diff --git a/data/Dockerfiles/acme/docker-entrypoint.sh b/data/Dockerfiles/acme/docker-entrypoint.sh
index ea55b3ca..4009ca1f 100755
--- a/data/Dockerfiles/acme/docker-entrypoint.sh
+++ b/data/Dockerfiles/acme/docker-entrypoint.sh
@@ -1,6 +1,7 @@
 #!/bin/bash
 
 ACME_BASE=/var/lib/acme
+SSL_EXAMPLE=/var/lib/ssl-example
 mkdir -p ${ACME_BASE}/acme/private
 
 restart_containers(){
@@ -11,16 +12,32 @@ restart_containers(){
 	done
 }
 
-if [[ $(openssl x509 -in ${ACME_BASE}/cert.pem -noout -issuer) != *"Let's Encrypt"* &&
-      $(openssl x509 -in ${ACME_BASE}/cert.pem -noout -issuer) != *"mailcow"* ]]; then
-	echo "Skipping ACME client"
-	exit 0
+if [[ -f ${ACME_BASE}/cert.pem ]]; then
+	if [[ $(openssl x509 -in ${ACME_BASE}/cert.pem -noout -issuer) != *"Let's Encrypt"* &&
+		  $(openssl x509 -in ${ACME_BASE}/cert.pem -noout -issuer) != *"mailcow"* ]]; then
+		echo "Skipping ACME client"
+		exit 0
+	else
+		declare -a SAN_ARRAY_NOW
+		SAN_NAMES=$(openssl x509 -noout -text -in ${ACME_BASE}/cert.pem | awk '/X509v3 Subject Alternative Name/ {getline;gsub(/ /, "", $0); print}' | tr -d "DNS:")
+		if [[ ! -z ${SAN_NAMES} ]]; then
+			IFS=',' read -a SAN_ARRAY_NOW <<< ${SAN_NAMES}
+		fi
+	fi
+else
+	if [[ -f ${ACME_BASE}/acme/fullchain.pem ]] && [[ -f ${ACME_BASE}/acme/private/privkey.pem ]]; then
+		cp ${ACME_BASE}/acme/fullchain.pem ${ACME_BASE}/cert.pem
+		cp ${ACME_BASE}/acme/private/privkey.pem ${ACME_BASE}/key.pem
+	else
+		cp ${SSL_EXAMPLE}/cert.pem ${ACME_BASE}/cert.pem
+		cp ${SSL_EXAMPLE}/key.pem ${ACME_BASE}/key.pem
+	fi
 fi
 
 while true; do
 
 	declare -a SQL_DOMAIN_ARR
-    declare -a CONFIG_DOMAINS
+    declare -a VALIDATED_CONFIG_DOMAINS
 	declare -a ADDITIONAL_VALIDATED_SAN
 	IFS=' ' read -r -a ADDITIONAL_SAN_ARR <<< "${ADDITIONAL_SAN}"
 	IPV4=$(curl -4s https://mailcow.email/ip.php)
@@ -35,7 +52,7 @@ while true; do
 			echo "Found A record for autoconfig.${SQL_DOMAIN}: ${A_CONFIG}"
 			if [[ ${IPV4} == ${A_CONFIG} ]]; then
 				echo "Confirmed A record autoconfig.${SQL_DOMAIN}"
-				CONFIG_DOMAINS+=("autoconfig.${SQL_DOMAIN}")
+				VALIDATED_CONFIG_DOMAINS+=("autoconfig.${SQL_DOMAIN}")
 			else
 				echo "Cannot match Your IP against hostname autoconfig.${SQL_DOMAIN}"
 			fi
@@ -48,7 +65,7 @@ while true; do
 			echo "Found A record for autodiscover.${SQL_DOMAIN}: ${A_CONFIG}"
 			if [[ ${IPV4} == ${A_DISCOVER} ]]; then
 				echo "Confirmed A record autodiscover.${SQL_DOMAIN}"
-				CONFIG_DOMAINS+=("autodiscover.${SQL_DOMAIN}")
+				VALIDATED_CONFIG_DOMAINS+=("autodiscover.${SQL_DOMAIN}")
 			else
 				echo "Cannot match Your IP against hostname autodiscover.${SQL_DOMAIN}"
 			fi
@@ -72,12 +89,22 @@ while true; do
 		fi
 	done
 
+	ORPHANED_SAN=($(echo ${SAN_ARRAY_NOW[*]} ${VALIDATED_CONFIG_DOMAINS[*]} ${ADDITIONAL_VALIDATED_SAN[*]} ${MAILCOW_HOSTNAME} | tr ' ' '\n' | sort | uniq -u ))
+	if [[ ! -z ${ORPHANED_SAN[*]} ]]; then
+		DATE=$(date +%Y-%m-%d_%H_%M_%S)
+		echo "Found orphaned SAN in certificate, moving old files to ${ACME_BASE}/acme/private/${DATE}/"
+		mkdir -p ${ACME_BASE}/acme/private/${DATE}/
+		mv ${ACME_BASE}/acme/private/privkey.pem ${ACME_BASE}/acme/private/${DATE}/
+		mv ${ACME_BASE}/acme/fullchain.pem ${ACME_BASE}/acme/private/${DATE}/
+        mv ${ACME_BASE}/acme/cert.pem ${ACME_BASE}/acme/private/${DATE}/
+	fi
+
 	acme-client \
 		-v -e -b -N -n \
 		-f ${ACME_BASE}/acme/private/account.key \
 		-k ${ACME_BASE}/acme/private/privkey.pem \
 		-c ${ACME_BASE}/acme \
-		${MAILCOW_HOSTNAME} ${CONFIG_DOMAINS[*]} ${ADDITIONAL_VALIDATED_SAN[*]}
+		${MAILCOW_HOSTNAME} ${VALIDATED_CONFIG_DOMAINS[*]} ${ADDITIONAL_VALIDATED_SAN[*]}
 
 	case "$?" in
 		0) # new certs