diff --git a/release/README.md b/release/README.md
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+# Cody Release Captain CLI
+
+This directory contains automation scripts for Cody release captains.
+
+## release-captain.sh
+
+An interactive CLI workflow that follows the [Release Captain Playbook](https://www.notion.so/sourcegraph/Release-Captain-Playbook-13ba8e112658800d877ce7b4e8413935) and guides release captains through the complete Cody release process.
+
+### Prerequisites
+
+- Git CLI
+- GitHub CLI (`gh`)
+- `jq` for JSON processing
+- Write access to the Cody repository
+- JetBrains account with admin access (for JetBrains releases)
+- `GITHUB_TOKEN` environment variable set
+
+### Usage
+
+```bash
+./release/release-captain.sh
+```
+
+The script provides an interactive menu with these options:
+
+1. **Day 1: Create release branch** - Creates release branch, backport labels, and prerelease builds
+2. **Day 2-6: Stabilize release branch** - Helps create new prerelease builds after backports
+3. **Day 7: Ship stable release** - Guides through stable release process for VSCode, JetBrains, and Agent
+4. **Emergency patch release** - Creates emergency patch releases when needed
+5. **Check prerequisites** - Validates required tools and permissions
+
+### Environment Variables
+
+- `MILESTONE` - The milestone number (e.g., 66). If not set, the script will prompt for it.
+
+### Example
+
+```bash
+# Set milestone and run
+export MILESTONE=66
+./release/release-captain.sh
+```
+
+### Manual Steps Still Required
+
+The script automates most tasks but still requires manual steps for:
+
+- Reviewing and organizing generated changelogs
+- JetBrains Marketplace management (unhiding releases, writing release notes)
+- Community notifications and QA coordination
+- Monitoring workflow statuses
+- Final release verification
+
+### Copy-Paste Templates
+
+#### 1. Notify #team-cody-core (Day 1)
+
+```text
+Hey team! 👋 I'm the release captain for milestone {MILESTONE}.
+
+We've branched from commit {COMMIT_HASH} for M{MILESTONE}, which will produce:
+- VSCode v1.{MILESTONE}.0 
+- JetBrains v7.{MILESTONE}.0
+
+**For ship-blocking fixes**: Add the `backport M{MILESTONE}` label to your PRs.
+
+**Prerelease versions for dogfooding**:
+- VSCode Insiders: v1.{MILESTONE_MINUS_ONE}.{BUILD} 
+- JetBrains Nightly: v7.{MILESTONE_MINUS_ONE}.0-nightly
+
+Please update your extensions and help us test! 🧪
+
+Next opportunity to reach stable: land code by {NEXT_BRANCH_DATE}, ships {NEXT_RELEASE_DATE}.
+```
+
+#### 2. Request QA (#ext-qa-fibilabs-sourcegraph)
+
+```text
+Hi QA team! 👋
+
+New prerelease builds are ready for testing:
+- **JetBrains**: v7.{MILESTONE_MINUS_ONE}.0-nightly
+- **VSCode Insiders**: v1.{MILESTONE_MINUS_ONE}.{BUILD}
+
+Please QA these versions and report any issues. Thanks! 🙏
+```
+
+#### 3. Introduce to Community Support (#discuss-community-support)
+
+```text
+Hi community support team! 👋
+
+I'm the release captain for Cody milestone {MILESTONE}. 
+
+**Current prerelease versions**:
+- VSCode Insiders: v1.{MILESTONE_MINUS_ONE}.{BUILD}
+- JetBrains Nightly: v7.{MILESTONE_MINUS_ONE}.0-nightly
+
+Please flag any issues you see with these versions - especially helpful since prerelease has fewer users. Thanks for the partnership! 🤝
+```
+
+### Related Documentation
+
+- Main release guide: See the comprehensive release captain guide in the codebase
+- [Agent release guide](../agent/README.md#updating-the-polly-http-recordings)
+- [Cody Web publishing guide](../web/publish.md)
diff --git a/release/release-captain.sh b/release/release-captain.sh
new file mode 100755
index 000000000000..35f57b416777
--- /dev/null
+++ b/release/release-captain.sh
@@ -0,0 +1,366 @@
+#!/bin/bash
+
+# Cody Release Captain CLI Workflow
+# This script guides release captains through the Cody release process
+
+set -e
+
+# Colors for output
+RED='\033[0;31m'
+GREEN='\033[0;32m'
+YELLOW='\033[1;33m'
+BLUE='\033[0;34m'
+NC='\033[0m' # No Color
+
+# Helper function to print colored output
+print_step() {
+    echo -e "${BLUE}📋 $1${NC}"
+}
+
+print_success() {
+    echo -e "${GREEN}✅ $1${NC}"
+}
+
+print_warning() {
+    echo -e "${YELLOW}⚠️  $1${NC}"
+}
+
+print_error() {
+    echo -e "${RED}❌ $1${NC}"
+}
+
+# Helper function to confirm before proceeding
+confirm() {
+    read -p "$(echo -e "${YELLOW}❓ $1 (y/N): ${NC}")" -n 1 -r
+    echo
+    if [[ ! $REPLY =~ ^[Yy]$ ]]; then
+        exit 1
+    fi
+}
+
+# Check prerequisites
+check_prerequisites() {
+    print_step "Checking prerequisites..."
