diff --git a/nixos/modules/security/acme.nix b/nixos/modules/security/acme.nix
index b321c04e574c49..e08c7e965eef9f 100644
--- a/nixos/modules/security/acme.nix
+++ b/nixos/modules/security/acme.nix
@@ -69,9 +69,9 @@ let
       plugins = mkOption {
         type = types.listOf (types.enum [
           "cert.der" "cert.pem" "chain.pem" "external.sh"
-          "fullchain.pem" "full.pem" "key.der" "key.pem" "account_key.json"
+          "fullchain.pem" "full.pem" "key.der" "key.pem" "account_key.json" "account_reg.json"
         ]);
-        default = [ "fullchain.pem" "full.pem" "key.pem" "account_key.json" ];
+        default = [ "fullchain.pem" "full.pem" "key.pem" "account_key.json" "account_reg.json" ];
         description = ''
           Plugins to enable. With default settings simp_le will
           store public certificate bundle in <filename>fullchain.pem</filename>,
@@ -203,6 +203,11 @@ in
                   description = "Renew ACME Certificate for ${cert}";
                   after = [ "network.target" "network-online.target" ];
                   wants = [ "network-online.target" ];
+                  # simp_le uses requests, which uses certifi under the hood,
+                  # which doesn't respect the system trust store.
+                  # At least in the acme test, we provision a fake CA, impersonating the LE endpoint.
+                  # REQUESTS_CA_BUNDLE is a way to teach python requests to use something else
+                  environment.REQUESTS_CA_BUNDLE = "/etc/ssl/certs/ca-certificates.crt";
                   serviceConfig = {
                     Type = "oneshot";
                     SuccessExitStatus = [ "0" "1" ];
diff --git a/nixos/tests/acme.nix b/nixos/tests/acme.nix
index 8cfdea4a16ef6e..85d32d10944221 100644
--- a/nixos/tests/acme.nix
+++ b/nixos/tests/acme.nix
@@ -80,7 +80,7 @@ in import ./make-test.nix {
     client = commonConfig;
   };
 
-  testScript = {nodes, ...}: 
+  testScript = {nodes, ...}:
     let
       newServerSystem = nodes.webserver2.config.system.build.toplevel;
       switchToNewServer = "${newServerSystem}/bin/switch-to-configuration test";
@@ -91,9 +91,12 @@ in import ./make-test.nix {
     # get pulled in by the oneshot units. The target units linger after activation, and hence we
     # can use them to probe that a oneshot fired. It is a bit ugly, but it is the best we can do
     ''
-      $client->waitForUnit("default.target");
+      $client->start;
+      $letsencrypt->start;
+      $acmeStandalone->start;
+
       $letsencrypt->waitForUnit("default.target");
-      $letsencrypt->waitForUnit("boulder.service");
+      $letsencrypt->waitForUnit("pebble.service");
 
       subtest "can request certificate with HTTPS-01 challenge", sub {
         $acmeStandalone->waitForUnit("default.target");
@@ -101,15 +104,20 @@ in import ./make-test.nix {
         $acmeStandalone->waitForUnit("acme-finished-standalone.com.target");
       };
 
+      $client->waitForUnit("default.target");
+
+      $client->succeed('curl https://acme-v02.api.letsencrypt.org:15000/roots/0 > /tmp/ca.crt');
+      $client->succeed('curl https://acme-v02.api.letsencrypt.org:15000/intermediate-keys/0 >> /tmp/ca.crt');
+
       subtest "Can request certificate for nginx service", sub {
         $webserver->waitForUnit("acme-finished-a.example.com.target");
-        $client->succeed('curl https://a.example.com/ | grep -qF "hello world"');
+        $client->succeed('curl --cacert /tmp/ca.crt https://a.example.com/ | grep -qF "hello world"');
       };
 
       subtest "Can add another certificate for nginx service", sub {
         $webserver->succeed("/run/current-system/fine-tune/child-1/bin/switch-to-configuration test");
         $webserver->waitForUnit("acme-finished-b.example.com.target");
-        $client->succeed('curl https://b.example.com/ | grep -qF "hello world"');
+        $client->succeed('curl --cacert /tmp/ca.crt https://b.example.com/ | grep -qF "hello world"');
       };
     '';
 }
diff --git a/nixos/tests/common/letsencrypt/0001-Change-ACME-directory-endpoint-to-directory.patch b/nixos/tests/common/letsencrypt/0001-Change-ACME-directory-endpoint-to-directory.patch
new file mode 100644
index 00000000000000..9d4a483dd88922
--- /dev/null
+++ b/nixos/tests/common/letsencrypt/0001-Change-ACME-directory-endpoint-to-directory.patch
@@ -0,0 +1,25 @@
+From c3b4004386074342d22cab5e129c1f7e623f4272 Mon Sep 17 00:00:00 2001
+From: =?UTF-8?q?F=C3=A9lix=20Baylac-Jacqu=C3=A9?= <felix@alternativebit.fr>
+Date: Mon, 21 Oct 2019 10:56:13 +0200
+Subject: [PATCH] Change ACME directory endpoint to /directory
+
+---
+ wfe/wfe.go | 2 +-
+ 1 file changed, 1 insertion(+), 1 deletion(-)
+
+diff --git a/wfe/wfe.go b/wfe/wfe.go
+index e24797f..10d29fb 100644
+--- a/wfe/wfe.go
++++ b/wfe/wfe.go
+@@ -39,7 +39,7 @@ const (
+ 	// Note: We deliberately pick endpoint paths that differ from Boulder to
+ 	// exercise clients processing of the /directory response
+ 	// We export the DirectoryPath so that the pebble binary can reference it
+-	DirectoryPath     = "/dir"
++	DirectoryPath     = "/directory"
+ 	noncePath         = "/nonce-plz"
+ 	newAccountPath    = "/sign-me-up"
+ 	acctPath          = "/my-account/"
+-- 
+2.23.0
+
diff --git a/nixos/tests/common/letsencrypt/common.nix b/nixos/tests/common/letsencrypt/common.nix
index 798a749f7f9b7c..c530de817bf2d9 100644
--- a/nixos/tests/common/letsencrypt/common.nix
+++ b/nixos/tests/common/letsencrypt/common.nix
@@ -1,27 +1,9 @@
-{ lib, nodes, ... }: {
+{ lib, nodes, pkgs, ... }: let
+  letsencrypt-ca = nodes.letsencrypt.config.test-support.letsencrypt.caCert;
+in {
   networking.nameservers = [
     nodes.letsencrypt.config.networking.primaryIPAddress
   ];
 
