rails-upgrade

Analyze Rails application upgrade path. Checks current version, finds latest release, fetches upgrade notes and diffs, then performs selective upgrade preserving local customizations.

SKILL.md

---
name: rails-upgrade
description: Analyze Rails application upgrade path. Checks current version, finds latest release, fetches upgrade notes and diffs, then performs selective upgrade preserving local customizations.
---

# Rails Upgrade Analyzer

Analyze the current Rails application and provide a comprehensive upgrade assessment with selective file merging.

## Step 1: Verify Rails Application

Check that we're in a Rails application by looking for these files:
- `Gemfile` (must exist and contain 'rails')
- `config/application.rb` (Rails application config)
- `config/environment.rb` (Rails environment)

If any of these are missing or don't indicate a Rails app, stop and inform the user this doesn't appear to be a Rails application.

## Step 2: Get Current Rails Version

Extract the current Rails version from:
1. First, check `Gemfile.lock` for the exact installed version (look for `rails (x.y.z)`)
2. If not found, check `Gemfile` for the version constraint

Report the exact current version (e.g., `7.1.3`).

## Step 3: Find Latest Rails Version

Use the GitHub CLI to fetch the latest Rails release:

```bash
gh api repos/rails/rails/releases/latest --jq '.tag_name'
```

This returns the latest stable version tag (e.g., `v8.0.1`). Strip the 'v' prefix for comparison.

Also check recent tags to understand the release landscape:

```bash
gh api repos/rails/rails/tags --jq '.[0:10] | .[].name'
```

## Step 4: Determine Upgrade Type

Compare current and latest versions to classify the upgrade:

- **Patch upgrade**: Same major.minor, different patch (e.g., 7.1.3 → 7.1.5)
- **Minor upgrade**: Same major, different minor (e.g., 7.1.3 → 7.2.0)
- **Major upgrade**: Different major version (e.g., 7.1.3 → 8.0.0)

## Step 5: Fetch Upgrade Guide

Use WebFetch to get the official Rails upgrade guide:

URL: `https://guides.rubyonrails.org/upgrading_ruby_on_rails.html`

Look for sections relevant to the version jump. The guide is organized by target version with sections like:
- "Upgrading from Rails X.Y to Rails X.Z"
- Breaking changes
- Deprecation warnings
- Configuration changes
- Required migrations

Extract and summarize the relevant sections for the user's specific upgrade path.

## Step 6: Fetch Rails Diff

Use WebFetch to get the diff between versions from railsdiff.org:

URL: `https://railsdiff.org/{current_version}/{target_version}`

For example: `https://railsdiff.org/7.1.3/8.0.0`

This shows:
- Changes to default configuration files
- New files that need to be added
- Modified initializers
- Updated dependencies
- Changes to bin/ scripts

Summarize the key file changes.

## Step 7: Check JavaScript Dependencies

Rails applications often include JavaScript packages that should be updated alongside Rails. Check for and report on these dependencies.

### 7.1: Identify JS Package Manager

Check which package manager the app uses:

```bash
# Check for package.json (npm/yarn)
ls package.json 2>/dev/null

# Check for importmap (Rails 7+)
ls config/importmap.rb 2>/dev/null
```

### 7.2: Check Rails-Related JS Packages

If `package.json` exists, check for these Rails-related packages:

```bash
# Extract current versions of Rails-related packages
cat package.json | grep -E '"@hotwired/|"@rails/|"stimulus"|"turbo-rails"' || echo "No Rails JS packages found"
```

**Key packages to check:**

| Package | Purpose | Version Alignment |
|---------|---------|-------------------|
| `@hotwired/turbo-rails` | Turbo Drive/Frames/Streams | Should match Rails version era |
| `@hotwired/stimulus` | Stimulus JS framework | Generally stable across Rails versions |
| `@rails/actioncable` | WebSocket support | Should match Rails version |
| `@rails/activestorage` | Direct uploads | Should match Rails version |
| `@rails/actiontext` | Rich text editing | Should match Rails version |
| `@rails/request.js` | Rails UJS replacement | Should match Rails version era |

