diff --git a/target/start-mailserver.sh b/target/start-mailserver.sh
index 8178844d..43b71c9e 100644
--- a/target/start-mailserver.sh
+++ b/target/start-mailserver.sh
@@ -1043,34 +1043,48 @@ function _setup_ssl() {
 	# SSL certificate Configuration
 	case $SSL_TYPE in
 		"letsencrypt" )
-			# letsencrypt folders and files mounted in /etc/letsencrypt
-			if [ -e "/etc/letsencrypt/live/$HOSTNAME/fullchain.pem" ]; then
-				KEY=""
-				if [ -e "/etc/letsencrypt/live/$HOSTNAME/privkey.pem" ]; then
-					KEY="privkey"
-				elif [ -e "/etc/letsencrypt/live/$HOSTNAME/key.pem" ]; then
-					KEY="key"
-				else
-					notify 'err' "Cannot access '/etc/letsencrypt/live/"$HOSTNAME"/privkey.pem' nor 'key.pem'"
-				fi
-				if [ -n "$KEY" ]; then
-					notify 'inf' "Adding $HOSTNAME SSL certificate"
+      notify 'inf' "Configuring SSL using 'letsecnrypt'"
+      # letsencrypt folders and files mounted in /etc/letsencrypt
+      local LETSENCRYPT_DOMAIN=""
+      local LETSENCRYPT_KEY=""
 
-					# Postfix configuration
-					sed -i -r 's~smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem~smtpd_tls_cert_file=/etc/letsencrypt/live/'$HOSTNAME'/fullchain.pem~g' /etc/postfix/main.cf
-					sed -i -r 's~smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key~smtpd_tls_key_file=/etc/letsencrypt/live/'$HOSTNAME'/'"$KEY"'\.pem~g' /etc/postfix/main.cf
-
-					# Dovecot configuration
-					sed -i -e 's~ssl_cert = </etc/dovecot/ssl/dovecot\.pem~ssl_cert = </etc/letsencrypt/live/'$HOSTNAME'/fullchain\.pem~g' /etc/dovecot/conf.d/10-ssl.conf
-					sed -i -e 's~ssl_key = </etc/dovecot/ssl/dovecot\.key~ssl_key = </etc/letsencrypt/live/'$HOSTNAME'/'"$KEY"'\.pem~g' /etc/dovecot/conf.d/10-ssl.conf
-
-					notify 'inf' "SSL configured with 'letsencrypt' certificates"
-				else
-					notify 'err' "Key filename not set!"
-				fi
+      # first determine the letsencrypt domain by checking both the full hostname or just the domainname if a SAN is used in the cert
+      if [ -e "/etc/letsencrypt/live/$HOSTNAME/fullchain.pem" ]; then
+        LETSENCRYPT_DOMAIN=$HOSTNAME
+      elif [ -e "/etc/letsencrypt/live/$DOMAINNAME/fullchain.pem" ]; then
+        LETSENCRYPT_DOMAIN=$DOMAINNAME
 			else
-				notify 'err' "Cannot access '/etc/letsencrypt/live/"$HOSTNAME"/fullchain.pem'"
+				notify 'err' "Cannot access '/etc/letsencrypt/live/"$HOSTNAME"/fullchain.pem' or '/etc/letsencrypt/live/"$DOMAINNAME"/fullchain.pem'"
+        return 1
 			fi
+
+      # then determine the keyfile to use
+			if [ -n "$LETSENCRYPT_DOMAIN" ]; then
+				if [ -e "/etc/letsencrypt/live/$LETSENCRYPT_DOMAIN/privkey.pem" ]; then
+					LETSENCRYPT_KEY="privkey"
+				elif [ -e "/etc/letsencrypt/live/$LETSENCRYPT_DOMAIN/key.pem" ]; then
+					LETSENCRYPT_KEY="key"
+				else
+					notify 'err' "Cannot access '/etc/letsencrypt/live/"$LETSENCRYPT_DOMAIN"/privkey.pem' nor 'key.pem'"
+          return 1
+				fi
+      fi
+
+      # finally, make the changes to the postfix and dovecot configurations
