diff --git a/.agent/scripts/tool-version-check.sh b/.agent/scripts/tool-version-check.sh
index 408971c26..5f15462c6 100755
--- a/.agent/scripts/tool-version-check.sh
+++ b/.agent/scripts/tool-version-check.sh
@@ -1,9 +1,14 @@
 #!/bin/bash
 # Tool Version Check
-# Checks versions of key MCP tools and flags outdated ones
+# Checks versions of key tools and flags outdated ones
 #
-# Usage: tool-version-check.sh [--update]
-#   --update  Automatically update outdated tools
+# Usage: 
+#   tool-version-check.sh              # Check all tools
+#   tool-version-check.sh --update     # Check and update outdated tools
+#   tool-version-check.sh --category npm  # Check only npm tools
+#   tool-version-check.sh --json       # Output as JSON
+#
+# Categories: npm, brew, pip, all (default)
 
 set -euo pipefail
 
@@ -12,86 +17,340 @@ readonly GREEN='\033[0;32m'
 readonly YELLOW='\033[1;33m'
 readonly RED='\033[0;31m'
 readonly BLUE='\033[0;34m'
+readonly CYAN='\033[0;36m'
+readonly BOLD='\033[1m'
 readonly NC='\033[0m'
 
-AUTO_UPDATE="${1:-}"
+# Parse arguments
+AUTO_UPDATE=false
+CATEGORY="all"
+JSON_OUTPUT=false
+QUIET=false
+
+while [[ $# -gt 0 ]]; do
+    case "$1" in
+        --update|-u)
+            AUTO_UPDATE=true
+            shift
+            ;;
+        --category|-c)
+            if [[ -z "${2:-}" ]]; then
+                echo "Error: --category requires a value (npm, brew, pip, all)"
+                exit 1
+            fi
+            CATEGORY="$2"
+            shift 2
+            ;;
+        --json|-j)
+            JSON_OUTPUT=true
+            shift
+            ;;
+        --quiet|-q)
+            QUIET=true
+            shift
+            ;;
+        --help|-h)
+            echo "Usage: tool-version-check.sh [OPTIONS]"
+            echo ""
+            echo "Options:"
+            echo "  --update, -u       Automatically update outdated tools"
+            echo "  --category, -c     Check only specific category (npm, brew, pip, all)"
+            echo "  --json, -j         Output results as JSON"
+            echo "  --quiet, -q        Only show outdated tools"
+            echo "  --help, -h         Show this help"
+            exit 0
+            ;;
+        *)
+            echo "Unknown option: $1"
+            exit 1
+            ;;
+    esac
+done
+
+# Tool definitions
+# Format: category|display_name|cli_command|version_flag|package_name|update_command
 
-# Tools to check: display_name|cli_command|version_flag|npm_package
-# Version flag can be --version or -V or custom
-TOOLS=(
-    "osgrep|osgrep|--version|osgrep"
-    "augment|auggie|--version|@augmentcode/auggie"
-    "repomix|repomix|--version|repomix"
-    "stagehand|stagehand|--version|@anthropic-ai/stagehand"
+NPM_TOOLS=(
+    "npm|osgrep|osgrep|--version|osgrep|npm update -g osgrep"
+    "npm|Augment CLI|auggie|--version|@augmentcode/auggie@prerelease|npm update -g @augmentcode/auggie@prerelease"
+    "npm|Repomix|repomix|--version|repomix|npm update -g repomix"
+    "npm|DSPyGround|dspyground|--version|dspyground|npm update -g dspyground"
+    "npm|LocalWP MCP|mcp-local-wp|--version|@verygoodplugins/mcp-local-wp|npm update -g @verygoodplugins/mcp-local-wp"
+    "npm|Beads UI|beads-ui|--version|beads-ui|npm update -g beads-ui"
+    "npm|BDUI|bdui|--version|bdui|npm update -g bdui"
+    "npm|OpenCode|opencode|--version|opencode|npm update -g opencode"
 )
 
