diff --git a/src/main/agent-launch/agent-launch-executor.test.ts b/src/main/agent-launch/agent-launch-executor.test.ts
index c0451a4f6b2..a95e71a30ef 100644
--- a/src/main/agent-launch/agent-launch-executor.test.ts
+++ b/src/main/agent-launch/agent-launch-executor.test.ts
@@ -463,6 +463,29 @@ describe('caller-supplied launch inputs', () => {
     expect(h.createStructuredSession).not.toHaveBeenCalled()
   })
 
+  it('still opens a structured session when the cwd names the workspace root', async () => {
+    // The root the RPC layer resolved rides on the target, so a cwd spelled as the root is not a
+    // custom directory and does not decide the route.
+    const h = harness({})
+    const result = await h.run({
+      agent: 'claude',
+      target: { kind: 'existing', worktree: 'wt-7', workspacePath: '/repo' },
+      cwd: '/repo/'
+    })
+    expect(result.outcome.kind).toBe('structured')
+    expect(result.receipt).toMatchObject({ mode: 'structured' })
+  })
+
+  it('still downgrades for a subdirectory of a resolved root', async () => {
+    const h = harness({})
+    const result = await h.run({
+      agent: 'claude',
+      target: { kind: 'existing', worktree: 'wt-7', workspacePath: '/repo' },
+      cwd: '/repo/packages/api'
+    })
+    expect(result.receipt).toMatchObject({ mode: 'terminal', reason: 'tui_launch_command' })
+  })
+
   it('still opens a structured session when the cwd is only whitespace', async () => {
     const h = harness({})
     const result = await h.run({ agent: 'claude', target: EXISTING, cwd: '   ' })
diff --git a/src/main/agent-launch/agent-launch-executor.ts b/src/main/agent-launch/agent-launch-executor.ts
index be85a4168ba..090a65f7650 100644
--- a/src/main/agent-launch/agent-launch-executor.ts
+++ b/src/main/agent-launch/agent-launch-executor.ts
@@ -83,7 +83,10 @@ export async function executeAgentLaunch(
       agent: intent.agent,
       workspaceKind: launchWorkspaceKind(intent.target),
       ...(intent.reuseTerminal ? { terminal: intent.reuseTerminal.handle } : {}),
-      ...(intent.cwd ? { cwd: intent.cwd } : {})
+      ...(intent.cwd ? { cwd: intent.cwd } : {}),
+      ...(intent.target.kind === 'existing' && intent.target.workspacePath
+        ? { workspacePath: intent.target.workspacePath }
+        : {})
     },
     settings,
     vocabulary
diff --git a/src/main/agent-launch/agent-launch-mode.ts b/src/main/agent-launch/agent-launch-mode.ts
index 99711cc1293..b3d954944b5 100644
--- a/src/main/agent-launch/agent-launch-mode.ts
+++ b/src/main/agent-launch/agent-launch-mode.ts
@@ -17,6 +17,7 @@
  * records; every other surface says "chat session" / "terminal agent".
  */
 
+import { requestsCwdOutsideWorkspaceRoot } from '../../shared/terminal-startup-cwd'
 import type {
   AgentLaunchMode,
   AgentLaunchModeReason,
@@ -72,10 +73,14 @@ export type AgentLaunchModePlacement = {
    *  resolved — never accepted from a caller, which would let one route around this decision.
