diff --git a/README.md b/README.md
index 11b1bc7..6f944af 100644
--- a/README.md
+++ b/README.md
@@ -75,6 +75,20 @@ tags: ["nature", "sunset"]
 ---
 ```
 
+### Internal Link Formats
+
+Canonical formats for new content:
+
+- Post links: `/YYYY/MM/DD/slug` (example: `/2025/02/16/my-post`)
+- Media links: `/media/YYYY/MM/file.ext` (example: `/media/2025/02/photo.jpg`)
+
+Also supported (legacy/alternative input formats):
+
+- Post links: `/posts/slug`, `/posts/YYYY/MM/slug`, `post/slug`, `post/YYYY/MM/slug`
+- Media links: `media/YYYY/MM/file.ext`
+
+Preview HTML generation rewrites supported post/media link formats to preview-routable URLs. Markdown source remains unchanged except when inserting new media links from the editor, which now use `/media/...`.
+
 ## Development
 
 ### Prerequisites
diff --git a/src/main/engine/PreviewServer.ts b/src/main/engine/PreviewServer.ts
index 906f2b5..f916838 100644
--- a/src/main/engine/PreviewServer.ts
+++ b/src/main/engine/PreviewServer.ts
@@ -1,7 +1,9 @@
 import { createServer, type IncomingMessage, type Server, type ServerResponse } from 'http';
 import { readFile } from 'node:fs/promises';
+import path from 'node:path';
 import { marked } from 'marked';
 import { getMetaEngine, type ProjectMetadata } from './MetaEngine';
+import { getMediaEngine, type MediaData } from './MediaEngine';
 import { getPostEngine, type PostData, type PostFilter } from './PostEngine';
 import { getProjectEngine } from './ProjectEngine';
 
@@ -25,10 +27,21 @@ interface MetaEngineContract {
 
 interface PreviewServerDependencies {
   postEngine: PostEngineContract;
+  mediaEngine: MediaEngineContract;
   settingsEngine: MetaEngineContract;
   getActiveProjectContext: () => Promise<ActiveProjectContext>;
 }
 
+interface HtmlRewriteContext {
+  canonicalPostPathBySlug: Map<string, string>;
+  canonicalMediaPathBySourcePath: Map<string, string>;
+}
+
+interface MediaEngineContract {
+  getAllMedia: () => Promise<MediaData[]>;
+  setProjectContext?: (projectId: string, dataDir?: string, internalDir?: string) => void;
+}
+
 const DEFAULT_MAX_POSTS_PER_PAGE = 50;
 const MIN_MAX_POSTS_PER_PAGE = 1;
 const MAX_MAX_POSTS_PER_PAGE = 500;
@@ -106,6 +119,102 @@ function parseMacroParams(paramString: string | undefined): Record<string, strin
   return params;
 }
 
+function isExternalOrSpecialUrl(value: string): boolean {
+  const normalized = value.trim();
+  if (!normalized) return false;
+  if (normalized.startsWith('#') || normalized.startsWith('//')) return true;
+  return /^[a-z][a-z0-9+.-]*:/i.test(normalized);
+}
+
+function splitPathSuffix(value: string): { pathPart: string; suffix: string } {
+  const match = value.match(/^([^?#]*)([?#].*)?$/);
+  return {
+    pathPart: match?.[1] ?? value,
+    suffix: match?.[2] ?? '',
+  };
+}
+
+function normalizePreviewHref(rawHref: string, rewriteContext: HtmlRewriteContext): string {
+  if (!rawHref || isExternalOrSpecialUrl(rawHref)) {
+    return rawHref;
+  }
+
+  const { pathPart, suffix } = splitPathSuffix(rawHref.trim());
+
+  const canonicalDayRouteMatch = pathPart.match(/^\/(\d{4})\/(\d{1,2})\/(\d{1,2})\/([a-z0-9-]+)(?:\.html?)?$/i);
+  if (canonicalDayRouteMatch) {
+    const [, year, month, day, slug] = canonicalDayRouteMatch;
+    const normalizedMonth = String(Number(month)).padStart(2, '0');
+    const normalizedDay = String(Number(day)).padStart(2, '0');
+    return `/${year}/${normalizedMonth}/${normalizedDay}/${slug}${suffix}`;
+  }
+
