diff --git a/README.md b/README.md
index c05bbe66..4d413e30 100644
--- a/README.md
+++ b/README.md
@@ -8,7 +8,7 @@
 
 It handles the automated creation, renewal and use of Let's Encrypt certificates for proxyed Docker containers.
 
-Please note that [letsencrypt-nginx-proxy-companion does not work with ACME v2 endpoints yet](https://github.com/JrCs/docker-letsencrypt-nginx-proxy-companion/issues/319).
+Please note that **letsencrypt-nginx-proxy-companion** no longer supports ACME v1 endpoints. The last tagged version that supports ACME v1 is [v1.11](https://github.com/JrCs/docker-letsencrypt-nginx-proxy-companion/releases/tag/v1.11.2).
 
 ### Features:
 * Automated creation/renewal of Let's Encrypt (or other ACME CAs) certificates using [**simp_le**](https://github.com/zenhack/simp_le).
diff --git a/app/entrypoint.sh b/app/entrypoint.sh
index c8a5cab1..9834b36e 100755
--- a/app/entrypoint.sh
+++ b/app/entrypoint.sh
@@ -135,10 +135,11 @@ function check_default_cert_key {
 source /app/functions.sh
 
 if [[ "$*" == "/bin/bash /app/start.sh" ]]; then
-    acmev2_re='https://acme-.*v02\.api\.letsencrypt\.org/directory'
-    if [[ "${ACME_CA_URI:-}" =~ $acmev2_re ]]; then
-        echo "Error: ACME v2 API is not yet supported by simp_le."
-        echo "See https://github.com/zenhack/simp_le/issues/101"
+    acmev1_r='acme-(v01\|staging)\.api\.letsencrypt\.org'
+    if [[ "${ACME_CA_URI:-}" =~ $acmev1_r ]]; then
+        echo "Error: the ACME v1 API is no longer supported by simp_le."
+        echo "See https://github.com/zenhack/simp_le/pull/119"
+        echo "Please use one of Let's Encrypt ACME v2 endpoints instead."
         exit 1
     fi
     check_docker_socket
diff --git a/app/functions.sh b/app/functions.sh
index 64ed07da..fe2d31bc 100644
--- a/app/functions.sh
+++ b/app/functions.sh
@@ -285,6 +285,8 @@ function set_ownership_and_permissions {
     return 1
   fi
 
+  [[ "$(lc $DEBUG)" == true ]] && echo "Debug: checking $path ownership and permissions."
+
   # Find the user numeric ID if the FILES_UID environment variable isn't numeric.
   if [[ "$user" =~ ^[0-9]+$ ]]; then
     user_num="$user"
@@ -329,7 +331,7 @@ function set_ownership_and_permissions {
       fi
     # If the path is a file, check and modify permissions if required.
     elif [[ -f "$path" ]]; then
-      # Use different permissions for private files (private keys and ACME account keys) ...
+      # Use different permissions for private files (private keys and ACME account files) ...
       if [[ "$path" =~ ^.*(default\.key|key\.pem|\.json)$ ]]; then
         if [[ "$(stat -c %a "$path")" != "$f_perms" ]]; then
           [[ "$(lc $DEBUG)" == true ]] && echo "Debug: setting $path permissions to $f_perms."
diff --git a/app/letsencrypt_service b/app/letsencrypt_service
index 8f770347..d316251a 100755
--- a/app/letsencrypt_service
+++ b/app/letsencrypt_service
@@ -4,7 +4,7 @@
 source /app/functions.sh
 
 seconds_to_wait=3600
-ACME_CA_URI="${ACME_CA_URI:-https://acme-v01.api.letsencrypt.org/directory}"
+ACME_CA_URI="${ACME_CA_URI:-https://acme-v02.api.letsencrypt.org/directory}"
 DEFAULT_KEY_SIZE=4096
 REUSE_ACCOUNT_KEYS="$(lc ${REUSE_ACCOUNT_KEYS:-true})"
 REUSE_PRIVATE_KEYS="$(lc ${REUSE_PRIVATE_KEYS:-false})"
@@ -158,7 +158,7 @@ function update_certs {
         fi
 
         test_certificate_varname="LETSENCRYPT_${cid}_TEST"
-        le_staging_uri="https://acme-staging.api.letsencrypt.org/directory"
+        le_staging_uri="https://acme-staging-v02.api.letsencrypt.org/directory"
         if [[ $(lc "${!test_certificate_varname:-}") == true ]] || \
           [[ "$ACME_CA_URI" == "$le_staging_uri" ]]; then
             # Use staging Let's Encrypt ACME end point
@@ -215,27 +215,39 @@ function update_certs {
             add_location_configuration "$domain" || reload_nginx
         done
 