    *  Absent means the kind was never established, and is not read as any particular kind. */
   workspaceKind?: WorkspaceLaunchKind
-  /** A start directory other than the workspace root. It belongs here, unlike `model` or `effort`,
-   *  because a structured session has no way to apply one — it runs in its workspace — so honouring
-   *  it and honouring the chat preference are mutually exclusive rather than merely awkward. */
+  /** A requested start directory. It belongs here, unlike `model` or `effort`, because a structured
+   *  session has no way to apply one — it runs in its workspace — so honouring it and honouring the
+   *  chat preference are mutually exclusive rather than merely awkward. Read against
+   *  `workspacePath`: a cwd that names the root asks for nothing and decides nothing. */
   cwd?: string
+  /** The root of the workspace the launch lands in, when the host has resolved it. Without it a
+   *  requested `cwd` cannot be proven to name the root and is read as custom. */
+  workspacePath?: string
 }
 
 const DOWNGRADE_DETAIL: Record<Exclude<AgentLaunchModeReason, 'user_default'>, string> = {
@@ -145,10 +150,11 @@ export function decideAgentLaunchMode(args: {
     // the create-support probe reads the resolved workspace rather than guessing from a
     // client-side project runtime.
     ...(placement.workspaceKind ? { workspaceKind: placement.workspaceKind } : {}),
-    // Mirrors the renderer's own route input (`agent-launch-route-input.ts`), which has always
-    // treated a requested cwd as terminal-only; the host simply had no way to be told about one.
+    // Mirrors the renderer's own route input (`agent-launch-route-input.ts`): a cwd is terminal-only
+    // when it names somewhere other than the workspace root, by the same shared rule.
     requiresTuiLaunchCommand:
-      Boolean(placement.cwd?.trim()) || hasExplicitTuiLaunchCommand(settings, agent)
+      requestsCwdOutsideWorkspaceRoot(placement.workspacePath, placement.cwd) ||
+      hasExplicitTuiLaunchCommand(settings, agent)
   })
   if (!support.supported) {
     return downgraded(BLOCKER_REASON[support.blocker], vocabulary)
diff --git a/src/main/runtime/rpc/methods/agent-launch.test.ts b/src/main/runtime/rpc/methods/agent-launch.test.ts
index f592c4fe1b7..f44ddb4978b 100644
--- a/src/main/runtime/rpc/methods/agent-launch.test.ts
+++ b/src/main/runtime/rpc/methods/agent-launch.test.ts
@@ -579,6 +579,15 @@ describe('launch inputs that cross the wire', () => {
     expect(terminalOptions(runtime)).not.toHaveProperty('telemetry')
   })
 
+  it('keeps a structured preference when the cwd names the workspace root', async () => {
+    // The scope the handler resolves for the target carries the root the fixture reports.
+    const runtime = runtimeStub({})
+    const result = await launch({ ...EXISTING_LAUNCH, cwd: '/tmp/wt-7/' }, runtime)
+
+    expect(result.outcome.kind).toBe('structured')
+    expect(result.receipt).toMatchObject({ mode: 'structured' })
+  })
+
   it('routes a structured preference to a terminal when the launch names a cwd', async () => {
     const runtime = runtimeStub({})
     const result = await launch({ ...EXISTING_LAUNCH, cwd: '/repo/packages/api' }, runtime)
@@ -587,4 +596,18 @@ describe('launch inputs that cross the wire', () => {
     expect(result.receipt).toMatchObject({ preferred: 'structured', reason: 'tui_launch_command' })
     expect(createStructuredSession).not.toHaveBeenCalled()
   })
+
