diff --git a/src/main/native-chat/claude-structured-managed-account-support.test.ts b/src/main/native-chat/claude-structured-managed-account-support.test.ts
index aa3d55907ef..f647579d03e 100644
--- a/src/main/native-chat/claude-structured-managed-account-support.test.ts
+++ b/src/main/native-chat/claude-structured-managed-account-support.test.ts
@@ -90,12 +90,43 @@ describe('structuredClaudeMatchesActiveManagedAccount', () => {
     expect(structuredClaudeMatchesActiveManagedAccount(undefined)).toBe(false)
   })
 
-  it('fails closed when managed accounts exist but no host account is selected', () => {
+  /** The four states this gate exists to tell apart, pinned together so a change to one is visible
+   *  against the others. */
+  it.each([
+    ['no managed accounts', [], null, true],
+    ['accounts present, none active, no WSL account', [account('host-1', 'host')], null, true],
+    ['host account selected', [account('host-1', 'host')], 'host-1', true],
+    ['WSL-only, normalized to no host selection', [account('wsl-1', 'wsl')], null, false]
+  ] as const)('resolves %s', (_name, claudeManagedAccounts, activeId, expected) => {
     expect(
       structuredClaudeMatchesActiveManagedAccount(
-        settings({ claudeManagedAccounts: [account('host-1', 'host')] })
+        settings({
+          claudeManagedAccounts: [...claudeManagedAccounts],
+          activeClaudeManagedAccountIdsByRuntime: { host: activeId, wsl: {} }
+        })
       )
-    ).toBe(false)
+    ).toBe(expected)
+  })
+
+  /** THE discriminator, and the whole of this rule. With nothing selected for the host runtime the
+   *  settings alone cannot distinguish honest deselection from the WSL-only steady state, because
+   *  `pruneInvalidClaudeRuntimeSelection` empties the host slot in the second case and persists it.
+   *  So the presence of ANY WSL-bound account decides. Simplifying this to "none active ->
+   *  supported" re-opens the auth-identity misrepresentation this gate exists to prevent. */
+  it('splits none-active on whether a WSL-bound account exists at all', () => {
+    const noneActive = (accounts: ReturnType<typeof account>[]) =>
+      structuredClaudeMatchesActiveManagedAccount(
+        settings({
+          claudeManagedAccounts: accounts,
+          activeClaudeManagedAccountIdsByRuntime: { host: null, wsl: {} }
+        })
+      )
+
+    expect(noneActive([account('host-1', 'host')])).toBe(true)
+    expect(noneActive([account('host-1', 'host'), account('host-2', 'host')])).toBe(true)
+    expect(noneActive([account('wsl-1', 'wsl')])).toBe(false)
+    // Mixed list still refuses: the WSL account is present and nothing is selected.
+    expect(noneActive([account('host-1', 'host'), account('wsl-1', 'wsl')])).toBe(false)
   })
 
   /** The gate and the auth policy must resolve the SAME account. A legacy settings blob carries the
diff --git a/src/main/native-chat/claude-structured-managed-account-support.ts b/src/main/native-chat/claude-structured-managed-account-support.ts
index a4709c0a629..dccf6216bda 100644
--- a/src/main/native-chat/claude-structured-managed-account-support.ts
+++ b/src/main/native-chat/claude-structured-managed-account-support.ts
@@ -39,7 +39,11 @@ export function structuredClaudeMatchesActiveManagedAccount(
   }
   const activeHostId = getSelectedClaudeAccountIdForTarget(settings, { runtime: 'host' })
   if (!activeHostId) {
-    return false
+    // Nothing selected for the host runtime is two different states that the settings cannot tell
+    // apart after the fact: honest deselection, where ambient auth is the truth and the UI names no
+    // identity, and the WSL-only case, where the prune emptied the host slot and persisted null
+    // while the UI still names the WSL account. The presence of any WSL-bound account decides.
+    return !accounts.some((candidate) => candidate.managedAuthRuntime === 'wsl')
   }
   const active = accounts.find((candidate) => candidate.id === activeHostId)
   return active ? active.managedAuthRuntime !== 'wsl' : false
diff --git a/src/main/runtime/orca-runtime-structured-claude-account-gate.test.ts b/src/main/runtime/orca-runtime-structured-claude-account-gate.test.ts
index 4ac7bea17bd..64b451e9ea9 100644
--- a/src/main/runtime/orca-runtime-structured-claude-account-gate.test.ts
+++ b/src/main/runtime/orca-runtime-structured-claude-account-gate.test.ts
@@ -30,6 +30,14 @@ const WSL_ONLY: ClaudeManagedAccountGateSettings = {
   activeClaudeManagedAccountIdsByRuntime: { host: null, wsl: { Ubuntu: 'wsl-1' } }
 }
 
+/** Registered Claude accounts with none selected: ambient auth, and the UI names no host identity,
+ *  so this must reach structured rather than silently falling back to a terminal session. */
+const ACCOUNTS_PRESENT_NONE_ACTIVE: ClaudeManagedAccountGateSettings = {
+  claudeManagedAccounts: [managedAccount('host-1', 'host'), managedAccount('host-2', 'host')],
+  activeClaudeManagedAccountId: null,
+  activeClaudeManagedAccountIdsByRuntime: { host: null, wsl: {} }
+}
+
 const HOST_SELECTED: ClaudeManagedAccountGateSettings = {
   claudeManagedAccounts: [managedAccount('host-1', 'host')],
   activeClaudeManagedAccountId: 'host-1',
@@ -72,6 +80,13 @@ describe('structured Claude managed-account gate', () => {
     ).resolves.toMatchObject({ supported: false })
   })
 
+  it('supports Claude when accounts are registered but none is selected', async () => {
+    const runtime = runtimeWithAccounts(ACCOUNTS_PRESENT_NONE_ACTIVE)
+    await expect(
+      runtime.getStructuredAgentSessionCreateSupport('id:workspace-1', 'claude')
+    ).resolves.toMatchObject({ supported: true })
+  })
+
   it('still supports Claude under a selected host managed account', async () => {
     const runtime = runtimeWithAccounts(HOST_SELECTED)
     await expect(