diff --git a/postgres/config.json b/postgres/config.json
index 6f36be607..5448079eb 100644
--- a/postgres/config.json
+++ b/postgres/config.json
@@ -38,5 +38,5 @@
   "slug": "postgres",
   "udev": true,
   "url": "https://github.com/alexbelgium/hassio-addons/tree/master/postgres",
-  "version": "15.7-20"
+  "version": "15.7-21"
 }
diff --git a/postgres/rootfs/etc/cont-init.d/99-run.sh b/postgres/rootfs/etc/cont-init.d/99-run.sh
index e3a707cf5..41ad83a34 100755
--- a/postgres/rootfs/etc/cont-init.d/99-run.sh
+++ b/postgres/rootfs/etc/cont-init.d/99-run.sh
@@ -2,7 +2,22 @@
 # shellcheck shell=bash
 set -e
 
+###############################
+# Configuration & Setup       #
+###############################
+
 CONFIG_HOME="/config"
+PGDATA="${PGDATA:-/config/database}"
+PG_VERSION_FILE="$PGDATA/pg_major_version"
+VECTOR_VERSION_FILE="$PGDATA/pgvector_version"
+
+# Define current versions
+PG_MAJOR_VERSION="${PG_MAJOR:-15}"
+if [ ! -f "$PG_VERSION_FILE" ]; then
+    echo "$PG_MAJOR_VERSION" > "$PG_VERSION_FILE"
+fi
+
+# Create necessary directories
 mkdir -p "$CONFIG_HOME"
 if [ ! -f "$CONFIG_HOME/postgresql.conf" ]; then
     if [ -f /usr/local/share/postgresql/postgresql.conf.sample ]; then
@@ -26,50 +41,171 @@ chmod 700 "$PGDATA"
 # Set permissions
 chmod -R 755 "$CONFIG_HOME"
 
-##############
-# Launch App #
-##############
+###############################
+# Launch PostgreSQL           #
+###############################
 
 cd /config || true
 
-bashio::log.info "Starting the app"
+bashio::log.info "Starting PostgreSQL..."
 
 # Start background tasks
 if [ "$(bashio::info.arch)" = "armv7" ]; then
     bashio::log.warning "ARMv7 detected: Starting without vectors.so"
     docker-entrypoint.sh postgres & true
     exit 0
+else
+    docker-entrypoint.sh postgres -c shared_preload_libraries=vectors.so -c search_path="public, vectors" & true
 fi
 
 # If not armv7
 docker-entrypoint.sh postgres -c shared_preload_libraries=vectors.so -c search_path="public, vectors" & true
 
-####################
-# Enable vector.rs #
-####################
+###############################
+# Wait for PostgreSQL Startup #
+###############################
 
-bashio::log.info "Waiting for port 5432 to open..."
+( bashio::log.info "Waiting for PostgreSQL to start..."
+bashio::net.wait_for 5432 localhost 900
 
-# Wait for transmission to become available
-( bashio::net.wait_for 5432 localhost 900
+###############################
+# PostgreSQL Major Version Upgrade Check #
+###############################
 
-bashio::log.info "Enabling vector.rs"
+OLD_PG_VERSION=$(cat "$PG_VERSION_FILE")
+if [ "$OLD_PG_VERSION" != "$PG_MAJOR_VERSION" ]; then
+    bashio::log.warning "PostgreSQL major version changed ($OLD_PG_VERSION → $PG_MAJOR_VERSION). Running upgrade..."
 
-# Set variables for vector.rs
+    # Note: Ensure pg_upgrade is installed and the paths below match your environment.
+    pg_upgrade --old-datadir="$PGDATA" \
+               --new-datadir="$PGDATA-new" \
+               --old-bindir="/usr/lib/postgresql/$OLD_PG_VERSION/bin" \
+               --new-bindir="/usr/lib/postgresql/$PG_MAJOR_VERSION/bin"
+
+    # Replace old data directory with upgraded one
+    mv "$PGDATA" "$PGDATA-old"
+    mv "$PGDATA-new" "$PGDATA"
+    rm -rf "$PGDATA-old"
+
+    # Update the version file
+    echo "$PG_MAJOR_VERSION" > "$PG_VERSION_FILE"
+fi
+
+#####################################
+# Enable & Upgrade pgvector.rs      #
+#####################################
+
+# Set connection variables for Postgres
 DB_PORT=5432
 DB_HOSTNAME=localhost
 DB_PASSWORD="$(bashio::config 'POSTGRES_PASSWORD')"
-if bashio::config.has_value "POSTGRES_USER"; then DB_USERNAME="$(bashio::config "POSTGRES_USER")"; else DB_USERNAME=postgres; fi
+DB_USERNAME=postgres
+if bashio::config.has_value "POSTGRES_USER"; then
+    DB_USERNAME="$(bashio::config "POSTGRES_USER")"
+fi
+export DB_PORT DB_HOSTNAME DB_USERNAME DB_PASSWORD
 
