diff --git a/.gitignore b/.gitignore
index 341843f98..38c95986c 100644
--- a/.gitignore
+++ b/.gitignore
@@ -6,6 +6,7 @@ dist*/
 /venv*/
 /kgs/
 /.tox/
+/releases/
 letsencrypt.log
 
 # coverage
diff --git a/acme/setup.py b/acme/setup.py
index 5a77f8a67..0843288e6 100644
--- a/acme/setup.py
+++ b/acme/setup.py
@@ -18,7 +18,9 @@ install_requires = [
     'pyrfc3339',
     'pytz',
     'requests',
-    'setuptools',  # pkg_resources
+    # For pkg_resources. >=1.0 so pip resolves it to a version cryptography
+    # will tolerate; see #2599:
+    'setuptools>=1.0',
     'six',
 ]
 
diff --git a/letsencrypt-apache/setup.py b/letsencrypt-apache/setup.py
index a8e010f0e..46f4da54c 100644
--- a/letsencrypt-apache/setup.py
+++ b/letsencrypt-apache/setup.py
@@ -11,7 +11,9 @@ install_requires = [
     'acme=={0}'.format(version),
     'letsencrypt=={0}'.format(version),
     'python-augeas',
-    'setuptools',  # pkg_resources
+    # For pkg_resources. >=1.0 so pip resolves it to a version cryptography
+    # will tolerate; see #2599:
+    'setuptools>=1.0',
     'zope.component',
     'zope.interface',
 ]
diff --git a/letsencrypt-auto b/letsencrypt-auto
index 9218bdc52..86367a5c0 100755
--- a/letsencrypt-auto
+++ b/letsencrypt-auto
@@ -18,25 +18,31 @@ set -e  # Work even if somebody does "sh thisscript.sh".
 XDG_DATA_HOME=${XDG_DATA_HOME:-~/.local/share}
 VENV_NAME="letsencrypt"
 VENV_PATH=${VENV_PATH:-"$XDG_DATA_HOME/$VENV_NAME"}
-VENV_BIN=${VENV_PATH}/bin
-LE_AUTO_VERSION="0.4.0"
+VENV_BIN="$VENV_PATH/bin"
+LE_AUTO_VERSION="0.4.1"
 
 # This script takes the same arguments as the main letsencrypt program, but it
 # additionally responds to --verbose (more output) and --debug (allow support
 # for experimental platforms)
 for arg in "$@" ; do
-  # This first clause is redundant with the third, but hedging on portability
-  if [ "$arg" = "-v" ] || [ "$arg" = "--verbose" ] || echo "$arg" | grep -E -- "-v+$" ; then
-    VERBOSE=1
-  elif [ "$arg" = "--no-self-upgrade" ] ; then
-    # Do not upgrade this script (also prevents client upgrades, because each
-    # copy of the script pins a hash of the python client)
-    NO_SELF_UPGRADE=1
-  elif [ "$arg" = "--os-packages-only" ] ; then
-    OS_PACKAGES_ONLY=1
-  elif [ "$arg" = "--debug" ]; then
-    DEBUG=1
-  fi
+  case "$arg" in
+    --debug)
+      DEBUG=1;;
+    --os-packages-only)
+      OS_PACKAGES_ONLY=1;;
+    --no-self-upgrade)
+      # Do not upgrade this script (also prevents client upgrades, because each
+      # copy of the script pins a hash of the python client)
+      NO_SELF_UPGRADE=1;;
+    --verbose)
+      VERBOSE=1;;
+    [!-]*|-*[!v]*|-)
+      # Anything that isn't -v, -vv, etc.: that is, anything that does not
+      # start with a -, contains anything that's not a v, or is just "-"
+      ;;
+    *)  # -v+ remains.
+      VERBOSE=1;;
+  esac
 done
 
 # letsencrypt-auto needs root access to bootstrap OS dependencies, and
@@ -91,21 +97,18 @@ ExperimentalBootstrap() {
 }
 
 DeterminePythonVersion() {
-  if command -v python2.7 > /dev/null ; then
-    export LE_PYTHON=${LE_PYTHON:-python2.7}
-  elif command -v python27 > /dev/null ; then
-    export LE_PYTHON=${LE_PYTHON:-python27}
-  elif command -v python2 > /dev/null ; then
-    export LE_PYTHON=${LE_PYTHON:-python2}
-  elif command -v python > /dev/null ; then
-    export LE_PYTHON=${LE_PYTHON:-python}
-  else
-    echo "Cannot find any Pythons... please install one!"
+  for LE_PYTHON in "$LE_PYTHON" python2.7 python27 python2 python; do
+    # Break (while keeping the LE_PYTHON value) if found.
+    command -v "$LE_PYTHON" > /dev/null && break
+  done
+  if [ "$?" != "0" ]; then
+    echo "Cannot find any Pythons; please install one!"
     exit 1
   fi
+  export LE_PYTHON
 
-  PYVER=`"$LE_PYTHON" --version 2>&1 | cut -d" " -f 2 | cut -d. -f1,2 | sed 's/\.//'`
-  if [ $PYVER -lt 26 ]; then
+  PYVER=`"$LE_PYTHON" -V 2>&1 | cut -d" " -f 2 | cut -d. -f1,2 | sed 's/\.//'`
+  if [ "$PYVER" -lt 26 ]; then
     echo "You have an ancient version of Python entombed in your operating system..."
     echo "This isn't going to work; you'll need at least version 2.6."
     exit 1
@@ -165,7 +168,7 @@ BootstrapDebCommon() {
                   /bin/echo '(Backports are only installed if explicitly requested via "apt-get install -t wheezy-backports")'
               fi
 
-              sudo sh -c "echo $BACKPORT_SOURCELINE >> /etc/apt/sources.list.d/$BACKPORT_NAME.list"
+              $SUDO sh -c "echo $BACKPORT_SOURCELINE >> /etc/apt/sources.list.d/$BACKPORT_NAME.list"
               $SUDO apt-get update
           fi
       fi
@@ -304,10 +307,11 @@ BootstrapArchCommon() {
     pkg-config
   "
 
-  missing=$("$SUDO" pacman -T $deps)
+  # pacman -T exits with 127 if there are missing dependencies
+  missing=$($SUDO pacman -T $deps) || true
 
   if [ "$missing" ]; then
-    "$SUDO" pacman -S --needed $missing
+    $SUDO pacman -S --needed $missing
   fi
 }
 
@@ -324,19 +328,19 @@ BootstrapGentooCommon() {
 
   case "$PACKAGE_MANAGER" in
     (paludis)
-      "$SUDO" cave resolve --keep-targets if-possible $PACKAGES -x
+      $SUDO cave resolve --preserve-world --keep-targets if-possible $PACKAGES -x
       ;;
     (pkgcore)
-      "$SUDO" pmerge --noreplace $PACKAGES
+      $SUDO pmerge --noreplace --oneshot $PACKAGES
       ;;
     (portage|*)
-      "$SUDO" emerge --noreplace $PACKAGES
+      $SUDO emerge --noreplace --oneshot $PACKAGES
       ;;
   esac
 }
 
 BootstrapFreeBsd() {
-  "$SUDO" pkg install -Ay \
+  $SUDO pkg install -Ay \
     python \
     py27-virtualenv \
     augeas \
@@ -345,20 +349,27 @@ BootstrapFreeBsd() {
 
 BootstrapMac() {
   if ! hash brew 2>/dev/null; then
-      echo "Homebrew Not Installed\nDownloading..."
+      echo "Homebrew not installed.\nDownloading..."
       ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)"
   fi
 
-  brew install augeas
-  brew install dialog
+  if [ -z "$(brew list --versions augeas)" ]; then
+      echo "augeas not installed.\nInstalling augeas from Homebrew..."
+      brew install augeas
+  fi
 
-  if ! hash pip 2>/dev/null; then
-      echo "pip Not Installed\nInstalling python from Homebrew..."
+  if [ -z "$(brew list --versions dialog)" ]; then
+      echo "dialog not installed.\nInstalling dialog from Homebrew..."
+      brew install dialog
+  fi
+
+  if [ -z "$(brew list --versions python)" ]; then
+      echo "python not installed.\nInstalling python from Homebrew..."
       brew install python
   fi
 
   if ! hash virtualenv 2>/dev/null; then
-      echo "virtualenv Not Installed\nInstalling with pip"
+      echo "virtualenv not installed.\nInstalling with pip..."
       pip install virtualenv
   fi
 }
@@ -412,9 +423,10 @@ TempDir() {
 
 
 
-if [ "$NO_SELF_UPGRADE" = 1 ]; then
+if [ "$1" = "--le-auto-phase2" ]; then
   # Phase 2: Create venv, install LE, and run.
 