+  it('ignores a caller-supplied root, so a subdirectory cannot claim to be one', async () => {
+    const runtime = runtimeStub({})
+    const result = await launch(
+      {
+        ...EXISTING_LAUNCH,
+        target: { ...EXISTING_LAUNCH.target, workspacePath: '/repo/packages/api' },
+        cwd: '/repo/packages/api'
+      },
+      runtime
+    )
+
+    expect(result.receipt).toMatchObject({ mode: 'terminal', reason: 'tui_launch_command' })
+  })
 })
diff --git a/src/main/runtime/rpc/methods/agent-launch.ts b/src/main/runtime/rpc/methods/agent-launch.ts
index eed47a746af..eee9f2a48c1 100644
--- a/src/main/runtime/rpc/methods/agent-launch.ts
+++ b/src/main/runtime/rpc/methods/agent-launch.ts
@@ -83,7 +83,7 @@ async function agentLaunchTarget(
     return { kind: 'create-worktree', create: { ...params.target.create } }
   }
   const workspace = await runtime.showTerminalWorkspaceLaunchScope(params.target.worktree)
-  return { kind: 'existing', worktree: workspace.id }
+  return { kind: 'existing', worktree: workspace.id, workspacePath: workspace.path }
 }
 
 async function agentLaunchIntent(
diff --git a/src/renderer/src/lib/agent-launch-route-input.test.ts b/src/renderer/src/lib/agent-launch-route-input.test.ts
index 2ea4c568243..6eb91bbc72e 100644
--- a/src/renderer/src/lib/agent-launch-route-input.test.ts
+++ b/src/renderer/src/lib/agent-launch-route-input.test.ts
@@ -33,6 +33,7 @@ vi.mock('@/lib/structured-agent-launch-settlement', () => ({
   settleStructuredAgentLaunch: vi.fn()
 }))
 
+import { folderWorkspaceKey } from '../../../shared/workspace-scope'
 import {
   buildAgentLaunchRouteInput,
   workspaceKindForWorktreeId,
@@ -74,17 +75,19 @@ function store(settings: Record<string, unknown> = STRUCTURED_SETTINGS): AgentLa
   return { settings } as unknown as AgentLaunchRouteStore
 }
 
+function stageLocalStructuredHost(): void {
+  vi.clearAllMocks()
+  mocks.getExecutionHostIdForWorktree.mockReturnValue('local')
+  mocks.getConnectionIdFromState.mockReturnValue(null)
+  mocks.getLocalProjectExecutionRuntimeContext.mockReturnValue(undefined)
+  mocks.getLocalRepoProjectExecutionRuntimeContext.mockReturnValue(undefined)
+  mocks.readLocalRuntimeCapabilitiesOrUnknown.mockReturnValue([
+    STRUCTURED_AGENT_SESSION_RUNTIME_CAPABILITY
+  ])
+}
+
 describe('buildAgentLaunchRouteInput', () => {
-  beforeEach(() => {
-    vi.clearAllMocks()
-    mocks.getExecutionHostIdForWorktree.mockReturnValue('local')
-    mocks.getConnectionIdFromState.mockReturnValue(null)
-    mocks.getLocalProjectExecutionRuntimeContext.mockReturnValue(undefined)
-    mocks.getLocalRepoProjectExecutionRuntimeContext.mockReturnValue(undefined)
-    mocks.readLocalRuntimeCapabilitiesOrUnknown.mockReturnValue([
-      STRUCTURED_AGENT_SESSION_RUNTIME_CAPABILITY
-    ])
-  })
+  beforeEach(stageLocalStructuredHost)
 
   it('gathers the full input set for an existing local git worktree', () => {
     mocks.getLocalProjectExecutionRuntimeContext.mockReturnValue(WSL_RUNTIME)
@@ -343,3 +346,62 @@ describe('workspaceKindForWorktreeId', () => {
     expect(workspaceKindForWorktreeId(worktreeId)).toBe(kind)
   })
 })
+
+describe('a cwd that names the workspace root', () => {
+  // "Continue in New Session…" always names a cwd; at the root it must not force a terminal.
+  beforeEach(stageLocalStructuredHost)
+
+  const withRoot = (): AgentLaunchRouteStore =>
+    // oxlint-disable-next-line typescript/consistent-type-assertions -- SAFETY: the route store is the app state narrowed to the slices the input reads; only those are staged.