-echo -e "${BLUE}=== Tool Version Check ===${NC}"
-echo ""
+BREW_TOOLS=(
+    "brew|GitHub CLI|gh|--version|gh|brew upgrade gh"
+    "brew|GitLab CLI|glab|--version|glab|brew upgrade glab"
+    "brew|Beads CLI|bd|version|steveyegge/beads/bd|brew upgrade steveyegge/beads/bd"
+    "brew|jq|jq|--version|jq|brew upgrade jq"
+    "brew|ShellCheck|shellcheck|--version|shellcheck|brew upgrade shellcheck"
+)
 
+PIP_TOOLS=(
+    "pip|Beads Viewer|beads_viewer|--version|beads-viewer|pip install --upgrade beads-viewer"
+    "pip|DSPy|dspy|--version|dspy-ai|pip install --upgrade dspy-ai"
+    "pip|Crawl4AI|crawl4ai|--version|crawl4ai|pip install --upgrade crawl4ai"
+)
+
+# Counters
 OUTDATED_COUNT=0
+INSTALLED_COUNT=0
+NOT_INSTALLED_COUNT=0
 declare -a OUTDATED_PACKAGES=()
+declare -a JSON_RESULTS=()
 
-for tool_spec in "${TOOLS[@]}"; do
-    IFS='|' read -r name cmd ver_flag npm_pkg <<< "$tool_spec"
+# Get installed version
+get_installed_version() {
+    local cmd="$1"
+    local ver_flag="$2"
     
-    # Get installed version
     if command -v "$cmd" &>/dev/null; then
-        installed=$("$cmd" "$ver_flag" 2>/dev/null | head -1 | grep -oE '[0-9]+\.[0-9]+\.[0-9]+' | head -1 || echo "unknown")
+        local version
+        # shellcheck disable=SC2086
+        version=$("$cmd" $ver_flag 2>/dev/null | head -1 | grep -oE '[0-9]+\.[0-9]+\.[0-9]+' | head -1 || echo "")
+        if [[ -z "$version" ]]; then
+            # Try alternative patterns
+            # shellcheck disable=SC2086
+            version=$("$cmd" $ver_flag 2>/dev/null | head -1 | grep -oE '[0-9]+\.[0-9]+' | head -1 || echo "unknown")
+        fi
+        echo "$version"
+    else
+        echo "not installed"
+    fi
+}
+
+# Get latest npm version
+get_npm_latest() {
+    local pkg="$1"
+    npm view "$pkg" version 2>/dev/null || echo "unknown"
+}
+
+# Get latest brew version
+get_brew_latest() {
+    local pkg="$1"
+    if command -v brew &>/dev/null; then
+        brew info "$pkg" 2>/dev/null | head -1 | grep -oE '[0-9]+\.[0-9]+\.[0-9]+' | head -1 || echo "unknown"
     else
-        installed="not installed"
+        echo "unknown"
     fi
+}
+
+# Get latest pip version
+get_pip_latest() {
+    local pkg="$1"
+    pip index versions "$pkg" 2>/dev/null | head -1 | grep -oE '[0-9]+\.[0-9]+\.[0-9]+' | head -1 || echo "unknown"
+}
+
+# Compare versions (returns 0 if v1 < v2)
+version_lt() {
+    local v1="$1"
+    local v2="$2"
+    
+    if [[ "$v1" == "$v2" ]]; then
+        return 1
+    fi
+    
+    # Use sort -V for version comparison
+    local lowest
+    lowest=$(printf '%s\n%s' "$v1" "$v2" | sort -V | head -1)
+    [[ "$lowest" == "$v1" ]]
+}
+
+# Check a single tool
+check_tool() {
+    local category="$1"
+    local name="$2"
+    local cmd="$3"
+    local ver_flag="$4"
+    local pkg="$5"
+    local update_cmd="$6"
     
-    # Get latest version from npm
-    latest=$(npm view "$npm_pkg" version 2>/dev/null || echo "unknown")
+    local installed
+    installed=$(get_installed_version "$cmd" "$ver_flag")
+    
+    local latest="unknown"
+    case "$category" in
+        npm) latest=$(get_npm_latest "$pkg") ;;
+        brew) latest=$(get_brew_latest "$pkg") ;;
+        pip) latest=$(get_pip_latest "$pkg") ;;
+    esac
+    
+    local status="up_to_date"
+    local icon="✓"
+    local color="$GREEN"
     