-  nixpkgs.overlays = lib.singleton (self: super: {
-    cacert = super.cacert.overrideDerivation (drv: {
-      installPhase = (drv.installPhase or "") + ''
-        cat "${nodes.letsencrypt.config.test-support.letsencrypt.caCert}" \
-          >> "$out/etc/ssl/certs/ca-bundle.crt"
-      '';
-    });
-
-    # Override certifi so that it accepts fake certificate for Let's Encrypt
-    # Need to override the attribute used by simp_le, which is python3Packages
-    python3Packages = (super.python3.override {
-      packageOverrides = lib.const (pysuper: {
-        certifi = pysuper.certifi.overridePythonAttrs (attrs: {
-          postPatch = (attrs.postPatch or "") + ''
-            cat "${self.cacert}/etc/ssl/certs/ca-bundle.crt" \
-              > certifi/cacert.pem
-          '';
-        });
-      });
-    }).pkgs;
-  });
+  security.pki.certificateFiles = [ letsencrypt-ca ];
 }
diff --git a/nixos/tests/common/letsencrypt/default.nix b/nixos/tests/common/letsencrypt/default.nix
index 58d87c64e34456..aaf2896f21cbfe 100644
--- a/nixos/tests/common/letsencrypt/default.nix
+++ b/nixos/tests/common/letsencrypt/default.nix
@@ -1,6 +1,3 @@
-# Fully pluggable module to have Letsencrypt's Boulder ACME service running in
-# a test environment.
-#
 # The certificate for the ACME service is exported as:
 #
 #   config.test-support.letsencrypt.caCert
@@ -54,277 +51,45 @@
 # that it has to be started _before_ the ACME service.
 { config, pkgs, lib, ... }:
 