+  const postBySlugMatch = pathPart.match(/^\/?post\/([a-z0-9-]+(?:\.html?)?)$/i);
+  if (postBySlugMatch) {
+    const slug = postBySlugMatch[1].replace(/\.html?$/i, '');
+    const canonical = rewriteContext.canonicalPostPathBySlug.get(slug);
+    return `${canonical ?? `/posts/${slug}`}${suffix}`;
+  }
+
+  const postByYearMonthSlugMatch = pathPart.match(/^\/?post\/(\d{4})\/(\d{1,2})\/([a-z0-9-]+(?:\.html?)?)$/i);
+  if (postByYearMonthSlugMatch) {
+    const [, , , rawSlug] = postByYearMonthSlugMatch;
+    const slug = rawSlug.replace(/\.html?$/i, '');
+    const canonical = rewriteContext.canonicalPostPathBySlug.get(slug);
+    return `${canonical ?? `/posts/${slug}`}${suffix}`;
+  }
+
+  const postsBySlugMatch = pathPart.match(/^\/?posts\/([a-z0-9-]+(?:\.html?)?)$/i);
+  if (postsBySlugMatch) {
+    const slug = postsBySlugMatch[1].replace(/\.html?$/i, '');
+    const canonical = rewriteContext.canonicalPostPathBySlug.get(slug);
+    return `${canonical ?? `/posts/${slug}`}${suffix}`;
+  }
+
+  const postsByYearMonthSlugMatch = pathPart.match(/^\/?posts\/(\d{4})\/(\d{1,2})\/([a-z0-9-]+(?:\.html?)?)$/i);
+  if (postsByYearMonthSlugMatch) {
+    const [, , , rawSlug] = postsByYearMonthSlugMatch;
+    const slug = rawSlug.replace(/\.html?$/i, '');
+    const canonical = rewriteContext.canonicalPostPathBySlug.get(slug);
+    return `${canonical ?? `/posts/${slug}`}${suffix}`;
+  }
+
+  return rawHref;
+}
+
+function normalizePreviewSrc(rawSrc: string, rewriteContext: HtmlRewriteContext): string {
+  if (!rawSrc || isExternalOrSpecialUrl(rawSrc)) {
+    return rawSrc;
+  }
+
+  const { pathPart, suffix } = splitPathSuffix(rawSrc.trim());
+  const mediaMatch = pathPart.match(/^\/?media\/(\d{4})\/(\d{2})\/([^\s]+)$/i);
+  if (!mediaMatch) {
+    return rawSrc;
+  }
+
+  const [, year, month, filename] = mediaMatch;
+  const sourceKey = `media/${year}/${month}/${filename}`.toLowerCase();
+  const canonicalPath = rewriteContext.canonicalMediaPathBySourcePath.get(sourceKey);
+  if (canonicalPath) {
+    return `${canonicalPath}${suffix}`;
+  }
+
+  return `/media/${year}/${month}/${filename}${suffix}`;
+}
+
+function rewriteRenderedHtmlUrls(html: string, rewriteContext: HtmlRewriteContext): string {
+  return html
+    .replace(/\bhref=(['"])(.*?)\1/gi, (_fullMatch, quote: string, href: string) => {
+      const rewritten = normalizePreviewHref(href, rewriteContext);
+      return `href=${quote}${rewritten}${quote}`;
+    })
+    .replace(/\bsrc=(['"])(.*?)\1/gi, (_fullMatch, quote: string, src: string) => {
+      const rewritten = normalizePreviewSrc(src, rewriteContext);
+      return `src=${quote}${rewritten}${quote}`;
+    });
+}
+
 function renderMacro(name: string, params: Record<string, string>, postId: string): string {
   if (name === 'youtube') {
     const id = escapeHtml(params.id || '');
@@ -136,14 +245,22 @@ function renderMacro(name: string, params: Record<string, string>, postId: strin
   return '';
 }
 
-async function renderPostHtml(post: PostData): Promise<string> {
+async function renderPostHtml(post: PostData, rewriteContext: HtmlRewriteContext): Promise<string> {
   const withMacros = post.content.replace(/\[\[(\w+)(?:\s+([^\]]+))?\]\]/g, (_match, macroName: string, rawParams: string | undefined) => {
     const params = parseMacroParams(rawParams);
     return renderMacro(macroName.toLowerCase(), params, post.id);
   });
 
   const markdownHtml = await marked.parse(withMacros, { async: true, gfm: true, breaks: false });