-    # Compare and report
     if [[ "$installed" == "not installed" ]]; then
-        echo -e "${YELLOW}⚠️  $name: not installed${NC}"
-        echo "   Latest: $latest"
-        echo "   Install: npm install -g $npm_pkg"
-    elif [[ "$installed" == "$latest" ]]; then
-        echo -e "${GREEN}✓  $name: $installed (up to date)${NC}"
-    elif [[ "$latest" == "unknown" ]]; then
-        echo -e "${YELLOW}?  $name: $installed (could not check latest)${NC}"
-    else
-        echo -e "${RED}⬆️  $name: $installed → $latest (UPDATE AVAILABLE)${NC}"
+        status="not_installed"
+        icon="○"
+        color="$YELLOW"
+        ((NOT_INSTALLED_COUNT++)) || true
+    elif [[ "$installed" == "unknown" || "$latest" == "unknown" ]]; then
+        status="unknown"
+        icon="?"
+        color="$YELLOW"
+        ((INSTALLED_COUNT++)) || true
+    elif [[ "$installed" != "$latest" ]] && version_lt "$installed" "$latest"; then
+        status="outdated"
+        icon="⬆"
+        color="$RED"
         ((OUTDATED_COUNT++)) || true
-        OUTDATED_PACKAGES+=("$npm_pkg")
+        OUTDATED_PACKAGES+=("$update_cmd")
+    else
+        ((INSTALLED_COUNT++)) || true
     fi
-done
-
-echo ""
+    
+    # JSON output (escape special characters for valid JSON)
+    if [[ "$JSON_OUTPUT" == "true" ]]; then
+        # Escape backslashes and double quotes for JSON safety
+        local json_name="${name//\\/\\\\}"
+        json_name="${json_name//\"/\\\"}"
+        local json_update="${update_cmd//\\/\\\\}"
+        json_update="${json_update//\"/\\\"}"
+        JSON_RESULTS+=("{\"name\":\"$json_name\",\"category\":\"$category\",\"installed\":\"$installed\",\"latest\":\"$latest\",\"status\":\"$status\",\"update_cmd\":\"$json_update\"}")
+    else
+        # Console output
+        if [[ "$QUIET" == "true" && "$status" != "outdated" ]]; then
+            return
+        fi
+        
+        case "$status" in
+            not_installed)
+                echo -e "${color}${icon}  $name: not installed${NC}"
+                if [[ "$QUIET" != "true" ]]; then
+                    echo "   Latest: $latest"
+                fi
+                ;;
+            outdated)
+                echo -e "${color}${icon}  $name: $installed → $latest (UPDATE AVAILABLE)${NC}"
+                ;;
+            unknown)
+                echo -e "${color}${icon}  $name: $installed (could not check latest)${NC}"
+                ;;
+            up_to_date)
+                echo -e "${color}${icon}  $name: $installed${NC}"
+                ;;
+        esac
+    fi
+}
 
-# Determine package manager (prefer bun)
-if command -v bun &> /dev/null; then
-    PKG_MGR="bun"
-    PKG_UPDATE="bun update -g"
-else
-    PKG_MGR="npm"
-    PKG_UPDATE="npm update -g"
-fi
+# Check tools by category
+check_category() {
+    local cat_name="$1"
+    shift
+    local tools=("$@")
+    
+    if [[ "$JSON_OUTPUT" != "true" && "$QUIET" != "true" ]]; then
+        echo ""
+        echo -e "${BOLD}${CYAN}=== $cat_name Tools ===${NC}"
+    fi
+    
+    for tool_spec in "${tools[@]}"; do
+        IFS='|' read -r category name cmd ver_flag pkg update_cmd <<< "$tool_spec"
+        check_tool "$category" "$name" "$cmd" "$ver_flag" "$pkg" "$update_cmd"
+    done
+}
 
