000
+export const SYSTEM_SSH_LOOPBACK_ROUTE_PROBE_TIMEOUT_MS = 15_000
+const LOOPBACK_ROUTE_PROBE_MARKER = 'ORCA-SYSTEM-SSH-LOOPBACK-OK'
+
+export type SystemSshLoopbackRoute = {
+  args: SystemSshLoopbackRouteArgs
+  onExit: (callback: () => void) => void
+  dispose: () => void
+}
+
+export function shouldUseSystemSshLoopbackRoute(
+  target: SshTarget,
+  resolved: SshResolvedConfig | null,
+  options: SystemSshBuildArgsOptions,
+  platform: NodeJS.Platform = process.platform
+): boolean {
+  if (platform !== 'win32' || target.systemSshConnectionReuse === false) {
+    return false
+  }
+  // Why: Kerberos derives the service principal from the dialled host name, which becomes 127.0.0.1.
+  if (options.gssapiOnly || target.gssapiAuthentication || resolved?.gssapiAuthentication) {
+    return false
+  }
+  // Why: an unclaimed alias already rewrites HostName/Port to the stored endpoint.
+  if (options.aliasClaimedByConfig === false) {
+    return false
+  }
+  return Boolean(
+    resolved?.proxyCommand || resolved?.proxyJump || target.proxyCommand || target.jumpHost
+  )
+}
+
+/** Known-hosts name OpenSSH would have used for the proxied route, so trust carries over. */
+export function getLoopbackRouteHostKeyAlias(
+  target: SshTarget,
+  resolved: SshResolvedConfig | null
+): string {
+  if (resolved?.hostKeyAlias) {
+    return resolved.hostKeyAlias
+  }
+  const host = resolved?.hostname || target.host
+  const port = resolved?.port || target.port || 22
+  return port === 22 ? host : `[${host}]:${port}`
+}
+
+export async function startSystemSshLoopbackRoute(
+  target: SshTarget,
+  resolved: SshResolvedConfig | null,
+  options: SystemSshBuildArgsOptions,
+  platform: NodeJS.Platform = process.platform
+): Promise<SystemSshLoopbackRoute> {
+  const remotePort = resolved?.port || target.port || 22
+  // Why: the forward itself must take the real proxy route, never an existing loopback one.
+  const forward = await startSystemSshPortForwardProcess(target, 0, 'localhost', remotePort, {
+    ...options,
+    loopbackRoute: undefined
+  })
+  const dispose = (): void => stopLoopbackForward(forward.process, forward.dispose, platform)
+  try {
+    await waitForSystemSshForwardStartup(
+      forward.process,
+      forward.localPort,
+      SYSTEM_SSH_LOOPBACK_ROUTE_LISTEN_TIMEOUT_MS
+    )
+    const args = {
+      localPort: forward.localPort,
+      hostKeyAlias: getLoopbackRouteHostKeyAlias(target, resolved)
+    }
+    // Why: a listening forward does not prove sshd allows it (AllowTcpForwarding) or that auth works over it.
+    await probeLoopbackRoute(target, { ...options, loopbackRoute: args })
+    return {
+      args,
+      onExit: (callback) => {
+        forward.process.once('exit', callback)
+      },
+      dispose
+    }
+  } catch (error) {
+    dispose()
+    throw error
+  }
+}
+
+function stopLoopbackForward(
+  forwardProcess: ChildProcess,
+  killForward: () => void,
+  platform: NodeJS.Platform
+): void {
+  const pid = forwardProcess.pid
+  if (platform !== 'win32' || !pid) {
+    killForward()
+    return
+  }
+  // Why: Windows does not end a killed ssh's ProxyCommand child, which would keep the proxy tunnel open.
+  void terminateWindowsProcessTree(pid, { site: 'system-ssh-loopback-route' }).then((stopped) => {
+    if (!stopped) {
+      killForward()
+    }
+  })
+}
+
+function probeLoopbackRoute(target: SshTarget, options: SystemSshBuildArgsOptions): Promise<void> {
+  const channel = spawnSystemSshCommand(target, `echo ${LOOPBACK_ROUTE_PROBE_MARKER}`, {
+    ...options,
+    nonInteractive: true,
+    wrapCommand: false
+  })
+  return new Promise((resolve, reject) => {
+    let stdout = ''
+    const timeout = setTimeout(() => {
+      channel.close()
+      reject(new Error('System SSH loopback route probe timed out'))
+    }, SYSTEM_SSH_LOOPBACK_ROUTE_PROBE_TIMEOUT_MS)
+    channel.on('data', (data: Buffer) => {
+      stdout += data.toString('utf-8')
+    })
+    channel.stderr.resume()
+    channel.once('error', (error: Error) => {
+      clearTimeout(timeout)
+      reject(error)
+    })
+    channel.once('close', (code: number | null) => {
+      clearTimeout(timeout)
+      if (code === 0 && stdout.includes(LOOPBACK_ROUTE_PROBE_MARKER)) {
+        resolve()
+        return
+      }
+      reject(new Error(`System SSH loopback route probe failed (exit ${code ?? 'unknown'})`))
+    })
+  })
+}