+  shift 1  # the --le-auto-phase2 arg
   if [ -f "$VENV_BIN/letsencrypt" ]; then
     INSTALLED_VERSION=$("$VENV_BIN/letsencrypt" --version 2>&1 | cut -d " " -f 2)
   else
@@ -609,10 +621,6 @@ traceback2==1.4.0
 # sha256: IogqDkGMKE4fcYqCKzsCKUTVPS2QjhaQsxmp0-ssBXk
 unittest2==1.1.0
 
-# sha256: aUkbUwUVfDxuDwSnAZhNaud_1yn8HJrNJQd_HfOFMms
-# sha256: 619wCpv8lkILBVY1r5AC02YuQ9gMP_0x8iTCW8DV9GI
-Werkzeug==0.11.3
-
 # sha256: KCwRK1XdjjyGmjVx-GdnwVCrEoSprOK97CJsWSrK-Bo
 zope.component==4.2.2
 
@@ -638,22 +646,25 @@ zope.event==4.1.0
 # sha256: sJyMHUezUxxADgGVaX8UFKYyId5u9HhZik8UYPfZo5I
 zope.interface==4.1.3
 
-# sha256: ilvjjTWOS86xchl0WBZ0YOAw_0rmqdnjNsxb1hq2RD8
-# sha256: T37KMj0TnsuvHIzCCmoww2fpfpOBTj7cd4NAqucXcpw
-acme==0.4.0
-
-# sha256: 33BQiANlNLGqGpirTfdCEElTF9YbpaKiYpTbK4zeGD8
-# sha256: lwsV1OdEzzlMeb08C_PRxaCXZ2vOk_1AI2755rZHmPM
-letsencrypt==0.4.0
-
-# sha256: D3YDaVFjLsMSEfjI5B5D5tn5FeWUtNHYXCObw3ih2tg
-# sha256: VTgvsePYGRmI4IOSAnxoYFHd8KciD73bxIuIHtbVFd8
-letsencrypt-apache==0.4.0
-
 # sha256: uDndLZwRfHAUMMFJlWkYpCOphjtIsJyQ4wpgE-fS9E8
 # sha256: j4MIDaoknQNsvM-4rlzG_wB7iNbZN1ITca-r57Gbrbw
 mock==1.0.1
 
+# THE LINES BELOW ARE EDITED BY THE RELEASE SCRIPT;
+# ADD ALL DEPENDENCIES ABOVE
+
+# sha256: zd_qpRKPaFs00y5hex5Rbu5CVLWzed7pBGL28juxoHM
+# sha256: 18Gfo85AbZXE46GyTkyePthTNiUeoGTQNcXlSvmRQvM
+acme==0.4.1
+
+# sha256: wIuGh8yh1TeOClXW0qLz70bKeM9Ax4bfFNrkKSDjbbo
+# sha256: 7TeAUt8cZ0IZQuQNuUm8MoH8vPWlKaCrwWAkdCEs_5s
+letsencrypt==0.4.1
+
+# sha256: bnpKXJTXy9cFSktJLtvTCTovJJybc__Ivqs6XaXxk9U
+# sha256: bcvJ6j5UB8sOJ_M88DAsqvmaLxD2UnAP9ys-_J6Bdcc
+letsencrypt-apache==0.4.1
+
 UNLIKELY_EOF
     # -------------------------------------------------------------------------
     cat << "UNLIKELY_EOF" > "$TEMP_DIR/peep.py"
@@ -745,6 +756,7 @@ except ImportError:
         from pip.util import url_to_path  # 0.7.0
     except ImportError:
         from pip.util import url_to_filename as url_to_path  # 0.6.2
+from pip.exceptions import InstallationError
 from pip.index import PackageFinder, Link
 try:
     from pip.log import logger
@@ -763,7 +775,7 @@ except ImportError:
 
     DownloadProgressBar = DownloadProgressSpinner = NullProgressBar
 
-__version__ = 3, 0, 0
+__version__ = 3, 1, 1
 
 try:
     from pip.index import FormatControl  # noqa
@@ -781,6 +793,7 @@ ITS_FINE_ITS_FINE = 0
 SOMETHING_WENT_WRONG = 1
 # "Traditional" for command-line errors according to optparse docs:
 COMMAND_LINE_ERROR = 2
+UNHANDLED_EXCEPTION = 3
 
 ARCHIVE_EXTENSIONS = ('.tar.bz2', '.tar.gz', '.tgz', '.tar', '.zip')
 
@@ -1543,7 +1556,7 @@ def peep_install(argv):
             first_every_last(buckets[SatisfiedReq], *printers)
 
         return ITS_FINE_ITS_FINE
-    except (UnsupportedRequirementError, DownloadError) as exc:
+    except (UnsupportedRequirementError, InstallationError, DownloadError) as exc:
         out(str(exc))
         return SOMETHING_WENT_WRONG
     finally:
@@ -1563,16 +1576,23 @@ def peep_port(paths):
         print('Please specify one or more requirements files so I have '
               'something to port.\n')
         return COMMAND_LINE_ERROR
+
+    comes_from = None
     for req in chain.from_iterable(
             _parse_requirements(path, package_finder(argv)) for path in paths):
+        req_path, req_line = path_and_line(req)
         hashes = [hexlify(urlsafe_b64decode((hash + '=').encode('ascii'))).decode('ascii')
-                  for hash in hashes_above(*path_and_line(req))]
+                  for hash in hashes_above(req_path, req_line)]
+        if req_path != comes_from:
+            print()
+            print('# from %s' % req_path)
+            print()
+            comes_from = req_path
+
         if not hashes:
             print(req.req)
-        elif len(hashes) == 1:
-            print('%s --hash=sha256:%s' % (req.req, hashes[0]))
         else:
-            print('%s' % req.req, end='')
+            print('%s' % (req.link if getattr(req, 'link', None) else req.req), end='')
             for hash in hashes:
                 print(' \\')
                 print('    --hash=sha256:%s' % hash, end='')
@@ -1617,7 +1637,7 @@ if __name__ == '__main__':
         exit(main())
     except Exception:
         exception_handler(*sys.exc_info())
-        exit(SOMETHING_WENT_WRONG)
+        exit(UNHANDLED_EXCEPTION)
 
 UNLIKELY_EOF
     # -------------------------------------------------------------------------
@@ -1630,8 +1650,10 @@ UNLIKELY_EOF
       # Report error. (Otherwise, be quiet.)
       echo "Had a problem while downloading and verifying Python packages:"
       echo "$PEEP_OUT"
+      rm -rf "$VENV_PATH"
       exit 1
     fi
+    echo "Installation succeeded."
   fi
   echo "Requesting root privileges to run letsencrypt..."
   echo "  " $SUDO "$VENV_BIN/letsencrypt" "$@"
@@ -1653,10 +1675,11 @@ else
     exit 0
   fi
 