+    
+    # Check if git is available
+    if ! command -v git &> /dev/null; then
+        print_error "git is required but not installed"
+        exit 1
+    fi
+    
+    # Check if gh CLI is available
+    if ! command -v gh &> /dev/null; then
+        print_error "GitHub CLI (gh) is required but not installed"
+        exit 1
+    fi
+    
+    # Check if jq is available
+    if ! command -v jq &> /dev/null; then
+        print_error "jq is required but not installed"
+        exit 1
+    fi
+    
+    # Check if we're in the right repo
+    if [[ ! -f "package.json" ]] || ! grep -q "@sourcegraph/cody" package.json; then
+        print_error "This script must be run from the root of the Cody repository"
+        exit 1
+    fi
+    
+    print_success "Prerequisites check passed"
+}
+
+# Get milestone from user
+get_milestone() {
+    if [[ -z "$MILESTONE" ]]; then
+        read -p "$(echo -e "${BLUE}Enter milestone number (e.g., 66): ${NC}")" MILESTONE
+        if [[ ! "$MILESTONE" =~ ^[0-9]+$ ]]; then
+            print_error "Milestone must be a number"
+            exit 1
+        fi
+    fi
+    
+    export MILESTONE
+    export MILESTONE_MINUS_ONE=$((MILESTONE - 1))
+    export MILESTONE_MINUS_TWO=$((MILESTONE - 2))
+    
+    print_success "Working on milestone $MILESTONE"
+}
+
+# Day 1: Create release branch
+day1_create_branch() {
+    print_step "DAY 1: Creating release branch for milestone $MILESTONE"
+    
+    confirm "Have you confirmed the branch date and version from the release calendar?"
+    confirm "Has the previous release captain produced the stable VSCode release?"
+    
+    print_step "Fetching latest main and creating release branch..."
+    git fetch origin main
+    
+    print_step "Latest commits on main:"
+    git log --oneline FETCH_HEAD -5
+    
+    confirm "Proceed with creating release branch from the latest main commit?"
+    
+    # Create release branch
+    git push origin FETCH_HEAD:refs/heads/M$MILESTONE
+    print_success "Created release branch M$MILESTONE"
+    
+    # Create backport label
+    gh label create "backport M$MILESTONE" --color "0366d6" --description "Backport to milestone $MILESTONE" || print_warning "Label may already exist"
+    print_success "Created backport label"
+    
+    # Create prerelease builds
+    print_step "Creating prerelease builds..."
+    
+    git tag jb-v7.${MILESTONE_MINUS_ONE}.0-nightly FETCH_HEAD
+    git push origin tag jb-v7.${MILESTONE_MINUS_ONE}.0-nightly
+    print_success "Created JetBrains nightly tag"
+    
+    gh workflow run release-vscode-prerelease --ref jb-v7.${MILESTONE_MINUS_ONE}.0-nightly
+    print_success "Triggered VSCode prerelease workflow"
+    
+    print_step "Monitor workflow status with:"
+    echo "  gh workflow view release-jetbrains-prerelease"
+    echo "  gh workflow view release-vscode-prerelease"
+    
+    print_step "Collect VSCode Insiders version with:"
+    echo "  git ls-remote | grep refs/tags/vscode-insiders-v1\\.$MILESTONE_MINUS_ONE\\."
+    
+    # Get the branch point commit for templates
+    BRANCH_COMMIT=$(git rev-parse --short FETCH_HEAD)
+    
+    print_warning "Next steps - Copy and paste these messages:"
+    
+    echo
+    echo "=== 1. Notify #team-cody-core ==="
+    echo "Hey team! 👋 I'm the release captain for milestone $MILESTONE."
