diff --git a/apps/x/apps/renderer/src/lib/wiki-links.ts b/apps/x/apps/renderer/src/lib/wiki-links.ts
index 4b429a05..0e376cc9 100644
--- a/apps/x/apps/renderer/src/lib/wiki-links.ts
+++ b/apps/x/apps/renderer/src/lib/wiki-links.ts
@@ -9,8 +9,7 @@ export const normalizeWikiPath = (input: string) => {
 }
 
 export const ensureMarkdownExtension = (path: string) => {
-  const lastSegment = path.split('/').pop() ?? path
-  if (lastSegment.includes('.')) return path
+  if (path.toLowerCase().endsWith('.md')) return path
   return `${path}.md`
 }
 
diff --git a/apps/x/packages/core/src/workspace/wiki-link-rewrite.ts b/apps/x/packages/core/src/workspace/wiki-link-rewrite.ts
new file mode 100644
index 00000000..68edbb9a
--- /dev/null
+++ b/apps/x/packages/core/src/workspace/wiki-link-rewrite.ts
@@ -0,0 +1,148 @@
+import fs from 'node:fs/promises';
+import path from 'node:path';
+
+const WIKI_LINK_REGEX = /\[\[([^[\]]+)\]\]/g;
+const KNOWLEDGE_PREFIX = 'knowledge/';
+const MARKDOWN_EXTENSION = '.md';
+
+function normalizeRelPath(relPath: string): string {
+  return relPath.replace(/\\/g, '/');
+}
+
+function isKnowledgeMarkdownPath(relPath: string): boolean {
+  const normalized = normalizeRelPath(relPath).replace(/^\/+/, '');
+  const lower = normalized.toLowerCase();
+  return lower.startsWith(KNOWLEDGE_PREFIX) && lower.endsWith(MARKDOWN_EXTENSION);
+}
+
+function stripKnowledgePrefix(relPath: string): string {
+  const normalized = normalizeRelPath(relPath).replace(/^\/+/, '');
+  if (!normalized.toLowerCase().startsWith(KNOWLEDGE_PREFIX)) return normalized;
+  return normalized.slice(KNOWLEDGE_PREFIX.length);
+}
+
+function stripMarkdownExtension(wikiPath: string): string {
+  return wikiPath.toLowerCase().endsWith(MARKDOWN_EXTENSION)
+    ? wikiPath.slice(0, -MARKDOWN_EXTENSION.length)
+    : wikiPath;
+}
+
+function toWikiPathCompareKey(wikiPath: string): string {
+  return stripMarkdownExtension(wikiPath).toLowerCase();
+}
+
+function splitWikiPathPrefix(rawPath: string): { pathWithoutPrefix: string; hadKnowledgePrefix: boolean } {
+  let normalized = rawPath.trim().replace(/^\/+/, '').replace(/^\.\//, '');
+  const hadKnowledgePrefix = /^knowledge\//i.test(normalized);
+  if (hadKnowledgePrefix) {
+    normalized = normalized.slice(KNOWLEDGE_PREFIX.length);
+  }
+  return { pathWithoutPrefix: normalized, hadKnowledgePrefix };
+}
+
+function rewriteWikiLinksInMarkdown(markdown: string, fromWikiPath: string, toWikiPath: string): string {
+  const fromCompareKey = toWikiPathCompareKey(fromWikiPath);
+  const toWikiPathWithoutExtension = stripMarkdownExtension(toWikiPath);
+
+  return markdown.replace(WIKI_LINK_REGEX, (fullMatch, innerRaw: string) => {
+    const pipeIndex = innerRaw.indexOf('|');
+    const pathAndAnchor = pipeIndex >= 0 ? innerRaw.slice(0, pipeIndex) : innerRaw;
+    const aliasSuffix = pipeIndex >= 0 ? innerRaw.slice(pipeIndex) : '';
+
+    const hashIndex = pathAndAnchor.indexOf('#');
+    const pathPart = hashIndex >= 0 ? pathAndAnchor.slice(0, hashIndex) : pathAndAnchor;
+    const anchorSuffix = hashIndex >= 0 ? pathAndAnchor.slice(hashIndex) : '';
+
+    const leadingWhitespace = pathPart.match(/^\s*/)?.[0] ?? '';
+    const trailingWhitespace = pathPart.match(/\s*$/)?.[0] ?? '';
+    const rawPath = pathPart.trim();
+    if (!rawPath) return fullMatch;
+
+    const { pathWithoutPrefix, hadKnowledgePrefix } = splitWikiPathPrefix(rawPath);
+    if (!pathWithoutPrefix) return fullMatch;
+
+    if (toWikiPathCompareKey(pathWithoutPrefix) !== fromCompareKey) {
+      return fullMatch;
+    }
+
+    const preserveMarkdownExtension = rawPath.toLowerCase().endsWith(MARKDOWN_EXTENSION);
+    const rewrittenPath = preserveMarkdownExtension ? toWikiPath : toWikiPathWithoutExtension;
+    const finalPath = hadKnowledgePrefix ? `${KNOWLEDGE_PREFIX}${rewrittenPath}` : rewrittenPath;
+
+    return `[[${leadingWhitespace}${finalPath}${trailingWhitespace}${anchorSuffix}${aliasSuffix}]]`;
+  });
+}
+
+async function collectKnowledgeMarkdownFiles(workspaceRoot: string): Promise<string[]> {
+  const knowledgeRoot = path.join(workspaceRoot, 'knowledge');
+  try {
+    const stat = await fs.lstat(knowledgeRoot);
+    if (!stat.isDirectory()) return [];
+  } catch {
+    return [];
+  }
+
+  const markdownFiles: string[] = [];
+  const pendingDirectories: string[] = [knowledgeRoot];
+
+  while (pendingDirectories.length > 0) {
+    const currentDirectory = pendingDirectories.pop();
+    if (!currentDirectory) continue;
+
+    const entries = await fs.readdir(currentDirectory, { withFileTypes: true });
+    for (const entry of entries) {
+      if (entry.name.startsWith('.')) continue;
+
+      const absolutePath = path.join(currentDirectory, entry.name);
+      if (entry.isDirectory()) {
+        pendingDirectories.push(absolutePath);
+        continue;
+      }
+      if (!entry.isFile()) continue;
+      if (!entry.name.toLowerCase().endsWith(MARKDOWN_EXTENSION)) continue;
+
+      const relativePath = normalizeRelPath(path.relative(workspaceRoot, absolutePath));
+      markdownFiles.push(relativePath);
+    }
+  }
+
+  return markdownFiles;
+}
+
+export async function rewriteWikiLinksForRenamedKnowledgeFile(
+  workspaceRoot: string,
+  fromRelPath: string,
+  toRelPath: string
+): Promise<number> {
+  const normalizedFrom = normalizeRelPath(fromRelPath);
+  const normalizedTo = normalizeRelPath(toRelPath);
+
+  if (!isKnowledgeMarkdownPath(normalizedFrom) || !isKnowledgeMarkdownPath(normalizedTo)) {
+    return 0;
+  }
+
+  const fromWikiPath = stripKnowledgePrefix(normalizedFrom);
+  const toWikiPath = stripKnowledgePrefix(normalizedTo);
+  if (toWikiPathCompareKey(fromWikiPath) === toWikiPathCompareKey(toWikiPath)) return 0;
+
+  const markdownFiles = await collectKnowledgeMarkdownFiles(workspaceRoot);
+  let rewrittenFiles = 0;
+
+  for (const relativePath of markdownFiles) {
+    const absolutePath = path.join(workspaceRoot, ...relativePath.split('/'));
+    try {
+      const markdown = await fs.readFile(absolutePath, 'utf8');
+      if (!markdown.includes('[[')) continue;
+
+      const rewritten = rewriteWikiLinksInMarkdown(markdown, fromWikiPath, toWikiPath);
+      if (rewritten === markdown) continue;
+
+      await fs.writeFile(absolutePath, rewritten, 'utf8');
+      rewrittenFiles += 1;
+    } catch (error) {
+      console.error('Failed to rewrite wiki links in file:', relativePath, error);
+    }
+  }
+
+  return rewrittenFiles;
+}
diff --git a/apps/x/packages/core/src/workspace/workspace.ts b/apps/x/packages/core/src/workspace/workspace.ts
index 59910bdb..cd872f39 100644
--- a/apps/x/packages/core/src/workspace/workspace.ts
+++ b/apps/x/packages/core/src/workspace/workspace.ts
@@ -5,6 +5,7 @@ import { workspace } from '@x/shared';
 import { z } from 'zod';
 import { RemoveOptions, WriteFileOptions, WriteFileResult } from 'packages/shared/dist/workspace.js';
 import { WorkDir } from '../config/config.js';
+import { rewriteWikiLinksForRenamedKnowledgeFile } from './wiki-link-rewrite.js';
 