-  echo "Checking for new version..."
-  TEMP_DIR=$(TempDir)
-  # ---------------------------------------------------------------------------
-  cat << "UNLIKELY_EOF" > "$TEMP_DIR/fetch.py"
+  if [ "$NO_SELF_UPGRADE" != 1 ]; then
+    echo "Checking for new version..."
+    TEMP_DIR=$(TempDir)
+    # ---------------------------------------------------------------------------
+    cat << "UNLIKELY_EOF" > "$TEMP_DIR/fetch.py"
 """Do downloading and JSON parsing without additional dependencies. ::
 
     # Print latest released version of LE to stdout:
@@ -1785,25 +1808,36 @@ if __name__ == '__main__':
     exit(main())
 
 UNLIKELY_EOF
-  # ---------------------------------------------------------------------------
-  DeterminePythonVersion
-  REMOTE_VERSION=`"$LE_PYTHON" "$TEMP_DIR/fetch.py" --latest-version`
-  if [ "$LE_AUTO_VERSION" != "$REMOTE_VERSION" ]; then
-    echo "Upgrading letsencrypt-auto $LE_AUTO_VERSION to $REMOTE_VERSION..."
+    # ---------------------------------------------------------------------------
+    DeterminePythonVersion
+    REMOTE_VERSION=`"$LE_PYTHON" "$TEMP_DIR/fetch.py" --latest-version`
+    if [ "$LE_AUTO_VERSION" != "$REMOTE_VERSION" ]; then
+      echo "Upgrading letsencrypt-auto $LE_AUTO_VERSION to $REMOTE_VERSION..."
 
-    # Now we drop into Python so we don't have to install even more
-    # dependencies (curl, etc.), for better flow control, and for the option of
-    # future Windows compatibility.
-    "$LE_PYTHON" "$TEMP_DIR/fetch.py" --le-auto-script "v$REMOTE_VERSION"
+      # Now we drop into Python so we don't have to install even more
+      # dependencies (curl, etc.), for better flow control, and for the option of
+      # future Windows compatibility.
+      "$LE_PYTHON" "$TEMP_DIR/fetch.py" --le-auto-script "v$REMOTE_VERSION"
 
-    # Install new copy of letsencrypt-auto. This preserves permissions and
-    # ownership from the old copy.
-    # TODO: Deal with quotes in pathnames.
-    echo "Replacing letsencrypt-auto..."
-    echo "  " $SUDO cp "$TEMP_DIR/letsencrypt-auto" "$0"
-    $SUDO cp "$TEMP_DIR/letsencrypt-auto" "$0"
-    # TODO: Clean up temp dir safely, even if it has quotes in its path.
-    rm -rf "$TEMP_DIR"
-  fi  # should upgrade
-  "$0" --no-self-upgrade "$@"
+      # Install new copy of letsencrypt-auto.
+      # TODO: Deal with quotes in pathnames.
+      echo "Replacing letsencrypt-auto..."
+      # Clone permissions with cp. chmod and chown don't have a --reference
+      # option on OS X or BSD, and stat -c on Linux is stat -f on OS X and BSD:
+      echo "  " $SUDO cp -p "$0" "$TEMP_DIR/letsencrypt-auto.permission-clone"
+      $SUDO cp -p "$0" "$TEMP_DIR/letsencrypt-auto.permission-clone"
+      echo "  " $SUDO cp "$TEMP_DIR/letsencrypt-auto" "$TEMP_DIR/letsencrypt-auto.permission-clone"
+      $SUDO cp "$TEMP_DIR/letsencrypt-auto" "$TEMP_DIR/letsencrypt-auto.permission-clone"
+      # Using mv rather than cp leaves the old file descriptor pointing to the
+      # original copy so the shell can continue to read it unmolested. mv across
+      # filesystems is non-atomic, doing `rm dest, cp src dest, rm src`, but the
+      # cp is unlikely to fail (esp. under sudo) if the rm doesn't.
+      echo "  " $SUDO mv -f "$TEMP_DIR/letsencrypt-auto.permission-clone" "$0"
+      $SUDO mv -f "$TEMP_DIR/letsencrypt-auto.permission-clone" "$0"
+      # TODO: Clean up temp dir safely, even if it has quotes in its path.
+      rm -rf "$TEMP_DIR"
+    fi  # A newer version is available.
+  fi  # Self-upgrading is allowed.
+
+  "$0" --le-auto-phase2 "$@"
 fi
diff --git a/letsencrypt-auto-source/letsencrypt-auto b/letsencrypt-auto-source/letsencrypt-auto
index 8e9882ffe..9b05092ed 100755
--- a/letsencrypt-auto-source/letsencrypt-auto
+++ b/letsencrypt-auto-source/letsencrypt-auto
@@ -421,6 +421,19 @@ TempDir() {
   mktemp -d 2>/dev/null || mktemp -d -t 'le'  # Linux || OS X
 }
 
+InstallRequirements() {
+    set +e
+    PEEP_OUT=`"$VENV_BIN/python" "$TEMP_DIR/peep.py" install -r "$TEMP_DIR/$1"`
+    PEEP_STATUS=$?
+    set -e
+    if [ "$PEEP_STATUS" != 0 ]; then
+      # Report error. (Otherwise, be quiet.)
+      echo "Had a problem while downloading and verifying Python packages:"
+      echo "$PEEP_OUT"
+      rm -rf "$VENV_PATH"
+      exit 1
+    fi
+}
 
 
 if [ "$1" = "--le-auto-phase2" ]; then
@@ -444,7 +457,17 @@ if [ "$1" = "--le-auto-phase2" ]; then
 
     echo "Installing Python packages..."
     TEMP_DIR=$(TempDir)
+    trap "rm -rf '$TEMP_DIR'" EXIT
     # There is no $ interpolation due to quotes on starting heredoc delimiter.
+    # -------------------------------------------------------------------------
+    cat << "UNLIKELY_EOF" > "$TEMP_DIR/setuptools-requirements.txt"
+# cryptography requires a more modern version of setuptools.
+# sha256: _ANFf7h6utSdwJ-cMTOGNpPn3bbKgrtQpzmnc3nOWpo
+# sha256: JPz8FTZKn-CaIg830tztyEl5Xj3j5LOT7piOZqnL2Fo
+# sha256: gJaELiTE8ddN_xKr6Qwm0S8F0NmlbtXgb8qm-qHkC2o
+setuptools==20.2.2
+
+UNLIKELY_EOF
     # -------------------------------------------------------------------------
     cat << "UNLIKELY_EOF" > "$TEMP_DIR/letsencrypt-auto-requirements.txt"
 # This is the flattened list of packages letsencrypt-auto installs. To generate
@@ -455,6 +478,11 @@ if [ "$1" = "--le-auto-phase2" ]; then
 # sha256: YrCJpVvh2JSc0rx-DfC9254Cj678jDIDjMhIYq791uQ
 argparse==1.4.0
 
+# This comes before cffi because cffi will otherwise install an unchecked
+# version via setup_requires.
+# sha256: eVm0p0q9wnsxL-0cIebK-TCc4LKeqGtZH9Lpns3yf3M
+pycparser==2.14
+
 # sha256: U8HJ3bMEMVE-t_PN7wo-BrDxJSGIqqd0SvD1pM1F268
 # sha256: pWj0nfyhKo2fNwGHJX78WKOBCeHu5xTZKFYdegGKZPg
 # sha256: gJxsqM-8ruv71DK0V2ABtA04_yRjdzy1dXfXXhoCC8M
@@ -479,28 +507,28 @@ ConfigArgParse==0.10.0
 # sha256: ovVlB3DhyH-zNa8Zqbfrc_wFzPIhROto230AzSvLCQI
 configobj==5.0.6
 