-if [[ $OUTDATED_COUNT -gt 0 ]]; then
-    echo -e "${YELLOW}Found $OUTDATED_COUNT outdated tool(s)${NC}"
-    echo ""
+# Main
+main() {
+    if [[ "$JSON_OUTPUT" != "true" && "$QUIET" != "true" ]]; then
+        echo -e "${BOLD}${BLUE}Tool Version Check${NC}"
+        echo "=================="
+    fi
     
-    if [[ "$AUTO_UPDATE" == "--update" ]]; then
-        echo "Updating outdated tools using $PKG_MGR..."
-        for pkg in "${OUTDATED_PACKAGES[@]}"; do
-            echo "  Updating $pkg..."
-            $PKG_UPDATE "$pkg" 2>&1 | tail -1
+    # Check requested categories
+    case "$CATEGORY" in
+        npm)
+            check_category "NPM" "${NPM_TOOLS[@]}"
+            ;;
+        brew)
+            check_category "Homebrew" "${BREW_TOOLS[@]}"
+            ;;
+        pip)
+            check_category "Python/Pip" "${PIP_TOOLS[@]}"
+            ;;
+        all|*)
+            if [[ ${#NPM_TOOLS[@]} -gt 0 ]]; then
+                check_category "NPM" "${NPM_TOOLS[@]}"
+            fi
+            if command -v brew &>/dev/null && [[ ${#BREW_TOOLS[@]} -gt 0 ]]; then
+                check_category "Homebrew" "${BREW_TOOLS[@]}"
+            fi
+            if command -v pip &>/dev/null && [[ ${#PIP_TOOLS[@]} -gt 0 ]]; then
+                check_category "Python/Pip" "${PIP_TOOLS[@]}"
+            fi
+            ;;
+    esac
+    
+    # Output results
+    if [[ "$JSON_OUTPUT" == "true" ]]; then
+        echo "{"
+        echo "  \"summary\": {"
+        echo "    \"installed\": $INSTALLED_COUNT,"
+        echo "    \"outdated\": $OUTDATED_COUNT,"
+        echo "    \"not_installed\": $NOT_INSTALLED_COUNT"
+        echo "  },"
+        echo "  \"tools\": ["
+        local first=true
+        for result in "${JSON_RESULTS[@]}"; do
+            if [[ "$first" == "true" ]]; then
+                first=false
+            else
+                echo ","
+            fi
+            echo -n "    $result"
         done
         echo ""
-        echo -e "${GREEN}Updates complete. Re-run to verify.${NC}"
-    else
-        echo "To update all outdated tools, run:"
-        echo "  tool-version-check.sh --update"
+        echo "  ]"
+        echo "}"
+        return 0
+    fi
+    
+    # Summary (skip in quiet mode if nothing outdated)
+    if [[ "$QUIET" == "true" && $OUTDATED_COUNT -eq 0 ]]; then
+        return 0
+    fi
+    
+    if [[ "$QUIET" != "true" ]]; then
+        echo ""
+        echo -e "${BOLD}Summary${NC}"
+        echo "  Installed & up to date: $INSTALLED_COUNT"
+        echo "  Outdated: $OUTDATED_COUNT"
+        echo "  Not installed: $NOT_INSTALLED_COUNT"
         echo ""
-        echo "Or update individually:"
-        for pkg in "${OUTDATED_PACKAGES[@]}"; do
-            echo "  $PKG_UPDATE $pkg"
-        done
     fi
-else
-    echo -e "${GREEN}All tools are up to date!${NC}"
-fi
+    
+    # Handle updates
+    if [[ $OUTDATED_COUNT -gt 0 ]]; then
+        if [[ "$AUTO_UPDATE" == "true" ]]; then
+            echo -e "${BLUE}Updating outdated tools...${NC}"
+            echo ""
+            for update_cmd in "${OUTDATED_PACKAGES[@]}"; do
+                echo "  Running: $update_cmd"
+                # Run update command directly (not via eval for security)
+                # Commands are hardcoded in tool definitions, not user input
+                if bash -c "$update_cmd" 2>&1 | tail -2; then
+                    echo -e "  ${GREEN}✓ Updated${NC}"
+                else
+                    echo -e "  ${RED}✗ Failed${NC}"
+                fi
+                echo ""
+            done
+            echo -e "${GREEN}Updates complete. Re-run to verify.${NC}"
+        else
+            echo "To update all outdated tools, run:"
+            echo "  tool-version-check.sh --update"
+            echo ""
+            echo "Or update individually:"
+            for update_cmd in "${OUTDATED_PACKAGES[@]}"; do
+                echo "  $update_cmd"
+            done
+        fi
+    else
+        echo -e "${GREEN}All installed tools are up to date!${NC}"
+    fi
+}
+
+main
diff --git a/aidevops.sh b/aidevops.sh
index a64811c0b..664ebf192 100755
--- a/aidevops.sh
+++ b/aidevops.sh
@@ -809,6 +809,24 @@ cmd_features() {
     echo ""
 }
 