 // ============================================================================
 // Path Utilities
@@ -58,6 +59,11 @@ export function absToRelPosix(absPath: string): string | null {
   return relPath.split(path.sep).join('/');
 }
 
+function isKnowledgeMarkdownRelPath(relPath: string): boolean {
+  const normalized = relPath.replace(/\\/g, '/').replace(/^\/+/, '').toLowerCase();
+  return normalized.startsWith('knowledge/') && normalized.endsWith('.md');
+}
+
 // ============================================================================
 // File System Utilities
 // ============================================================================
@@ -286,6 +292,7 @@ export async function rename(
 
   // Check if source exists
   await fs.access(fromPath);
+  const fromStats = await fs.lstat(fromPath);
 
   // Check if destination exists (only if overwrite is false)
   if (!overwrite) {
@@ -309,6 +316,19 @@ export async function rename(
   await fs.mkdir(path.dirname(toPath), { recursive: true });
 
   await fs.rename(fromPath, toPath);
+
+  if (
+    fromStats.isFile()
+    && isKnowledgeMarkdownRelPath(from)
+    && isKnowledgeMarkdownRelPath(to)
+  ) {
+    try {
+      await rewriteWikiLinksForRenamedKnowledgeFile(WorkDir, from, to);
+    } catch (error) {
+      console.error('Failed to rewrite wiki backlinks after file rename:', error);
+    }
+  }
+
   return { ok: true as const };
 }
 
@@ -383,4 +403,4 @@ export async function remove(
   }
 
   return { ok: true as const };
-}
\ No newline at end of file
+}