diff --git a/desktop/src/lib/assistantOutputTargets.test.ts b/desktop/src/lib/assistantOutputTargets.test.ts
new file mode 100644
index 00000000..1fe3427a
--- /dev/null
+++ b/desktop/src/lib/assistantOutputTargets.test.ts
@@ -0,0 +1,221 @@
+import { describe, expect, it } from 'vitest'
+import { extractAssistantOutputTargets } from './assistantOutputTargets'
+
+const workDir = '/Users/nanmi/project/demo'
+
+describe('extractAssistantOutputTargets', () => {
+  it('extracts markdown links for workspace html, markdown, and images', () => {
+    const content = [
+      '已完成：',
+      '- [index.html](/Users/nanmi/project/demo/index.html)',
+      '- [notes](docs/result.md)',
+      '- [preview](assets/hero.png)',
+    ].join('\n')
+
+    const targets = extractAssistantOutputTargets(content, { workDir })
+
+    expect(targets.map((target) => [target.kind, target.href, target.normalizedPath])).toEqual([
+      ['local-html', '/Users/nanmi/project/demo/index.html', 'index.html'],
+      ['markdown', 'docs/result.md', 'docs/result.md'],
+      ['image', 'assets/hero.png', 'assets/hero.png'],
+    ])
+  })
+
+  it('normalizes markdown destinations with angle brackets, spaces, and line suffixes', () => {
+    const content = [
+      '[html](</Users/nanmi/project/demo/My Page/index.html>)',
+      '[lined](/Users/nanmi/project/demo/index.html:12)',
+    ].join('\n')
+
+    const targets = extractAssistantOutputTargets(content, { workDir })
+
+    expect(targets.map((target) => [target.href, target.normalizedPath])).toEqual([
+      ['/Users/nanmi/project/demo/My Page/index.html', 'My Page/index.html'],
+      ['/Users/nanmi/project/demo/index.html', 'index.html'],
+    ])
+  })
+
+  it('accepts safe Windows workspace paths with case-insensitive segments', () => {
+    const targets = extractAssistantOutputTargets(
+      '[Preview](C:/users/nanmi/project/demo/out/index.html)',
+      { workDir: 'C:/Users/nanmi/project/demo' },
+    )
+
+    expect(targets).toMatchObject([
+      {
+        kind: 'local-html',
+        href: 'C:/users/nanmi/project/demo/out/index.html',
+        normalizedPath: 'out/index.html',
+      },
+    ])
+  })
+
+  it('accepts absolute paths when the workdir is filesystem root', () => {
+    const targets = extractAssistantOutputTargets(
+      '[Preview](/tmp/demo/index.html)',
+      { workDir: '/' },
+    )
+
+    expect(targets).toMatchObject([
+      {
+        kind: 'local-html',
+        href: '/tmp/demo/index.html',
+        normalizedPath: 'tmp/demo/index.html',
+      },
+    ])
+  })
+
+  it('extracts naked localhost and loopback URLs', () => {
+    const targets = extractAssistantOutputTargets(
+      'Open http://localhost:5173 and http://127.0.0.1:3000/app and http://[::1]:4173/app now.',
+      { workDir },
+    )
+
+    expect(targets).toMatchObject([
+      { kind: 'localhost-url', href: 'http://localhost:5173' },
+      { kind: 'localhost-url', href: 'http://127.0.0.1:3000/app' },
+      { kind: 'localhost-url', href: 'http://[::1]:4173/app' },
+    ])
+  })
+
+  it('trims markdown/code punctuation around naked localhost URLs', () => {
+    const targets = extractAssistantOutputTargets(
+      '地址：`http://localhost:9527/`，备用：http://127.0.0.1:3000/app)。',
+      { workDir },
+    )
+
+    expect(targets.map((target) => target.href)).toEqual([
+      'http://localhost:9527/',
+      'http://127.0.0.1:3000/app',
+    ])
+  })
+