+# Update tools command - check and update installed tools
+# Passes all arguments through to tool-version-check.sh
+cmd_update_tools() {
+    print_header "Tool Version Check"
+    echo ""
+    
+    local tool_check_script="$AGENTS_DIR/scripts/tool-version-check.sh"
+    
+    if [[ ! -f "$tool_check_script" ]]; then
+        print_error "Tool version check script not found"
+        print_info "Run 'aidevops update' first to get the latest scripts"
+        return 1
+    fi
+    
+    # Pass all arguments through to the script
+    bash "$tool_check_script" "$@"
+}
+
 # Help command
 cmd_help() {
     local version
@@ -822,7 +840,8 @@ cmd_help() {
     echo "  init [features]  Initialize aidevops in current project"
     echo "  features         List available features for init"
     echo "  status           Check installation status of all components"
-    echo "  update           Update to the latest version (alias: upgrade)"
+    echo "  update           Update aidevops to the latest version"
+    echo "  update-tools     Check for outdated tools (--update to auto-update)"
     echo "  uninstall        Remove aidevops from your system"
     echo "  version          Show version information"
     echo "  help             Show this help message"
@@ -832,7 +851,9 @@ cmd_help() {
     echo "  aidevops init planning       # Initialize with planning only"
     echo "  aidevops features            # List available features"
     echo "  aidevops status              # Check what's installed"
-    echo "  aidevops update              # Update to latest version"
+    echo "  aidevops update              # Update aidevops to latest version"
+    echo "  aidevops update-tools        # Check for outdated tools"
+    echo "  aidevops update-tools -u     # Update all outdated tools"
     echo "  aidevops uninstall           # Remove aidevops"
     echo ""
     echo "Quick install:"
@@ -873,6 +894,10 @@ main() {
         update|upgrade|u)
             cmd_update
             ;;
+        update-tools|tools)
+            shift
+            cmd_update_tools "$@"
+            ;;
         uninstall|remove)
             cmd_uninstall
             ;;
diff --git a/setup.sh b/setup.sh
index facddf55e..d95f1c001 100755
--- a/setup.sh
+++ b/setup.sh
@@ -19,6 +19,7 @@ NC='\033[0m' # No Color
 # Global flags
 CLEAN_MODE=false
 INTERACTIVE_MODE=false
+UPDATE_TOOLS_MODE=false
 REPO_URL="https://github.com/marcusquinn/aidevops.git"
 INSTALL_DIR="$HOME/Git/aidevops"
 
