diff --git a/templates/docker-compose/MAINTENANCE.md b/templates/docker-compose/MAINTENANCE.md
index 63b3b14..590f638 100644
--- a/templates/docker-compose/MAINTENANCE.md
+++ b/templates/docker-compose/MAINTENANCE.md
@@ -28,7 +28,7 @@ make restore
    ```bash
    make backup
    ```
-2. Run the `upgrade` command:
+2. Consider upgrading dependencies (MySQL, Redis, Meilisearch, etc) to new supported versions, and then run the `upgrade` command:
    ```bash
    make upgrade
    ```
diff --git a/templates/docker-monolithic/upgrade.sh b/templates/docker-monolithic/upgrade.sh
index 403cd19..a12097a 100644
--- a/templates/docker-monolithic/upgrade.sh
+++ b/templates/docker-monolithic/upgrade.sh
@@ -1,6 +1,37 @@
 #!/bin/bash
 set -eu -o pipefail
 
+# Generate unique log filename
+generate_log_filename() {
+    local base_name="upgrade"
+    local ext="log"
+    local filename="${base_name}.${ext}"
+    local counter=1
+
+    while [ -f "$filename" ]; do
+        filename="${base_name}-${counter}.${ext}"
+        ((counter++))
+    done
+
+    echo "$filename"
+}
+
+# Initialize log file
+LOG_FILE="$(generate_log_filename)"
+touch "$LOG_FILE"
+
+# Log function - writes to log file
+log_debug() {
+    echo "[$(date '+%Y-%m-%d %H:%M:%S')] $*" >> "$LOG_FILE"
+}
+
+# Error exit function - notifies user about log file
+error_exit() {
+    echo "ERROR: $1" >&2
+    echo "A debug log is available in: $LOG_FILE"
+    exit 1
+}
+
 usage="Options:
     -h,--help                  Display this help and exit.
     -r,--ref=5.x               Git ref (commit sha, ref name, tag) to run the script on.
@@ -37,6 +68,8 @@ while [[ "$#" -gt 0 ]]; do
     shift
 done
 
+COMPOSE_FILE_DOWNLOAD_URL="https://raw.githubusercontent.com/supportpal/helpdesk-install/${ref}/templates/docker-monolithic/docker-compose.yml"
+
 # usage: version_ge <installed_version> <minimum_version>
 version_ge() {
     if ! [ "$(printf '%s\n' "$2" "$1" | sort -V | head -n1)" = "$2" ]; then
@@ -81,7 +114,7 @@ backup() {
 }
 
 update_compose_files() {
-    curl -fLsS https://raw.githubusercontent.com/supportpal/helpdesk-install/"${ref}"/templates/docker-monolithic/docker-compose.yml -o docker-compose.yml
+    curl -fLsS "${COMPOSE_FILE_DOWNLOAD_URL}" -o docker-compose.yml
 }
 