+      if [ -n "$LETSENCRYPT_KEY" ]; then
+        notify 'inf' "Adding $LETSENCRYPT_DOMAIN SSL certificate to the postfix and dovecot configuration"
+
+        # Postfix configuration
+        sed -i -r 's~smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem~smtpd_tls_cert_file=/etc/letsencrypt/live/'$LETSENCRYPT_DOMAIN'/fullchain.pem~g' /etc/postfix/main.cf
+        sed -i -r 's~smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key~smtpd_tls_key_file=/etc/letsencrypt/live/'$LETSENCRYPT_DOMAIN'/'"$LETSENCRYPT_KEY"'\.pem~g' /etc/postfix/main.cf
+
+        # Dovecot configuration
+        sed -i -e 's~ssl_cert = </etc/dovecot/ssl/dovecot\.pem~ssl_cert = </etc/letsencrypt/live/'$LETSENCRYPT_DOMAIN'/fullchain\.pem~g' /etc/dovecot/conf.d/10-ssl.conf
+        sed -i -e 's~ssl_key = </etc/dovecot/ssl/dovecot\.key~ssl_key = </etc/letsencrypt/live/'$LETSENCRYPT_DOMAIN'/'"$LETSENCRYPT_KEY"'\.pem~g' /etc/dovecot/conf.d/10-ssl.conf
+
+        notify 'inf' "SSL configured with 'letsencrypt' certificates"
+      fi
+      return 0
 		;;
 	"custom" )
 		# Adding CA signed SSL certificate if provided in 'postfix/ssl' folder
diff --git a/test/config/letsencrypt/my-domain.com/cert.pem b/test/config/letsencrypt/my-domain.com/cert.pem
new file mode 100644
index 00000000..1e391e01
--- /dev/null
+++ b/test/config/letsencrypt/my-domain.com/cert.pem
@@ -0,0 +1,30 @@
+-----BEGIN CERTIFICATE-----
+MIIFGTCCBAGgAwIBAgISA50jj6A/ilExMla41PwSejyBMA0GCSqGSIb3DQEBCwUA
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+TKdnq/QFhHWVZUr3hg==
+-----END CERTIFICATE-----
\ No newline at end of file
diff --git a/test/config/letsencrypt/my-domain.com/chain.pem b/test/config/letsencrypt/my-domain.com/chain.pem
new file mode 100644
index 00000000..edb593bc
--- /dev/null
+++ b/test/config/letsencrypt/my-domain.com/chain.pem
@@ -0,0 +1,27 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
\ No newline at end of file
diff --git a/test/config/letsencrypt/my-domain.com/fullchain.pem b/test/config/letsencrypt/my-domain.com/fullchain.pem
new file mode 100644
index 00000000..9060829b
--- /dev/null
+++ b/test/config/letsencrypt/my-domain.com/fullchain.pem
@@ -0,0 +1,57 @@
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
+-----BEGIN CERTIFICATE-----
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+-----END CERTIFICATE-----
\ No newline at end of file
diff --git a/test/config/letsencrypt/my-domain.com/key.pem b/test/config/letsencrypt/my-domain.com/key.pem
new file mode 100644
index 00000000..54394e92
--- /dev/null
+++ b/test/config/letsencrypt/my-domain.com/key.pem
@@ -0,0 +1,28 @@
+-----BEGIN PRIVATE KEY-----
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+kBfZ8GZztQKBgEVSdw6/vjpdxV9lrMws10fxoN4TrAaI5JY0TM71KTlybWWS1qLr
+dZ3riWCfAHKSbIk70+p/KtCUKbRvid9M4AqUKWYy2A0BW8IbEz0K8DFouPPUkSEo
+cM4poZzpn+ZS3lncNyQcZHVAMJsNpLWBcknYqVZ4u0j0WJZZRDsOQ8tBAoGBAK2p
+BH9+iFI/ZG5IbCDBdr6x1NhqxQk/GOyzU4sy0V81j1OMiagCAMlqe0p6g/UaY4SV
