diff --git a/.github/workflows/README.md b/.github/workflows/README.md
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+# GitHub Actions Workflows
+
+This directory contains automated workflows for the master-plan repository.
+
+## Sync Roadmap Workflow
+
+**File:** `sync-roadmap.yml`
+
+### Purpose
+
+Automatically synchronizes the roadmap section in `README.md` with the actual state of GitHub issues across the deep-assistant organization.
+
+### How It Works
+
+1. **Triggers:**
+   - Runs daily at 00:00 UTC (scheduled)
+   - Can be manually triggered from the Actions tab
+   - Automatically runs when issues are opened, closed, reopened, edited, or deleted
+
+2. **Process:**
+   - Scans `README.md` for issue references in the roadmap section
+   - Fetches current state of each issue from GitHub API
+   - Updates checkboxes: `[ ]` for open issues, `[x]` for closed issues
+   - Commits changes if any updates are detected
+
+3. **Script:** `sync-roadmap.js`
+   - Node.js script that performs the actual synchronization
+   - Parses markdown to find issue links
+   - Uses GitHub API to check issue states
+   - Preserves existing roadmap structure and formatting
+
+### Manual Execution
+
+You can manually trigger this workflow from the GitHub Actions tab:
+
+1. Go to the repository's Actions tab
+2. Select "Sync Master Plan Roadmap" workflow
+3. Click "Run workflow" button
+
+### Configuration
+
+The workflow requires:
+- `contents: write` permission to commit changes
+- `issues: read` permission to fetch issue states
+- `GITHUB_TOKEN` secret (automatically provided by GitHub Actions)
+
+### Maintenance
+
+To update the roadmap structure or add new issues:
+1. Manually edit the `README.md` file
+2. Add issue references in the format: `[#123](https://github.com/deep-assistant/repo-name/issues/123)`
+3. The workflow will automatically sync checkbox states on the next run
diff --git a/.github/workflows/sync-roadmap.js b/.github/workflows/sync-roadmap.js
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+#!/usr/bin/env node
+
+/**
+ * Sync Master Plan Roadmap Script
+ *
+ * This script automatically updates the roadmap section in README.md
+ * by synchronizing checkbox states with actual GitHub issue states.
+ *
+ * Features:
+ * - Updates checkboxes: [ ] for open issues, [x] for closed issues
+ * - Preserves the existing roadmap structure and formatting
+ * - Works with issues from multiple repositories
+ */
+
+const fs = require('fs');
+const https = require('https');
+
+const GITHUB_TOKEN = process.env.GITHUB_TOKEN;
+const ORG_NAME = 'deep-assistant';
+
+/**
+ * Fetch data from GitHub API
+ */
+function fetchGitHub(path) {
+  return new Promise((resolve, reject) => {
+    const options = {
+      hostname: 'api.github.com',
+      path: path,
+      method: 'GET',
+      headers: {
+        'User-Agent': 'Master-Plan-Sync-Bot',
+        'Authorization': `token ${GITHUB_TOKEN}`,
+        'Accept': 'application/vnd.github.v3+json'
+      }
+    };
+
+    https.get(options, (res) => {
+      let data = '';
+      res.on('data', chunk => data += chunk);
+      res.on('end', () => {
+        if (res.statusCode === 200) {
+          resolve(JSON.parse(data));
+        } else {
+          reject(new Error(`GitHub API error: ${res.statusCode} - ${data}`));
+        }
+      });
+    }).on('error', reject);
+  });
+}
+
+/**
+ * Get issue state (open/closed) from GitHub
+ */
+async function getIssueState(repo, issueNumber) {
+  try {
+    const issue = await fetchGitHub(`/repos/${ORG_NAME}/${repo}/issues/${issueNumber}`);
+    return issue.state === 'closed' ? 'closed' : 'open';
+  } catch (error) {
+    console.error(`Error fetching issue ${repo}#${issueNumber}:`, error.message);
+    return 'open'; // Default to open if we can't fetch
+  }
+}
+
+/**
+ * Parse issue reference from markdown link
+ * Returns: { repo: string, number: number } or null
+ */
+function parseIssueLink(line) {
+  // Match patterns like:
+  // - **Link:** [#46](https://github.com/deep-assistant/telegram-bot/issues/46)
