diff --git a/Dockerfile b/Dockerfile
index 116631f60..33d0eeee3 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -17,6 +17,11 @@ ARG FOREGO_VERSION="0.17.2"
 # See: https://github.com/hairyhenderson/gomplate
 ARG GOMPLATE_VERSION="v3.11.6"
 
+# See: https://github.com/dotenv-linter/dotenv-linter/releases
+#
+# WARN: v3.3.0 and above requires newer libc version than Ubuntu ships with
+ARG DOTENV_LINTER_VERSION="v3.2.0"
+
 ###
 # PHP base configuration
 ###
@@ -99,8 +104,10 @@ ARG PHP_VERSION
 ARG RUNTIME_GID
 ARG RUNTIME_UID
 ARG TARGETPLATFORM
+ARG DOTENV_LINTER_VERSION
 
 ENV DEBIAN_FRONTEND="noninteractive"
+ENV DOTENV_LINTER_VERSION="${DOTENV_LINTER_VERSION}"
 
 # Ensure we run all scripts through 'bash' rather than 'sh'
 SHELL ["/bin/bash", "-c"]
diff --git a/docker/shared/root/docker/entrypoint.d/00-check-config.sh b/docker/shared/root/docker/entrypoint.d/00-check-config.sh
new file mode 100755
index 000000000..36244f6ca
--- /dev/null
+++ b/docker/shared/root/docker/entrypoint.d/00-check-config.sh
@@ -0,0 +1,18 @@
+#!/bin/bash
+source /docker/helpers.sh
+
+entrypoint-set-script-name "$0"
+
+# Validating dot-env files for any issues
+for file in "${dot_env_files[@]}"; do
+    if file-exists "$file"; then
+        log-warning "Could not source file [${file}]: does not exists"
+        continue
+    fi
+
+    log-info "Linting dotenv file ${file}"
+    dotenv-linter --skip=QuoteCharacter --skip=UnorderedKey "${file}"
+done
+
+# Write the config cache
+run-as-runtime-user php artisan config:cache
diff --git a/docker/shared/root/docker/entrypoint.d/05-templating.sh b/docker/shared/root/docker/entrypoint.d/05-templating.sh
index cafb9d133..1bb62aae6 100755
--- a/docker/shared/root/docker/entrypoint.d/05-templating.sh
+++ b/docker/shared/root/docker/entrypoint.d/05-templating.sh
@@ -49,7 +49,7 @@ find "${ENTRYPOINT_TEMPLATE_DIR}" -follow -type f -print | while read -r templat
     cat "${template_file}" | gomplate >"${output_file_path}"
 
     # Show the diff from the envsubst command
-    if [[ ${ENTRYPOINT_SHOW_TEMPLATE_DIFF:-1} = 1 ]]; then
-        git --no-pager diff --color=always "${template_file}" "${output_file_path}" || :
+    if is-true "${ENTRYPOINT_SHOW_TEMPLATE_DIFF}"; then
+        git --no-pager diff --color=always "${template_file}" "${output_file_path}" || : # ignore diff exit code
     fi
 done
diff --git a/docker/shared/root/docker/entrypoint.d/11-first-time-setup.sh b/docker/shared/root/docker/entrypoint.d/11-first-time-setup.sh
index 529c1d0cf..f9fd6a61b 100755
--- a/docker/shared/root/docker/entrypoint.d/11-first-time-setup.sh
+++ b/docker/shared/root/docker/entrypoint.d/11-first-time-setup.sh
@@ -10,13 +10,3 @@ only-once "storage:link" run-as-runtime-user php artisan storage:link
 only-once "key:generate" run-as-runtime-user php artisan key:generate
 only-once "initial:migrate" run-as-runtime-user php artisan migrate --force
 only-once "import:cities" run-as-runtime-user php artisan import:cities
-
-# if [ ! -e "./storage/docker-instance-actor-has-run" ]; then
-#     run-as-runtime-user php artisan instance:actor
-#     touch "./storage/docker-instance-actor-has-run"
-# fi
-
-# if [ ! -e "./storage/docker-passport-keys-has-run" ]; then
-#     run-as-runtime-user php artisan instance:actor
-#     touch "./storage/docker-passport-keys-has-run"
-# fi
diff --git a/docker/shared/root/docker/entrypoint.d/12-migrations.sh b/docker/shared/root/docker/entrypoint.d/12-migrations.sh
index 68008c596..20cbe3a31 100755
--- a/docker/shared/root/docker/entrypoint.d/12-migrations.sh
+++ b/docker/shared/root/docker/entrypoint.d/12-migrations.sh
@@ -6,13 +6,6 @@ entrypoint-set-script-name "$0"
 # Allow automatic applying of outstanding/new migrations on startup
 : ${DOCKER_APPLY_NEW_MIGRATIONS_AUTOMATICALLY:=0}
 