 update_volumes() {
@@ -107,21 +140,216 @@ update_env() {
     fi
 }
 
+drop_meilisearch_data() {
+    echo "Preparing Meilisearch for upgrade..."
+
+    # Stop Meilisearch service
+    echo "Stopping Meilisearch service..."
+    if ! docker compose exec supportpal sudo sv stop 00meilisearch; then
+        error_exit "Failed to stop Meilisearch service"
+    fi
+    echo "✓ Meilisearch service stopped"
+
+    # Clear Meilisearch database directory (including hidden files)
+    echo "Clearing Meilisearch database directory..."
+    if ! docker compose exec supportpal bash -c 'sudo rm -rf "${MEILI_DB_PATH:?}"/* "${MEILI_DB_PATH:?}"/.[!.]*'; then
+        error_exit "Failed to clear Meilisearch database directory"
+    fi
+    echo "✓ Meilisearch database directory cleared"
+}
+
+# Helper function to parse version from meilisearch --version output
+parse_meilisearch_version() {
+    local version_output="$1"
+    local pkg_version
+
+    log_debug "Raw version output: $version_output"
+
+    # Extract version number from output like "meilisearch 1.10.3"
+    if ! pkg_version="$(echo "$version_output" | grep -oE '[0-9]+\.[0-9]+\.[0-9]+')"; then
+        log_debug "Expected format: 'meilisearch x.y.z'"
+        log_debug "Actual output: $version_output"
+        error_exit "Failed to parse version from meilisearch --version output"
+    fi
+
+    log_debug "Extracted Meilisearch version: $pkg_version"
+    echo "$pkg_version"
+}
+
+# Usage: get_current_meilisearch_version <container_id>
+get_current_meilisearch_version() {
+    local cid="$1"
+    local version
+
+    log_debug "Getting Meilisearch version from container: $cid"
+
+    # Get version directly using meilisearch --version command
+    if ! version="$(docker exec "$cid" meilisearch --version 2>&1)"; then
+        log_debug "Make sure the container is running and has meilisearch binary"
+        log_debug "Container logs:"
+        docker logs --tail 10 "$cid" >> "$LOG_FILE" 2>&1 || true
+        error_exit "Failed to get Meilisearch version from container $cid"
+    fi
+
+    parse_meilisearch_version "$version"
+}
+
+get_next_meilisearch_version() {
+    log_debug "Fetching next Meilisearch version from docker-compose file..."
+    log_debug "Download URL: $COMPOSE_FILE_DOWNLOAD_URL"
+
+    local image
+    if ! image=$(curl -fsSL "${COMPOSE_FILE_DOWNLOAD_URL}" 2>&1 | grep -m1 -E '^[[:space:]]*image:' | sed -E "s/^[[:space:]]*image:[[:space:]]*//; s/^['\"]//; s/['\"]$//"); then
+        log_debug "URL: $COMPOSE_FILE_DOWNLOAD_URL"
+        log_debug "Check if the URL is accessible and contains valid YAML"
+        error_exit "Failed to fetch or parse docker-compose file"
+    fi
+
+    if [ -z "$image" ]; then
+        log_debug "Expected to find a line like 'image: supportpal/helpdesk:latest'"
+        error_exit "Could not extract image name from docker-compose file"
+    fi
+
+    log_debug "Found image: $image"
+
+    # Get version directly using meilisearch --version without starting the full container
+    log_debug "Getting Meilisearch version from image..."
+
+    local version
+    if ! version="$(docker run --rm --entrypoint meilisearch "$image" --version 2>&1)"; then
+        log_debug "Check if the image exists and contains meilisearch binary"
+        log_debug "Docker run output: $version"
+        error_exit "Failed to get Meilisearch version from image: $image"
+    fi
+
+    parse_meilisearch_version "$version"
+}
+
+# Check if a version requires data dumping for upgrade
+meili_requires_upgrade() {
+    local MEILISEARCH_DUMPLESS_VERSION="1.12.0"
+    local from_version="$1"
+    local to_version="$2"
+
+    log_debug "Checking if Meilisearch requires upgrading"
+    log_debug "Current version: $from_version"
+    log_debug "Target version: $to_version"
+    log_debug "Dumpless version threshold: $MEILISEARCH_DUMPLESS_VERSION"
+
+    # Validate input versions
+    if [ -z "$from_version" ] || [ -z "$to_version" ]; then
+        log_debug "from_version='$from_version', to_version='$to_version'"
+        error_exit "Both from_version and to_version must be provided"
+    fi
+
+    # Check if versions are equal - no dump needed if not upgrading
+    if [ "$from_version" = "$to_version" ]; then
+        log_debug "No dump required - versions are identical (no upgrade needed)"