+    echo
+    echo "We've branched from commit $BRANCH_COMMIT for M$MILESTONE, which will produce:"
+    echo "- VSCode v1.$MILESTONE.0"
+    echo "- JetBrains v7.$MILESTONE.0"
+    echo
+    echo "**For ship-blocking fixes**: Add the \`backport M$MILESTONE\` label to your PRs."
+    echo
+    echo "**Prerelease versions for dogfooding**:"
+    echo "- VSCode Insiders: v1.$MILESTONE_MINUS_ONE.{BUILD} (check: git ls-remote | grep vscode-insiders-v1\\\\.$MILESTONE_MINUS_ONE\\\\.)"
+    echo "- JetBrains Nightly: v7.$MILESTONE_MINUS_ONE.0-nightly"
+    echo
+    echo "Please update your extensions and help us test! 🧪"
+    echo
+    echo "Next opportunity to reach stable: land code by {NEXT_BRANCH_DATE}, ships {NEXT_RELEASE_DATE}."
+    echo
+    echo "=== 2. Request QA (#ext-qa-fibilabs-sourcegraph) ==="
+    echo "Hi QA team! 👋"
+    echo
+    echo "New prerelease builds are ready for testing:"
+    echo "- **JetBrains**: v7.$MILESTONE_MINUS_ONE.0-nightly"
+    echo "- **VSCode Insiders**: v1.$MILESTONE_MINUS_ONE.{BUILD} (get version from command above)"
+    echo
+    echo "Please QA these versions and report any issues. Thanks! 🙏"
+    echo
+    echo "=== 3. Introduce to Community Support (#discuss-community-support) ==="
+    echo "Hi community support team! 👋"
+    echo
+    echo "I'm the release captain for Cody milestone $MILESTONE."
+    echo
+    echo "**Current prerelease versions**:"
+    echo "- VSCode Insiders: v1.$MILESTONE_MINUS_ONE.{BUILD} (get version from command above)"
+    echo "- JetBrains Nightly: v7.$MILESTONE_MINUS_ONE.0-nightly"
+    echo
+    echo "Please flag any issues you see with these versions - especially helpful since prerelease has fewer users. Thanks for the partnership! 🤝"
+    echo
+}
+
+# Day 2-6: Stabilize release branch
+day2_6_stabilize() {
+    print_step "DAY 2-6: Stabilizing release branch M$MILESTONE"
+    
+    echo "Use this phase to:"
+    echo "1. Monitor issues from QA, GitHub, community support"
+    echo "2. Identify ship blockers"
+    echo "3. Backport fixes using 'backport M$MILESTONE' label"
+    echo "4. Cut new prerelease builds after backports"
+    
+    confirm "Create new prerelease builds now?"
+    
+    # Create new prerelease builds
+    git fetch origin M$MILESTONE
+    git checkout FETCH_HEAD
+    
+    # JetBrains
+    cd jetbrains
+    ./scripts/push-git-tag-for-next-release.sh --patch --nightly
+    cd ..
+    
+    # VSCode
+    gh workflow run release-vscode-prerelease --ref M$MILESTONE
+    
+    print_success "Created new prerelease builds"
+    print_step "Monitor workflows and notify QA team to test"
+}
+
+# Day 7: Ship stable release
+day7_ship_stable() {
+    print_step "DAY 7: Shipping stable release for milestone $MILESTONE"
+    
+    confirm "Have you done a final check for ship blockers?"
+    confirm "Are you ready to ship the stable release?"
+    
+    # Create release thread
+    print_warning "Create a thread in #team-cody-core for this release"
+    
+    # Ship VSCode to stable
+    print_step "Shipping VSCode to stable..."
+    
+    # Generate changelog
+    print_step "Running changelog generation workflow..."
+    confirm "Run the vscode-generate-changelog workflow on GitHub Actions?"
+    
+    echo "1. Go to: https://github.com/sourcegraph/cody/actions/workflows/generate-changelog.yml"
+    echo "2. Click 'Run workflow'"
+    echo "3. Select branch: M$MILESTONE"
+    echo "4. Enter version: 1.$MILESTONE.0"
+    echo "5. Review and merge the generated PR"
+    
+    confirm "Has the changelog PR been merged and backported to M$MILESTONE?"
