diff --git a/src/cli/format.ts b/src/cli/format.ts
index cae419094d2..1487a69eea0 100644
--- a/src/cli/format.ts
+++ b/src/cli/format.ts
@@ -245,6 +245,9 @@ function formatHostConnection(host: HostListEntry): string {
   if (host.kind !== 'ssh') {
     return ''
   }
+  if (host.connected === undefined) {
+    return `connection unknown${host.connectionStatus ? ` (${host.connectionStatus})` : ''}`
+  }
   return host.connected
     ? `connected${host.connectionStatus ? ` (${host.connectionStatus})` : ''}`
     : `not connected${host.connectionStatus ? ` (${host.connectionStatus})` : ''}`
diff --git a/src/cli/handlers/environment.ts b/src/cli/handlers/environment.ts
index a597df8669e..181b2947f98 100644
--- a/src/cli/handlers/environment.ts
+++ b/src/cli/handlers/environment.ts
@@ -51,7 +51,7 @@ export const ENVIRONMENT_HANDLERS: Record<string, CommandHandler> = {
       name: target.label,
       id: target.id,
       selector: `--host ssh:${target.id}`,
-      connected: target.connected ?? false,
+      ...(target.connected === undefined ? {} : { connected: target.connected }),
       ...(target.connectionStatus ? { connectionStatus: target.connectionStatus } : {}),
       ...(target.remotePlatform ? { platform: target.remotePlatform } : {})
     }))
diff --git a/src/cli/host-selector-alternatives.test.ts b/src/cli/host-selector-alternatives.test.ts
index bc4fadd05c1..9460931a083 100644
--- a/src/cli/host-selector-alternatives.test.ts
+++ b/src/cli/host-selector-alternatives.test.ts
@@ -118,6 +118,24 @@ describe('listSshTargets', () => {
     expect(call).toHaveBeenCalledWith('ssh.listTargets')
   })
 
+  it('enriches legacy target rows from host-owned connection state', async () => {
+    const { RuntimeClientError } = await import('./runtime/types.js')
+    const call = vi.fn(async (method: string) => {
+      if (method === 'ssh.listTargetSummaries') {
+        throw new RuntimeClientError('method_not_found', 'Unknown method')
+      }
+      if (method === 'ssh.getState') {
+        return { result: { state: { status: 'connected', remotePlatform: 'win32' } } }
+      }
+      return { result: { targets: SSH_TARGETS } }
+    })
+
+    await expect(listSshTargets({ call } as unknown as RuntimeClient)).resolves.toEqual([
+      { ...SSH_TARGETS[0], connected: true, connectionStatus: 'connected', remotePlatform: 'win32' }
+    ])
+    expect(call).toHaveBeenCalledWith('ssh.getState', { targetId: SSH_TARGETS[0].id })
+  })
+
   // Why: this only ever runs to enrich an error we are already reporting; a failure here must
   // not replace that error with a confusing one about SSH enumeration.
   it('returns nothing rather than masking the error it was enriching', async () => {
diff --git a/src/cli/host-selector-alternatives.ts b/src/cli/host-selector-alternatives.ts
index 564fbef5bd9..f42fec88aee 100644
--- a/src/cli/host-selector-alternatives.ts
+++ b/src/cli/host-selector-alternatives.ts
@@ -112,7 +112,7 @@ export async function listSshTargets(client: RuntimeClient): Promise<SshTargetSu
     if (error instanceof Error && 'code' in error && error.code === 'method_not_found') {
       try {
         const legacy = await client.call<{ targets: SshTargetSummary[] }>('ssh.listTargets')
-        return legacy.result.targets
+        return await enrichLegacySshTargetStates(client, legacy.result.targets)
       } catch {
         return []
       }
@@ -121,6 +121,34 @@ export async function listSshTargets(client: RuntimeClient): Promise<SshTargetSu
   }
 }
 
+async function enrichLegacySshTargetStates(
+  client: RuntimeClient,
+  targets: SshTargetSummary[]
+): Promise<SshTargetSummary[]> {
+  return Promise.all(
+    targets.map(async (target) => {
+      try {
+        const response = await client.call<{
+          state: {
+            status?: string
+            remotePlatform?: 'linux' | 'darwin' | 'win32'
+          } | null
+        }>('ssh.getState', { targetId: target.id })
+        const state = response.result.state
+        return {
+          ...target,
+          ...(state?.status === undefined
+            ? {}
+            : { connected: state.status === 'connected', connectionStatus: state.status }),
+          ...(state?.remotePlatform === undefined ? {} : { remotePlatform: state.remotePlatform })
+        }
+      } catch {
+        return target
+      }
+    })
+  )
+}
+
 // Why: `--host ssh:<id>` was never validated, so an unknown target answered ok:true with an
 // empty list — the same silent wrong-machine answer that `runtime:` ids used to give. And since
 // target ids are machine-generated (`ssh-<timestamp>-<random>`), the label a caller actually