-  return `<div class="post">${markdownHtml}</div>`;
+  const rewrittenHtml = rewriteRenderedHtmlUrls(markdownHtml, rewriteContext);
+  return `<div class="post">${rewrittenHtml}</div>`;
+}
+
+function buildCanonicalPostPath(post: PostData): string {
+  const year = post.createdAt.getFullYear();
+  const month = String(post.createdAt.getMonth() + 1).padStart(2, '0');
+  const day = String(post.createdAt.getDate()).padStart(2, '0');
+  return `/${year}/${month}/${day}/${post.slug}`;
 }
 
 function getPageHtml(content: string, title: string): string {
@@ -175,6 +292,7 @@ function getPageHtml(content: string, title: string): string {
 
 export class PreviewServer {
   private readonly postEngine: PostEngineContract;
+  private readonly mediaEngine: MediaEngineContract;
   private readonly settingsEngine: MetaEngineContract;
   private readonly getActiveProjectContext: () => Promise<ActiveProjectContext>;
   private server: Server | null = null;
@@ -182,6 +300,7 @@ export class PreviewServer {
 
   constructor(dependencies?: Partial<PreviewServerDependencies>) {
     this.postEngine = dependencies?.postEngine ?? getPostEngine();
+    this.mediaEngine = dependencies?.mediaEngine ?? getMediaEngine();
     this.settingsEngine = dependencies?.settingsEngine ?? getMetaEngine();
     this.getActiveProjectContext = dependencies?.getActiveProjectContext ?? (async () => {
       const projectEngine = getProjectEngine();
@@ -278,10 +397,12 @@ export class PreviewServer {
     try {
       const context = await this.getActiveProjectContext();
       this.postEngine.setProjectContext(context.projectId, context.dataDir);
+      this.mediaEngine.setProjectContext?.(context.projectId, context.dataDir, context.dataDir);
       this.settingsEngine.setProjectContext(context.projectId, context.dataDir);
 
       const metadata = await this.settingsEngine.getProjectMetadata();
       const maxPostsPerPage = clampMaxPostsPerPage(metadata?.maxPostsPerPage);
+      const htmlRewriteContext = await this.buildHtmlRewriteContext();
 
       const requestUrl = new URL(req.url || '/', 'http://127.0.0.1');
       const pathname = decodeURIComponent(requestUrl.pathname.replace(/\/+$/, '') || '/');
@@ -292,7 +413,13 @@ export class PreviewServer {
         return;
       }
 
-      const result = await this.resolveRoute(pathname, maxPostsPerPage);
+      const mediaAsset = await this.resolveMediaAsset(pathname, context.dataDir);
+      if (mediaAsset) {
+        this.respondAsset(res, mediaAsset.contentType, mediaAsset.body);
+        return;
+      }
+
+      const result = await this.resolveRoute(pathname, maxPostsPerPage, htmlRewriteContext);
       if (!result) {
         this.respond(res, 404, 'Not Found');
         return;
@@ -305,24 +432,62 @@ export class PreviewServer {
     }
   }
 
-  private async resolveRoute(pathname: string, maxPostsPerPage: number): Promise<string | null> {
+  private async resolveRoute(pathname: string, maxPostsPerPage: number, rewriteContext: HtmlRewriteContext): Promise<string | null> {
+        const postsYearMonthSlugMatch = pathname.match(/^\/posts\/(\d{4})\/(\d{1,2})\/([^/]+)$/);
+        if (postsYearMonthSlugMatch) {
+          const year = Number(postsYearMonthSlugMatch[1]);
+          const month = Number(postsYearMonthSlugMatch[2]);
+          const slug = postsYearMonthSlugMatch[3].replace(/\.html?$/i, '');
+          if (month < 1 || month > 12) return null;