+    
+    # Create VSCode stable release
+    git fetch origin M$MILESTONE
+    git checkout FETCH_HEAD
+    
+    VSCODE_VERSION=$(jq -r .version vscode/package.json)
+    git tag vscode-v$VSCODE_VERSION
+    git push origin tag vscode-v$VSCODE_VERSION
+    print_success "Created VSCode stable tag: vscode-v$VSCODE_VERSION"
+    
+    print_step "Monitor VSCode stable release workflow"
+    gh workflow view release-vscode-stable
+    
+    # Ship JetBrains to stable
+    print_step "Shipping JetBrains to stable..."
+    
+    confirm "Do you have JDK installed and GITHUB_TOKEN exported?"
+    
+    git ls-remote | grep 'refs/tags/jb-v.*\..*\..*-nightly' | tail -5
+    print_step "Latest nightly versions shown above"
+    
+    cd jetbrains
+    ./scripts/push-git-tag-for-next-release.sh --minor --dry-run
+    confirm "Does the dry-run look correct for v7.$MILESTONE.0?"
+    
+    ./scripts/push-git-tag-for-next-release.sh --minor
+    gh workflow run release-jetbrains-stable --ref jb-v7.$MILESTONE.0
+    cd ..
+    
+    print_success "Created JetBrains stable release"
+    
+    # Ship agent CLI
+    print_step "Shipping agent CLI..."
+    ./agent/scripts/minor-release.sh
+    print_success "Created agent CLI release"
+    
+    # Ship Cody Web
+    print_step "Ship Cody Web following: web/publish.md"
+    
+    print_warning "Manual steps remaining:"
+    echo "1. Update JetBrains Marketplace (unhide stable version)"
+    echo "2. Write JetBrains release notes on GitHub"
+    echo "3. Monitor JetBrains Marketplace approval (up to 48 hours)"
+    echo "4. Notify #team-cody-core when complete"
+}
+
+# Emergency patch release
+emergency_patch() {
+    print_step "EMERGENCY: Creating patch release"
+    
+    confirm "Are you sure you need an emergency patch release?"
+    
+    get_milestone
+    
+    print_step "Creating patch release for milestone $MILESTONE"
+    
+    # Determine patch version
+    CURRENT_PATCH=$(git ls-remote | grep "refs/tags/vscode-v1\\.$MILESTONE\\." | wc -l)
+    PATCH_VERSION=$((CURRENT_PATCH + 1))
+    
+    print_step "This will be patch version 1.$MILESTONE.$PATCH_VERSION"
+    confirm "Proceed with patch release?"
+    
+    # Update VSCode version
+    git checkout M$MILESTONE
+    git pull origin M$MILESTONE
+    
+    # Update package.json version
+    jq ".version = \"1.$MILESTONE.$PATCH_VERSION\"" vscode/package.json > tmp.json && mv tmp.json vscode/package.json
+    
+    git add vscode/package.json
+    git commit -m "chore: bump version to 1.$MILESTONE.$PATCH_VERSION for patch release"
+    git push origin M$MILESTONE
+    
+    # Create tags and release
+    git tag vscode-v1.$MILESTONE.$PATCH_VERSION
+    git push origin tag vscode-v1.$MILESTONE.$PATCH_VERSION
+    
+    # JetBrains patch
+    cd jetbrains
+    ./scripts/push-git-tag-for-next-release.sh --patch
+    cd ..
+    
+    print_success "Emergency patch release created"
+}
+
+# Main menu
+show_menu() {
+    echo
+    echo "=== Cody Release Captain CLI ==="
+    echo "1. Day 1: Create release branch"
+    echo "2. Day 2-6: Stabilize release branch (create new prerelease)"
+    echo "3. Day 7: Ship stable release"
+    echo "4. Emergency patch release"
+    echo "5. Check prerequisites"
+    echo "6. Exit"
+    echo
+}
+
+# Main script
+main() {
+    check_prerequisites
+    get_milestone
+    
+    while true; do
+        show_menu
+        read -p "$(echo -e "${BLUE}Select option (1-6): ${NC}")" choice
+        case $choice in
+            1)
+                day1_create_branch
+                ;;
+            2)
+                day2_6_stabilize
+                ;;
+            3)
+                day7_ship_stable
+                ;;
+            4)
+                emergency_patch
+                ;;
+            5)
+                check_prerequisites
+                ;;
+            6)
+                print_success "Goodbye! 🚀"
+                exit 0
+                ;;
+            *)
+                print_error "Invalid option. Please select 1-6."
+                ;;
+        esac
+        
+        echo
+        read -p "$(echo -e "${YELLOW}Press Enter to continue...${NC}")"
+    done
+}
+
+# Run if called directly
+if [[ "${BASH_SOURCE[0]}" == "${0}" ]]; then
+    main "$@"
+fi