-        # The ACME account key full path is derived from the endpoint URI
-        # + the account alias (set to 'default' if no alias is provided)
-        account_key_dir="../accounts/${acme_ca_uri#*://}"
-        account_key_full_path="${account_key_dir}/${account_alias}.json"
+        if [[ -e "./account_key.json" ]] && [[ ! -e "./account_reg.json" ]]; then
+          # If there is an account key present without account registration, this is
+          # a leftover from the ACME v1 version of simp_le. Remove this account key.
+          rm -f ./account_key.json
+          [[ "$(lc $DEBUG)" == true ]] \
+            && echo "Debug: removed ACME v1 account key $certificate_dir/account_key.json"
+        fi
+
+        # The ACME account key and registration full path are derived from the
+        # endpoint URI + the account alias (set to 'default' if no alias is provided)
+        account_dir="../accounts/${acme_ca_uri#*://}"
         if [[ $REUSE_ACCOUNT_KEYS == true ]]; then
-            if [[ -f "$account_key_full_path" ]]; then
-                # If there is no symlink to the account key, create it
-                if [[ ! -L ./account_key.json ]]; then
-                    ln -sf "$account_key_full_path" ./account_key.json \
-                      && set_ownership_and_permissions ./account_key.json
-                # If the symlink target the wrong account key, replace it
-                elif [[ "$(readlink -f ./account_key.json)" != "$account_key_full_path" ]]; then
-                    ln -sf "$account_key_full_path" ./account_key.json \
-                      && set_ownership_and_permissions ./account_key.json
+            for type in "key" "reg"; do
+                file_full_path="${account_dir}/${account_alias}_${type}.json"
+                simp_le_file="./account_${type}.json"
+                if [[ -f "$file_full_path" ]]; then
+                    # If there is no symlink to the account file, create it
+                    if [[ ! -L "$simp_le_file" ]]; then
+                        ln -sf "$file_full_path" "$simp_le_file" \
+                          && set_ownership_and_permissions "$simp_le_file"
+                    # If the symlink target the wrong account file, replace it
+                    elif [[ "$(readlink -f "$simp_le_file")" != "$file_full_path" ]]; then
+                        ln -sf "$file_full_path" "$simp_le_file" \
+                          && set_ownership_and_permissions "$simp_le_file"
+                    fi
                 fi
-            fi
+            done
         fi
 
         echo "Creating/renewal $base_domain certificates... (${hosts_array_expanded[*]})"
         /usr/bin/simp_le \
-            -f account_key.json -f key.pem -f chain.pem -f fullchain.pem -f cert.pem \
+            -f account_key.json -f account_reg.json \
+            -f key.pem -f chain.pem -f fullchain.pem -f cert.pem \
             $params_d_str \
             --cert_key_size=$cert_keysize \
             --server=$acme_ca_uri \
@@ -244,13 +256,17 @@ function update_certs {
         simp_le_return=$?
 
         if [[ $REUSE_ACCOUNT_KEYS == true ]]; then
-            # If the account key to be reused does not exist yet, copy it
-            # from the CWD and replace the file in CWD with a symlink
-            if [[ ! -f "$account_key_full_path" && -f ./account_key.json ]]; then
-                mkdir -p "$account_key_dir"
-                cp ./account_key.json "$account_key_full_path"
-                ln -sf "$account_key_full_path" ./account_key.json
-            fi
+            mkdir -p "$account_dir"
+            for type in "key" "reg"; do
+                file_full_path="${account_dir}/${account_alias}_${type}.json"
+                simp_le_file="./account_${type}.json"
+                # If the account file to be reused does not exist yet, copy it
+                # from the CWD and replace the file in CWD with a symlink
+                if [[ ! -f "$file_full_path" && -f "$simp_le_file" ]]; then
+                    cp "$simp_le_file" "$file_full_path"
+                    ln -sf "$file_full_path" "$simp_le_file"
+                fi
+            done
         fi
 