+          const post = await this.findPublishedPostBySlug(slug, { year, month: month - 1 });
+          if (!post) return null;
+          return this.renderPostList([post], rewriteContext);
+        }
+
+        const postsSlugMatch = pathname.match(/^\/posts\/([^/]+)$/);
+        if (postsSlugMatch) {
+          const slug = postsSlugMatch[1].replace(/\.html?$/i, '');
+          const post = await this.findPublishedPostBySlug(slug);
+          if (!post) return null;
+          return this.renderPostList([post], rewriteContext);
+        }
+
+        const legacyPostsYearMonthSlugMatch = pathname.match(/^\/post\/(\d{4})\/(\d{1,2})\/([^/]+)$/);
+        if (legacyPostsYearMonthSlugMatch) {
+          const year = Number(legacyPostsYearMonthSlugMatch[1]);
+          const month = Number(legacyPostsYearMonthSlugMatch[2]);
+          const slug = legacyPostsYearMonthSlugMatch[3].replace(/\.html?$/i, '');
+          if (month < 1 || month > 12) return null;
+          const post = await this.findPublishedPostBySlug(slug, { year, month: month - 1 });
+          if (!post) return null;
+          return this.renderPostList([post], rewriteContext);
+        }
+
+        const legacyPostsSlugMatch = pathname.match(/^\/post\/([^/]+)$/);
+        if (legacyPostsSlugMatch) {
+          const slug = legacyPostsSlugMatch[1].replace(/\.html?$/i, '');
+          const post = await this.findPublishedPostBySlug(slug);
+          if (!post) return null;
+          return this.renderPostList([post], rewriteContext);
+        }
+
     if (pathname === '/') {
       const posts = await this.loadPublishedPosts({ status: 'published' }, maxPostsPerPage);
-      return this.renderPostList(posts);
+      return this.renderPostList(posts, rewriteContext);
     }
 
     const tagMatch = pathname.match(/^\/tag\/([^/]+)$/);
     if (tagMatch) {
       const tag = tagMatch[1];
       const posts = await this.loadPublishedPosts({ status: 'published', tags: [tag] }, maxPostsPerPage);
-      return this.renderPostList(posts);
+      return this.renderPostList(posts, rewriteContext);
     }
 
     const categoryMatch = pathname.match(/^\/category\/([^/]+)$/);
     if (categoryMatch) {
       const category = categoryMatch[1];
       const posts = await this.loadPublishedPosts({ status: 'published', categories: [category] }, maxPostsPerPage);
-      return this.renderPostList(posts);
+      return this.renderPostList(posts, rewriteContext);
     }
 
     const daySlugMatch = pathname.match(/^\/(\d{4})\/(\d{1,2})\/(\d{1,2})\/([^/]+)$/);
@@ -334,7 +499,7 @@ export class PreviewServer {
       const posts = await this.loadPostsForDay(year, month, day, maxPostsPerPage);
       const post = posts.find((candidate) => candidate.slug === slug) || null;
       if (!post) return null;
-      return this.renderPostList([post]);
+      return this.renderPostList([post], rewriteContext);
     }
 
     const dayMatch = pathname.match(/^\/(\d{4})\/(\d{1,2})\/(\d{1,2})$/);
@@ -343,7 +508,7 @@ export class PreviewServer {
       const month = Number(dayMatch[2]);
       const day = Number(dayMatch[3]);
       const posts = await this.loadPostsForDay(year, month, day, maxPostsPerPage);
-      return this.renderPostList(posts);
+      return this.renderPostList(posts, rewriteContext);
     }
 
     const monthMatch = pathname.match(/^\/(\d{4})\/(\d{1,2})$/);
@@ -352,14 +517,14 @@ export class PreviewServer {
       const month = Number(monthMatch[2]);
       if (month < 1 || month > 12) return null;