-# sha256: 1U_hszrB4J8cEj4vl0948z6V1h1PSALdISIKXD6MEX0
-# sha256: B1X2aE4RhSAFs2MTdh7ctbqEOmTNAizhrC3L1JqTYG0
-# sha256: zjhNo4lZlluh90VKJfVp737yqxRd8ueiml4pS3TgRnc
-# sha256: GvQDkV3LmWHDB2iuZRr6tpKC0dpaut-mN1IhrBGHdQM
-# sha256: ag08d91PH-W8ZfJ--3fsjQSjiNpesl66DiBAwJgZ30o
-# sha256: KdelgcO6_wTh--IAaltHjZ7cfPmib8ijWUkkf09lA3k
-# sha256: IPAWEKpAh_bVadjMIMR4uB8DhIYnWqqx3Dx12VAsZ-A
-# sha256: l9hGUIulDVomml82OK4cFmWbNTFaH0B_oVF2cH2j0Jc
-# sha256: djfqRMLL1NsvLKccsmtmPRczORqnafi8g2xZVilbd5g
-# sha256: gR-eqJVbPquzLgQGU0XDB4Ui5rPuPZLz0n08fNcWpjM
-# sha256: DXCMjYz97Qm4fCoLqHY856ZjWG4EPmrEL9eDHpKQHLY
-# sha256: Efnq11YqPgATWGytM5o_em9Yg8zhw7S5jhrGnft3p_Y
-# sha256: dNhnm55-0ePs-wq1NNyTUruxz3PTYsmQkJTAlyivqJY
-# sha256: z1Hd-123eBaiB1OKZgEUuC4w4IAD_uhJmwILi4SA2sU
-# sha256: 47DEQpj8HBSa-_TImW-5JCeuQeRkm5NMpJWZG3hSuFU
-# sha256: dITvgYGUFB3_eUdf-74vd6-FHiw7v-Lk1ZEjEi-KTjM
-# sha256: 7gLB6J7l7pUBV6VK1YTXN8Ec83putMCFPozz8n6WLcA
-# sha256: pfGPaxhQpVVKV9v2YsrSUSpGBW5paHJqmFjngN1bnQo
-# sha256: 26GA8xrb5xi6qdbPirY0hJSwlLK4GAL_8zvVDSfRPnM
-# sha256: 5RinlLjzjoOC9_B3kUGBPOtIE6z9MRVBwNsOGJ69eN4
-# sha256: f1FFn4TWcERCdeYVg59FQsk1R6Euk4oKSQba_l994VM
-cryptography==1.1.2
+# sha256: Axk49zpcXrPoCeGP98rraGU1GHFBe-YFDLjIapogK5o
+# sha256: oXmjjVD41otJHXoxPbePjKvikIQs7N3dx7NNQI5Z2wo
+# sha256: kGyIsqrc-Zz6uyQJgmPRv2WrDIaIrN4Q2uHwnYZZIPE
+# sha256: bnBsXGCIdwsdG2NOlZ4hlj4xWwJV9fR3cSWtPVQIKXc
+# sha256: 9ev44xxI-HB5Idyg6ZTed4E6nJub8DwRnF3fl73P_nM
+# sha256: x7ieQiiMx_vuOBLpnvXHRPIkUuEdaCL2gHr8bWs76D4
+# sha256: hAjSmGWUcQnYto8YN6fN4apNyG4Peco7pYwMRORD1qU
+# sha256: x-ds88PZJd0x-iOM-4Bs_7pxjA8IcH13pTh2hHeWmVY
+# sha256: fY3jU4DzFwJ1i3dTu1xAcjgyxzAG3tsvkJm_YaN_coc
+# sha256: XtvucfrlRp7oP-CjeGa5OYyM46RjJcJPzt-_CXu0ihk
+# sha256: WU7a_kgBwTvcHMMF53BKkMGWF-lZNvarRX7k_-AAulA
+# sha256: t_2xagp_SBvkLadEv-HqIWMCXeIfkPLGiKMW88NU2pw
+# sha256: IHuL8P4JBzNt84tzO0h1Ic-eE4GJq6kjStVP5UXdDbg
+# sha256: UJovBThicM94OZPJDUn_77PdYq7kW_HqjOPSzecnHCE
+# sha256: rGm2XdGvAXnt5AyfFXiMiPc-Yo6mwFGd44OOJ5uziMY
+# sha256: jfb61sauEv1wBOopNX8KK003dOrsp2VlMNCNLZDNQao
+# sha256: C4uW3YHMFTOgTzA4LA_iHBly4Yn3lNDEJhoYzsCP2bU
+# sha256: yuj8oYg_I8UOp42J3m_k_v20zqgxd3YPRxd1WUFN7ZM
+# sha256: GkccpXapzc4bHNnzoisdCe5E1GhiA3VX3heRnA20RCU
+# sha256: jsTo49RTs6G2O19Xc3pDTc8e5KLyb2_3xaN8P2eRBNI
+# sha256: jrEcd92Oc_SN9rL3p-Fhc_4P6P3-JmIygy6IR34IRU4
+cryptography==1.2.3
 
 # sha256: JHXX_N31lR6S_1RpcnWIAt5SYL9Akxmp8ZNOa7yLHcc
 # sha256: NZB977D5krdat3iPZf7cHPIP-iJojg5vbxKvwGs-pQE
@@ -528,9 +556,9 @@ ndg-httpsclient==0.4.0
 # sha256: HDW0rCBs7y0kgWyJ-Jzyid09OM98RJuz-re_bUPwGx8
 ordereddict==1.1
 
-# sha256: OnTxAPkNZZGDFf5kkHca0gi8PxOv0y01_P5OjQs7gSs
-# sha256: Paa-K-UG9ZzOMuGeMOIBBT4btNB-JWaJGOAPikmtQKs
-parsedatetime==1.5
+# sha256: zp1CIWXPbpY5Bc1fdPJ06_fMmMlBkWFpF475Pw5VeDg
+# sha256: F8V4d1UgyZExY04Jz8paBeqeG9KgXNBpZ-vs4Q33ry0
+parsedatetime==2.1
 
 # sha256: Rsjbda51oFa9HMB_ohc0_i5gPRGgeDPswe63TDXHLgw
 # sha256: 4hJ2JqkebIhduJZol22zECDwry2nKJJLVkgPx8zwlkk
@@ -572,9 +600,6 @@ psutil==3.3.0
 # sha256: hTys2W0fcB3dZ6oD7MBfUYkBNbcmLpInEBEvEqLtKn8
 pyasn1==0.1.9
 
-# sha256: eVm0p0q9wnsxL-0cIebK-TCc4LKeqGtZH9Lpns3yf3M
-pycparser==2.14
-
 # sha256: iORea7Jd_tJyoe8ucoRh1EtjTCzWiemJtuVqNJxaOuU
 # sha256: 8KJgcNbbCIHei8x4RpNLfDyTDY-cedRYg-5ImEvA1nI
 pyOpenSSL==0.15.1
@@ -646,22 +671,25 @@ zope.event==4.1.0
 # sha256: sJyMHUezUxxADgGVaX8UFKYyId5u9HhZik8UYPfZo5I
 zope.interface==4.1.3
 