-export DB_PORT
-export DB_HOSTNAME
-export DB_USERNAME
-export DB_PASSWORD
-echo "DROP EXTENSION IF EXISTS vectors;
-    CREATE EXTENSION vectors;
-\q" > /setup_postgres.sql
+# Function: Check if the "vectors" extension is enabled
+check_vector_extension() {
+    bashio::log.info "Checking if 'vectors' extension is enabled..."
+    local result
+    result=$(psql "postgres://$DB_USERNAME:$DB_PASSWORD@$DB_HOSTNAME:$DB_PORT" \
+               -tAc "SELECT extname FROM pg_extension WHERE extname = 'vectors';")
+    if [[ "$result" == "vectors" ]]; then
+        bashio::log.info "'vectors' extension is enabled."
+        return 0
+    else
+        bashio::log.error "'vectors' extension is NOT enabled."
+        return 1
+    fi
+}
 
-# Enable vectors
-psql "postgres://$DB_USERNAME:$DB_PASSWORD@$DB_HOSTNAME:$DB_PORT" < /setup_postgres.sql >/dev/null || true
-rm /setup_postgres.sql || true
-) & true
+# Function: Enable (or re-create) the "vectors" extension
+enable_vector_extension() {
+    bashio::log.info "Enabling 'vectors' extension..."
+    cat <<EOF > /setup_postgres.sql
+DROP EXTENSION IF EXISTS vectors;
+CREATE EXTENSION vectors;
+EOF
+    psql "postgres://$DB_USERNAME:$DB_PASSWORD@$DB_HOSTNAME:$DB_PORT" < /setup_postgres.sql >/dev/null 2>&1
+    rm /setup_postgres.sql || true
+}
+
+# Function: Store the current pgvector.rs extension version in a file
+store_vector_version() {
+    local version
+    version=$(psql "postgres://$DB_USERNAME:$DB_PASSWORD@$DB_HOSTNAME:$DB_PORT" \
+               -tAc "SELECT extversion FROM pg_extension WHERE extname = 'vectors';")
+    echo "$version" > "$VECTOR_VERSION_FILE"
+}
+
+# Function: Cleanup outdated vector indexes (adjust as needed)
+cleanup_vector_indexes() {
+    bashio::log.info "Cleaning up outdated vector indexes..."
+    psql "postgres://$DB_USERNAME:$DB_PASSWORD@$DB_HOSTNAME:$DB_PORT" \
+         -c "DROP INDEX IF EXISTS clip_index;" >/dev/null 2>&1
+}
+
+# Function: Upgrade the "vectors" extension if a desired version is provided
+upgrade_vector_extension() {
+    local current_version desired_version
+    current_version=$(psql "postgres://$DB_USERNAME:$DB_PASSWORD@$DB_HOSTNAME:$DB_PORT" \
+                     -tAc "SELECT extversion FROM pg_extension WHERE extname = 'vectors';")
+    # Use the desired version from config; if not set, use current version
+    desired_version=$(bashio::config 'VECTOR_EXTENSION_VERSION' || echo "$current_version")
+
+    if [[ "$current_version" != "$desired_version" ]]; then
+        bashio::log.warning "Upgrading 'vectors' extension from version $current_version to $desired_version..."
+        psql "postgres://$DB_USERNAME:$DB_PASSWORD@$DB_HOSTNAME:$DB_PORT" \
+             -c "ALTER EXTENSION vectors UPDATE TO '$desired_version';" >/dev/null 2>&1
+        cleanup_vector_indexes
+        echo "$desired_version" > "$VECTOR_VERSION_FILE"
+    else
+        bashio::log.info "'vectors' extension is already at the desired version ($desired_version)."
+    fi
+}
+
+# Function: Troubleshooting routine if extension checks fail
+troubleshoot_vector_extension() {
+    bashio::log.error "Troubleshooting pgvector.rs installation:"
+
+    bashio::log.info "Checking if PostgreSQL is running..."
+    if ! pg_isready -h "$DB_HOSTNAME" -p "$DB_PORT" -U "$DB_USERNAME" >/dev/null 2>&1; then
+        bashio::log.error "PostgreSQL is not running or unreachable. Start the database and check network settings."
+        exit 1
+    else
+        bashio::log.info "PostgreSQL is running."
+    fi
+
+    bashio::log.info "Verifying availability of the 'vectors' extension..."
+    local ext_check
+    ext_check=$(psql "postgres://$DB_USERNAME:$DB_PASSWORD@$DB_HOSTNAME:$DB_PORT" \
+                -tAc "SELECT count(*) FROM pg_available_extensions WHERE name = 'vectors';")
+    if [[ "$ext_check" -eq 0 ]]; then
+        bashio::log.error "'vectors' extension is not available. Ensure that the pgvector.rs extension is installed."
+        bashio::log.error "Try running: ALTER SYSTEM SET shared_preload_libraries = 'vectors'; then restart PostgreSQL."
+        exit 1
+    else
+        bashio::log.info "'vectors' extension is available."
+    fi
+}
+
+###################################
+# Main Extension Handling         #
+###################################
+
+# If the extension isn’t enabled, create it.
+if ! check_vector_extension; then
+    enable_vector_extension
+fi
+
+# Store the initial pgvector.rs version
+store_vector_version
+
+# If a desired version is provided, attempt to upgrade.
+upgrade_vector_extension
+
+# Verify that the extension is enabled (and upgraded, if needed).
+check_vector_extension || troubleshoot_vector_extension
+
+echo "All initialization steps done" ) & true