       const posts = await this.loadPublishedPosts({ status: 'published', year, month: month - 1 }, maxPostsPerPage);
-      return this.renderPostList(posts);
+      return this.renderPostList(posts, rewriteContext);
     }
 
     const yearMatch = pathname.match(/^\/(\d{4})$/);
     if (yearMatch) {
       const year = Number(yearMatch[1]);
       const posts = await this.loadPublishedPosts({ status: 'published', year }, maxPostsPerPage);
-      return this.renderPostList(posts);
+      return this.renderPostList(posts, rewriteContext);
     }
 
     const pageSlugMatch = pathname.match(/^\/([^/]+)$/);
@@ -368,12 +533,27 @@ export class PreviewServer {
       const pages = await this.loadPublishedPosts({ status: 'published', categories: ['page'] }, maxPostsPerPage);
       const page = pages.find((candidate) => candidate.slug === slug) || null;
       if (!page) return null;
-      return this.renderPostList([page]);
+      return this.renderPostList([page], rewriteContext);
     }
 
     return null;
   }
 
+  private async findPublishedPostBySlug(slug: string, dateFilter?: { year: number; month: number }): Promise<PostData | null> {
+    if (!slug) return null;
+
+    const filter: PostFilter = {
+      status: 'published',
+      ...(dateFilter ? { year: dateFilter.year, month: dateFilter.month } : {}),
+    };
+
+    const candidates = await this.postEngine.getPostsFiltered(filter);
+    const match = candidates.find((candidate) => candidate.slug === slug);
+    if (!match) return null;
+
+    return (await this.postEngine.getPost(match.id)) ?? match;
+  }
+
   private async loadPostsForDay(year: number, month: number, day: number, maxPostsPerPage: number): Promise<PostData[]> {
     if (month < 1 || month > 12 || day < 1 || day > 31) {
       return [];
@@ -410,11 +590,43 @@ export class PreviewServer {
     return withContent;
   }
 
-  private async renderPostList(posts: PostData[]): Promise<string> {
-    const rendered = await Promise.all(posts.map((post) => renderPostHtml(post)));
+  private async renderPostList(posts: PostData[], rewriteContext: HtmlRewriteContext): Promise<string> {
+    const rendered = await Promise.all(posts.map((post) => renderPostHtml(post, rewriteContext)));
     return rendered.join('\n');
   }
 
+  private async buildHtmlRewriteContext(): Promise<HtmlRewriteContext> {
+    const publishedPosts = await this.postEngine.getPostsFiltered({ status: 'published' });
+    const canonicalPostPathBySlug = new Map<string, string>();
+
+    for (const post of publishedPosts) {
+      canonicalPostPathBySlug.set(post.slug, buildCanonicalPostPath(post));
+    }
+
+    const canonicalMediaPathBySourcePath = new Map<string, string>();
+    try {
+      const mediaItems = await this.mediaEngine.getAllMedia();
+      for (const media of mediaItems) {
+        const year = media.createdAt.getFullYear();
+        const month = String(media.createdAt.getMonth() + 1).padStart(2, '0');
+        const canonicalPath = `/media/${year}/${month}/${media.filename}`;
+
+        const originalNameKey = `media/${year}/${month}/${media.originalName}`.toLowerCase();
+        const filenameKey = `media/${year}/${month}/${media.filename}`.toLowerCase();
+
+        canonicalMediaPathBySourcePath.set(originalNameKey, canonicalPath);
+        canonicalMediaPathBySourcePath.set(filenameKey, canonicalPath);
+      }
+    } catch {
+      // Keep media map empty if media metadata cannot be loaded.