-let
-  softhsm = pkgs.stdenv.mkDerivation rec {
-    pname = "softhsm";
-    version = "1.3.8";
-
-    src = pkgs.fetchurl {
-      url = "https://dist.opendnssec.org/source/${pname}-${version}.tar.gz";
-      sha256 = "0flmnpkgp65ym7w3qyg78d3fbmvq3aznmi66rgd420n33shf7aif";
-    };
-
-    configureFlags = [ "--with-botan=${pkgs.botan}" ];
-    buildInputs = [ pkgs.sqlite ];
-  };
-
-  pkcs11-proxy = pkgs.stdenv.mkDerivation {
-    name = "pkcs11-proxy";
-
-    src = pkgs.fetchFromGitHub {
-      owner = "SUNET";
-      repo = "pkcs11-proxy";
-      rev = "944684f78bca0c8da6cabe3fa273fed3db44a890";
-      sha256 = "1nxgd29y9wmifm11pjcdpd2y293p0dgi0x5ycis55miy97n0f5zy";
-    };
-
-    postPatch = "patchShebangs mksyscalls.sh";
-
-    nativeBuildInputs = [ pkgs.cmake ];
-    buildInputs = [ pkgs.openssl pkgs.libseccomp ];
-  };
-
-  mkGoDep = { goPackagePath, url ? "https://${goPackagePath}", rev, sha256 }: {
-    inherit goPackagePath;
-    src = pkgs.fetchgit { inherit url rev sha256; };
-  };
-
-  goose = let
-    owner = "liamstask";
-    repo = "goose";
-    rev = "8488cc47d90c8a502b1c41a462a6d9cc8ee0a895";
-    version = "20150116";
-
-  in pkgs.buildGoPackage rec {
-    name = "${repo}-${version}";
-
-    src = pkgs.fetchFromBitbucket {
-      name = "${name}-src";
-      inherit rev owner repo;
-      sha256 = "1jy0pscxjnxjdg3hj111w21g8079rq9ah2ix5ycxxhbbi3f0wdhs";
-    };
-
-    goPackagePath = "bitbucket.org/${owner}/${repo}";
-    subPackages = [ "cmd/goose" ];
-    extraSrcs = map mkGoDep [
-      { goPackagePath = "github.com/go-sql-driver/mysql";
-        rev = "2e00b5cd70399450106cec6431c2e2ce3cae5034";
-        sha256 = "085g48jq9hzmlcxg122n0c4pi41sc1nn2qpx1vrl2jfa8crsppa5";
-      }
-      { goPackagePath = "github.com/kylelemons/go-gypsy";
-        rev = "08cad365cd28a7fba23bb1e57aa43c5e18ad8bb8";
-        sha256 = "1djv7nii3hy451n5jlslk0dblqzb1hia1cbqpdwhnps1g8hqjy8q";
-      }
-      { goPackagePath = "github.com/lib/pq";
-        rev = "ba5d4f7a35561e22fbdf7a39aa0070f4d460cfc0";
-        sha256 = "1mfbqw9g00bk24bfmf53wri5c2wqmgl0qh4sh1qv2da13a7cwwg3";
-      }
-      { goPackagePath = "github.com/mattn/go-sqlite3";
-        rev = "2acfafad5870400156f6fceb12852c281cbba4d5";
-        sha256 = "1rpgil3w4hh1cibidskv1js898hwz83ps06gh0hm3mym7ki8d5h7";
-      }
-      { goPackagePath = "github.com/ziutek/mymysql";
-        rev = "0582bcf675f52c0c2045c027fd135bd726048f45";
-        sha256 = "0bkc9x8sgqbzgdimsmsnhb0qrzlzfv33fgajmmjxl4hcb21qz3rf";
-      }
-      { goPackagePath = "golang.org/x/net";
-        url = "https://go.googlesource.com/net";
-        rev = "10c134ea0df15f7e34d789338c7a2d76cc7a3ab9";
-        sha256 = "14cbr2shl08gyg85n5gj7nbjhrhhgrd52h073qd14j97qcxsakcz";
-      }
-    ];
-  };
-
-  boulder = let
-    owner = "letsencrypt";
-    repo = "boulder";
-    rev = "9c6a1f2adc4c26d925588f5ae366cfd4efb7813a";
-    version = "20180129";
-
-  in pkgs.buildGoPackage rec {
-    name = "${repo}-${version}";
-
-    src = pkgs.fetchFromGitHub {
-      name = "${name}-src";
-      inherit rev owner repo;
-      sha256 = "09kszswrifm9rc6idfaq0p1mz5w21as2qbc8gd5pphrq9cf9pn55";
-    };
-
-    postPatch = ''
-      # compat for go < 1.8
-      sed -i -e 's/time\.Until(\([^)]\+\))/\1.Sub(time.Now())/' \
-        test/ocsp/helper/helper.go
-
-      find test -type f -exec sed -i -e '/libpkcs11-proxy.so/ {
-        s,/usr/local,${pkcs11-proxy},
-      }' {} +
-
-      sed -i -r \
-        -e '/^def +install/a \    return True' \
-        -e 's,exec \./bin/,,' \
-        test/startservers.py
-
-      cat ${lib.escapeShellArg snakeOilCerts.ca.key} > test/test-ca.key
-      cat ${lib.escapeShellArg snakeOilCerts.ca.cert} > test/test-ca.pem
-    '';
-
-    # Until vendored pkcs11 is go 1.9 compatible
-    preBuild = ''
-      rm -r go/src/github.com/letsencrypt/boulder/vendor/github.com/miekg/pkcs11
-    '';
-
-    # XXX: Temporarily brought back putting the source code in the output,
-    # since e95f17e2720e67e2eabd59d7754c814d3e27a0b2 was removing that from
-    # buildGoPackage.
-    preInstall = ''
-      mkdir -p $out
-      pushd "$NIX_BUILD_TOP/go"
-      while read f; do
-        echo "$f" | grep -q '^./\(src\|pkg/[^/]*\)/${goPackagePath}' \
-          || continue
-        mkdir -p "$(dirname "$out/share/go/$f")"
-        cp "$NIX_BUILD_TOP/go/$f" "$out/share/go/$f"
-      done < <(find . -type f)
-      popd
-    '';
-
-    extraSrcs = map mkGoDep [
-      { goPackagePath = "github.com/miekg/pkcs11";
-        rev           = "6dbd569b952ec150d1425722dbbe80f2c6193f83";
-        sha256        = "1m8g6fx7df6hf6q6zsbyw1icjmm52dmsx28rgb0h930wagvngfwb";
-      }
-    ];
-
-    goPackagePath = "github.com/${owner}/${repo}";
-    buildInputs = [ pkgs.libtool ];
-  };
-
-  boulderSource = "${boulder.out}/share/go/src/${boulder.goPackagePath}";
-
-  softHsmConf = pkgs.writeText "softhsm.conf" ''
-    0:/var/lib/softhsm/slot0.db
-    1:/var/lib/softhsm/slot1.db
-  '';
 
+let
   snakeOilCerts = import ./snakeoil-certs.nix;
 
-  wfeDomain = "acme-v01.api.letsencrypt.org";
+  wfeDomain = "acme-v02.api.letsencrypt.org";
   wfeCertFile = snakeOilCerts.${wfeDomain}.cert;
   wfeKeyFile = snakeOilCerts.${wfeDomain}.key;
 
   siteDomain = "letsencrypt.org";
   siteCertFile = snakeOilCerts.${siteDomain}.cert;
   siteKeyFile = snakeOilCerts.${siteDomain}.key;
-
-  # Retrieved via:
-  # curl -s -I https://acme-v01.api.letsencrypt.org/terms \
-  #   | sed -ne 's/^[Ll]ocation: *//p'
-  tosUrl = "https://letsencrypt.org/documents/2017.11.15-LE-SA-v1.2.pdf";
-  tosPath = builtins.head (builtins.match "https?://[^/]+(.*)" tosUrl);
-
-  tosFile = pkgs.fetchurl {
-    url = tosUrl;
-    sha256 = "0yvyckqzj0b1xi61sypcha82nanizzlm8yqy828h2jbza7cxi26c";
-  };
+  pebble = pkgs.pebble.overrideAttrs (attrs: {
+    # The pebble directory endpoint is /dir when the bouder (official
+    # ACME server) is /directory. Sadly, this endpoint is hardcoded,
+    # we have to patch it.
+    #
+    # Tried to upstream, that said upstream maintainers rather keep
+    # this custom endpoint to test ACME clients robustness. See
+    # https://github.com/letsencrypt/pebble/issues/283#issuecomment-545123242
+    patches = [ ./0001-Change-ACME-directory-endpoint-to-directory.patch ];
+  });
 
   resolver = let
     message = "You need to define a resolver for the letsencrypt test module.";
     firstNS = lib.head config.networking.nameservers;
   in if config.networking.nameservers == [] then throw message else firstNS;
 