++mX/5Pj5GvM84iyD/N+dYVjw7wEJbzGWtKm5LJfrT0pMWFGDrluE3uVwVlwWihn7
+NaecuatRxyhxk7O76U4PHuQkAsdrFi+yDcetLJIBAoGBAJHUMttKQ9/sc6EYgdym
+u8hMi/WGrt5eOOAJ17lY53eRZLci7s1mfsWIF9b0N50iE60SaFADQiMRAUtkJXNI
+a55qdpalVHsAE4Wwh7nlKLkaDEartx5X1qSTFw4fTMyKNOveiggQ/i9LZpFxsz22
+3V+7jPJaCNyPbmOevXGhBEjr
+-----END PRIVATE KEY-----
\ No newline at end of file
diff --git a/test/mail_pop3.bats b/test/mail_pop3.bats
index 45bbea27..5f183fea 100644
--- a/test/mail_pop3.bats
+++ b/test/mail_pop3.bats
@@ -12,14 +12,11 @@ function setup_file() {
     docker run -d --name mail_pop3 \
 		-v "`pwd`/test/config":/tmp/docker-mailserver \
 		-v "`pwd`/test/test-files":/tmp/docker-mailserver-test:ro \
-		-v "`pwd`/test/config/letsencrypt":/etc/letsencrypt/live \
 		-e ENABLE_POP3=1 \
 		-e DMS_DEBUG=0 \
-		-e SSL_TYPE=letsencrypt \
 		-h mail.my-domain.com -t ${NAME}
 
     wait_for_finished_setup_in_container mail_pop3
-    
 }
 
 function teardown_file() {
@@ -64,24 +61,6 @@ function teardown_file() {
   assert_success
 }
 
-#
-# ssl
-#
-
-@test "checking ssl: letsencrypt configuration is correct" {
-  run docker exec mail_pop3 /bin/sh -c 'grep -ir "/etc/letsencrypt/live/mail.my-domain.com/" /etc/postfix/main.cf | wc -l'
-  assert_success
-  assert_output 2
-  run docker exec mail_pop3 /bin/sh -c 'grep -ir "/etc/letsencrypt/live/mail.my-domain.com/" /etc/dovecot/conf.d/10-ssl.conf | wc -l'
-  assert_success
-  assert_output 2
-}
-
-@test "checking ssl: letsencrypt cert works correctly" {
-  run docker exec mail_pop3 /bin/sh -c "timeout 1 openssl s_client -connect 0.0.0.0:587 -starttls smtp -CApath /etc/ssl/certs/ | grep 'Verify return code: 10 (certificate has expired)'"
-  assert_success
-}
-
 #
 # system
 #
diff --git a/test/mail_ssl_letsencrypt.bats b/test/mail_ssl_letsencrypt.bats
new file mode 100644
index 00000000..01c7a742
--- /dev/null
+++ b/test/mail_ssl_letsencrypt.bats
@@ -0,0 +1,84 @@
+load 'test_helper/common'
+
+function setup() {
+  run_setup_file_if_necessary
+}
+
+function teardown() {
+  run_teardown_file_if_necessary
+}
+
+function setup_file() {
+  docker run -d --name mail_lets_domain \
+  -v "`pwd`/test/config":/tmp/docker-mailserver \
+  -v "`pwd`/test/test-files":/tmp/docker-mailserver-test:ro \
+  -v "`pwd`/test/config/letsencrypt/my-domain.com":/etc/letsencrypt/live/my-domain.com \
+  -e DMS_DEBUG=0 \
+  -e SSL_TYPE=letsencrypt \
+  -h mail.my-domain.com -t ${NAME}
+  wait_for_finished_setup_in_container mail_lets_domain
+
+  docker run -d --name mail_lets_hostname \
+  -v "`pwd`/test/config":/tmp/docker-mailserver \
+  -v "`pwd`/test/test-files":/tmp/docker-mailserver-test:ro \
+  -v "`pwd`/test/config/letsencrypt/mail.my-domain.com":/etc/letsencrypt/live/mail.my-domain.com \
+  -e DMS_DEBUG=0 \
+  -e SSL_TYPE=letsencrypt \
+  -h mail.my-domain.com -t ${NAME}
+  wait_for_finished_setup_in_container mail_lets_hostname
+}
+
+function teardown_file() {
+  docker rm -f mail_lets_domain
