diff --git a/.github/scripts/coderabbit_plan_trigger.js b/.github/scripts/coderabbit_plan_trigger.js
new file mode 100644
index 000000000..ca6eefd02
--- /dev/null
+++ b/.github/scripts/coderabbit_plan_trigger.js
@@ -0,0 +1,83 @@
+// Script to trigger CodeRabbit plan for intermediate and advanced issues
+
+const marker = '<!-- CodeRabbit Plan Trigger -->';
+
+async function triggerCodeRabbitPlan(github, owner, repo, issue, marker) {
+  const comment = `${marker} @coderabbitai plan`;
+
+  try {
+    await github.rest.issues.createComment({
+      owner,
+      repo,
+      issue_number: issue.number,
+      body: comment,
+    });
+    console.log(`Triggered CodeRabbit plan for issue #${issue.number}`);
+    return true;
+  } catch (commentErr) {
+    console.log(`Failed to trigger CodeRabbit plan for issue #${issue.number}:`, commentErr.message || commentErr);
+    return false;
+  }
+}
+
+function hasIntermediateOrAdvancedLabel(issue, label) {
+  // Check if issue has intermediate or advanced label (case-insensitive)
+  const hasIntermediateLabel = issue.labels?.some(l => l?.name?.toLowerCase() === 'intermediate');
+  const hasAdvancedLabel = issue.labels?.some(l => l?.name?.toLowerCase() === 'advanced');
+  
+  // Also check if newly added label is intermediate/advanced
+  const isNewLabelIntermediate = label?.name?.toLowerCase() === 'intermediate';
+  const isNewLabelAdvanced = label?.name?.toLowerCase() === 'advanced';
+  
+  return hasIntermediateLabel || hasAdvancedLabel || isNewLabelIntermediate || isNewLabelAdvanced;
+}
+
+async function hasExistingCodeRabbitPlan(github, owner, repo, issueNumber) {
+  // Check for existing CodeRabbit plan comment (limited to first 500 comments)
+  const comments = [];
+  const iterator = github.paginate.iterator(github.rest.issues.listComments, {
+    owner, repo, issue_number: issueNumber, per_page: 100
+  });
+  
+  let count = 0;
+  for await (const { data: page } of iterator) {
+    comments.push(...page);
+    count += page.length;
+    if (count >= 500) break; // Hard upper bound to prevent unbounded pagination
+  }
+  
+  return comments.some(c => c.body?.includes('@coderabbitai plan'));
+}
+
+function logSummary(owner, repo, issue) {
+  console.log('=== Summary ===');
+  console.log(`Repository: ${owner}/${repo}`);
+  console.log(`Issue Number: ${issue.number}`);
+  console.log(`Issue Title: ${issue.title || '(no title)'}`);
+  console.log(`Labels: ${issue.labels?.map(l => l.name).join(', ') || 'none'}`);
+}
+
+module.exports = async ({ github, context }) => {
+  try {
+    const { owner, repo } = context.repo;
+    const { issue, label } = context.payload;
+
+    // Validations
+    if (!issue?.number) return console.log('No issue in payload');
+    
+    if (!hasIntermediateOrAdvancedLabel(issue, label)) {
+      return console.log('Issue does not have intermediate or advanced label');
+    }
+
+    if (await hasExistingCodeRabbitPlan(github, owner, repo, issue.number)) {
+      return console.log(`CodeRabbit plan already triggered for #${issue.number}`);
+    }
+
+    // Post CodeRabbit plan trigger
+    await triggerCodeRabbitPlan(github, owner, repo, issue, marker);
+
+    logSummary(owner, repo, issue);
+  } catch (err) {
+    console.log('❌ Error:', err.message);
+  }
+};
diff --git a/.github/workflows/bot-coderabbit-plan-trigger.yml b/.github/workflows/bot-coderabbit-plan-trigger.yml
new file mode 100644
index 000000000..ac1bde8ed
--- /dev/null
+++ b/.github/workflows/bot-coderabbit-plan-trigger.yml
@@ -0,0 +1,43 @@
+# This workflow automatically triggers CodeRabbit's plan feature for intermediate and advanced issues.
+name: CodeRabbit Plan Trigger
+on:
+  issues:
+    types: [opened, labeled]
+
+permissions:
+  issues: write
+  contents: read
+
+jobs:
+  coderabbit_plan_trigger:
+    runs-on: ubuntu-latest
+    concurrency:
+      group: coderabbit-plan-${{ github.event.issue.number }}
+      cancel-in-progress: false
+    # Only run for issues labeled with 'intermediate' or 'advanced' (case-insensitive)
+    if: >
+      (github.event_name == 'issues' && (
+        contains(github.event.issue.labels.*.name, 'intermediate') || 
+        contains(github.event.issue.labels.*.name, 'advanced') ||
+        contains(github.event.issue.labels.*.name, 'Intermediate') || 
+        contains(github.event.issue.labels.*.name, 'Advanced') ||
+        (github.event.label && (github.event.label.name == 'intermediate' || github.event.label.name == 'advanced' || github.event.label.name == 'Intermediate' || github.event.label.name == 'Advanced'))
+      ))
+
+    steps:
+      - name: Harden the runner
+        uses: step-security/harden-runner@20cf305ff2072d973412fa9b1e3a4f227bda3c76 # v2.14.0
+        with:
+          egress-policy: audit
+
+      - name: Checkout repository
+        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 #v6.0.1
+
+      - name: Trigger CodeRabbit Plan
+        env: 
+          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        uses: actions/github-script@ed597411d8f924073f98dfc5c65a23a2325f34cd #v8.0.0
+        with:
+          script: |
+            const script = require('./.github/scripts/coderabbit_plan_trigger.js');      
+            await script({ github, context});
diff --git a/CHANGELOG.md b/CHANGELOG.md
index ba152e27d..d2c16f2d3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -22,6 +22,8 @@ This changelog is based on [Keep a Changelog](https://keepachangelog.com/en/1.1.
 - Added method chaining examples to the developer training guide (`docs/sdk_developers/training/coding_token_transactions.md`) (#1194)
 - Added documentation explaining how to pin GitHub Actions to specific commit SHAs (`docs/sdk_developers/how-to-pin-github-actions.md`)(#1211)
 - examples/mypy.ini for stricter type checking in example scripts
+- Formatted examples/tokens directory using black code formatter for consistent code style
+- Added `.github/workflows/bot-coderabbit-plan-trigger.yml` to automatically invoke CodeRabbit's plan feature on intermediate and advanced issues, providing implementation guidance to help contributors assess complexity and understand requirements. (#1289)
 - Added a GitHub Actions workflow that reminds contributors to link pull requests to issues.
 - Added `__str__` and `__repr__` methods to `AccountInfo` class for improved logging and debugging experience (#1098)
 - Added Good First Issue (GFI) management and frequency documentation to clarify maintainer expectations and SDK-level GFI governance.