-  cfgDir = pkgs.stdenv.mkDerivation {
-    name = "boulder-config";
-    src = "${boulderSource}/test/config";
-    nativeBuildInputs = [ pkgs.jq ];
-    phases = [ "unpackPhase" "patchPhase" "installPhase" ];
-    postPatch = ''
-      sed -i -e 's/5002/80/' -e 's/5002/443/' va.json
-      sed -i -e '/listenAddress/s/:4000/:80/' wfe.json
-      sed -i -r \
-        -e ${lib.escapeShellArg "s,http://boulder:4000/terms/v1,${tosUrl},g"} \
-        -e 's,http://(boulder|127\.0\.0\.1):4000,https://${wfeDomain},g' \
-        -e '/dnsResolver/s/127\.0\.0\.1:8053/${resolver}:53/' \
-        *.json
-      if grep 4000 *.json; then exit 1; fi
-
-      # Change all ports from 1909X to 909X, because the 1909X range of ports is
-      # allocated by startservers.py in order to intercept gRPC communication.
-      sed -i -e 's/\<1\(909[0-9]\)\>/\1/' *.json
-
-      # Patch out all additional issuer certs
-      jq '. + {ca: (.ca + {Issuers:
-        [.ca.Issuers[] | select(.CertFile == "test/test-ca.pem")]
-      })}' ca.json > tmp
-      mv tmp ca.json
-    '';
-    installPhase = "cp -r . \"$out\"";
-  };
-
-  components = {
-    gsb-test-srv.args = "-apikey my-voice-is-my-passport";
-    gsb-test-srv.waitForPort = 6000;
-    gsb-test-srv.first = true;
-    boulder-sa.args = "--config ${cfgDir}/sa.json";
-    boulder-wfe.args = "--config ${cfgDir}/wfe.json";
-    boulder-ra.args = "--config ${cfgDir}/ra.json";
-    boulder-ca.args = "--config ${cfgDir}/ca.json";
-    boulder-va.args = "--config ${cfgDir}/va.json";
-    boulder-publisher.args = "--config ${cfgDir}/publisher.json";
-    boulder-publisher.waitForPort = 9091;
-    ocsp-updater.args = "--config ${cfgDir}/ocsp-updater.json";
-    ocsp-updater.after = [ "boulder-publisher" ];
-    ocsp-responder.args = "--config ${cfgDir}/ocsp-responder.json";
-    ct-test-srv = {};
-    mail-test-srv.args = let
-      key = "${boulderSource}/test/mail-test-srv/minica-key.pem";
-      crt = "${boulderSource}/test/mail-test-srv/minica.pem";
-     in
-      "--closeFirst 5 --cert ${crt} --key ${key}";
+  pebbleConf.pebble = {
+    listenAddress = "0.0.0.0:443";
+    managementListenAddress = "0.0.0.0:15000";
+    certificate = snakeOilCerts.${wfeDomain}.cert;
+    privateKey = snakeOilCerts.${wfeDomain}.key;
+    httpPort = 80;
+    tlsPort = 443;
+    ocspResponderURL = "http://0.0.0.0:4002";
   };
 
-  commonPath = [ softhsm pkgs.mariadb goose boulder ];
-
-  mkServices = a: b: with lib; listToAttrs (concatLists (mapAttrsToList a b));
-
-  componentServices = mkServices (name: attrs: let
-    mkSrvName = n: "boulder-${n}.service";
-    firsts = lib.filterAttrs (lib.const (c: c.first or false)) components;
-    firstServices = map mkSrvName (lib.attrNames firsts);
-    firstServicesNoSelf = lib.remove "boulder-${name}.service" firstServices;
-    additionalAfter = firstServicesNoSelf ++ map mkSrvName (attrs.after or []);
-    needsPort = attrs ? waitForPort;
-    inits = map (n: "boulder-init-${n}.service") [ "mysql" "softhsm" ];
-    portWaiter = {
-      name = "boulder-${name}";
-      value = {
-        description = "Wait For Port ${toString attrs.waitForPort} (${name})";
-        after = [ "boulder-real-${name}.service" "bind.service" ];
-        requires = [ "boulder-real-${name}.service" ];
-        requiredBy = [ "boulder.service" ];
-        serviceConfig.Type = "oneshot";
-        serviceConfig.RemainAfterExit = true;
-        script = let
-          netcat = "${pkgs.libressl.nc}/bin/nc";
-          portCheck = "${netcat} -z 127.0.0.1 ${toString attrs.waitForPort}";
-        in "while ! ${portCheck}; do :; done";
-      };
-    };
-  in lib.optional needsPort portWaiter ++ lib.singleton {
-    name = if needsPort then "boulder-real-${name}" else "boulder-${name}";
-    value = {
-      description = "Boulder ACME Component (${name})";
-      after = inits ++ additionalAfter;
-      requires = inits;
-      requiredBy = [ "boulder.service" ];
-      path = commonPath;
-      environment.GORACE = "halt_on_error=1";
-      environment.SOFTHSM_CONF = softHsmConf;
-      environment.PKCS11_PROXY_SOCKET = "tcp://127.0.0.1:5657";
-      serviceConfig.WorkingDirectory = boulderSource;
-      serviceConfig.ExecStart = "${boulder}/bin/${name} ${attrs.args or ""}";
-      serviceConfig.Restart = "on-failure";
-    };
-  }) components;
+  pebbleConfFile = pkgs.writeText "pebble.conf" (builtins.toJSON pebbleConf);
+  pebbleDataDir = "/root/pebble";
 
