diff --git a/web/e2e/skill-detail-relative-links.spec.ts b/web/e2e/skill-detail-relative-links.spec.ts
index 5f1f353c..89164c02 100644
--- a/web/e2e/skill-detail-relative-links.spec.ts
+++ b/web/e2e/skill-detail-relative-links.spec.ts
@@ -28,8 +28,12 @@ test.describe('Skill Detail Relative Links (Real API)', () => {
         extraFiles: [
           {
             path: 'docs/usage.md',
-            content: '# Usage\n\nThis is linked documentation.',
+            content: '# Usage\n\nThis is linked documentation.\n\n[Nested](nested.md)',
           },
+          {
+            path: 'docs/nested.md',
+            content: '# Nested\n\nSecond-level linked documentation.',
+          }
         ],
       })
 
@@ -40,6 +44,11 @@ test.describe('Skill Detail Relative Links (Real API)', () => {
       await page.getByRole('link', { name: 'Usage' }).click()
       await expect(page.getByRole('dialog')).toContainText('usage.md')
       await expect(page.getByRole('dialog')).toContainText('This is linked documentation.')
+      await expect(page.getByRole('dialog').getByRole('link', { name: 'Nested' })).toBeVisible()
+
+      await page.getByRole('dialog').getByRole('link', { name: 'Nested' }).click()
+      await expect(page.getByRole('dialog')).toContainText('nested.md')
+      await expect(page.getByRole('dialog')).toContainText('Second-level linked documentation.')
 
       await page.getByRole('button', { name: 'Close' }).click()
       await expect(page.getByRole('dialog')).toBeHidden()
diff --git a/web/src/features/skill/file-preview-dialog.tsx b/web/src/features/skill/file-preview-dialog.tsx
index 14bba880..21aabbfa 100644
--- a/web/src/features/skill/file-preview-dialog.tsx
+++ b/web/src/features/skill/file-preview-dialog.tsx
@@ -1,4 +1,4 @@
-import { useState } from 'react'
+import { useState, type MouseEvent } from 'react'
 import { Copy, Check, Download, X } from 'lucide-react'
 import { useTranslation } from 'react-i18next'
 import { Dialog, DialogContent } from '@/shared/ui/dialog'
@@ -18,6 +18,7 @@ interface FilePreviewDialogProps {
   isLoading: boolean
   error: Error | null
   onDownload: () => void
+  onLinkClick?: (href: string, event: MouseEvent<HTMLAnchorElement>) => void
 }
 
 /**
@@ -33,6 +34,7 @@ export function FilePreviewDialog({
   isLoading,
   error,
   onDownload,
+  onLinkClick,
 }: FilePreviewDialogProps) {
   const { t } = useTranslation()
   // Tracks the copy animation state: idle → spinning → done
@@ -143,7 +145,7 @@ export function FilePreviewDialog({
               <Button onClick={onDownload}>{t('filePreview.downloadHint', { name: node.name })}</Button>
             </div>
           ) : content && isMarkdown ? (
-            <MarkdownRenderer content={content} />
+            <MarkdownRenderer content={content} onLinkClick={onLinkClick} />
           ) : content && shouldHighlight ? (
             <CodeRenderer code={content} language={language} />
           ) : content ? (
diff --git a/web/src/pages/skill-detail.test.tsx b/web/src/pages/skill-detail.test.tsx
index 1c6374ce..8da128c0 100644
--- a/web/src/pages/skill-detail.test.tsx
+++ b/web/src/pages/skill-detail.test.tsx
@@ -127,8 +127,27 @@ vi.mock('@/features/skill/markdown-renderer', () => ({
 }))
 
 vi.mock('@/features/skill/file-preview-dialog', () => ({
-  FilePreviewDialog: ({ open, node }: { open: boolean; node: { path: string } | null }) => (
-    open && node ? <div role="dialog">preview:{node.path}</div> : null
+  FilePreviewDialog: ({
+    open,
+    node,
+    onLinkClick,
+  }: {
+    open: boolean
+    node: { path: string } | null
+    onLinkClick?: (href: string, event: MouseEvent<HTMLAnchorElement>) => void
+  }) => (
+    open && node
+      ? (
+          <div role="dialog">
+            preview:{node.path}
+            {onLinkClick && (
+              <a href="nested.md" onClick={(event) => onLinkClick('nested.md', event)}>
+                Nested
+              </a>
+            )}
+          </div>
+        )
+      : null
   ),
 }))
 
@@ -490,6 +509,25 @@ describe('SkillDetailPage', () => {
     expect(toastMocks.error).not.toHaveBeenCalled()
   })
 
+  it('resolves links inside previewed markdown files against the previewed file path', () => {
+    useSkillFilesMock.mockReturnValue({
+      data: [
+        createSkillFile('README.md'),
+        createSkillFile('docs/usage.md'),
+        createSkillFile('docs/nested.md'),
+      ],
+    })
+
+    render(<SkillDetailPage />)
+    fireEvent.click(screen.getByRole('link', { name: 'Usage' }))
+    expect(screen.getByRole('dialog').textContent).toContain('preview:docs/usage.md')
+
+    fireEvent.click(screen.getByRole('link', { name: 'Nested' }))
+
+    expect(screen.getByRole('dialog').textContent).toContain('preview:docs/nested.md')
+    expect(toastMocks.error).not.toHaveBeenCalled()
+  })
+
   it('keeps the viewer on the detail page and shows a toast for missing package files', () => {
     useSkillFilesMock.mockReturnValue({
       data: [
diff --git a/web/src/pages/skill-detail.tsx b/web/src/pages/skill-detail.tsx
index 77b0c291..ca62eb49 100644
--- a/web/src/pages/skill-detail.tsx
+++ b/web/src/pages/skill-detail.tsx
@@ -300,8 +300,12 @@ export function SkillDetailPage() {
     setPreviewDialogOpen(true)
   }
 
-  const handleOverviewLinkClick = (href: string, event: MouseEvent<HTMLAnchorElement>) => {
-    const resolution = resolvePackageRelativeLink(href, documentationPath, files)
+  const handlePackageMarkdownLinkClick = (
+    href: string,
+    event: MouseEvent<HTMLAnchorElement>,
+    currentFilePath: string | null | undefined,
+  ) => {
+    const resolution = resolvePackageRelativeLink(href, currentFilePath, files)
 
     if (resolution.status === 'ignored') {
       return
@@ -318,6 +322,14 @@ export function SkillDetailPage() {
     toast.error(t('skillDetail.packageLinkMissingTitle'), t('skillDetail.packageLinkMissingDescription'))
   }
 
+  const handleOverviewLinkClick = (href: string, event: MouseEvent<HTMLAnchorElement>) => {
+    handlePackageMarkdownLinkClick(href, event, documentationPath)
+  }
+
+  const handlePreviewLinkClick = (href: string, event: MouseEvent<HTMLAnchorElement>) => {
+    handlePackageMarkdownLinkClick(href, event, previewNode?.path)
+  }
+
   // Download a single file from the skill version
   const handleDownloadFile = () => {
     const isAnonymousAllowed = namespace === 'global' && skill?.visibility === 'PUBLIC'
@@ -1652,6 +1664,7 @@ export function SkillDetailPage() {
         isLoading={isLoadingPreview}
         error={previewError}
         onDownload={handleDownloadFile}
+        onLinkClick={handlePreviewLinkClick}
       />
     </div>
   )