-# sha256: ilvjjTWOS86xchl0WBZ0YOAw_0rmqdnjNsxb1hq2RD8
-# sha256: T37KMj0TnsuvHIzCCmoww2fpfpOBTj7cd4NAqucXcpw
-acme==0.4.0
-
-# sha256: 33BQiANlNLGqGpirTfdCEElTF9YbpaKiYpTbK4zeGD8
-# sha256: lwsV1OdEzzlMeb08C_PRxaCXZ2vOk_1AI2755rZHmPM
-letsencrypt==0.4.0
-
-# sha256: D3YDaVFjLsMSEfjI5B5D5tn5FeWUtNHYXCObw3ih2tg
-# sha256: VTgvsePYGRmI4IOSAnxoYFHd8KciD73bxIuIHtbVFd8
-letsencrypt-apache==0.4.0
-
 # sha256: uDndLZwRfHAUMMFJlWkYpCOphjtIsJyQ4wpgE-fS9E8
 # sha256: j4MIDaoknQNsvM-4rlzG_wB7iNbZN1ITca-r57Gbrbw
 mock==1.0.1
 
+# THE LINES BELOW ARE EDITED BY THE RELEASE SCRIPT;
+# ADD ALL DEPENDENCIES ABOVE
+
+# sha256: zd_qpRKPaFs00y5hex5Rbu5CVLWzed7pBGL28juxoHM
+# sha256: 18Gfo85AbZXE46GyTkyePthTNiUeoGTQNcXlSvmRQvM
+acme==0.4.1
+
+# sha256: wIuGh8yh1TeOClXW0qLz70bKeM9Ax4bfFNrkKSDjbbo
+# sha256: 7TeAUt8cZ0IZQuQNuUm8MoH8vPWlKaCrwWAkdCEs_5s
+letsencrypt==0.4.1
+
+# sha256: bnpKXJTXy9cFSktJLtvTCTovJJybc__Ivqs6XaXxk9U
+# sha256: bcvJ6j5UB8sOJ_M88DAsqvmaLxD2UnAP9ys-_J6Bdcc
+letsencrypt-apache==0.4.1
+
 UNLIKELY_EOF
     # -------------------------------------------------------------------------
     cat << "UNLIKELY_EOF" > "$TEMP_DIR/peep.py"
@@ -1638,18 +1666,8 @@ if __name__ == '__main__':
 
 UNLIKELY_EOF
     # -------------------------------------------------------------------------
-    set +e
-    PEEP_OUT=`"$VENV_BIN/python" "$TEMP_DIR/peep.py" install -r "$TEMP_DIR/letsencrypt-auto-requirements.txt"`
-    PEEP_STATUS=$?
-    set -e
-    rm -rf "$TEMP_DIR"
-    if [ "$PEEP_STATUS" != 0 ]; then
-      # Report error. (Otherwise, be quiet.)
-      echo "Had a problem while downloading and verifying Python packages:"
-      echo "$PEEP_OUT"
-      rm -rf "$VENV_PATH"
-      exit 1
-    fi
+    InstallRequirements "setuptools-requirements.txt"
+    InstallRequirements "letsencrypt-auto-requirements.txt"
     echo "Installation succeeded."
   fi
   echo "Requesting root privileges to run letsencrypt..."
diff --git a/letsencrypt-auto-source/letsencrypt-auto.sig b/letsencrypt-auto-source/letsencrypt-auto.sig
index 532a48207..e6d597298 100644
Binary files a/letsencrypt-auto-source/letsencrypt-auto.sig and b/letsencrypt-auto-source/letsencrypt-auto.sig differ
diff --git a/letsencrypt-auto-source/letsencrypt-auto.sig.lzma.base64 b/letsencrypt-auto-source/letsencrypt-auto.sig.lzma.base64
new file mode 100644
index 000000000..829e274f0
--- /dev/null
+++ b/letsencrypt-auto-source/letsencrypt-auto.sig.lzma.base64
@@ -0,0 +1,6 @@
+XQAAAAT//////////wBCghGWcdbIc2Jwx9eNx/8BCz2bNPFlhMANgkl2y9DXQ35eeVwpAz1hka/X
+mbAtebf8wyUrVCYJ295X4aa52T2/hffWukE1K2mV5ZNV2IstEohx5ghX536mksyW2pLB5K6pttTs
+Zg4DW17p/vWM/VczjT5yhIlR+ZAKcSKGSiMhJXLnvF0UKcQ6RJ2CFdfQhPkEEtjHlWPPlLRc8K9/
+DyPI1KeAoER9MMl/sZELr7gRJh8vpDV9XtVwQ0RhH59/Xze6s/WvaMf2C08IWysSW/BulLu9YbEs
+oOiW7OKECzryCNcg4+QISNcoiKUEDGUYbQWMfcB1I0hYjl5HZ332R1ljr9UbdGGdUAF0zby+LvrT
+///9TmAA
diff --git a/letsencrypt-auto-source/letsencrypt-auto.template b/letsencrypt-auto-source/letsencrypt-auto.template
index ea4d064b7..291d2ee9e 100755
--- a/letsencrypt-auto-source/letsencrypt-auto.template
+++ b/letsencrypt-auto-source/letsencrypt-auto.template
@@ -169,6 +169,19 @@ TempDir() {
   mktemp -d 2>/dev/null || mktemp -d -t 'le'  # Linux || OS X
 }
 
+InstallRequirements() {
+    set +e
+    PEEP_OUT=`"$VENV_BIN/python" "$TEMP_DIR/peep.py" install -r "$TEMP_DIR/$1"`
+    PEEP_STATUS=$?
+    set -e
+    if [ "$PEEP_STATUS" != 0 ]; then
+      # Report error. (Otherwise, be quiet.)
+      echo "Had a problem while downloading and verifying Python packages:"
+      echo "$PEEP_OUT"
+      rm -rf "$VENV_PATH"
+      exit 1
+    fi
+}
 
 
 if [ "$1" = "--le-auto-phase2" ]; then
@@ -192,7 +205,12 @@ if [ "$1" = "--le-auto-phase2" ]; then
 
     echo "Installing Python packages..."
     TEMP_DIR=$(TempDir)
+    trap "rm -rf '$TEMP_DIR'" EXIT
     # There is no $ interpolation due to quotes on starting heredoc delimiter.
+    # -------------------------------------------------------------------------
+    cat << "UNLIKELY_EOF" > "$TEMP_DIR/setuptools-requirements.txt"
+{{ setuptools-requirements.txt }}
+UNLIKELY_EOF
     # -------------------------------------------------------------------------
     cat << "UNLIKELY_EOF" > "$TEMP_DIR/letsencrypt-auto-requirements.txt"
 {{ letsencrypt-auto-requirements.txt }}
@@ -202,18 +220,8 @@ UNLIKELY_EOF
 {{ peep.py }}
 UNLIKELY_EOF
     # -------------------------------------------------------------------------
-    set +e
-    PEEP_OUT=`"$VENV_BIN/python" "$TEMP_DIR/peep.py" install -r "$TEMP_DIR/letsencrypt-auto-requirements.txt"`
-    PEEP_STATUS=$?
-    set -e
-    rm -rf "$TEMP_DIR"
-    if [ "$PEEP_STATUS" != 0 ]; then
-      # Report error. (Otherwise, be quiet.)
-      echo "Had a problem while downloading and verifying Python packages:"
-      echo "$PEEP_OUT"
-      rm -rf "$VENV_PATH"
-      exit 1
-    fi
+    InstallRequirements "setuptools-requirements.txt"
+    InstallRequirements "letsencrypt-auto-requirements.txt"
     echo "Installation succeeded."
   fi
   echo "Requesting root privileges to run letsencrypt..."
diff --git a/letsencrypt-auto-source/pieces/letsencrypt-auto-requirements.txt b/letsencrypt-auto-source/pieces/letsencrypt-auto-requirements.txt
index b258fcfad..381759a5c 100644
--- a/letsencrypt-auto-source/pieces/letsencrypt-auto-requirements.txt
+++ b/letsencrypt-auto-source/pieces/letsencrypt-auto-requirements.txt
@@ -6,6 +6,11 @@
 # sha256: YrCJpVvh2JSc0rx-DfC9254Cj678jDIDjMhIYq791uQ
 argparse==1.4.0
 