 in {
   imports = [ ../resolver.nix ];
@@ -352,94 +117,29 @@ in {
     networking.firewall.enable = false;
 
     networking.extraHosts = ''
-      127.0.0.1 ${toString [
-        "sa.boulder" "ra.boulder" "wfe.boulder" "ca.boulder" "va.boulder"
-        "publisher.boulder" "ocsp-updater.boulder" "admin-revoker.boulder"
-        "boulder" "boulder-mysql" wfeDomain
-      ]}
+      127.0.0.1 ${wfeDomain}
       ${config.networking.primaryIPAddress} ${wfeDomain} ${siteDomain}
     '';
 
-    services.mysql.enable = true;
-    services.mysql.package = pkgs.mariadb;
-
-    services.nginx.enable = true;
-    services.nginx.recommendedProxySettings = true;
-    # This fixes the test on i686
-    services.nginx.commonHttpConfig = ''
-      server_names_hash_bucket_size 64;
-    '';
-    services.nginx.virtualHosts.${wfeDomain} = {
-      onlySSL = true;
-      enableACME = false;
-      sslCertificate = wfeCertFile;
-      sslCertificateKey = wfeKeyFile;
-      locations."/".proxyPass = "http://127.0.0.1:80";
-    };
-    services.nginx.virtualHosts.${siteDomain} = {
-      onlySSL = true;
-      enableACME = false;
-      sslCertificate = siteCertFile;
-      sslCertificateKey = siteKeyFile;
-      locations."= ${tosPath}".alias = tosFile;
-    };
-
     systemd.services = {
-      pkcs11-daemon = {
-        description = "PKCS11 Daemon";
-        after = [ "boulder-init-softhsm.service" ];
-        before = map (n: "${n}.service") (lib.attrNames componentServices);
-        wantedBy = [ "multi-user.target" ];
-        environment.SOFTHSM_CONF = softHsmConf;
-        environment.PKCS11_DAEMON_SOCKET = "tcp://127.0.0.1:5657";
-        serviceConfig.ExecStart = let
-          softhsmLib = "${softhsm}/lib/softhsm/libsofthsm.so";
-        in "${pkcs11-proxy}/bin/pkcs11-daemon ${softhsmLib}";
-      };
-
-      boulder-init-mysql = {
-        description = "Boulder ACME Init (MySQL)";
-        after = [ "mysql.service" ];
-        serviceConfig.Type = "oneshot";
-        serviceConfig.RemainAfterExit = true;
-        serviceConfig.WorkingDirectory = boulderSource;
-        path = commonPath;
-        script = "${pkgs.bash}/bin/sh test/create_db.sh";
-      };
-
-      boulder-init-softhsm = {
-        description = "Boulder ACME Init (SoftHSM)";
-        environment.SOFTHSM_CONF = softHsmConf;
-        serviceConfig.Type = "oneshot";
-        serviceConfig.RemainAfterExit = true;
-        serviceConfig.WorkingDirectory = boulderSource;
-        preStart = "mkdir -p /var/lib/softhsm";
-        path = commonPath;
+      pebble = {
+        enable = true;
+        description = "Pebble ACME server";
+        requires = [ ];
+        wantedBy = [ "network.target" ];
+        preStart = ''
+          mkdir ${pebbleDataDir}
+        '';
         script = ''
-          softhsm --slot 0 --init-token \
-            --label intermediate --pin 5678 --so-pin 1234
-          softhsm --slot 0 --import test/test-ca.key \
-            --label intermediate_key --pin 5678 --id FB
-          softhsm --slot 1 --init-token \
-            --label root --pin 5678 --so-pin 1234
-          softhsm --slot 1 --import test/test-root.key \
-            --label root_key --pin 5678 --id FA
+          cd ${pebbleDataDir}
+          ${pebble}/bin/pebble -config ${pebbleConfFile}
         '';
+        serviceConfig = {
+          # Required to bind on privileged ports.
+          User = "root";
+          Group = "root";
+        };
       };
-
-      boulder = {
-        description = "Boulder ACME Server";
-        after = map (n: "${n}.service") (lib.attrNames componentServices);
-        wantedBy = [ "multi-user.target" ];
-        serviceConfig.Type = "oneshot";
-        serviceConfig.RemainAfterExit = true;
-        script = let
-          ports = lib.range 8000 8005 ++ lib.singleton 80;
-          netcat = "${pkgs.libressl.nc}/bin/nc";
-          mkPortCheck = port: "${netcat} -z 127.0.0.1 ${toString port}";
-          checks = "(${lib.concatMapStringsSep " && " mkPortCheck ports})";
-        in "while ! ${checks}; do :; done";
-      };
-    } // componentServices;
+    };
   };
 }
diff --git a/nixos/tests/common/letsencrypt/mkcerts.nix b/nixos/tests/common/letsencrypt/mkcerts.nix
index 3b4a589e41427d..e7ac2bae46bd25 100644
--- a/nixos/tests/common/letsencrypt/mkcerts.nix
+++ b/nixos/tests/common/letsencrypt/mkcerts.nix
@@ -1,7 +1,7 @@
 { pkgs ? import <nixpkgs> {}
 , lib ? pkgs.lib
 