+  it('keeps markdown localhost links as markdown-link targets with authored labels', () => {
+    const targets = extractAssistantOutputTargets(
+      '[Preview](http://localhost:4173) then http://localhost:4173',
+      { workDir },
+    )
+
+    expect(targets).toMatchObject([
+      {
+        kind: 'localhost-url',
+        href: 'http://localhost:4173',
+        title: 'Preview',
+        source: 'markdown-link',
+      },
+    ])
+    expect(targets).toHaveLength(1)
+  })
+
+  it('rejects paths outside the active workspace', () => {
+    const targets = extractAssistantOutputTargets(
+      '[secret](/Users/nanmi/private/secret.html) [ok](/Users/nanmi/project/demo/public/index.html)',
+      { workDir },
+    )
+
+    expect(targets).toHaveLength(1)
+    expect(targets[0]).toMatchObject({
+      kind: 'local-html',
+      normalizedPath: 'public/index.html',
+    })
+  })
+
+  it('deduplicates repeated targets while preserving order', () => {
+    const content = [
+      '[index](index.html)',
+      'Again: http://localhost:5173',
+      '[index copy](./index.html)',
+      'Again: http://localhost:5173',
+    ].join('\n')
+
+    const targets = extractAssistantOutputTargets(content, { workDir })
+
+    expect(targets.map((target) => target.href)).toEqual(['index.html', 'http://localhost:5173'])
+  })
+
+  it('extracts files from absolute-root directory trees inside code blocks', () => {
+    const targets = extractAssistantOutputTargets(
+      [
+        '目录结构',
+        '```',
+        '/Users/nanmi/project/demo/generated/',
+        '├── README.md                    # Markdown 说明文件',
+        '├── index.html                   # 静态页面',
+        '└── todo-app/',
+        '    └── index.html',
+        '```',
+      ].join('\n'),
+      { workDir },
+    )
+
+    expect(targets.map((target) => [target.href, target.normalizedPath])).toEqual([
+      ['/Users/nanmi/project/demo/generated/README.md', 'generated/README.md'],
+      ['/Users/nanmi/project/demo/generated/index.html', 'generated/index.html'],
+      ['/Users/nanmi/project/demo/generated/todo-app/index.html', 'generated/todo-app/index.html'],
+    ])
+  })
+
+  it('ignores orphan preview file names inside code blocks', () => {
+    const targets = extractAssistantOutputTargets(
+      ['```', 'index.html', 'README.md', '```'].join('\n'),
+      { workDir },
+    )
+
+    expect(targets).toEqual([])
+  })
+
+  it('preserves first-seen order across mixed target types', () => {
+    const targets = extractAssistantOutputTargets(
+      'Open http://localhost:5173 first, then [index](index.html), then docs/guide.md.',
+      { workDir },
+    )
+
+    expect(targets.map((target) => target.href)).toEqual([
+      'http://localhost:5173',
+      'index.html',
+      'docs/guide.md',
+    ])
+  })
+
+  it('limits the result set to high-confidence preview targets', () => {
+    const targets = extractAssistantOutputTargets(
+      'Read https://example.com and maybe file:///etc/passwd, but use report.pdf only externally.',
+      { workDir },
+    )
+
+    expect(targets).toEqual([])
+  })
+
+  it('caps results at 6 by default', () => {
+    const targets = extractAssistantOutputTargets(
+      [
+        '[one](one.html)',
+        '[two](two.html)',
+        '[three](three.html)',
+        '[four](four.html)',
+        '[five](five.html)',
+        '[six](six.html)',
+        '[seven](seven.html)',
+      ].join('\n'),
+      { workDir },