         popd || return
@@ -262,20 +278,21 @@ function update_certs {
             else
               create_links "$base_domain" "$domain" && should_reload_nginx='true' && should_restart_container='true'
             fi
-            touch "${certificate_dir}/.companion"
-            set_ownership_and_permissions "${certificate_dir}/.companion"
           done
-          # Make private key root readable only
-          for file in cert.pem key.pem chain.pem fullchain.pem account_key.json; do
+          touch "${certificate_dir}/.companion"
+          # Set ownership and permissions of the files inside $certificate_dir
+          for file in .companion cert.pem key.pem chain.pem fullchain.pem account_key.json account_reg.json; do
             set_ownership_and_permissions "${certificate_dir}/${file}"
           done
-          # Make the account key and its parent folders (up to
-          # /etc/nginx/certs/accounts included) root readable only
-          account_key_perm_path="/etc/nginx/certs/accounts/${acme_ca_uri#*://}/${account_alias}.json"
+          # Set ownership and permissions of the ACME account key and its parent
+          # folders (up to /etc/nginx/certs/accounts included)
+          account_key_perm_path="/etc/nginx/certs/accounts/${acme_ca_uri#*://}/${account_alias}_key.json"
           until [[ "$account_key_perm_path" == /etc/nginx/certs ]]; do
             set_ownership_and_permissions "$account_key_perm_path"
             account_key_perm_path="$(dirname "$account_key_perm_path")"
           done
+          # Set ownership and permissions of the ACME account registration
+          set_ownership_and_permissions "/etc/nginx/certs/accounts/${acme_ca_uri#*://}/${account_alias}_reg.json"
           # Queue nginx reload if a certificate was issued or renewed
           [[ $simp_le_return -eq 0 ]] && should_reload_nginx='true' && should_restart_container='true'
         fi
diff --git a/install_simp_le.sh b/install_simp_le.sh
index a527a4a8..b57e3809 100755
--- a/install_simp_le.sh
+++ b/install_simp_le.sh
@@ -10,7 +10,7 @@ apk add --update python3 git gcc musl-dev libffi-dev python3-dev openssl-dev
 [[ -e /usr/bin/python ]] || ln -sf /usr/bin/python3 /usr/bin/python
 
 # Get Let's Encrypt simp_le client source
-branch="0.14.0"
+branch="0.16.0"
 mkdir -p /src
 git -C /src clone --depth=1 --branch $branch https://github.com/zenhack/simp_le.git
 
diff --git a/test/setup/setup-boulder.sh b/test/setup/setup-boulder.sh
index 46cd8ba0..34604b29 100755
--- a/test/setup/setup-boulder.sh
+++ b/test/setup/setup-boulder.sh
@@ -2,7 +2,7 @@
 
 set -e
 
-acme_endpoint='http://boulder:4000/directory'
+acme_endpoint='http://boulder:4001/directory'
 
 setup_boulder() {
   export GOPATH=${TRAVIS_BUILD_DIR}/go
@@ -10,7 +10,7 @@ setup_boulder() {
     && git clone https://github.com/letsencrypt/boulder \
       $GOPATH/src/github.com/letsencrypt/boulder
   pushd $GOPATH/src/github.com/letsencrypt/boulder
-  git checkout release-2019-06-17
+  git checkout release-2019-10-07
   if [[ "$(uname)" == 'Darwin' ]]; then
     # Set Standard Ports
     sed -i '' 's/ 5002/ 80/g' test/config/va.json
diff --git a/test/tests/permissions_custom/run.sh b/test/tests/permissions_custom/run.sh
index a43595be..dddfa55b 100755
--- a/test/tests/permissions_custom/run.sh
+++ b/test/tests/permissions_custom/run.sh
@@ -42,8 +42,8 @@ wait_for_symlink "${domains[0]}" "$le_container_name"
 # Array of folder paths to test
 folders=( \
   [0]="/etc/nginx/certs/accounts" \
-  [1]="/etc/nginx/certs/accounts/boulder:4000" \
-  [2]="/etc/nginx/certs/accounts/boulder:4000/directory" \
+  [1]="/etc/nginx/certs/accounts/boulder:4001" \
+  [2]="/etc/nginx/certs/accounts/boulder:4001/directory" \
   [3]="/etc/nginx/certs/${domains[0]}" \
   )
 
@@ -62,6 +62,7 @@ symlinks=( \
   [2]="/etc/nginx/certs/${domains[0]}.chain.pem" \
   [3]="/etc/nginx/certs/${domains[0]}.dhparam.pem" \
   [4]="/etc/nginx/certs/${domains[0]}/account_key.json" \
+  [5]="/etc/nginx/certs/${domains[0]}/account_reg.json" \
   )
 
   # Test symlinks paths
@@ -75,8 +76,9 @@ symlinks=( \
 # Array of private file paths to test
 private_files=( \
   [0]="/etc/nginx/certs/default.key" \
-  [1]="/etc/nginx/certs/accounts/boulder:4000/directory/default.json" \
-  [2]="/etc/nginx/certs/${domains[0]}/key.pem" \
+  [1]="/etc/nginx/certs/accounts/boulder:4001/directory/default_key.json" \
+  [2]="/etc/nginx/certs/accounts/boulder:4001/directory/default_reg.json" \
+  [3]="/etc/nginx/certs/${domains[0]}/key.pem" \
   )
 