+    ({
+      settings: STRUCTURED_SETTINGS,
+      worktreesByRepo: { 'repo-1': [{ id: 'wt-1', path: '/repo/app' }] },
+      folderWorkspaces: [{ id: 'folder-1', folderPath: '/srv/notes' }]
+    }) as unknown as AgentLaunchRouteStore
+
+  it.each(['/repo/app', '/repo/app/', '.'])(
+    'routes structured under the chat default for cwd %s',
+    (cwd) => {
+      const args = {
+        agent: 'codex' as const,
+        workspace: { kind: 'git-worktree' as const, worktreeId: 'wt-1' },
+        tuiCustomization: { cwd }
+      }
+      expect(buildAgentLaunchRouteInput(withRoot(), args).requiresTuiLaunchCommand).toBe(false)
+      expect(routeFor(withRoot(), args)).toBe('structured-native-chat')
+    }
+  )
+
+  it('still requires a terminal for a subdirectory, which a structured session cannot start in', () => {
+    const args = {
+      agent: 'codex' as const,
+      workspace: { kind: 'git-worktree' as const, worktreeId: 'wt-1' },
+      tuiCustomization: { cwd: '/repo/app/packages/web' }
+    }
+    expect(buildAgentLaunchRouteInput(withRoot(), args).requiresTuiLaunchCommand).toBe(true)
+    expect(routeFor(withRoot(), args)).not.toBe('structured-native-chat')
+  })
+
+  it('reads a folder workspace root the same way', () => {
+    const workspaceId = folderWorkspaceKey('folder-1')
+    const at = (cwd: string) =>
+      buildAgentLaunchRouteInput(withRoot(), {
+        agent: 'codex',
+        workspace: { kind: 'folder', worktreeId: workspaceId },
+        tuiCustomization: { cwd }
+      }).requiresTuiLaunchCommand
+    expect(at('/srv/notes/')).toBe(false)
+    expect(at('/srv/notes/drafts')).toBe(true)
+  })
+
+  it('keeps a cwd custom when the store holds no root for the workspace', () => {
+    // The existing "requires a terminal for a cwd" case above pins this against an empty store.
+    expect(
+      buildAgentLaunchRouteInput(store(), {
+        agent: 'codex',
+        workspace: { kind: 'git-worktree', worktreeId: 'wt-1' },
+        tuiCustomization: { cwd: '/repo/app' }
+      }).requiresTuiLaunchCommand
+    ).toBe(true)
+  })
+})
diff --git a/src/renderer/src/lib/agent-launch-route-input.ts b/src/renderer/src/lib/agent-launch-route-input.ts
index 2f0c1e083f4..9e46494fa0c 100644
--- a/src/renderer/src/lib/agent-launch-route-input.ts
+++ b/src/renderer/src/lib/agent-launch-route-input.ts
@@ -3,6 +3,9 @@ import {
   parseExecutionHostId,
   toRuntimeExecutionHostId
 } from '../../../shared/execution-host'
+import type { AppState } from '@/store/types'
+import { findWorktreeById } from '@/store/slices/worktree-helpers'
+import { requestsCwdOutsideWorkspaceRootForWorkspace } from '../../../shared/terminal-startup-cwd'
 import type { TuiAgent } from '../../../shared/tui-agent'
 import { workspaceKindForWorktreeId } from '../../../shared/workspace-launch-kind'
 import {
@@ -40,11 +43,15 @@ export type ProspectiveWorkspace = {
   runtimeEnvironmentId?: string | null
 }
 
-export type AgentLaunchRouteStore = Parameters<typeof getExecutionHostIdForWorktree>[0] &
+export type AgentLaunchRouteStore = {
+  settings?: AgentLaunchRoutingInput['settings']
+  /** Where each workspace's root is, so a cwd naming it is not read as a custom directory. First
+   *  in the intersection so these lookups resolve to the full records. */
+  worktreesByRepo?: AppState['worktreesByRepo']
+  folderWorkspaces?: AppState['folderWorkspaces']
+} & Parameters<typeof getExecutionHostIdForWorktree>[0] &
   Parameters<typeof getLocalProjectExecutionRuntimeContext>[0] &
-  Parameters<typeof getConnectionIdFromState>[0] & {
-    settings?: AgentLaunchRoutingInput['settings']
-  }
+  Parameters<typeof getConnectionIdFromState>[0]
 
 export type AgentLaunchRouteArgs = {
   agent: TuiAgent
@@ -123,8 +130,18 @@ export function buildAgentLaunchRouteInput(
       workspace,
       executionHostId
     ),
+    // A cwd decides the route only when it names somewhere other than the workspace root; the
+    // host applies the same rule (`agent-launch-mode.ts`), so the two never disagree on it.