+    )
+
+    expect(targets.map((target) => target.href)).toEqual([
+      'one.html',
+      'two.html',
+      'three.html',
+      'four.html',
+      'five.html',
+      'six.html',
+    ])
+  })
+
+  it('respects an explicit limit override', () => {
+    const targets = extractAssistantOutputTargets(
+      '[one](one.html) [two](two.html) [three](three.html)',
+      { workDir, limit: 2 },
+    )
+
+    expect(targets.map((target) => target.href)).toEqual(['one.html', 'two.html'])
+  })
+})
diff --git a/desktop/src/lib/assistantOutputTargets.ts b/desktop/src/lib/assistantOutputTargets.ts
new file mode 100644
index 00000000..34768447
--- /dev/null
+++ b/desktop/src/lib/assistantOutputTargets.ts
@@ -0,0 +1,666 @@
+export type AssistantOutputTargetKind =
+  | 'local-html'
+  | 'localhost-url'
+  | 'image'
+  | 'markdown'
+
+export type AssistantOutputTargetSource =
+  | 'markdown-link'
+  | 'plain-url'
+  | 'plain-path'
+
+export type AssistantOutputTarget = {
+  id: string
+  kind: AssistantOutputTargetKind
+  title: string
+  subtitle?: string
+  href: string
+  normalizedPath?: string
+  confidence: 'high'
+  source: AssistantOutputTargetSource
+}
+
+export type ExtractAssistantOutputTargetOptions = {
+  workDir?: string | null
+  limit?: number
+}
+
+type FileTargetMatch = {
+  kind: Exclude<AssistantOutputTargetKind, 'localhost-url'>
+  normalizedPath: string
+}
+
+type LocalhostTargetMatch = {
+  kind: 'localhost-url'
+  href: string
+}
+
+type CandidateTarget = {
+  key: string
+  position: number
+  order: number
+  target: AssistantOutputTarget
+}
+
+type MarkdownLinkMatch = {
+  title: string
+  href: string
+  start: number
+  end: number
+}
+
+type FencedCodeBlock = {
+  start: number
+  end: number
+  contentStart: number
+  text: string
+}
+
+type DirectoryTreeFileMatch = {
+  href: string
+  position: number
+}
+
+const localhostUrlPattern =
+  /https?:\/\/(?:localhost|127\.0\.0\.1|\[::1\])(?::\d+)?(?:\/[^\s`"'<>，。；、）\])}]*)?/gi
+const previewablePathPattern =
+  /(^|[\s("'`[])((?:\.{1,2}\/)?(?:[\w.-]+\/)*[\w.-]+\.(?:html?|md|markdown|png|jpe?g|gif|webp|svg))(?![\w/-])/gi
+
+export function extractAssistantOutputTargets(
+  content: string,
+  options: ExtractAssistantOutputTargetOptions = {},
+): AssistantOutputTarget[] {
+  const workDir = options.workDir ? resolveFilePath(options.workDir) : null
+  const limit = options.limit ?? 6
+  const candidates: CandidateTarget[] = []
+  const results: AssistantOutputTarget[] = []
+  const seen = new Set<string>()
+  const markdownLinks = extractMarkdownLinks(content)
+  const codeBlocks = extractFencedCodeBlocks(content)
+  let order = 0
+
+  const queueTarget = (target: AssistantOutputTarget, key: string, position: number) => {
+    candidates.push({
+      key,
+      position,
+      order,
+      target,
+    })
+    order += 1
+  }
+
+  for (const match of markdownLinks) {
+    const title = match.title
+    const href = match.href
+    const localhostTarget = toLocalhostTarget(href)
+    const fileTarget = toWorkspaceFileTarget(href, workDir)
+
+    if (!title) {
+      continue
+    }
+
+    if (localhostTarget) {
+      queueTarget({
+        id: createId(localhostTarget.kind, localhostTarget.href),
+        kind: localhostTarget.kind,
+        title,
+        href: localhostTarget.href,
+        confidence: 'high',
+        source: 'markdown-link',
+      }, createLocalhostKey(localhostTarget.href), match.start)