+    }
+
+    return {
+      canonicalPostPathBySlug,
+      canonicalMediaPathBySourcePath,
+    };
+  }
+
   private async resolveAsset(pathname: string): Promise<{ contentType: string; body: Buffer } | null> {
     const match = pathname.match(/^\/assets\/([^/]+)$/);
     if (!match) return null;
@@ -436,6 +648,65 @@ export class PreviewServer {
     }
   }
 
+  private async resolveMediaAsset(pathname: string, dataDir?: string): Promise<{ contentType: string; body: Buffer } | null> {
+    const match = pathname.match(/^\/media\/(.+)$/);
+    if (!match || !dataDir) return null;
+
+    const relativeMediaPath = path.posix.normalize(`media/${match[1]}`);
+    if (!relativeMediaPath.startsWith('media/')) {
+      return null;
+    }
+
+    const absoluteDataDir = path.resolve(dataDir);
+    const mediaRoot = path.resolve(absoluteDataDir, 'media');
+    const absoluteMediaPath = path.resolve(absoluteDataDir, relativeMediaPath);
+
+    if (absoluteMediaPath !== mediaRoot && !absoluteMediaPath.startsWith(`${mediaRoot}${path.sep}`)) {
+      return null;
+    }
+
+    try {
+      const body = await readFile(absoluteMediaPath);
+      return {
+        contentType: this.getMediaContentType(absoluteMediaPath),
+        body,
+      };
+    } catch {
+      return null;
+    }
+  }
+
+  private getMediaContentType(filePath: string): string {
+    const extension = path.extname(filePath).toLowerCase();
+    switch (extension) {
+      case '.jpg':
+      case '.jpeg':
+        return 'image/jpeg';
+      case '.png':
+        return 'image/png';
+      case '.gif':
+        return 'image/gif';
+      case '.webp':
+        return 'image/webp';
+      case '.svg':
+        return 'image/svg+xml';
+      case '.bmp':
+        return 'image/bmp';
+      case '.avif':
+        return 'image/avif';
+      case '.mp4':
+        return 'video/mp4';
+      case '.webm':
+        return 'video/webm';
+      case '.mov':
+        return 'video/quicktime';
+      case '.pdf':
+        return 'application/pdf';
+      default:
+        return 'application/octet-stream';
+    }
+  }
+
   private respond(res: ServerResponse, status: number, body: string): void {
     res.statusCode = status;
     res.setHeader('Content-Type', 'text/html; charset=utf-8');
diff --git a/src/main/ipc/handlers.ts b/src/main/ipc/handlers.ts
index 034a0e5..d3bddd1 100644
--- a/src/main/ipc/handlers.ts
+++ b/src/main/ipc/handlers.ts
@@ -475,10 +475,12 @@ export function registerIpcHandlers(): void {
 
   safeHandle('media:getUrl', async (_, id: string) => {
     // Returns the relative path for a media item (e.g. media/2025/01/uuid.jpg)
-    // This is the format used in markdown content for image references
+    // and exposes it as an absolute preview path (e.g. /media/2025/01/uuid.jpg)
+    // so inserted markdown uses root-absolute URLs.
     const engine = getMediaEngine();
     const relativePath = await engine.getRelativePath(id);
-    return relativePath ?? `media/${id}`;
+    const normalized = relativePath ?? `media/${id}`;
+    return normalized.startsWith('/') ? normalized : `/${normalized}`;
   });
 
   safeHandle('media:getFilePath', async (_, id: string) => {
diff --git a/src/renderer/components/InsertModal/InsertModal.css b/src/renderer/components/InsertModal/InsertModal.css
index de7bb1e..99456ff 100644
--- a/src/renderer/components/InsertModal/InsertModal.css
+++ b/src/renderer/components/InsertModal/InsertModal.css
@@ -203,6 +203,13 @@
   justify-content: center;
 }
 
+.insert-modal-footer-content {
+  display: flex;
+  flex-direction: column;
+  align-items: center;
+  gap: 4px;
+}
+
 .insert-modal-hint {
   font-size: 11px;
   color: var(--color-text-muted, #888);
@@ -210,6 +217,12 @@
   letter-spacing: 0.5px;
 }
 
+.insert-modal-format-hint {
+  font-size: 11px;
+  color: var(--color-text-muted, #888);
+  font-family: 'Cascadia Code', 'Consolas', 'Courier New', monospace;
+}
+
 /* Scrollbar styling */
 .insert-modal-results::-webkit-scrollbar {
   width: 8px;
diff --git a/src/renderer/components/InsertModal/InsertModal.tsx b/src/renderer/components/InsertModal/InsertModal.tsx