 # Test private file paths
@@ -89,11 +91,12 @@ done
 
 # Array of public files paths to test
 public_files=( \
-  [0]="/etc/nginx/certs/${domains[0]}/cert.pem" \
-  [1]="/etc/nginx/certs/${domains[0]}/chain.pem" \
-  [2]="/etc/nginx/certs/${domains[0]}/fullchain.pem" \
-  [3]="/etc/nginx/certs/default.crt" \
-  [4]="/etc/nginx/certs/dhparam.pem" \
+  [0]="/etc/nginx/certs/${domains[0]}/.companion" \
+  [1]="/etc/nginx/certs/${domains[0]}/cert.pem" \
+  [2]="/etc/nginx/certs/${domains[0]}/chain.pem" \
+  [3]="/etc/nginx/certs/${domains[0]}/fullchain.pem" \
+  [4]="/etc/nginx/certs/default.crt" \
+  [5]="/etc/nginx/certs/dhparam.pem" \
   )
 
 # Test public file paths
diff --git a/test/tests/permissions_default/run.sh b/test/tests/permissions_default/run.sh
index 1e3ebea9..f4402159 100755
--- a/test/tests/permissions_default/run.sh
+++ b/test/tests/permissions_default/run.sh
@@ -36,8 +36,8 @@ wait_for_symlink "${domains[0]}" "$le_container_name"
 # Array of folder paths to test
 folders=( \
   [0]="/etc/nginx/certs/accounts" \
-  [1]="/etc/nginx/certs/accounts/boulder:4000" \
-  [2]="/etc/nginx/certs/accounts/boulder:4000/directory" \
+  [1]="/etc/nginx/certs/accounts/boulder:4001" \
+  [2]="/etc/nginx/certs/accounts/boulder:4001/directory" \
   [3]="/etc/nginx/certs/${domains[0]}" \
   )
 
@@ -56,6 +56,7 @@ symlinks=( \
   [2]="/etc/nginx/certs/${domains[0]}.chain.pem" \
   [3]="/etc/nginx/certs/${domains[0]}.dhparam.pem" \
   [4]="/etc/nginx/certs/${domains[0]}/account_key.json" \
+  [5]="/etc/nginx/certs/${domains[0]}/account_reg.json" \
   )
 
   # Test symlinks paths
@@ -69,8 +70,9 @@ symlinks=( \
 # Array of private file paths to test
 private_files=( \
   [0]="/etc/nginx/certs/default.key" \
-  [1]="/etc/nginx/certs/accounts/boulder:4000/directory/default.json" \
-  [2]="/etc/nginx/certs/${domains[0]}/key.pem" \
+  [1]="/etc/nginx/certs/accounts/boulder:4001/directory/default_key.json" \
+  [2]="/etc/nginx/certs/accounts/boulder:4001/directory/default_reg.json" \
+  [3]="/etc/nginx/certs/${domains[0]}/key.pem" \
   )
 
 # Test private file paths
@@ -83,11 +85,12 @@ done
 
 # Array of public files paths to test
 public_files=( \
-  [0]="/etc/nginx/certs/${domains[0]}/cert.pem" \
-  [1]="/etc/nginx/certs/${domains[0]}/chain.pem" \
-  [2]="/etc/nginx/certs/${domains[0]}/fullchain.pem" \
-  [3]="/etc/nginx/certs/default.crt" \
-  [4]="/etc/nginx/certs/dhparam.pem" \
+  [0]="/etc/nginx/certs/${domains[0]}/.companion" \
+  [1]="/etc/nginx/certs/${domains[0]}/cert.pem" \
+  [2]="/etc/nginx/certs/${domains[0]}/chain.pem" \
+  [3]="/etc/nginx/certs/${domains[0]}/fullchain.pem" \
+  [4]="/etc/nginx/certs/default.crt" \
+  [5]="/etc/nginx/certs/dhparam.pem" \
   )
 
 # Test public file paths
diff --git a/test/tests/test-functions.sh b/test/tests/test-functions.sh
index 6bda4531..308de6c4 100755
--- a/test/tests/test-functions.sh
+++ b/test/tests/test-functions.sh
@@ -24,7 +24,7 @@ function run_le_container {
     $cli_args \
     --env "DHPARAM_BITS=256" \
     --env "DEBUG=true" \
-    --env "ACME_CA_URI=http://boulder:4000/directory" \
+    --env "ACME_CA_URI=http://boulder:4001/directory" \
     --label com.github.jrcs.letsencrypt_nginx_proxy_companion.test_suite \
     --network boulder_bluenet \
     "$image" > /dev/null && echo "Started letsencrypt container for test ${name%%_2*}"