+      continue
+    }
+
+    if (!fileTarget) {
+      continue
+    }
+
+    queueTarget({
+      id: createId(fileTarget.kind, fileTarget.normalizedPath),
+      kind: fileTarget.kind,
+      title,
+      subtitle: fileTarget.normalizedPath,
+      href,
+      normalizedPath: fileTarget.normalizedPath,
+      confidence: 'high',
+      source: 'markdown-link',
+    }, createFileKey(fileTarget), match.start)
+  }
+
+  for (const match of content.matchAll(localhostUrlPattern)) {
+    const position = match.index ?? 0
+
+    if (isInMarkdownLink(position, markdownLinks)) {
+      continue
+    }
+
+    const href = trimTrailingPunctuation(match[0] ?? '')
+
+    if (!href) {
+      continue
+    }
+
+    queueTarget({
+      id: createId('localhost-url', href),
+      kind: 'localhost-url',
+      title: href,
+      href,
+      confidence: 'high',
+      source: 'plain-url',
+    }, createLocalhostKey(href), position)
+  }
+
+  for (const treeMatch of extractDirectoryTreeFileMatches(codeBlocks)) {
+    const fileTarget = toWorkspaceFileTarget(treeMatch.href, workDir)
+
+    if (!fileTarget) {
+      continue
+    }
+
+    queueTarget({
+      id: createId(fileTarget.kind, fileTarget.normalizedPath),
+      kind: fileTarget.kind,
+      title: getBasename(fileTarget.normalizedPath),
+      subtitle: fileTarget.normalizedPath,
+      href: treeMatch.href,
+      normalizedPath: fileTarget.normalizedPath,
+      confidence: 'high',
+      source: 'plain-path',
+    }, createFileKey(fileTarget), treeMatch.position)
+  }
+
+  for (const match of content.matchAll(previewablePathPattern)) {
+    const position = match.index ?? 0
+
+    if (isInMarkdownLink(position, markdownLinks)) {
+      continue
+    }
+
+    if (isInCodeBlock(position, codeBlocks)) {
+      continue
+    }
+
+    const href = trimTrailingPunctuation(match[2] ?? '')
+    const fileTarget = toWorkspaceFileTarget(href, workDir)
+
+    if (!fileTarget) {
+      continue
+    }
+
+    queueTarget({
+      id: createId(fileTarget.kind, fileTarget.normalizedPath),
+      kind: fileTarget.kind,
+      title: getBasename(fileTarget.normalizedPath),
+      subtitle: fileTarget.normalizedPath,
+      href,
+      normalizedPath: fileTarget.normalizedPath,
+      confidence: 'high',
+      source: 'plain-path',
+    }, createFileKey(fileTarget), position)
+  }
+
+  candidates.sort((left, right) => {
+    if (left.position !== right.position) {
+      return left.position - right.position
+    }
+
+    return left.order - right.order
+  })
+
+  for (const candidate of candidates) {
+    if (results.length >= limit || seen.has(candidate.key)) {
+      continue
+    }
+
+    seen.add(candidate.key)
+    results.push(candidate.target)
+  }
+
+  return results
+}
+
+function toWorkspaceFileTarget(candidate: string, workDir: string | null): FileTargetMatch | null {
+  if (!candidate || candidate.startsWith('file://') || isExternalUrl(candidate)) {
+    return null
+  }
+
+  const kind = classifyFileTarget(candidate)
+
+  if (!kind) {
+    return null
+  }
+
+  if (isAbsoluteFilePath(candidate)) {
+    if (!workDir) {
+      return null
+    }
+
+    const absoluteCandidate = resolveFilePath(candidate)
+
+    if (!isWithinWorkDir(absoluteCandidate, workDir)) {
+      return null
+    }
+
+    return {
+      kind,
+      normalizedPath: relativeFilePath(workDir, absoluteCandidate),
+    }
+  }
+
+  const baseDir = workDir ?? '.'