+# This comes before cffi because cffi will otherwise install an unchecked
+# version via setup_requires.
+# sha256: eVm0p0q9wnsxL-0cIebK-TCc4LKeqGtZH9Lpns3yf3M
+pycparser==2.14
+
 # sha256: U8HJ3bMEMVE-t_PN7wo-BrDxJSGIqqd0SvD1pM1F268
 # sha256: pWj0nfyhKo2fNwGHJX78WKOBCeHu5xTZKFYdegGKZPg
 # sha256: gJxsqM-8ruv71DK0V2ABtA04_yRjdzy1dXfXXhoCC8M
@@ -30,28 +35,28 @@ ConfigArgParse==0.10.0
 # sha256: ovVlB3DhyH-zNa8Zqbfrc_wFzPIhROto230AzSvLCQI
 configobj==5.0.6
 
-# sha256: 1U_hszrB4J8cEj4vl0948z6V1h1PSALdISIKXD6MEX0
-# sha256: B1X2aE4RhSAFs2MTdh7ctbqEOmTNAizhrC3L1JqTYG0
-# sha256: zjhNo4lZlluh90VKJfVp737yqxRd8ueiml4pS3TgRnc
-# sha256: GvQDkV3LmWHDB2iuZRr6tpKC0dpaut-mN1IhrBGHdQM
-# sha256: ag08d91PH-W8ZfJ--3fsjQSjiNpesl66DiBAwJgZ30o
-# sha256: KdelgcO6_wTh--IAaltHjZ7cfPmib8ijWUkkf09lA3k
-# sha256: IPAWEKpAh_bVadjMIMR4uB8DhIYnWqqx3Dx12VAsZ-A
-# sha256: l9hGUIulDVomml82OK4cFmWbNTFaH0B_oVF2cH2j0Jc
-# sha256: djfqRMLL1NsvLKccsmtmPRczORqnafi8g2xZVilbd5g
-# sha256: gR-eqJVbPquzLgQGU0XDB4Ui5rPuPZLz0n08fNcWpjM
-# sha256: DXCMjYz97Qm4fCoLqHY856ZjWG4EPmrEL9eDHpKQHLY
-# sha256: Efnq11YqPgATWGytM5o_em9Yg8zhw7S5jhrGnft3p_Y
-# sha256: dNhnm55-0ePs-wq1NNyTUruxz3PTYsmQkJTAlyivqJY
-# sha256: z1Hd-123eBaiB1OKZgEUuC4w4IAD_uhJmwILi4SA2sU
-# sha256: 47DEQpj8HBSa-_TImW-5JCeuQeRkm5NMpJWZG3hSuFU
-# sha256: dITvgYGUFB3_eUdf-74vd6-FHiw7v-Lk1ZEjEi-KTjM
-# sha256: 7gLB6J7l7pUBV6VK1YTXN8Ec83putMCFPozz8n6WLcA
-# sha256: pfGPaxhQpVVKV9v2YsrSUSpGBW5paHJqmFjngN1bnQo
-# sha256: 26GA8xrb5xi6qdbPirY0hJSwlLK4GAL_8zvVDSfRPnM
-# sha256: 5RinlLjzjoOC9_B3kUGBPOtIE6z9MRVBwNsOGJ69eN4
-# sha256: f1FFn4TWcERCdeYVg59FQsk1R6Euk4oKSQba_l994VM
-cryptography==1.1.2
+# sha256: Axk49zpcXrPoCeGP98rraGU1GHFBe-YFDLjIapogK5o
+# sha256: oXmjjVD41otJHXoxPbePjKvikIQs7N3dx7NNQI5Z2wo
+# sha256: kGyIsqrc-Zz6uyQJgmPRv2WrDIaIrN4Q2uHwnYZZIPE
+# sha256: bnBsXGCIdwsdG2NOlZ4hlj4xWwJV9fR3cSWtPVQIKXc
+# sha256: 9ev44xxI-HB5Idyg6ZTed4E6nJub8DwRnF3fl73P_nM
+# sha256: x7ieQiiMx_vuOBLpnvXHRPIkUuEdaCL2gHr8bWs76D4
+# sha256: hAjSmGWUcQnYto8YN6fN4apNyG4Peco7pYwMRORD1qU
+# sha256: x-ds88PZJd0x-iOM-4Bs_7pxjA8IcH13pTh2hHeWmVY
+# sha256: fY3jU4DzFwJ1i3dTu1xAcjgyxzAG3tsvkJm_YaN_coc
+# sha256: XtvucfrlRp7oP-CjeGa5OYyM46RjJcJPzt-_CXu0ihk
+# sha256: WU7a_kgBwTvcHMMF53BKkMGWF-lZNvarRX7k_-AAulA
+# sha256: t_2xagp_SBvkLadEv-HqIWMCXeIfkPLGiKMW88NU2pw
+# sha256: IHuL8P4JBzNt84tzO0h1Ic-eE4GJq6kjStVP5UXdDbg
+# sha256: UJovBThicM94OZPJDUn_77PdYq7kW_HqjOPSzecnHCE
+# sha256: rGm2XdGvAXnt5AyfFXiMiPc-Yo6mwFGd44OOJ5uziMY
+# sha256: jfb61sauEv1wBOopNX8KK003dOrsp2VlMNCNLZDNQao
+# sha256: C4uW3YHMFTOgTzA4LA_iHBly4Yn3lNDEJhoYzsCP2bU
+# sha256: yuj8oYg_I8UOp42J3m_k_v20zqgxd3YPRxd1WUFN7ZM
+# sha256: GkccpXapzc4bHNnzoisdCe5E1GhiA3VX3heRnA20RCU
+# sha256: jsTo49RTs6G2O19Xc3pDTc8e5KLyb2_3xaN8P2eRBNI
+# sha256: jrEcd92Oc_SN9rL3p-Fhc_4P6P3-JmIygy6IR34IRU4
+cryptography==1.2.3
 
 # sha256: JHXX_N31lR6S_1RpcnWIAt5SYL9Akxmp8ZNOa7yLHcc
 # sha256: NZB977D5krdat3iPZf7cHPIP-iJojg5vbxKvwGs-pQE
@@ -79,9 +84,9 @@ ndg-httpsclient==0.4.0
 # sha256: HDW0rCBs7y0kgWyJ-Jzyid09OM98RJuz-re_bUPwGx8
 ordereddict==1.1
 
-# sha256: OnTxAPkNZZGDFf5kkHca0gi8PxOv0y01_P5OjQs7gSs
-# sha256: Paa-K-UG9ZzOMuGeMOIBBT4btNB-JWaJGOAPikmtQKs
-parsedatetime==1.5
+# sha256: zp1CIWXPbpY5Bc1fdPJ06_fMmMlBkWFpF475Pw5VeDg
+# sha256: F8V4d1UgyZExY04Jz8paBeqeG9KgXNBpZ-vs4Q33ry0
+parsedatetime==2.1
 
 # sha256: Rsjbda51oFa9HMB_ohc0_i5gPRGgeDPswe63TDXHLgw
 # sha256: 4hJ2JqkebIhduJZol22zECDwry2nKJJLVkgPx8zwlkk
@@ -123,9 +128,6 @@ psutil==3.3.0
 # sha256: hTys2W0fcB3dZ6oD7MBfUYkBNbcmLpInEBEvEqLtKn8
 pyasn1==0.1.9
 
