diff --git a/bin/clean.sh b/bin/clean.sh
index cc2f1d9..df2a658 100755
--- a/bin/clean.sh
+++ b/bin/clean.sh
@@ -917,8 +917,9 @@ perform_cleanup() {
             brew_tmp_file=$(create_temp_file)
 
             # Run brew cleanup in background with manual timeout
-            # Clean old versions with --prune=all (default 2 minutes, configurable via MO_BREW_TIMEOUT)
-            (brew cleanup --prune=all > "$brew_tmp_file" 2>&1) &
+            # Clean old versions only (default 2 minutes, configurable via MO_BREW_TIMEOUT)
+            # Uses default 120-day threshold to avoid breaking zsh completions
+            (brew cleanup > "$brew_tmp_file" 2>&1) &
             local brew_pid=$!
             local elapsed=0
 
@@ -1002,17 +1003,38 @@ perform_cleanup() {
         MOLE_SPINNER_PREFIX="  "
         start_inline_spinner "Searching Next.js caches..."
     fi
-    while IFS= read -r next_dir; do
-        if [[ -d "$next_dir/cache" ]]; then
-            safe_clean "$next_dir/cache"/* "Next.js build cache" || true
-        fi
-    done < <(
-        find "$HOME" -type d -name ".next" -maxdepth 4 \
+
+    # Use timeout to prevent hanging on problematic directories
+    local nextjs_tmp_file
+    nextjs_tmp_file=$(create_temp_file)
+    (
+        find "$HOME" -P -mount -type d -name ".next" -maxdepth 3 \
             -not -path "*/Library/*" \
             -not -path "*/.Trash/*" \
             -not -path "*/node_modules/*" \
+            -not -path "*/.*" \
             2> /dev/null || true
-    )
+    ) > "$nextjs_tmp_file" 2>&1 &
+    local find_pid=$!
+    local find_timeout=10
+    local elapsed=0
+
+    while kill -0 $find_pid 2>/dev/null && [[ $elapsed -lt $find_timeout ]]; do
+        sleep 1
+        ((elapsed++))
+    done
+
+    if kill -0 $find_pid 2>/dev/null; then
+        kill -TERM $find_pid 2>/dev/null || true
+        wait $find_pid 2>/dev/null || true
+    else
+        wait $find_pid 2>/dev/null || true
+    fi
+
+    while IFS= read -r next_dir; do
+        [[ -d "$next_dir/cache" ]] && safe_clean "$next_dir/cache"/* "Next.js build cache" || true
+    done < "$nextjs_tmp_file"
+
     if [[ -t 1 ]]; then
         stop_inline_spinner
     fi
@@ -1022,15 +1044,38 @@ perform_cleanup() {
         MOLE_SPINNER_PREFIX="  "
         start_inline_spinner "Searching Python caches..."
     fi
-    while IFS= read -r pycache; do
-        safe_clean "$pycache"/* "Python bytecode cache" || true
-    done < <(
-        find "$HOME" -type d -name "__pycache__" -maxdepth 5 \
+
+    # Use timeout to prevent hanging on problematic directories
+    local pycache_tmp_file
+    pycache_tmp_file=$(create_temp_file)
+    (
+        find "$HOME" -P -mount -type d -name "__pycache__" -maxdepth 3 \
             -not -path "*/Library/*" \
             -not -path "*/.Trash/*" \
             -not -path "*/node_modules/*" \
+            -not -path "*/.*" \
             2> /dev/null || true
-    )
+    ) > "$pycache_tmp_file" 2>&1 &
+    local find_pid=$!
+    local find_timeout=10
+    local elapsed=0
+
+    while kill -0 $find_pid 2>/dev/null && [[ $elapsed -lt $find_timeout ]]; do
+        sleep 1
+        ((elapsed++))
+    done
+
+    if kill -0 $find_pid 2>/dev/null; then
+        kill -TERM $find_pid 2>/dev/null || true
+        wait $find_pid 2>/dev/null || true
+    else
+        wait $find_pid 2>/dev/null || true
+    fi
+
+    while IFS= read -r pycache; do
+        [[ -d "$pycache" ]] && safe_clean "$pycache"/* "Python bytecode cache" || true
+    done < "$pycache_tmp_file"
+
     if [[ -t 1 ]]; then
         stop_inline_spinner
     fi
diff --git a/lib/common.sh b/lib/common.sh
index 1aba377..b3eb5fb 100755
--- a/lib/common.sh
+++ b/lib/common.sh
@@ -575,11 +575,42 @@ update_via_homebrew() {
     else
         echo "Updating Homebrew..."
     fi
-    # Filter out common noise but show important info
-    brew update 2>&1 | grep -Ev "^(==>|Already up-to-date)" || true
+
+    # Run brew update with timeout to prevent hanging
+    # Use background process to allow interruption
+    local brew_update_timeout="${MO_BREW_UPDATE_TIMEOUT:-300}"
+    local brew_tmp_file
+    brew_tmp_file=$(mktemp -t mole-brew-update 2>/dev/null || echo "/tmp/mole-brew-update.$$")
+
+    (brew update > "$brew_tmp_file" 2>&1) &
+    local brew_pid=$!
+    local elapsed=0
+
+    # Wait for completion or timeout
+    while kill -0 $brew_pid 2>/dev/null; do
+        if [[ $elapsed -ge $brew_update_timeout ]]; then
+            kill -TERM $brew_pid 2>/dev/null || true
+            wait $brew_pid 2>/dev/null || true
+            if [[ -t 1 ]]; then stop_inline_spinner; fi
+            rm -f "$brew_tmp_file"
+            log_error "Homebrew update timed out (${brew_update_timeout}s)"
+            return 1
+        fi
+        sleep 1
+        ((elapsed++))
+    done
+
+    wait $brew_pid 2>/dev/null || {
+        if [[ -t 1 ]]; then stop_inline_spinner; fi
+        rm -f "$brew_tmp_file"
+        log_error "Homebrew update failed"
+        return 1
+    }
+
     if [[ -t 1 ]]; then
         stop_inline_spinner
     fi
+    rm -f "$brew_tmp_file"
 