+  const resolvedCandidate = resolveFilePath(candidate, baseDir)
+
+  if (workDir && !isWithinWorkDir(resolvedCandidate, workDir)) {
+    return null
+  }
+
+  const normalizedPath = workDir
+    ? relativeFilePath(workDir, resolvedCandidate)
+    : normalizeFilePath(candidate)
+
+  if (!normalizedPath || normalizedPath === '.' || normalizedPath.startsWith('../')) {
+    return null
+  }
+
+  return {
+    kind,
+    normalizedPath,
+  }
+}
+
+function classifyFileTarget(candidate: string): FileTargetMatch['kind'] | null {
+  const extension = getExtension(candidate).toLowerCase()
+
+  if (extension === '.html' || extension === '.htm') {
+    return 'local-html'
+  }
+
+  if (extension === '.md' || extension === '.markdown') {
+    return 'markdown'
+  }
+
+  if (['.png', '.jpg', '.jpeg', '.gif', '.webp', '.svg'].includes(extension)) {
+    return 'image'
+  }
+
+  return null
+}
+
+function toLocalhostTarget(candidate: string): LocalhostTargetMatch | null {
+  const href = trimTrailingPunctuation(candidate)
+
+  if (!localhostUrlPattern.test(href) || localhostUrlPattern.lastIndex !== href.length) {
+    localhostUrlPattern.lastIndex = 0
+    return null
+  }
+
+  localhostUrlPattern.lastIndex = 0
+
+  return {
+    kind: 'localhost-url',
+    href,
+  }
+}
+
+function isExternalUrl(candidate: string): boolean {
+  return /^[a-z][a-z0-9+.-]*:\/\//i.test(candidate)
+}
+
+function isWithinWorkDir(candidatePath: string, workDir: string): boolean {
+  const relativePath = relativeFilePath(workDir, candidatePath)
+
+  return relativePath === '' || (!relativePath.startsWith('..') && !isAbsoluteFilePath(relativePath))
+}
+
+function toPosixPath(value: string): string {
+  return value.replace(/\\/g, '/')
+}
+
+function trimTrailingPunctuation(value: string): string {
+  return value.replace(/[`'")\]\}>,.;!?，。；、）】》]+$/g, '')
+}
+
+function extractMarkdownLinks(content: string): MarkdownLinkMatch[] {
+  const matches: MarkdownLinkMatch[] = []
+
+  for (let index = 0; index < content.length; index += 1) {
+    if (content[index] !== '[') {
+      continue
+    }
+
+    const labelEnd = content.indexOf(']', index + 1)
+
+    if (labelEnd === -1 || content[labelEnd + 1] !== '(') {
+      continue
+    }
+
+    const destinationEnd = findMarkdownDestinationEnd(content, labelEnd + 2)
+
+    if (destinationEnd === -1) {
+      continue
+    }
+
+    const title = content.slice(index + 1, labelEnd).trim()
+    const rawDestination = content.slice(labelEnd + 2, destinationEnd)
+    const href = normalizeMarkdownDestination(rawDestination)
+
+    matches.push({
+      title,
+      href,
+      start: index,
+      end: destinationEnd + 1,
+    })
+
+    index = destinationEnd
+  }
+
+  return matches
+}
+
+function findMarkdownDestinationEnd(content: string, start: number): number {
+  let inAngleBrackets = false
+
+  for (let index = start; index < content.length; index += 1) {
+    const character = content[index]
+
+    if (character === '<') {
+      inAngleBrackets = true
+      continue
+    }
+
+    if (character === '>' && inAngleBrackets) {
+      inAngleBrackets = false
+      continue
+    }
+
+    if (character === ')' && !inAngleBrackets) {
+      return index
+    }
+  }
+
+  return -1
+}
+
+function normalizeMarkdownDestination(destination: string): string {
+  let normalized = destination.trim()
+
+  if (normalized.startsWith('<') && normalized.endsWith('>')) {
+    normalized = normalized.slice(1, -1).trim()
+  }
+
+  const lineSuffixMatch = normalized.match(/^(.*\.(?:html?|md|markdown|png|jpe?g|gif|webp|svg)):\d+$/i)
+  const lineSuffixedPath = lineSuffixMatch?.[1]
+
+  if (lineSuffixedPath && !isExternalUrl(lineSuffixedPath)) {
+    normalized = lineSuffixedPath
+  }
+
+  return trimTrailingPunctuation(normalized)
+}
+
+function isInMarkdownLink(position: number, markdownLinks: MarkdownLinkMatch[]): boolean {
+  return markdownLinks.some((link) => position >= link.start && position < link.end)
+}
+
+function isInCodeBlock(position: number, codeBlocks: FencedCodeBlock[]): boolean {