index 5d765dc..b5f7e9e 100644
--- a/src/renderer/components/InsertModal/InsertModal.tsx
+++ b/src/renderer/components/InsertModal/InsertModal.tsx
@@ -324,11 +324,20 @@ export const InsertModal: React.FC<InsertModalProps> = ({
         )}
 
         <div className="insert-modal-footer">
-          <span className="insert-modal-hint">
-            {activeTab === 'internal' 
-              ? 'Use ↑↓ to navigate, Enter to select, Esc to close'
-              : 'Enter URL and press Enter or click button, Esc to close'}
-          </span>
+          <div className="insert-modal-footer-content">
+            <span className="insert-modal-hint">
+              {activeTab === 'internal' 
+                ? 'Use ↑↓ to navigate, Enter to select, Esc to close'
+                : 'Enter URL and press Enter or click button, Esc to close'}
+            </span>
+            {activeTab === 'internal' && (
+              <span className="insert-modal-format-hint">
+                {mode === 'link'
+                  ? 'Canonical: /YYYY/MM/DD/slug'
+                  : 'Canonical: /media/YYYY/MM/file.ext'}
+              </span>
+            )}
+          </div>
         </div>
       </div>
     </div>
diff --git a/tests/engine/PreviewServer.test.ts b/tests/engine/PreviewServer.test.ts
index 787a793..8cdefac 100644
--- a/tests/engine/PreviewServer.test.ts
+++ b/tests/engine/PreviewServer.test.ts
@@ -1,4 +1,7 @@
 import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest';
+import { mkdtemp, mkdir, rm, writeFile } from 'node:fs/promises';
+import path from 'node:path';
+import { tmpdir } from 'node:os';
 import type { PostData, PostFilter } from '../../src/main/engine/PostEngine';
 import { PreviewServer } from '../../src/main/engine/PreviewServer';
 
@@ -84,13 +87,26 @@ function makeSettings(maxPostsPerPage = 50): SettingsEngineLike {
   };
 }
 
+function makeMediaEngine(mediaItems: Array<{ id: string; filename: string; originalName: string; createdAt: Date }>) {
+  return {
+    async getAllMedia() {
+      return mediaItems;
+    },
+  };
+}
+
 describe('PreviewServer', () => {
   let server: PreviewServer;
+  let tempDir: string | null = null;
 
   afterEach(async () => {
     if (server) {
       await server.stop();
     }
+    if (tempDir) {
+      await rm(tempDir, { recursive: true, force: true });
+      tempDir = null;
+    }
   });
 
   beforeEach(() => {
@@ -328,4 +344,91 @@ describe('PreviewServer', () => {
     expect(html).toContain('<title>Configured Project Name</title>');
     expect(html).not.toContain('<title>Blog Preview</title>');
   });
+
+  it('rewrites supported markdown links to preview-safe URLs while leaving external links unchanged', async () => {
+    const targetBySlug = makePost({
+      id: 'target-1',
+      slug: 'target-post',
+      title: 'Target Post',
+      createdAt: new Date('2025-02-14T10:00:00.000Z'),
+      content: '# Target',
+    });
+    const targetByYearMonth = makePost({
+      id: 'target-2',
+      slug: 'archive-post',
+      title: 'Archive Post',
+      createdAt: new Date('2025-02-10T10:00:00.000Z'),
+      content: '# Archive',
+    });
+    const legacyTarget = makePost({
+      id: 'target-3',
+      slug: 'legacy-post',
+      title: 'Legacy Post',
+      createdAt: new Date('2025-03-01T10:00:00.000Z'),
+      content: '# Legacy',
+    });
+
+    const post = makePost({
+      id: 'rewrite-1',
+      slug: 'rewrite-test',
+      title: 'Rewrite Test',
+      content: [
+        '[Post by slug](/posts/target-post)',
+        '[Post by year/month](/posts/2025/02/archive-post)',
+        '[Legacy post link](post/legacy-post)',
+        '![Local image](media/2025/02/example.jpg)',
+        '[External](https://example.com/path)',
+      ].join('\n\n'),
+    });
+
+    server = new PreviewServer({
+      postEngine: makeEngine([post, targetBySlug, targetByYearMonth, legacyTarget]),
+      mediaEngine: makeMediaEngine([
+        {
+          id: 'media-guid-1',
+          filename: '3b94f5d1-91f5-4c9b-a8d4-6f3bf8f045cf.jpg',
+          originalName: 'example.jpg',
