diff --git a/src/renderer/src/components/settings/CliSkillRuntimeSetup.test.tsx b/src/renderer/src/components/settings/CliSkillRuntimeSetup.test.tsx
index 6150bd808..269074ff8 100644
--- a/src/renderer/src/components/settings/CliSkillRuntimeSetup.test.tsx
+++ b/src/renderer/src/components/settings/CliSkillRuntimeSetup.test.tsx
@@ -243,6 +243,55 @@ describe('CliSkillRuntimeSetup runtime helpers', () => {
     }
   })
 
+  it('skips the Windows preflight when the configured Windows shell is POSIX-family', () => {
+    const installCommand = buildAgentFeatureSkillInstallCommand(['orchestration'])
+    const windowsHost = { runtime: 'host', label: 'Windows' } as const
+    const previous = useAppStore.getState()
+
+    try {
+      // MSYS rewrites cmd.exe's leading /d /s /c switches into drive paths, so
+      // the copied command must stay bare for a Git Bash / wsl.exe paste target.
+      for (const terminalWindowsShell of ['git-bash', 'C:\\Program Files\\Git\\bin\\bash.exe']) {
+        useAppStore.setState({
+          settings: { ...getDefaultSettings('/tmp'), terminalWindowsShell }
+        })
+        expect(buildSkillCommandForRuntime(installCommand, windowsHost, 'win32')).toBe(
+          installCommand
+        )
+      }
+
+      // cmd-family shells still need the preflight wrapper.
+      useAppStore.setState({
+        settings: { ...getDefaultSettings('/tmp'), terminalWindowsShell: 'cmd.exe' }
+      })
+      expect(buildSkillCommandForRuntime(installCommand, windowsHost, 'win32')).toBe(
+        `${windowsNpxPreflightPrefix}${windowsNpxGuidance}) else (${installCommand})"`
+      )
+    } finally {
+      useAppStore.setState({ settings: previous.settings })
+    }
+  })
+
+  it('keeps the bare reinstall rewrite for POSIX-family Windows skill updates', () => {
+    const installCommand = buildAgentFeatureSkillInstallCommand(['orchestration'])
+    const previous = useAppStore.getState()
+    useAppStore.setState({
+      settings: { ...getDefaultSettings('/tmp'), terminalWindowsShell: 'git-bash' }
+    })
+
+    try {
+      expect(
+        buildSkillCommandForRuntime(
+          'npx skills update orchestration --global',
+          { runtime: 'host', label: 'Windows' },
+          'win32'
+        )
+      ).toBe(installCommand)
+    } finally {
+      useAppStore.setState({ settings: previous.settings })
+    }
+  })
+
   it('does not wrap unrelated Windows host commands', () => {
     expect(
       buildSkillCommandForRuntime(
diff --git a/src/renderer/src/components/settings/CliSkillRuntimeSetup.tsx b/src/renderer/src/components/settings/CliSkillRuntimeSetup.tsx
index bee39049f..005b5dfc5 100644
--- a/src/renderer/src/components/settings/CliSkillRuntimeSetup.tsx
+++ b/src/renderer/src/components/settings/CliSkillRuntimeSetup.tsx
@@ -8,6 +8,7 @@ import {
   quotePowerShellNativeArgument
 } from '../../../../shared/powershell-native-argument'
 import { buildWslLoginShellCommand } from '../../../../shared/wsl-login-shell-command'
+import { resolveWindowsShellStartupFamily } from '../../../../shared/windows-terminal-shell'
 import { getProjectAgentSkillTerminalShellOverride } from '@/lib/project-skill-runtime'
 import { useAppStore } from '@/store'
 import { buildAgentFeatureSkillInstallCommand } from '../../../../shared/agent-feature-install-commands'
@@ -136,6 +137,10 @@ function wrapWindowsSkillCommandWithNpxPrerequisite(
     // Why: skill setup terminals spawn on the focused runtime environment, so a
     // Windows client must not hand a cmd.exe command to a remote host.
     isRemoteRuntimeEnvironmentFocused() ||
+    // Why: the copied command lands in the user's configured shell, and MSYS
+    // shells rewrite cmd.exe's leading /d /s /c switches into drive paths,
+    // starting an interactive cmd session instead of running the payload.
+    isPosixFamilyWindowsShellConfigured() ||
     !/^npx\s+skills\s+(?:add|update)\b/i.test(trimmedCommand)
   ) {
     return command
@@ -149,6 +154,13 @@ function wrapWindowsSkillCommandWithNpxPrerequisite(
   return `cmd.exe /d /s /c "where.exe npx >nul 2>nul & if errorlevel 1 (${missingNpxGuidance}) else (${trimmedCommand})"`
 }
 
+function isPosixFamilyWindowsShellConfigured(): boolean {
+  return (
+    resolveWindowsShellStartupFamily(useAppStore.getState().settings?.terminalWindowsShell) ===
+    'posix'
+  )
+}
+
 function isRemoteRuntimeEnvironmentFocused(): boolean {
   // Why: the terminal router also weighs how many environments are saved, but
   // that slice has no subscriber here. Read only the focused id, which every