+  return codeBlocks.some((block) => position >= block.start && position < block.end)
+}
+
+function extractFencedCodeBlocks(content: string): FencedCodeBlock[] {
+  const blocks: FencedCodeBlock[] = []
+  const lines = content.match(/[^\n]*\n|[^\n]+$/g) ?? []
+  let offset = 0
+  let active:
+    | { marker: '```' | '~~~'; start: number; contentStart: number }
+    | null = null
+
+  for (const line of lines) {
+    const trimmed = line.trimStart()
+
+    if (!active && (trimmed.startsWith('```') || trimmed.startsWith('~~~'))) {
+      active = {
+        marker: trimmed.startsWith('```') ? '```' : '~~~',
+        start: offset,
+        contentStart: offset + line.length,
+      }
+      offset += line.length
+      continue
+    }
+
+    if (active && trimmed.startsWith(active.marker)) {
+      blocks.push({
+        start: active.start,
+        end: offset + line.length,
+        contentStart: active.contentStart,
+        text: content.slice(active.contentStart, offset),
+      })
+      active = null
+    }
+
+    offset += line.length
+  }
+
+  return blocks
+}
+
+function extractDirectoryTreeFileMatches(codeBlocks: FencedCodeBlock[]): DirectoryTreeFileMatch[] {
+  const matches: DirectoryTreeFileMatch[] = []
+
+  for (const block of codeBlocks) {
+    matches.push(...extractDirectoryTreeFileMatchesFromBlock(block))
+  }
+
+  return matches
+}
+
+function extractDirectoryTreeFileMatchesFromBlock(block: FencedCodeBlock): DirectoryTreeFileMatch[] {
+  const matches: DirectoryTreeFileMatch[] = []
+  const lines = block.text.match(/[^\n]*\n|[^\n]+$/g) ?? []
+  const directoryStack: string[] = []
+  let rootPath: string | null = null
+  let offset = 0
+
+  for (const line of lines) {
+    const trimmed = line.trim()
+
+    if (!rootPath) {
+      const rootMatch = trimmed.match(/^((?:\/|[A-Za-z]:\/).*[\\/])$/)
+      if (rootMatch) {
+        rootPath = normalizeFilePath(rootMatch[1] ?? '')
+      }
+      offset += line.length
+      continue
+    }
+
+    const entryMatch = line.match(/^(\s*)(?:[│|]\s*)*[├└]──\s+(.+?)\s*$/u)
+    if (!entryMatch) {
+      offset += line.length
+      continue
+    }
+
+    const rawPrefix = entryMatch[1] ?? ''
+    const level = Math.floor(rawPrefix.replace(/[│|]/g, ' ').length / 4)
+    const entryName = stripTreeEntryComment(entryMatch[2] ?? '')
+
+    if (!entryName || entryName === '.' || entryName === '..') {
+      offset += line.length
+      continue
+    }
+
+    if (entryName.endsWith('/')) {
+      directoryStack[level] = entryName.replace(/\/+$/g, '')
+      directoryStack.length = level + 1
+      offset += line.length
+      continue
+    }
+
+    const relativeSegments = [...directoryStack.slice(0, level), entryName]
+    const href = resolveFilePath(relativeSegments.join('/'), rootPath)
+    if (classifyFileTarget(href)) {
+      matches.push({
+        href,
+        position: block.contentStart + offset,
+      })
+    }
+
+    offset += line.length
+  }
+
+  return matches
+}
+
+function stripTreeEntryComment(value: string): string {
+  return value.replace(/\s+#.*$/g, '').trim()
+}
+
+function createFileKey(target: FileTargetMatch): string {
+  return `file:${target.kind}:${target.normalizedPath}`
+}
+
+function createLocalhostKey(href: string): string {
+  return `url:${href}`
+}
+
+function createId(kind: AssistantOutputTargetKind, value: string): string {
+  return `${kind}:${value}`
+}
+
+function isAbsoluteFilePath(value: string): boolean {
+  return value.startsWith('/') || /^[A-Za-z]:\//.test(toPosixPath(value))
+}
+
+function normalizeFilePath(value: string): string {
+  const slashed = toPosixPath(value)
+  const { prefix, segments } = splitFilePath(slashed)
+  const normalizedSegments: string[] = []
+
+  for (const segment of segments) {
+    if (!segment || segment === '.') {
+      continue
+    }
+
+    if (segment === '..') {
+      const previous = normalizedSegments[normalizedSegments.length - 1]
+
+      if (previous && previous !== '..') {
+        normalizedSegments.pop()
+      } else if (!prefix) {
+        normalizedSegments.push('..')