-# sha256: eVm0p0q9wnsxL-0cIebK-TCc4LKeqGtZH9Lpns3yf3M
-pycparser==2.14
-
 # sha256: iORea7Jd_tJyoe8ucoRh1EtjTCzWiemJtuVqNJxaOuU
 # sha256: 8KJgcNbbCIHei8x4RpNLfDyTDY-cedRYg-5ImEvA1nI
 pyOpenSSL==0.15.1
@@ -197,18 +199,21 @@ zope.event==4.1.0
 # sha256: sJyMHUezUxxADgGVaX8UFKYyId5u9HhZik8UYPfZo5I
 zope.interface==4.1.3
 
-# sha256: ilvjjTWOS86xchl0WBZ0YOAw_0rmqdnjNsxb1hq2RD8
-# sha256: T37KMj0TnsuvHIzCCmoww2fpfpOBTj7cd4NAqucXcpw
-acme==0.4.0
-
-# sha256: 33BQiANlNLGqGpirTfdCEElTF9YbpaKiYpTbK4zeGD8
-# sha256: lwsV1OdEzzlMeb08C_PRxaCXZ2vOk_1AI2755rZHmPM
-letsencrypt==0.4.0
-
-# sha256: D3YDaVFjLsMSEfjI5B5D5tn5FeWUtNHYXCObw3ih2tg
-# sha256: VTgvsePYGRmI4IOSAnxoYFHd8KciD73bxIuIHtbVFd8
-letsencrypt-apache==0.4.0
-
 # sha256: uDndLZwRfHAUMMFJlWkYpCOphjtIsJyQ4wpgE-fS9E8
 # sha256: j4MIDaoknQNsvM-4rlzG_wB7iNbZN1ITca-r57Gbrbw
 mock==1.0.1
+
+# THE LINES BELOW ARE EDITED BY THE RELEASE SCRIPT;
+# ADD ALL DEPENDENCIES ABOVE
+
+# sha256: zd_qpRKPaFs00y5hex5Rbu5CVLWzed7pBGL28juxoHM
+# sha256: 18Gfo85AbZXE46GyTkyePthTNiUeoGTQNcXlSvmRQvM
+acme==0.4.1
+
+# sha256: wIuGh8yh1TeOClXW0qLz70bKeM9Ax4bfFNrkKSDjbbo
+# sha256: 7TeAUt8cZ0IZQuQNuUm8MoH8vPWlKaCrwWAkdCEs_5s
+letsencrypt==0.4.1
+
+# sha256: bnpKXJTXy9cFSktJLtvTCTovJJybc__Ivqs6XaXxk9U
+# sha256: bcvJ6j5UB8sOJ_M88DAsqvmaLxD2UnAP9ys-_J6Bdcc
+letsencrypt-apache==0.4.1
diff --git a/letsencrypt-auto-source/pieces/setuptools-requirements.txt b/letsencrypt-auto-source/pieces/setuptools-requirements.txt
new file mode 100644
index 000000000..ab9d30da2
--- /dev/null
+++ b/letsencrypt-auto-source/pieces/setuptools-requirements.txt
@@ -0,0 +1,5 @@
+# cryptography requires a more modern version of setuptools.
+# sha256: _ANFf7h6utSdwJ-cMTOGNpPn3bbKgrtQpzmnc3nOWpo
+# sha256: JPz8FTZKn-CaIg830tztyEl5Xj3j5LOT7piOZqnL2Fo
+# sha256: gJaELiTE8ddN_xKr6Qwm0S8F0NmlbtXgb8qm-qHkC2o
+setuptools==20.2.2
diff --git a/letsencrypt-nginx/setup.py b/letsencrypt-nginx/setup.py
index 656d6e04f..e53bef059 100644
--- a/letsencrypt-nginx/setup.py
+++ b/letsencrypt-nginx/setup.py
@@ -12,7 +12,9 @@ install_requires = [
     'letsencrypt=={0}'.format(version),
     'PyOpenSSL',
     'pyparsing>=1.5.5',  # Python3 support; perhaps unnecessary?
-    'setuptools',  # pkg_resources
+    # For pkg_resources. >=1.0 so pip resolves it to a version cryptography
+    # will tolerate; see #2599:
+    'setuptools>=1.0',
     'zope.interface',
 ]
 
diff --git a/letsencrypt/cli.py b/letsencrypt/cli.py
index 3551d5a10..024f53d0b 100644
--- a/letsencrypt/cli.py
+++ b/letsencrypt/cli.py
@@ -19,6 +19,7 @@ import traceback
 
 import configargparse
 import OpenSSL
+import six
 import zope.component
 import zope.interface.exceptions
 import zope.interface.verify
@@ -806,12 +807,18 @@ def _restore_required_config_elements(config, renewalparams):
     # int-valued items to add if they're present
     for config_item in INT_CONFIG_ITEMS:
         if config_item in renewalparams and not _set_by_cli(config_item):
-            try:
-                value = int(renewalparams[config_item])
-                setattr(config.namespace, config_item, value)
-            except ValueError:
-                raise errors.Error(
-                    "Expected a numeric value for {0}".format(config_item))
+            config_value = renewalparams[config_item]
+            # the default value for http01_port was None during private beta
+            if config_item == "http01_port" and config_value == "None":
+                logger.info("updating legacy http01_port value")
+                int_value = flag_default("http01_port")
+            else:
+                try:
+                    int_value = int(config_value)
+                except ValueError:
+                    raise errors.Error(
+                        "Expected a numeric value for {0}".format(config_item))
+            setattr(config.namespace, config_item, int_value)
 
 
 def _restore_plugin_configs(config, renewalparams):
@@ -842,7 +849,7 @@ def _restore_plugin_configs(config, renewalparams):
     if renewalparams.get("installer", None) is not None:
         plugin_prefixes.append(renewalparams["installer"])
     for plugin_prefix in set(plugin_prefixes):
-        for config_item, config_value in renewalparams.iteritems():
+        for config_item, config_value in six.iteritems(renewalparams):
             if config_item.startswith(plugin_prefix + "_") and not _set_by_cli(config_item):
                 # Values None, True, and False need to be treated specially,
                 # As they don't get parsed correctly based on type
@@ -1159,10 +1166,10 @@ class HelpfulArgumentParser(object):
 
     # List of topics for which additional help can be provided
     HELP_TOPICS = ["all", "security",
-                   "paths", "automation", "testing"] + VERBS.keys()
+                   "paths", "automation", "testing"] + list(six.iterkeys(VERBS))
 
     def __init__(self, args, plugins, detect_defaults=False):
-        plugin_names = [name for name, _p in plugins.iteritems()]
+        plugin_names = list(six.iterkeys(plugins))
         self.help_topics = self.HELP_TOPICS + plugin_names + [None]
         usage, short_usage = usage_strings(plugins)
         self.parser = configargparse.ArgParser(
@@ -1432,7 +1439,7 @@ class HelpfulArgumentParser(object):
         may or may not be displayed as help topics.
 