-if [[ $DOCKER_APPLY_NEW_MIGRATIONS_AUTOMATICALLY -eq 0 ]]; then
-    log-info "Automatic applying of new database migrations is disabled"
-    log-info "Please set [DOCKER_APPLY_NEW_MIGRATIONS_AUTOMATICALLY=1] in your [.env] file to enable this."
-
-    exit 0
-fi
-
 # Wait for the database to be ready
 await-database-ready
 
@@ -20,7 +13,7 @@ await-database-ready
 declare -i new_migrations=0
 run-as-runtime-user php artisan migrate:status | grep No && new_migrations=1
 
-if [[ $new_migrations -eq 0 ]]; then
+if is-true "${new_migrations}"; then
     log-info "No outstanding migrations detected"
 
     exit 0
@@ -28,4 +21,11 @@ fi
 
 log-warning "New migrations available, will automatically apply them now"
 
+if is-false "${DOCKER_APPLY_NEW_MIGRATIONS_AUTOMATICALLY}"; then
+    log-info "Automatic applying of new database migrations is disabled"
+    log-info "Please set [DOCKER_APPLY_NEW_MIGRATIONS_AUTOMATICALLY=1] in your [.env] file to enable this."
+
+    exit 0
+fi
+
 run-as-runtime-user php artisan migrate --force
diff --git a/docker/shared/root/docker/helpers.sh b/docker/shared/root/docker/helpers.sh
index 24bd7f1f8..e71b4f295 100644
--- a/docker/shared/root/docker/helpers.sh
+++ b/docker/shared/root/docker/helpers.sh
@@ -224,17 +224,17 @@ function load-config-files() {
     # Associative array (aka map/dictionary) holding the unique keys found in dot-env files
     local -A _tmp_dot_env_keys
 
-    for f in "${dot_env_files[@]}"; do
-        if [ ! -e "$f" ]; then
-            log-warning "Could not source file [${f}]: does not exists"
+    for file in "${dot_env_files[@]}"; do
+        if ! file-exists "${file}"; then
+            log-warning "Could not source file [${file}]: does not exists"
             continue
         fi
 
-        log-info "Sourcing ${f}"
-        source "${f}"
+        log-info "Sourcing ${file}"
+        source "${file}"
 
         # find all keys in the dot-env file and store them in our temp associative array
-        for k in "$(grep -v '^#' "${f}" | sed -E 's/(.*)=.*/\1/' | xargs)"; do
+        for k in "$(grep -v '^#' "${file}" | cut -d"=" -f1 | xargs)"; do
             _tmp_dot_env_keys[$k]=1
         done
     done
@@ -270,6 +270,21 @@ function is-writable() {
     [[ -w "$1" ]]
 }
 