+        return 1  # false - no dump required
+    fi
+
+    # Check version format (basic validation)
+    if ! echo "$from_version" | grep -qE '^[0-9]+\.[0-9]+\.[0-9]+'; then
+        log_debug "WARNING: from_version '$from_version' doesn't match expected format (x.y.z)"
+    fi
+
+    if ! echo "$to_version" | grep -qE '^[0-9]+\.[0-9]+\.[0-9]+'; then
+        log_debug "WARNING: to_version '$to_version' doesn't match expected format (x.y.z)"
+    fi
+
+    # If upgrading from < 1.12.0 to any version, dump is required
+    local comparison_result
+    comparison_result="$(printf '%s\n' "$from_version" "$MEILISEARCH_DUMPLESS_VERSION" | sort -V | head -n1)"
+
+    if [ "$comparison_result" = "$from_version" ] && [ "$from_version" != "$MEILISEARCH_DUMPLESS_VERSION" ]; then
+        log_debug "Upgrading from pre-$MEILISEARCH_DUMPLESS_VERSION version"
+        return 0  # true - dump required
+    else
+        log_debug "No dump required - version $from_version >= $MEILISEARCH_DUMPLESS_VERSION"
+        return 1  # false - no dump required
+    fi
+}
+
 upgrade() {
-    backup
-    docker compose down -v
+    echo "Starting upgrade process..."
+
+    # Get current Meilisearch version with error handling
+    echo "Checking current Meilisearch version..."
+    local current_container_id
+    if ! current_container_id=$(docker compose ps -q supportpal 2>/dev/null); then
+        log_debug "Ensure docker compose is running and supportpal service exists"
+        error_exit "Failed to get supportpal container ID"
+    fi
+
+    if [ -z "$current_container_id" ]; then
+        log_debug "Start the containers with: docker compose up -d"
+        error_exit "supportpal container is not running"
+    fi
+
+    log_debug "Found supportpal container: $current_container_id"
+
+    local current_meili_version
+    if ! current_meili_version="$(get_current_meilisearch_version "$current_container_id")"; then
+        log_debug "Check if Meilisearch is properly configured in the supportpal container"
+        error_exit "Failed to get current Meilisearch version"
+    fi
+
+    echo "✓ Current Meilisearch version: $current_meili_version"
+
+    # Get next Meilisearch version with error handling
+    echo "Checking target Meilisearch version..."
+    local next_meili_version
+    if ! next_meili_version="$(get_next_meilisearch_version)"; then
+        log_debug "Check network connectivity and docker image availability"
+        error_exit "Failed to get target Meilisearch version"
+    fi
+
+    echo "✓ Target Meilisearch version: $next_meili_version"
+
+    # Check if dump is required
+    if meili_requires_upgrade "$current_meili_version" "$next_meili_version"; then
+        echo "✓ Meilisearch upgrade is required."
+        echo "! The Meilisearch database will be dropped and re-indexed... cancel (CTRL+C) if you're not happy to proceed..."
+        sleep 10
+        drop_meilisearch_data
+    fi
+
+    echo "Stopping containers..."
+    if ! docker compose down -v; then
+        log_debug "Check docker compose status and try manually: docker compose down -v"
+        error_exit "Failed to stop containers"
+    fi
+
+    echo "Updating volumes..."
     update_volumes
+
+    echo "Updating environment configuration..."
     update_env
+
+    echo "Updating docker-compose files..."
     update_compose_files
+
     if [ "${only_files}" = true ]; then
+        echo "✓ Files updated successfully (--only-files specified)"
         exit 0
     fi
 
-    COMPOSE_PARALLEL_LIMIT=1 docker compose up -d
-    docker compose exec supportpal bash -c "bash /init/upgrade-helpdesk.sh"
+    echo "Starting upgraded containers..."
+    if ! COMPOSE_PARALLEL_LIMIT=1 docker compose up -d; then
+        log_debug "Check docker compose logs: docker compose logs"
+        error_exit "Failed to start upgraded containers"
+    fi
+
+    echo "Running helpdesk upgrade script..."
+    if ! docker compose exec supportpal bash -c "bash /init/upgrade-helpdesk.sh"; then
+        log_debug "Check container logs: docker compose logs supportpal"
+        error_exit "Helpdesk upgrade script failed"
+    fi
+
     echo
-    echo "Upgrade complete!"
+    echo "✓ Upgrade complete!"
 }
 
 check_docker_compose
+backup
 upgrade