+          createdAt: new Date('2025-02-03T10:00:00.000Z'),
+        },
+      ]) as any,
+      settingsEngine: makeSettings(50),
+      getActiveProjectContext: async () => ({ projectId: 'default' }),
+    });
+
+    await server.start(0);
+
+    const response = await fetch(`${server.getBaseUrl()}/`);
+    expect(response.status).toBe(200);
+    const html = await response.text();
+
+    expect(html).toContain('href="/2025/02/14/target-post"');
+    expect(html).toContain('href="/2025/02/10/archive-post"');
+    expect(html).toContain('href="/2025/03/01/legacy-post"');
+    expect(html).toContain('src="/media/2025/02/3b94f5d1-91f5-4c9b-a8d4-6f3bf8f045cf.jpg"');
+    expect(html).toContain('href="https://example.com/path"');
+  });
+
+  it('serves media files from the active project data directory at /media/...', async () => {
+    tempDir = await mkdtemp(path.join(tmpdir(), 'bds-preview-media-'));
+    const mediaDir = path.join(tempDir, 'media', '2025', '02');
+    await mkdir(mediaDir, { recursive: true });
+    await writeFile(path.join(mediaDir, 'sample.jpg'), Buffer.from('fake-image-bytes'));
+
+    server = new PreviewServer({
+      postEngine: makeEngine([makePost()]),
+      settingsEngine: makeSettings(50),
+      getActiveProjectContext: async () => ({
+        projectId: 'default',
+        dataDir: tempDir!,
+      }),
+    });
+
+    await server.start(0);
+
+    const response = await fetch(`${server.getBaseUrl()}/media/2025/02/sample.jpg`);
+    expect(response.status).toBe(200);
+    expect(response.headers.get('content-type')).toContain('image/jpeg');
+    const body = await response.text();
+    expect(body).toBe('fake-image-bytes');
+  });
 });
\ No newline at end of file
diff --git a/tests/ipc/handlers.test.ts b/tests/ipc/handlers.test.ts
index 945a983..64b1639 100644
--- a/tests/ipc/handlers.test.ts
+++ b/tests/ipc/handlers.test.ts
@@ -918,21 +918,21 @@ describe('IPC Handlers', () => {
     });
 
     describe('media:getUrl', () => {
-      it('should return relative media path', async () => {
+      it('should return absolute media path', async () => {
         mockMediaEngine.getRelativePath.mockResolvedValue('media/2025/01/media-123.jpg');
 
         const result = await invokeHandler('media:getUrl', 'media-123');
 
         expect(mockMediaEngine.getRelativePath).toHaveBeenCalledWith('media-123');
-        expect(result).toBe('media/2025/01/media-123.jpg');
+        expect(result).toBe('/media/2025/01/media-123.jpg');
       });
 
-      it('should fall back to media/{id} when relative path is not found', async () => {
+      it('should fall back to /media/{id} when relative path is not found', async () => {
         mockMediaEngine.getRelativePath.mockResolvedValue(null);
 
         const result = await invokeHandler('media:getUrl', 'media-unknown');
 
-        expect(result).toBe('media/media-unknown');
+        expect(result).toBe('/media/media-unknown');
       });
     });
 
diff --git a/tests/renderer/components/InsertModal.test.tsx b/tests/renderer/components/InsertModal.test.tsx
new file mode 100644
index 0000000..cfed947
--- /dev/null
+++ b/tests/renderer/components/InsertModal.test.tsx
@@ -0,0 +1,32 @@
+import React from 'react';
+import { describe, it, expect, vi } from 'vitest';
+import { render, screen } from '@testing-library/react';
+import { InsertModal } from '../../../src/renderer/components/InsertModal/InsertModal';
+
+describe('InsertModal format hints', () => {
+  it('shows canonical post link format hint in internal link mode', () => {
+    render(
+      <InsertModal
+        mode="link"
+        onInsertLink={vi.fn()}
+        onInsertImage={vi.fn()}
+        onClose={vi.fn()}
+      />
+    );
+
+    expect(screen.getByText('Canonical: /YYYY/MM/DD/slug')).toBeInTheDocument();
+  });
+
+  it('shows canonical media format hint in internal image mode', () => {
+    render(
+      <InsertModal
+        mode="image"
+        onInsertLink={vi.fn()}
+        onInsertImage={vi.fn()}
+        onClose={vi.fn()}
+      />
+    );
+
+    expect(screen.getByText('Canonical: /media/YYYY/MM/file.ext')).toBeInTheDocument();
+  });
+});