+  // - **Link:** [#10](https://github.com/deep-assistant/master-plan/issues/10)
+  const linkPattern = /\[#(\d+)\]\(https:\/\/github\.com\/deep-assistant\/([^\/]+)\/issues\/\d+\)/;
+  const match = line.match(linkPattern);
+
+  if (match) {
+    return {
+      repo: match[2],
+      number: parseInt(match[1], 10)
+    };
+  }
+
+  return null;
+}
+
+/**
+ * Update checkbox state in a task line
+ */
+function updateCheckbox(line, isClosed) {
+  const checkbox = isClosed ? '[x]' : '[ ]';
+  // Replace existing checkbox at the start of the line
+  return line.replace(/^(\s*)-\s*\[([ x])\]/, `$1- ${checkbox}`);
+}
+
+/**
+ * Main sync function
+ */
+async function syncRoadmap() {
+  console.log('🚀 Starting roadmap sync...');
+
+  // Read README.md
+  const readmePath = 'README.md';
+  let content = fs.readFileSync(readmePath, 'utf8');
+  const lines = content.split('\n');
+
+  let updated = false;
+  let currentIssue = null;
+
+  // Process each line
+  for (let i = 0; i < lines.length; i++) {
+    const line = lines[i];
+
+    // Check if this line contains an issue link
+    const issueRef = parseIssueLink(line);
+    if (issueRef) {
+      currentIssue = issueRef;
+      console.log(`📋 Found issue reference: ${issueRef.repo}#${issueRef.number}`);
+    }
+
+    // Check if this is a task line with a checkbox and we have a current issue
+    if (currentIssue && line.match(/^\s*-\s*\[([ x])\]/)) {
+      // Get the actual state from GitHub
+      const state = await getIssueState(currentIssue.repo, currentIssue.number);
+      const isClosed = state === 'closed';
+
+      // Update the checkbox if needed
+      const newLine = updateCheckbox(line, isClosed);
+      if (newLine !== line) {
+        console.log(`✅ Updating ${currentIssue.repo}#${currentIssue.number}: ${state}`);
+        lines[i] = newLine;
+        updated = true;
+      }
+
+      // Reset current issue after processing its task line
+      currentIssue = null;
+    }
+  }
+
+  // Write back if updated
+  if (updated) {
+    fs.writeFileSync(readmePath, lines.join('\n'), 'utf8');
+    console.log('✨ Roadmap successfully updated!');
+  } else {
+    console.log('✓ Roadmap is already up to date!');
+  }
+
+  return updated;
+}
+
+// Run the sync
+syncRoadmap().catch(error => {
+  console.error('❌ Error syncing roadmap:', error);
+  process.exit(1);
+});
diff --git a/.github/workflows/sync-roadmap.yml b/.github/workflows/sync-roadmap.yml
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+++ b/.github/workflows/sync-roadmap.yml
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+name: Sync Master Plan Roadmap
+
+on:
+  schedule:
+    # Run daily at 00:00 UTC
+    - cron: '0 0 * * *'
+  workflow_dispatch: # Allow manual trigger
+  issues:
+    types: [opened, closed, reopened, edited, deleted]
+
+permissions:
+  contents: write
+  issues: read
+
+jobs:
+  sync-roadmap:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@v4
+        with:
+          token: ${{ secrets.GITHUB_TOKEN }}
+          fetch-depth: 0
+
+      - name: Setup Node.js
+        uses: actions/setup-node@v4
+        with:
+          node-version: '20'
+
+      - name: Sync roadmap with issues
+        env:
+          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          node .github/workflows/sync-roadmap.js
+
+      - name: Check for changes
+        id: git-check
+        run: |
+          git diff --exit-code README.md || echo "changed=true" >> $GITHUB_OUTPUT
+
+      - name: Commit and push if changed
+        if: steps.git-check.outputs.changed == 'true'
+        run: |
+          git config user.name "github-actions[bot]"
+          git config user.email "github-actions[bot]@users.noreply.github.com"
+          git add README.md
+          git commit -m "chore: sync roadmap with GitHub issues
+
+          🤖 Automatically synchronized the roadmap section in README.md with the current state of GitHub issues across the organization.
+
+          🤖 Generated with GitHub Actions"
+          git push