@@ -2025,6 +2026,62 @@ setup_seo_mcps() {
     return 0
 }
 
+# Check for tool updates after setup
+check_tool_updates() {
+    print_info "Checking for tool updates..."
+    
+    local tool_check_script="$HOME/.aidevops/agents/scripts/tool-version-check.sh"
+    
+    if [[ ! -f "$tool_check_script" ]]; then
+        # Try local script if deployed version not available yet
+        tool_check_script=".agent/scripts/tool-version-check.sh"
+    fi
+    
+    if [[ ! -f "$tool_check_script" ]]; then
+        print_warning "Tool version check script not found - skipping update check"
+        return 0
+    fi
+    
+    # Run the check in quiet mode first to see if there are updates
+    # Capture both output and exit code
+    local outdated_output
+    local check_exit_code
+    outdated_output=$(bash "$tool_check_script" --quiet 2>&1) || check_exit_code=$?
+    check_exit_code=${check_exit_code:-0}
+    
+    # If the script failed, warn and continue
+    if [[ $check_exit_code -ne 0 ]]; then
+        print_warning "Tool version check encountered an error (exit code: $check_exit_code)"
+        print_info "Run 'aidevops update-tools' manually to check for updates"
+        return 0
+    fi
+    
+    if [[ -z "$outdated_output" ]]; then
+        print_success "All tools are up to date!"
+        return 0
+    fi
+    
+    # Show what's outdated
+    echo ""
+    print_warning "Some tools have updates available:"
+    echo ""
+    bash "$tool_check_script" --quiet
+    echo ""
+    
+    read -r -p "Update all outdated tools now? (y/n): " do_update
+    
+    if [[ "$do_update" == "y" || "$do_update" == "Y" ]]; then
+        print_info "Updating tools..."
+        bash "$tool_check_script" --update
+        print_success "Tool updates complete!"
+    else
+        print_info "Skipped tool updates"
+        print_info "Run 'aidevops update-tools' anytime to update tools"
+    fi
+    
+    return 0
+}
+
 # Parse command line arguments
 parse_args() {
     while [[ $# -gt 0 ]]; do
@@ -2037,6 +2094,10 @@ parse_args() {
                 INTERACTIVE_MODE=true
                 shift
                 ;;
+            --update|-u)
+                UPDATE_TOOLS_MODE=true
+                shift
+                ;;
             --help|-h)
                 echo "Usage: ./setup.sh [OPTIONS]"
                 echo ""
@@ -2044,11 +2105,14 @@ parse_args() {
                 echo "  --clean        Remove stale files before deploying (cleans ~/.aidevops/agents/)"
                 echo "  --interactive  Ask confirmation before each step"
                 echo "  -i             Short for --interactive"
+                echo "  --update       Check for and offer to update outdated tools after setup"
+                echo "  -u             Short for --update"
                 echo "  --help         Show this help message"
                 echo ""
                 echo "Default behavior adds/overwrites files without removing deleted agents."
                 echo "Use --clean after removing or renaming agents to sync deletions."
                 echo "Use --interactive to control each step individually."
+                echo "Use --update to check for tool updates after setup completes."
                 exit 0
                 ;;
             *)
@@ -2077,6 +2141,9 @@ main() {
         echo ""
         echo "Controls: [Y]es (default) / [n]o skip / [q]uit"
     fi
+    if [[ "$UPDATE_TOOLS_MODE" == "true" ]]; then
+        echo "Mode: Update (will check for tool updates after setup)"
+    fi
     echo ""
 
     # Required steps (always run)
@@ -2117,11 +2184,12 @@ main() {
     print_success "🎉 Setup complete!"
     echo ""
 echo "CLI Command:"
-echo "  aidevops init       - Initialize aidevops in a project"
-echo "  aidevops features   - List available features"
-echo "  aidevops status     - Check installation status"
-echo "  aidevops update     - Update to latest version"
-echo "  aidevops uninstall  - Remove aidevops"
+echo "  aidevops init         - Initialize aidevops in a project"
+echo "  aidevops features     - List available features"
+echo "  aidevops status       - Check installation status"
+echo "  aidevops update       - Update to latest version"
+echo "  aidevops update-tools - Check for and update installed tools"
+echo "  aidevops uninstall    - Remove aidevops"
     echo ""
     echo "Deployed to:"
     echo "  ~/.aidevops/agents/     - Agent files (main agents, subagents, scripts)"
@@ -2176,6 +2244,12 @@ echo "  aidevops uninstall  - Remove aidevops"
     echo "Happy server managing! 🚀"
     echo ""
     
+    # Check for tool updates if --update flag was passed
+    if [[ "$UPDATE_TOOLS_MODE" == "true" ]]; then
+        echo ""
+        check_tool_updates
+    fi
+    
     # Offer to launch onboarding for new users (only if not running inside OpenCode)
     if [[ -z "${OPENCODE_SESSION:-}" ]] && command -v opencode &>/dev/null; then
         echo "━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━"