### 7.3: Check for Updates

For npm/yarn projects, check for available updates:

```bash
# Using npm
npm outdated @hotwired/turbo-rails @hotwired/stimulus @rails/actioncable @rails/activestorage 2>/dev/null

# Or check latest versions directly
npm view @hotwired/turbo-rails version 2>/dev/null
npm view @rails/actioncable version 2>/dev/null
```

### 7.4: Check Importmap Pins (if applicable)

If the app uses importmap-rails, check `config/importmap.rb` for pinned versions:

```bash
cat config/importmap.rb | grep -E 'pin.*turbo|pin.*stimulus|pin.*@rails' || echo "No importmap pins found"
```

To update importmap pins:
```bash
bin/importmap pin @hotwired/turbo-rails
bin/importmap pin @hotwired/stimulus
```

### 7.5: JS Dependency Summary

Include in the upgrade summary:

```
### JavaScript Dependencies

**Package Manager**: [npm/yarn/importmap/none]

| Package | Current | Latest | Action |
|---------|---------|--------|--------|
| @hotwired/turbo-rails | 8.0.4 | 8.0.12 | Update recommended |
| @rails/actioncable | 7.1.0 | 8.0.0 | Update with Rails |
| ... | ... | ... | ... |

**Recommended JS Updates:**
- Run `npm update @hotwired/turbo-rails` (or yarn equivalent)
- Run `npm update @rails/actioncable @rails/activestorage` to match Rails version
```

---

## Step 8: Generate Upgrade Summary

Provide a comprehensive summary including all findings from Steps 1-7:

### Version Information
- Current version: X.Y.Z
- Latest version: A.B.C
- Upgrade type: [Patch/Minor/Major]

### Upgrade Complexity Assessment

Rate the upgrade as **Small**, **Medium**, or **Large** based on:

| Factor | Small | Medium | Large |
|--------|-------|--------|-------|
| Version jump | Patch only | Minor version | Major version |
| Breaking changes | None | Few, well-documented | Many, significant |
| Config changes | Minimal | Moderate | Extensive |
| Deprecations | None active | Some to address | Many requiring refactoring |
| Dependencies | Compatible | Some updates needed | Major dependency updates |

### Key Changes to Address

List the most important changes the user needs to handle:
1. Configuration file updates
2. Deprecated methods/features to update
3. New required dependencies
4. Database migrations needed
5. Breaking API changes

### Recommended Upgrade Steps

1. Update test suite and ensure passing
2. Review deprecation warnings in current version
3. Update Gemfile with new Rails version
4. Run `bundle update rails`
5. Update JavaScript dependencies (see JS Dependencies section)
6. **DO NOT run `rails app:update` directly** - use the selective merge process below
7. Run database migrations
8. Run test suite
9. Review and update deprecated code

### Resources

- Rails Upgrade Guide: https://guides.rubyonrails.org/upgrading_ruby_on_rails.html
- Rails Diff: https://railsdiff.org/{current}/{target}
- Release Notes: https://github.com/rails/rails/releases/tag/v{target}

---

## Step 9: Selective File Update (replaces `rails app:update`)

**IMPORTANT:** Do NOT run `rails app:update` as it overwrites files without considering local customizations. Instead, follow this selective merge process:

### 9.1: Detect Local Customizations

Before any upgrade, identify files with local customizations:

```bash
# Check for uncommitted changes
git status

# List config files that differ from a fresh Rails app
# These are the files we need to be careful with
git diff HEAD --name-only -- config/ bin/ public/
```

Create a mental list of files in these categories:
- **Custom config files**: Files with project-specific settings (i18n, mailer, etc.)
- **Modified bin scripts**: Scripts with custom behavior (bin/dev with foreman, etc.)
- **Standard files**: Files that haven't been customized