+      }
+
+      continue
+    }
+
+    normalizedSegments.push(segment)
+  }
+
+  if (!prefix && normalizedSegments.length === 0) {
+    return '.'
+  }
+
+  if (normalizedSegments.length === 0) {
+    return prefix
+  }
+
+  return `${prefix}${normalizedSegments.join('/')}`
+}
+
+function resolveFilePath(value: string, baseDir = '/'): string {
+  if (isAbsoluteFilePath(value)) {
+    return normalizeFilePath(value)
+  }
+
+  const normalizedBaseDir = normalizeFilePath(baseDir)
+  const separator = normalizedBaseDir === '/' || normalizedBaseDir.endsWith('/') ? '' : '/'
+
+  return normalizeFilePath(`${normalizedBaseDir}${separator}${value}`)
+}
+
+function relativeFilePath(from: string, to: string): string {
+  const fromParts = splitFilePath(normalizeFilePath(from))
+  const toParts = splitFilePath(normalizeFilePath(to))
+
+  if (fromParts.prefix.toLowerCase() !== toParts.prefix.toLowerCase()) {
+    return normalizeFilePath(to)
+  }
+
+  let sharedLength = 0
+
+  while (
+    sharedLength < fromParts.segments.length &&
+    sharedLength < toParts.segments.length &&
+    arePathSegmentsEqual(
+      fromParts.segments[sharedLength],
+      toParts.segments[sharedLength],
+      fromParts.prefix,
+    )
+  ) {
+    sharedLength += 1
+  }
+
+  const parentSegments = Array.from(
+    { length: fromParts.segments.length - sharedLength },
+    () => '..',
+  )
+  const childSegments = toParts.segments.slice(sharedLength)
+
+  return [...parentSegments, ...childSegments].join('/')
+}
+
+function getExtension(value: string): string {
+  const basename = getBasename(value)
+  const extensionIndex = basename.lastIndexOf('.')
+
+  if (extensionIndex <= 0) {
+    return ''
+  }
+
+  return basename.slice(extensionIndex)
+}
+
+function getBasename(value: string): string {
+  const normalized = toPosixPath(value).replace(/\/+$/g, '')
+  const segments = normalized.split('/')
+
+  return segments[segments.length - 1] || ''
+}
+
+function splitFilePath(value: string): { prefix: string, segments: string[] } {
+  const slashed = toPosixPath(value)
+
+  if (slashed.startsWith('/')) {
+    return {
+      prefix: '/',
+      segments: slashed.slice(1).split('/').filter(Boolean),
+    }
+  }
+
+  const driveMatch = slashed.match(/^([A-Za-z]:)\/?(.*)$/)
+
+  if (driveMatch) {
+    const drivePrefix = driveMatch[1] ?? ''
+    const driveSegments = driveMatch[2] ?? ''
+
+    return {
+      prefix: `${drivePrefix}/`,
+      segments: driveSegments.split('/').filter(Boolean),
+    }
+  }
+
+  return {
+    prefix: '',
+    segments: slashed.split('/').filter(Boolean),
+  }
+}
+
+function arePathSegmentsEqual(left: string | undefined, right: string | undefined, prefix: string): boolean {
+  if (!left || !right) {
+    return left === right
+  }
+
+  if (/^[A-Za-z]:\/$/.test(prefix)) {
+    return left.toLowerCase() === right.toLowerCase()
+  }
+
+  return left === right
+}