     requiresTuiLaunchCommand:
-      Boolean(tuiCustomization?.cwd?.trim()) || hasExplicitTuiLaunchCommand(store.settings, agent),
+      requestsCwdOutsideWorkspaceRootForWorkspace({
+        workspaceId: workspace.worktreeId,
+        requestedCwd: tuiCustomization?.cwd,
+        workspacePath: workspace.worktreeId
+          ? findWorktreeById(store.worktreesByRepo ?? {}, workspace.worktreeId)?.path
+          : undefined,
+        resolveFolderWorkspacePath: (folderWorkspaceId) =>
+          store.folderWorkspaces?.find((entry) => entry.id === folderWorkspaceId)?.folderPath
+      }) || hasExplicitTuiLaunchCommand(store.settings, agent),
     initialSessionOptions: args.initialSessionOptions
   }
 }
diff --git a/src/shared/agent-launch-intent.ts b/src/shared/agent-launch-intent.ts
index 87b5fc9ef68..7e68340fdba 100644
--- a/src/shared/agent-launch-intent.ts
+++ b/src/shared/agent-launch-intent.ts
@@ -39,7 +39,13 @@ export type AgentLaunchPrompt = {
  */
 export type AgentLaunchTarget =
   /** A workspace that already exists, addressed by any selector the runtime resolves. */
-  | { kind: 'existing'; worktree: string }
+  | {
+      kind: 'existing'
+      worktree: string
+      /** The workspace root the host resolved for that selector. Host-set, never accepted from a
+       *  caller: it decides whether a requested `cwd` names the root or somewhere else. */
+      workspacePath?: string
+    }
   /** A worktree this launch creates. `create` is the `worktree.create` request minus its agent
    *  fields — the launch owns those, so a caller cannot set a startup agent behind the router. */
   | { kind: 'create-worktree'; create: Readonly<Record<string, unknown>> }
diff --git a/src/shared/terminal-startup-cwd.test.ts b/src/shared/terminal-startup-cwd.test.ts
index 879465e4435..9e8f477c4a5 100644
--- a/src/shared/terminal-startup-cwd.test.ts
+++ b/src/shared/terminal-startup-cwd.test.ts
@@ -1,6 +1,8 @@
 import { describe, expect, it, vi } from 'vitest'
 import { FLOATING_TERMINAL_WORKTREE_ID } from './constants'
 import {
+  requestsCwdOutsideWorkspaceRoot,
+  requestsCwdOutsideWorkspaceRootForWorkspace,
   resolveTerminalStartupCwd,
   resolveTerminalStartupCwdForWorkspace
 } from './terminal-startup-cwd'
@@ -217,3 +219,106 @@ describe('resolveTerminalStartupCwd', () => {
     ).toBe('/repo/other')
   })
 })
+
+describe('requestsCwdOutsideWorkspaceRoot', () => {
+  it.each([
+    ['the root itself', '/repo/app', '/repo/app'],
+    ['the root with a trailing slash', '/repo/app', '/repo/app/'],
+    ['the root as a relative dot', '/repo/app', '.'],
+    ['a relative path that lands back on the root', '/repo/app', 'packages/..'],
+    ['a Windows root spelled with forward slashes', 'C:\\repo\\app', 'C:/repo/app/'],
+    ['a Windows root in another case', 'C:\\Repo\\App', 'c:\\repo\\app'],
+    [
+      'the other WSL UNC alias of the root',
+      '\\\\wsl$\\Ubuntu\\home\\ada\\app',
+      '\\\\wsl.localhost\\Ubuntu\\home\\ada\\app\\'
+    ],
+    ['an SSH-side root spelled with a trailing slash', '/home/ada/app', '/home/ada/app//'],
+    [