### 9.2: Analyze Required Changes from Railsdiff

Based on the railsdiff output from Step 6, categorize each changed file:

| Category | Action | Example |
|----------|--------|---------|
| **New files** | Create directly | `config/initializers/new_framework_defaults_X_Y.rb` |
| **Unchanged locally** | Safe to overwrite | `public/404.html` (if not customized) |
| **Customized locally** | Manual merge needed | `config/application.rb`, `bin/dev` |
| **Comment-only changes** | Usually skip | Minor comment updates in config files |

### 9.3: Create Upgrade Plan

Present the user with a clear upgrade plan:

```
## Upgrade Plan: Rails X.Y.Z → A.B.C

### New Files (will be created):
- config/initializers/new_framework_defaults_A_B.rb
- bin/ci (new CI script)

### Safe to Update (no local customizations):
- public/400.html
- public/404.html
- public/500.html

### Needs Manual Merge (local customizations detected):
- config/application.rb
  └─ Local: i18n configuration
  └─ Rails: [describe new Rails changes if any]

- config/environments/development.rb
  └─ Local: letter_opener mailer config
  └─ Rails: [describe new Rails changes]

- bin/dev
  └─ Local: foreman + Procfile.dev setup
  └─ Rails: changed to simple ruby script

### Skip (comment-only or irrelevant changes):
- config/puma.rb (only comment changes)
```

### 9.4: Execute Upgrade Plan

After user confirms the plan:

#### For New Files:
Create them directly using the content from railsdiff or by extracting from a fresh Rails app:

```bash
# Generate a temporary fresh Rails app to extract new files
cd /tmp && rails new rails_template --skip-git --skip-bundle
# Then copy needed files
```

Or use the Rails generator for specific files:
```bash
bin/rails app:update:configs  # Only updates config files, still interactive
```

#### For Safe Updates:
Overwrite these files as they have no local customizations.

#### For Manual Merges:
For each file needing merge, show the user:

1. **Current local version** (their customizations)
2. **New Rails default** (from railsdiff)
3. **Suggested merged version** that:
   - Keeps all local customizations
   - Adds only essential new Rails functionality
   - Removes deprecated settings

Example merge for `config/application.rb`:
```ruby
# KEEP local customizations:
config.i18n.available_locales = [:de, :en]
config.i18n.default_locale = :de
config.i18n.fallbacks = [:en]

# ADD new Rails 8.1 settings if needed:
# (usually none required - new defaults come via new_framework_defaults file)
```

### 9.5: Handle Active Storage Migrations

After file updates, run any new migrations:

```bash
bin/rails db:migrate
```

Check for new migrations that were added:
```bash
ls -la db/migrate/ | tail -10
```

### 9.6: Verify Upgrade

After completing the merge:

1. Start the Rails server and check for errors:
   ```bash
   bin/dev  # or bin/rails server
   ```

2. Check the Rails console:
   ```bash
   bin/rails console
   ```

3. Run the test suite:
   ```bash
   bin/rails test
   ```

4. Review deprecation warnings in logs

---

## Step 10: Finalize Framework Defaults

After verifying the app works:

1. Review `config/initializers/new_framework_defaults_X_Y.rb`
2. Enable each new default one by one, testing after each
3. Once all defaults are enabled and tested, update `config/application.rb`:
   ```ruby
   config.load_defaults X.Y  # Update to new version
   ```
4. Delete the `new_framework_defaults_X_Y.rb` file

---

## Error Handling

- If `gh` CLI is not authenticated, instruct the user to run `gh auth login`
- If railsdiff.org doesn't have the exact versions, try with major.minor.0 versions
- If the app is already on the latest version, congratulate the user and note any upcoming releases
- If local customizations would be lost, ALWAYS stop and show the user what would be overwritten before proceeding

## Key Principles

1. **Never overwrite without checking** - Always check for local customizations first
2. **Preserve user intent** - Local customizations exist for a reason
3. **Minimal changes** - Only add what's necessary for the new Rails version
4. **Transparency** - Show the user exactly what will change before doing it
5. **Reversibility** - User should be able to `git checkout` to restore if needed