-, domains ? [ "acme-v01.api.letsencrypt.org" "letsencrypt.org" ]
+, domains ? [ "acme-v02.api.letsencrypt.org" "letsencrypt.org" ]
 }:
 
 pkgs.runCommand "letsencrypt-snakeoil-ca" {
diff --git a/nixos/tests/common/letsencrypt/snakeoil-certs.nix b/nixos/tests/common/letsencrypt/snakeoil-certs.nix
index c3d29ab8f16333..ca4f71ae688a49 100644
--- a/nixos/tests/common/letsencrypt/snakeoil-certs.nix
+++ b/nixos/tests/common/letsencrypt/snakeoil-certs.nix
@@ -2,252 +2,253 @@
 {
   ca.key = builtins.toFile "ca.key" ''
     -----BEGIN PRIVATE KEY-----
-    MIIJQwIBADANBgkqhkiG9w0BAQEFAASCCS0wggkpAgEAAoICAQDfdVxC/4HwhuzD
-    9or9CDDu3TBQE5lirJI5KYmfMZtfgdzEjgOzmR9AVSkn2rQeCqzM5m+YCzPO+2y7
-    0Fdk7vDORi1OdhYfUQIW6/TZ27xEjx4t82j9i705yUqTJZKjMbD830geXImJ6VGj
-    Nv/WisTHmwBspWKefYQPN68ZvYNCn0d5rYJg9uROZPJHSI0MYj9iERWIPN+xhZoS
-    xN74ILJ0rEOQfx2GHDhTr99vZYAFqbAIfh35fYulRWarUSekI+rDxa83FD8q9cMg
-    OP84KkLep2dRXXTbUWErGUOpHP55M9M7ws0RVNdl9PUSbDgChl7yYlHCde3261q/
-    zGp5dMV/t/jXXNUgRurvXc4gUKKjS4Sffvg0XVnPs3sMlZ4JNmycK9klgISVmbTK
-    VcjRRJv8Bva2NQVsJ9TIryV0QEk94DucgsC3LbhQfQdmnWVcEdzwrZHNpk9az5mn
-    w42RuvZW9L19T7xpIrdLSHaOis4VEquZjkWIhfIz0DVMeXtYEQmwqFG23Ww0utcp
-    mCW4FPvpyYs5GAPmGWfrlMxsLD/7eteot3AheC+56ZBoVBnI8FFvIX2qci+gfVDu
-    CjvDmbyS/0NvxLGqvSC1GUPmWP3TR5Fb1H8Rp+39zJHRmH+qYWlhcv6p7FlY2/6d
-    9Rkw8WKRTSCB7yeUdNNPiPopk6N4NwIDAQABAoICAQCzV0ei5dntpvwjEp3eElLj
-    glYiDnjOPt5kTjgLsg6XCmyau7ewzrXMNgz/1YE1ky+4i0EI8AS2nAdafQ2HDlXp
-    11zJWfDLVYKtztYGe1qQU6TPEEo1I4/M7waRLliP7XO0n6cL5wzjyIQi0CNolprz
-    8CzZBasutGHmrLQ1nmnYcGk2+NBo7f2yBUaFe27of3mLRVbYrrKBkU5kveiNkABp
-    r0/SipKxbbivQbm7d+TVpqiHSGDaOa54CEksOcfs7n6efOvw8qj326KtG9GJzDE6
-    7XP4U19UHe40XuR0t7Zso/FmRyO6QzNUutJt5LjXHezZ75razTcdMyr0QCU8MUHH
-    jXZxQCsbt+9AmdxUMBm1SMNVBdHYM8oiNHynlgsEj9eM6jxDEss/Uc3FeKoHl+XL
-    L6m28guIB8NivqjVzZcwhxvdiQCzYxjyqMC+/eX7aaK4NIlX2QRMoDL6mJ58Bz/8
-    V2Qxp2UNVwKJFWAmpgXC+sq6XV/TP3HkOvd0OK82Nid2QxEvfE/EmOhU63qAjgUR
-    QnteLEcJ3MkGGurs05pYBDE7ejKVz6uu2tHahFMOv+yanGP2gfivnT9a323/nTqH
-    oR5ffMEI1u/ufpWU7sWXZfL/mH1L47x87k+9wwXHCPeSigcy+hFI7t1+rYsdCmz9
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-    fJ5sQ06aDBV2sqS4XnoWsHuJWUd39rulks8cg8WIQu8oJwVkFI9EpARt/+a1fRP0
-    Ncc9qiBdP6VctQGgKfe5KyOfMzIBUl3zj2cAmU6q+CW1OgdhnEl4QhgBe5XQGquZ
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-    XI+S2ZLyUn3WHYkaJqvUFrbfekgBBmbk5Ead6ImlsLsBla6MolKrVYV1kN6KT+Y+
-    plcxNpWY8bnWfw5058OWPLPa9LPfReu9rxAeGT2ZLmAhSkjGxQKCAQEA7BkBzT3m
-    SIzop9RKl5VzYbVysCYDjFU9KYMW5kBIw5ghSMnRmU7kXIZUkc6C1L/v9cTNFFLw
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-    u5WFOyGS5g1JtN0280yIcrmWeNPp8Q2Nq4wnNgMqDmeEnNFDOsmo1l6NqMC0NtrW
-    CdxyXj82aXSkRgMQSqw/zk7BmNkDV8VvyOqX/fHWQynnfuYmEco4Pd2UZQgadOW5
-    cVMCggEBANGz1fC+QQaangUzsVNOJwg2+CsUFYlAKYA3pRKZPIyMob2CBXk3Oln/
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+    Eq4OVTSu/s8gmY94tgbjeOaLUPEPmg==
     -----END PRIVATE KEY-----
   '';
   ca.cert = builtins.toFile "ca.cert" ''
     -----BEGIN CERTIFICATE-----
-    MIIFATCCAumgAwIBAgIJANydi4uFZr0LMA0GCSqGSIb3DQEBCwUAMBYxFDASBgNV
-    BAMMC1NuYWtlb2lsIENBMCAXDTE4MDcxMjAwMjIxNloYDzIxMTgwNjE4MDAyMjE2
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+    kgwJ
     -----END CERTIFICATE-----
   '';
-  "acme-v01.api.letsencrypt.org".key = builtins.toFile "acme-v01.api.letsencrypt.org.key" ''