+      'a WSL root spelled as its Linux path',
+      '\\\\wsl.localhost\\Ubuntu\\home\\ada\\app',
+      '/home/ada/app/'
+    ]
+  ])('reads %s as no custom cwd', (_name, root, cwd) => {
+    expect(requestsCwdOutsideWorkspaceRoot(root, cwd)).toBe(false)
+  })
+
+  it.each([
+    ['a subdirectory', '/repo/app', '/repo/app/packages/web'],
+    ['a relative subdirectory', '/repo/app', 'packages/web'],
+    ['a directory outside the root', '/repo/app', '/repo/other'],
+    [
+      'a POSIX root in another case, which is a different directory',
+      '/home/ada/app',
+      '/home/Ada/app'
+    ],
+    [
+      'a Linux subdirectory of a WSL root',
+      '\\\\wsl.localhost\\Ubuntu\\home\\ada\\app',
+      '/home/ada/app/src'
+    ]
+  ])('reads %s as a custom cwd', (_name, root, cwd) => {
+    expect(requestsCwdOutsideWorkspaceRoot(root, cwd)).toBe(true)
+  })
+
+  it('reads no cwd, or only whitespace, as no custom cwd', () => {
+    expect(requestsCwdOutsideWorkspaceRoot('/repo/app', undefined)).toBe(false)
+    expect(requestsCwdOutsideWorkspaceRoot('/repo/app', '   ')).toBe(false)
+  })
+
+  it('reads a cwd against an unknown root as custom, because it cannot prove otherwise', () => {
+    expect(requestsCwdOutsideWorkspaceRoot(undefined, '/repo/app')).toBe(true)
+  })
+})
+
+describe('requestsCwdOutsideWorkspaceRootForWorkspace', () => {
+  it('takes the root from the caller when it has one, else from the worktree id', () => {
+    expect(
+      requestsCwdOutsideWorkspaceRootForWorkspace({
+        workspaceId: 'wt-1',
+        workspacePath: '/repo/app',
+        requestedCwd: '/repo/app/'
+      })
+    ).toBe(false)
+    expect(
+      requestsCwdOutsideWorkspaceRootForWorkspace({
+        workspaceId: 'repo-1::/repo/app',
+        requestedCwd: '/repo/app'
+      })
+    ).toBe(false)
+    expect(
+      requestsCwdOutsideWorkspaceRootForWorkspace({
+        workspaceId: 'repo-1::/repo/app',
+        requestedCwd: '/repo/app/packages/web'
+      })
+    ).toBe(true)
+  })
+
+  it('resolves a folder workspace root through the caller', () => {
+    const workspaceId = folderWorkspaceKey('folder-1')
+    const resolveFolderWorkspacePath = (id: string) => (id === 'folder-1' ? '/srv/notes' : null)
+    expect(
+      requestsCwdOutsideWorkspaceRootForWorkspace({
+        workspaceId,
+        requestedCwd: '/srv/notes/',
+        resolveFolderWorkspacePath
+      })
+    ).toBe(false)
+    expect(
+      requestsCwdOutsideWorkspaceRootForWorkspace({
+        workspaceId,
+        requestedCwd: '/srv/notes/drafts',
+        resolveFolderWorkspacePath
+      })
+    ).toBe(true)
+  })
+
+  it('reads any cwd in the floating workspace as custom, since it has no root', () => {
+    expect(
+      requestsCwdOutsideWorkspaceRootForWorkspace({
+        workspaceId: FLOATING_TERMINAL_WORKTREE_ID,
+        requestedCwd: '/tmp'
+      })
+    ).toBe(true)
+  })
+})
diff --git a/src/shared/terminal-startup-cwd.ts b/src/shared/terminal-startup-cwd.ts
index 8344abf07cc..828e8e8ef65 100644
--- a/src/shared/terminal-startup-cwd.ts
+++ b/src/shared/terminal-startup-cwd.ts
@@ -1,6 +1,11 @@