+# @description Checks if $1 exists (directory or file)
+# @arg $1 string The path to check
+# @exitcode 0 If $1 exists
+# @exitcode 1 If $1 does *NOT* exists
+function path-exists() {
+    [[ -e "$1" ]]
+}
+
+# @description Checks if $1 exists (file only)
+# @arg $1 string The path to check
+# @exitcode 0 If $1 exists
+# @exitcode 1 If $1 does *NOT* exists
+function file-exists() {
+    [[ -f "$1" ]]
+}
 # @description Checks if $1 contains any files or not
 # @arg $1 string The path to check
 # @exitcode 0 If $1 contains files
@@ -328,7 +343,7 @@ function acquire-lock() {
     ensure-directory-exists "$(dirname "${file}")"
 
     log-info "🔑 Trying to acquire lock: ${file}: "
-    while [[ -e "${file}" ]]; do
+    while file-exists "${file}"; do
         log-info "🔒 Waiting on lock ${file}"
 
         staggered-sleep
@@ -384,15 +399,17 @@ declare -f -t on-trap
 function await-database-ready() {
     log-info "❓ Waiting for database to be ready"
 
+    load-config-files
+
     case "${DB_CONNECTION:-}" in
     mysql)
-        while ! echo "SELECT 1" | mysql --user="$DB_USERNAME" --password="$DB_PASSWORD" --host="$DB_HOST" "$DB_DATABASE" --silent >/dev/null; do
+        while ! echo "SELECT 1" | mysql --user="${DB_USERNAME}" --password="${DB_PASSWORD}" --host="${DB_HOST}" "${DB_DATABASE}" --silent >/dev/null; do
             staggered-sleep
         done
         ;;
 
     pgsql)
-        while ! echo "SELECT 1" | psql --user="$DB_USERNAME" --password="$DB_PASSWORD" --host="$DB_HOST" "$DB_DATABASE" >/dev/null; do
+        while ! echo "SELECT 1" | PGPASSWORD="${DB_PASSWORD}" psql --user="${DB_USERNAME}" --host="${DB_HOST}" "${DB_DATABASE}" >/dev/null; do
             staggered-sleep
         done
         ;;
@@ -453,3 +470,50 @@ function show-call-stack() {
         log-error "  at: ${func} ${src}:${lineno}"
     done
 }
+
+# @description Helper function see if $1 could be considered truthy
+# @arg $1 string The string to evaluate
+# @see as-boolean
+function is-true() {
+    as-boolean "${1:-}" && return 0
+}
+
+# @description Helper function see if $1 could be considered falsey
+# @arg $1 string The string to evaluate
+# @see as-boolean
+function is-false() {
+    as-boolean "${1:-}" || return 0
+}
+
+# @description Helper function see if $1 could be truethy or falsey.
+#   since this is a bash context, returning 0 is true and 1 is false
+#   so it works with [if is-false $input; then .... fi]
+#
+#   This is a bit confusing, *especially* in a PHP world where [1] would be truthy and
+#   [0] would be falsely as return values
+# @arg $1 string The string to evaluate
+function as-boolean() {
+    local input="${1:-}"
+    local var="${input,,}" # convert input to lower-case
+
+    case "$var" in
+    1 | true)
+        log-info "[as-boolean] variable [${var}] was detected as truthy/true, returning [0]"
+
+        return 0
+        ;;
+
+    0 | false)
+        log-info "[as-boolean] variable [${var}] was detected as falsey/false, returning [1]"
+
+        return 1
+        ;;
+
+    *)
+        log-warning "[as-boolean] variable [${var}] could not be detected as true or false, returning [1] (false) as default"
+
+        return 1
+        ;;
+
+    esac
+}
diff --git a/docker/shared/root/docker/install/base.sh b/docker/shared/root/docker/install/base.sh
index d3da207e5..5856836f9 100755
--- a/docker/shared/root/docker/install/base.sh
+++ b/docker/shared/root/docker/install/base.sh
@@ -83,3 +83,6 @@ apt-get install -y \
 
 locale-gen
 update-locale
+
+# Install dotenv linter (https://github.com/dotenv-linter/dotenv-linter)
+curl -sSfL https://raw.githubusercontent.com/dotenv-linter/dotenv-linter/master/install.sh | sh -s -- -b /usr/local/bin ${DOTENV_LINTER_VERSION}