     if [[ -t 1 ]]; then
         start_inline_spinner "Upgrading Mole..."
diff --git a/mole b/mole
index fecdd22..ccb7fbe 100755
--- a/mole
+++ b/mole
@@ -22,7 +22,7 @@ SCRIPT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")" && pwd)"
 source "$SCRIPT_DIR/lib/common.sh"
 
 # Version info
-VERSION="1.10.5"
+VERSION="1.10.6"
 MOLE_TAGLINE="can dig deep to clean your Mac."
 
 # Check if Touch ID is already configured
@@ -186,6 +186,10 @@ show_help() {
 
 # Simple update function
 update_mole() {
+    # Set up cleanup trap for update process
+    local update_interrupted=false
+    trap 'update_interrupted=true; echo ""; log_error "Update interrupted by user"; exit 130' INT TERM
+
     # Check if installed via Homebrew
     if is_homebrew_install; then
         update_via_homebrew "$VERSION"
@@ -198,6 +202,8 @@ update_mole() {
 
     if [[ -z "$latest" ]]; then
         log_error "Unable to check for updates. Check network connection."
+        echo -e "${YELLOW}Tip:${NC} Check if you can access GitHub (https://github.com)"
+        echo -e "${YELLOW}Tip:${NC} Try again with: ${GRAY}mo update${NC}"
         exit 1
     fi
 
@@ -222,25 +228,40 @@ update_mole() {
         exit 1
     }
 
-    # Download installer with progress
+    # Download installer with progress and better error handling
+    local download_error=""
     if command -v curl > /dev/null 2>&1; then
-        if ! curl -fsSL --connect-timeout 10 --max-time 60 "$installer_url" -o "$tmp_installer" 2>&1; then
+        download_error=$(curl -fsSL --connect-timeout 10 --max-time 60 "$installer_url" -o "$tmp_installer" 2>&1) || {
+            local curl_exit=$?
             if [[ -t 1 ]]; then stop_inline_spinner; fi
             rm -f "$tmp_installer"
-            log_error "Update failed. Check network connection."
+            log_error "Update failed (curl error: $curl_exit)"
+
+            # Provide helpful error messages based on curl exit codes
+            case $curl_exit in
+                6) echo -e "${YELLOW}Tip:${NC} Could not resolve host. Check DNS or network connection." ;;
+                7) echo -e "${YELLOW}Tip:${NC} Failed to connect. Check network or proxy settings." ;;
+                22) echo -e "${YELLOW}Tip:${NC} HTTP 404 Not Found. The installer may have moved." ;;
+                28) echo -e "${YELLOW}Tip:${NC} Connection timed out. Try again or check firewall." ;;
+                *) echo -e "${YELLOW}Tip:${NC} Check network connection and try again." ;;
+            esac
+            echo -e "${YELLOW}Tip:${NC} URL: $installer_url"
             exit 1
-        fi
+        }
     elif command -v wget > /dev/null 2>&1; then
-        if ! wget --timeout=10 --tries=3 -qO "$tmp_installer" "$installer_url" 2>&1; then
+        download_error=$(wget --timeout=10 --tries=3 -qO "$tmp_installer" "$installer_url" 2>&1) || {
             if [[ -t 1 ]]; then stop_inline_spinner; fi
             rm -f "$tmp_installer"
-            log_error "Update failed. Check network connection."
+            log_error "Update failed (wget error)"
+            echo -e "${YELLOW}Tip:${NC} Check network connection and try again."
+            echo -e "${YELLOW}Tip:${NC} URL: $installer_url"
             exit 1
-        fi
+        }
     else
         if [[ -t 1 ]]; then stop_inline_spinner; fi
         rm -f "$tmp_installer"
         log_error "curl or wget required"
+        echo -e "${YELLOW}Tip:${NC} Install curl with: ${GRAY}brew install curl${NC}"
         exit 1
     fi