+  docker rm -f mail_lets_hostname
+}
+
+# this test must come first to reliably identify when to run setup_file
+@test "first" {
+  skip 'Starting testing of letsencrypt SSL'
+}
+
+@test "checking ssl: letsencrypt configuration is correct" {
+  #test domain has certificate files
+  run docker exec mail_lets_domain /bin/sh -c 'postconf | grep "smtpd_tls_cert_file = /etc/letsencrypt/live/my-domain.com/fullchain.pem" | wc -l'
+  assert_success
+  assert_output 1
+  run docker exec mail_lets_domain /bin/sh -c 'postconf | grep "smtpd_tls_key_file = /etc/letsencrypt/live/my-domain.com/key.pem" | wc -l'
+  assert_success
+  assert_output 1
+  run docker exec mail_lets_domain /bin/sh -c 'doveconf | grep "ssl_cert = </etc/letsencrypt/live/my-domain.com/fullchain.pem" | wc -l'
+  assert_success
+  assert_output 1
+  run docker exec mail_lets_domain /bin/sh -c 'doveconf -P | grep "ssl_key = </etc/letsencrypt/live/my-domain.com/key.pem" | wc -l'
+  assert_success
+  assert_output 1
+  #test hostname has certificate files
+  run docker exec mail_lets_hostname /bin/sh -c 'postconf | grep "smtpd_tls_cert_file = /etc/letsencrypt/live/mail.my-domain.com/fullchain.pem" | wc -l'
+  assert_success
+  assert_output 1
+  run docker exec mail_lets_hostname /bin/sh -c 'postconf | grep "smtpd_tls_key_file = /etc/letsencrypt/live/mail.my-domain.com/privkey.pem" | wc -l'
+  assert_success
+  assert_output 1
+  run docker exec mail_lets_hostname /bin/sh -c 'doveconf | grep "ssl_cert = </etc/letsencrypt/live/mail.my-domain.com/fullchain.pem" | wc -l'
+  assert_success
+  assert_output 1
+  run docker exec mail_lets_hostname /bin/sh -c 'doveconf -P | grep "ssl_key = </etc/letsencrypt/live/mail.my-domain.com/privkey.pem" | wc -l'
+  assert_success
+  assert_output 1
+}
+
+@test "checking ssl: letsencrypt cert works correctly" {
+  run docker exec mail_lets_domain /bin/sh -c "timeout 1 openssl s_client -connect 0.0.0.0:587 -starttls smtp -CApath /etc/ssl/certs/ | grep 'Verify return code: 10 (certificate has expired)'"
+  assert_success
+  run docker exec mail_lets_domain /bin/sh -c "timeout 1 openssl s_client -connect 0.0.0.0:465 -CApath /etc/ssl/certs/ | grep 'Verify return code: 10 (certificate has expired)'"
+  assert_success
+  run docker exec mail_lets_hostname /bin/sh -c "timeout 1 openssl s_client -connect 0.0.0.0:587 -starttls smtp -CApath /etc/ssl/certs/ | grep 'Verify return code: 10 (certificate has expired)'"
+  assert_success
+  run docker exec mail_lets_hostname /bin/sh -c "timeout 1 openssl s_client -connect 0.0.0.0:465 -CApath /etc/ssl/certs/ | grep 'Verify return code: 10 (certificate has expired)'"
+  assert_success
+}
+
+ # this test is only there to reliably mark the end for the teardown_file
+@test "last" {
+  skip 'Finished testing of letsencrypt SSL'
+}
diff --git a/test/mail_manual_ssl.bats b/test/mail_ssl_manual.bats
similarity index 100%
rename from test/mail_manual_ssl.bats
rename to test/mail_ssl_manual.bats