+  "acme-v02.api.letsencrypt.org".key = builtins.toFile "acme-v02.api.letsencrypt.org.key" ''
     -----BEGIN RSA PRIVATE KEY-----
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     -----END RSA PRIVATE KEY-----
   '';
-  "acme-v01.api.letsencrypt.org".cert = builtins.toFile "acme-v01.api.letsencrypt.org.cert" ''
+  "acme-v02.api.letsencrypt.org".cert = builtins.toFile "acme-v02.api.letsencrypt.org.cert" ''
     -----BEGIN CERTIFICATE-----
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     -----END CERTIFICATE-----
   '';
   "letsencrypt.org".key = builtins.toFile "letsencrypt.org.key" ''
     -----BEGIN RSA PRIVATE KEY-----
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     -----END RSA PRIVATE KEY-----
   '';
   "letsencrypt.org".cert = builtins.toFile "letsencrypt.org.cert" ''
     -----BEGIN CERTIFICATE-----
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+    dzZZM+pUpIB5fEO5JfjiOEOKDdAvRSs0mTAVYZEokGkXSNWyylvEaA16mHtMgPjo
+    Lm75d0O66RfJDdd/hTl8umGpF7kEGW1qYk2QmuPr7AqOa8na7olL5fMPh6Q7yRqx
+    GIS9JKQ0fWl8Ngk09WfwUN/kEMcp9Jl5iunNRkbpUJIM/lHFkSA7yOFFL+dVWzd4
+    2r+ddJXTFzW8Rwt65l8SV2MEhijEamKva3mqKLIRWxDsfFVT1T04LWFtnzMW4Z29
+    UHF9Pi7XSyKz0Y/Lz31mNTkjJYbOvbnwok8lc3wFWHc+lummZk8IkCq8xfqzwmwX
+    Ow6EV+Q6VaQpOHumQZ12pBBLtL8DyDhWaRUgVy2vYpwYsMYa5BFMcKCynjlSewo9
+    G2hNoW45cQZP1qHltRR9Xad7SaP7iTETDCiR7AWOqSpDipSh9eMfVW97ZbSfz+vl
+    xl8PZEZMTRIIRVXsPP+E8gtDUhUQp2+Vcz8r6q71qslXM09xl/501uaNjCc3hH2R
+    iw2N77Lho1F3FrBbHdML3RYHZI55eC9iQw6R4S+R4b+iWLJoHzHrW61itg==
     -----END CERTIFICATE-----
   '';
 }
diff --git a/pkgs/tools/admin/certbot/0001-pebble_artifacts-hardcode-pebble-location.patch b/pkgs/tools/admin/certbot/0001-pebble_artifacts-hardcode-pebble-location.patch
new file mode 100644
index 00000000000000..33f0cd216c1d97
--- /dev/null
+++ b/pkgs/tools/admin/certbot/0001-pebble_artifacts-hardcode-pebble-location.patch
@@ -0,0 +1,24 @@
+From 8ddf2697508eca514a0dde4646ad14ac3ba34b2a Mon Sep 17 00:00:00 2001
+From: Florian Klink <flokli@flokli.de>
+Date: Fri, 18 Oct 2019 16:06:50 +0200
+Subject: [PATCH] pebble_artifacts: hardcode pebble location
+
+---
+ certbot-ci/certbot_integration_tests/utils/pebble_artifacts.py | 1 +
+ 1 file changed, 1 insertion(+)
+
+diff --git a/certbot-ci/certbot_integration_tests/utils/pebble_artifacts.py b/certbot-ci/certbot_integration_tests/utils/pebble_artifacts.py
+index 2b1557928..d2603c51a 100644
+--- a/certbot-ci/certbot_integration_tests/utils/pebble_artifacts.py
++++ b/certbot-ci/certbot_integration_tests/utils/pebble_artifacts.py
+@@ -22,6 +22,7 @@ def fetch(workspace):
+ 
+ 
+ def _fetch_asset(asset, suffix):
++    return "@pebble@"
+     asset_path = os.path.join(ASSETS_PATH, '{0}_{1}_{2}'.format(asset, PEBBLE_VERSION, suffix))
+     if not os.path.exists(asset_path):
+         asset_url = ('https://github.com/letsencrypt/pebble/releases/download/{0}/{1}_{2}'
+-- 
+2.23.0
+
diff --git a/pkgs/tools/admin/certbot/default.nix b/pkgs/tools/admin/certbot/default.nix
index 782af149ed6a89..3448e3c8183180 100644
--- a/pkgs/tools/admin/certbot/default.nix
+++ b/pkgs/tools/admin/certbot/default.nix
@@ -1,21 +1,27 @@
-{ stdenv, python3Packages, fetchFromGitHub, dialog }:
+{ stdenv, python37Packages, fetchFromGitHub, fetchurl, dialog, autoPatchelfHook, nginx, pebble }:
 