 import { FLOATING_TERMINAL_WORKTREE_ID } from './constants'
-import { resolveRuntimePath } from './cross-platform-path'
+import {
+  isWslUncPathForCallerLinuxPath,
+  normalizeRuntimePathForComparison,
+  resolveRuntimePath
+} from './cross-platform-path'
 import { parseWorkspaceKey } from './workspace-scope'
+import { parseWslUncPath } from './wsl-paths'
 import { splitWorktreeIdForFilesystem } from './worktree/id'
 
 export type TerminalStartupCwdMissingDirFallback = {
@@ -80,3 +85,58 @@ function resolveTerminalWorkspacePath(
   const worktreeId = scope?.type === 'worktree' ? scope.worktreeId : workspaceId
   return splitWorktreeIdForFilesystem(worktreeId)?.worktreePath ?? null
 }
+
+/**
+ * Whether a requested cwd would start the agent somewhere other than the workspace root.
+ *
+ * Only such a cwd is a reason to route a launch to a terminal: a structured session runs in its
+ * workspace and cannot honour any other directory. A cwd that names the root, however it is
+ * spelled — trailing slash, `.`, a relative path back to it, Windows separators or case, either WSL
+ * UNC alias or the distro's own Linux path — asks for nothing a structured session cannot give. An
+ * unknown root is read as a custom cwd: the launch cannot prove the request names the root, so it
+ * keeps the surface that can honour it.
+ */
+export function requestsCwdOutsideWorkspaceRoot(
+  workspacePath: string | null | undefined,
+  requestedCwd: string | null | undefined
+): boolean {
+  const trimmedCwd = requestedCwd?.trim()
+  if (!trimmedCwd) {
+    return false
+  }
+  if (!workspacePath) {
+    return true
+  }
+  const resolved = resolveTerminalStartupCwd(workspacePath, trimmedCwd) ?? trimmedCwd
+  if (
+    normalizeRuntimePathForComparison(resolved) === normalizeRuntimePathForComparison(workspacePath)
+  ) {
+    return false
+  }
+  // Why: an agent inside a WSL workspace records its cwd as a Linux path, which the workspace's
+  // own distro reads as the root.
+  const wslRoot = parseWslUncPath(workspacePath)
+  return !(wslRoot && isWslUncPathForCallerLinuxPath(workspacePath, trimmedCwd, wslRoot.distro))
+}
+
+/** `requestsCwdOutsideWorkspaceRoot` for a workspace named by id, with the root taken from the
+ *  caller's own record of it when one exists, else derived the way terminal creation derives it.
+ *  The floating workspace has no root, so any cwd there is custom. */
+export function requestsCwdOutsideWorkspaceRootForWorkspace(args: {
+  workspaceId?: string
+  requestedCwd?: string | null
+  /** The root as the caller already knows it; consulted before the id is parsed for one. */
+  workspacePath?: string | null
+  resolveFolderWorkspacePath?: (folderWorkspaceId: string) => string | null | undefined
+}): boolean {
+  if (!args.requestedCwd?.trim()) {
+    return false
+  }
+  if (args.workspaceId === FLOATING_TERMINAL_WORKTREE_ID) {
+    return true
+  }
+  const workspacePath =
+    args.workspacePath ??
+    resolveTerminalWorkspacePath(args.workspaceId, args.resolveFolderWorkspacePath)
+  return requestsCwdOutsideWorkspaceRoot(workspacePath, args.requestedCwd)
+}