-python3Packages.buildPythonApplication rec {
+
+python37Packages.buildPythonApplication rec {
   pname = "certbot";
-  version = "0.31.0";
+  version = "0.39.0";
 
   src = fetchFromGitHub {
     owner = pname;
     repo = pname;
     rev = "v${version}";
-    sha256 = "0rwjxmkpicyc9a5janvj1lfi430nq6ha94nyfgp11ds9fyydbh1s";
+    sha256 = "1s32xg2ljz7ci78wc8rqkjvgrz7vprb7fkznrlf9a4blm55pp54c";
   };
 
-  propagatedBuildInputs = with python3Packages; [
+  patches = [
+    ./0001-pebble_artifacts-hardcode-pebble-location.patch
+  ];
+
+  propagatedBuildInputs = with python37Packages; [
     ConfigArgParse
     acme
     configobj
     cryptography
+    distro
     josepy
     parsedatetime
     psutil
@@ -26,11 +32,19 @@ python3Packages.buildPythonApplication rec {
     zope_component
     zope_interface
   ];
-  buildInputs = [ dialog ] ++ (with python3Packages; [ mock gnureadline ]);
 
-  patchPhase = ''
+  buildInputs = [ dialog ] ++ (with python37Packages; [ mock gnureadline ]);
+
+  checkInputs = with python37Packages; [
+    pytest_xdist
+    pytest
+    dateutil
+  ];
+
+  postPatch = ''
     substituteInPlace certbot/notify.py --replace "/usr/sbin/sendmail" "/run/wrappers/bin/sendmail"
     substituteInPlace certbot/util.py --replace "sw_vers" "/usr/bin/sw_vers"
+    substituteInPlace certbot-ci/certbot_integration_tests/utils/pebble_artifacts.py --replace "@pebble@" "${pebble}/bin/pebble"
   '';
 
   postInstall = ''
@@ -40,7 +54,15 @@ python3Packages.buildPythonApplication rec {
     done
   '';
 
-  doCheck = !stdenv.isDarwin; # On Hydra Darwin tests fail with "Too many open files".
+  # tests currently time out, because they're trying to do network access
+  # Upstream issue: https://github.com/certbot/certbot/issues/7450
+  doCheck = false;
+
+  checkPhase = ''
+    PATH="$out/bin:${nginx}/bin:$PATH" pytest certbot-ci/certbot_integration_tests
+  '';
+
+  dontUseSetuptoolsCheck = true;
 
   meta = with stdenv.lib; {
     homepage = src.meta.homepage;
diff --git a/pkgs/tools/admin/pebble/default.nix b/pkgs/tools/admin/pebble/default.nix
new file mode 100644
index 00000000000000..5aa220fd89e68e
--- /dev/null
+++ b/pkgs/tools/admin/pebble/default.nix
@@ -0,0 +1,26 @@
+{ buildGoPackage
+, fetchFromGitHub
+, lib
+}:
+
+let
+  version = "v2.2.2";
+  pname = "pebble";
+in buildGoPackage {
+  inherit pname version;
+  goPackagePath = "github.com/letsencrypt/${pname}";
+
+  src = fetchFromGitHub {
+    owner = "letsencrypt";
+    repo = pname;
+    rev = version;
+    sha256 = "10g6ivdxxp3632wk0gvmp75v9x668kchhmlczbsq8qnsc8sb8pwf";
+  };
+
+  meta = {
+    homepage = "https://github.com/letsencrypt/boulder";
+    description = "A miniature version of Boulder, Pebble is a small RFC 8555 ACME test server not suited for a production CA";
+    license = [ lib.licenses.mpl20 ];
+    maintainers = [ ];
+  };
+}
diff --git a/pkgs/tools/admin/simp_le/default.nix b/pkgs/tools/admin/simp_le/default.nix
index f5be7719d0d21d..37f627a18f566f 100644
--- a/pkgs/tools/admin/simp_le/default.nix
+++ b/pkgs/tools/admin/simp_le/default.nix
@@ -2,16 +2,14 @@
 
 python3Packages.buildPythonApplication rec {
   pname = "simp_le-client";
-  version = "0.9.0";
+  version = "0.16.0";
 
   src = python3Packages.fetchPypi {
     inherit pname version;
-    sha256 = "1yxfznd78zkg2f657v520zj5w4dvq5n594d0kpm4lra8xnpg4zcv";
+    sha256 = "17azqlb1xsnh9p0m75apb19j7pramgj00cf5k6fwzz2zqz0x0hpp";
   };
 
   postPatch = ''
-    # drop upper bound of acme requirement
-    sed -ri "s/'(acme>=[^,]+),<[^']+'/'\1'/" setup.py
     # drop upper bound of idna requirement
     sed -ri "s/'(idna)<[^']+'/'\1'/" setup.py
     substituteInPlace simp_le.py \
diff --git a/pkgs/top-level/all-packages.nix b/pkgs/top-level/all-packages.nix
index f55bcd7a195013..32cf7b480e198a 100644
--- a/pkgs/top-level/all-packages.nix
+++ b/pkgs/top-level/all-packages.nix
@@ -922,6 +922,8 @@ in
 
   m-cli = callPackage ../os-specific/darwin/m-cli { };
 
+  pebble = callPackage ../tools/admin/pebble { };
+
   reattach-to-user-namespace = callPackage ../os-specific/darwin/reattach-to-user-namespace {};
 
   skhd = callPackage ../os-specific/darwin/skhd {