         """
-        for name, plugin_ep in plugins.iteritems():
+        for name, plugin_ep in six.iteritems(plugins):
             parser_or_group = self.add_group(name, description=plugin_ep.description)
             #print(parser_or_group)
             plugin_ep.plugin_cls.inject_parser_options(parser_or_group, name)
@@ -1827,7 +1834,7 @@ def _process_domain(args_or_config, domain_arg, webroot_path=None):
 class WebrootMapProcessor(argparse.Action):  # pylint: disable=missing-docstring
     def __call__(self, parser, args, webroot_map_arg, option_string=None):
         webroot_map = json.loads(webroot_map_arg)
-        for domains, webroot_path in webroot_map.iteritems():
+        for domains, webroot_path in six.iteritems(webroot_map):
             _process_domain(args, domains, [webroot_path])
 
 
diff --git a/letsencrypt/plugins/webroot_test.py b/letsencrypt/plugins/webroot_test.py
index 7a34b3fcc..8c1427340 100644
--- a/letsencrypt/plugins/webroot_test.py
+++ b/letsencrypt/plugins/webroot_test.py
@@ -1,4 +1,7 @@
 """Tests for letsencrypt.plugins.webroot."""
+
+from __future__ import print_function
+
 import errno
 import os
 import shutil
@@ -74,7 +77,7 @@ class AuthenticatorTest(unittest.TestCase):
         os.chmod(self.path, 0o000)
         try:
             open(permission_canary, "r")
-            print "Warning, running tests as root skips permissions tests..."
+            print("Warning, running tests as root skips permissions tests...")
         except IOError:
             # ok, permissions work, test away...
             self.assertRaises(errors.PluginError, self.auth.prepare)
diff --git a/letsencrypt/reporter.py b/letsencrypt/reporter.py
index 81106be34..147928e3c 100644
--- a/letsencrypt/reporter.py
+++ b/letsencrypt/reporter.py
@@ -4,10 +4,10 @@ from __future__ import print_function
 import collections
 import logging
 import os
-import Queue
 import sys
 import textwrap
 
+from six.moves import queue  # pylint: disable=import-error
 import zope.interface
 
 from letsencrypt import interfaces
@@ -21,7 +21,7 @@ logger = logging.getLogger(__name__)
 class Reporter(object):
     """Collects and displays information to the user.
 
-    :ivar `Queue.PriorityQueue` messages: Messages to be displayed to
+    :ivar `queue.PriorityQueue` messages: Messages to be displayed to
         the user.
 
     """
@@ -36,7 +36,7 @@ class Reporter(object):
     _msg_type = collections.namedtuple('ReporterMsg', 'priority text on_crash')
 
     def __init__(self):
-        self.messages = Queue.PriorityQueue()
+        self.messages = queue.PriorityQueue()
 
     def add_message(self, msg, priority, on_crash=True):
         """Adds msg to the list of messages to be printed.
diff --git a/letsencrypt/storage.py b/letsencrypt/storage.py
index 6786ac745..cff2d53e1 100644
--- a/letsencrypt/storage.py
+++ b/letsencrypt/storage.py
@@ -694,7 +694,7 @@ class RenewableCert(object):  # pylint: disable=too-many-instance-attributes
         for i in (cli_config.renewal_configs_dir, cli_config.archive_dir,
                   cli_config.live_dir):
             if not os.path.exists(i):
-                os.makedirs(i, 0700)
+                os.makedirs(i, 0o700)
                 logger.debug("Creating directory %s.", i)
         config_file, config_filename = le_util.unique_lineage_name(
             cli_config.renewal_configs_dir, lineagename)
diff --git a/letsencrypt/tests/cli_test.py b/letsencrypt/tests/cli_test.py
index aef3447c3..bfd3818c1 100644
--- a/letsencrypt/tests/cli_test.py
+++ b/letsencrypt/tests/cli_test.py
@@ -1,15 +1,18 @@
 """Tests for letsencrypt.cli."""
+
+from __future__ import print_function
+
 import argparse
 import functools
 import itertools
 import os
 import shutil
-import StringIO
 import traceback
 import tempfile
 import unittest
 
 import mock
+import six
 
 from acme import jose
 
@@ -81,7 +84,7 @@ class CLITest(unittest.TestCase):  # pylint: disable=too-many-public-methods
 
     def _help_output(self, args):
         "Run a command, and return the ouput string for scrutiny"
-        output = StringIO.StringIO()
+        output = six.StringIO()
         with mock.patch('letsencrypt.cli.sys.stdout', new=output):
             self.assertRaises(SystemExit, self._call_stdout, args)
             out = output.getvalue()
@@ -580,7 +583,7 @@ class CLITest(unittest.TestCase):  # pylint: disable=too-many-public-methods
                                 try:
                                     ret, _, _, _ = self._call(args)
                                     if ret:
-                                        print "Returned", ret
+                                        print("Returned", ret)
                                         raise AssertionError(ret)
                                     assert not error_expected, "renewal should have errored"
                                 except: # pylint: disable=bare-except
@@ -628,8 +631,8 @@ class CLITest(unittest.TestCase):  # pylint: disable=too-many-public-methods
 
     def _dump_log(self):
         with open(os.path.join(self.logs_dir, "letsencrypt.log")) as lf:
-            print "Logs:"
-            print lf.read()
+            print("Logs:")
+            print(lf.read())
 
 
     def _make_test_renewal_conf(self, testfile):
@@ -710,6 +713,12 @@ class CLITest(unittest.TestCase):  # pylint: disable=too-many-public-methods
         self._test_renew_common(renewalparams=renewalparams, error_expected=True,
                                 assert_oc_called=False)
 
+    def test_renew_with_nonetype_http01(self):
+        renewalparams = {'authenticator': 'webroot',
+                         'http01_port': 'None'}
+        self._test_renew_common(renewalparams=renewalparams, error_expected=False,
+                                assert_oc_called=True)
+
     def test_renew_with_bad_domain(self):
         renewalparams = {'authenticator': 'webroot'}
         names = ['*.example.com']
diff --git a/letsencrypt/tests/colored_logging_test.py b/letsencrypt/tests/colored_logging_test.py
index 5b49ec820..4080157fc 100644
--- a/letsencrypt/tests/colored_logging_test.py
+++ b/letsencrypt/tests/colored_logging_test.py
@@ -1,8 +1,9 @@
 """Tests for letsencrypt.colored_logging."""
 import logging
-import StringIO
 import unittest
 
+import six
+
 from letsencrypt import le_util
 
 
@@ -12,7 +13,7 @@ class StreamHandlerTest(unittest.TestCase):
     def setUp(self):
         from letsencrypt import colored_logging
 
-        self.stream = StringIO.StringIO()
+        self.stream = six.StringIO()
         self.stream.isatty = lambda: True
         self.handler = colored_logging.StreamHandler(self.stream)
 
diff --git a/letsencrypt/tests/le_util_test.py b/letsencrypt/tests/le_util_test.py
index 87894f837..191b70801 100644
--- a/letsencrypt/tests/le_util_test.py
+++ b/letsencrypt/tests/le_util_test.py
@@ -4,11 +4,11 @@ import errno
 import os
 import shutil
 import stat
-import StringIO
 import tempfile
 import unittest
 
 import mock
+import six
 
 from letsencrypt import errors
 
@@ -307,14 +307,14 @@ class AddDeprecatedArgumentTest(unittest.TestCase):
         self.assertTrue("--old-option is deprecated" in stderr)
 
     def _get_argparse_warnings(self, args):
-        stderr = StringIO.StringIO()
+        stderr = six.StringIO()
         with mock.patch("letsencrypt.le_util.sys.stderr", new=stderr):
             self.parser.parse_args(args)
         return stderr.getvalue()
 
     def test_help(self):
         self._call("--old-option", 2)
-        stdout = StringIO.StringIO()
+        stdout = six.StringIO()
         with mock.patch("letsencrypt.le_util.sys.stdout", new=stdout):
             try:
                 self.parser.parse_args(["-h"])
diff --git a/letsencrypt/tests/reporter_test.py b/letsencrypt/tests/reporter_test.py
index c848b1cab..26a1105c8 100644
--- a/letsencrypt/tests/reporter_test.py
+++ b/letsencrypt/tests/reporter_test.py
@@ -1,8 +1,9 @@
 """Tests for letsencrypt.reporter."""
-import StringIO
 import sys
 import unittest
 
+import six
+
 
 class ReporterTest(unittest.TestCase):
     """Tests for letsencrypt.reporter.Reporter."""
@@ -12,7 +13,7 @@ class ReporterTest(unittest.TestCase):
         self.reporter = reporter.Reporter()
 
         self.old_stdout = sys.stdout
-        sys.stdout = StringIO.StringIO()
+        sys.stdout = six.StringIO()
 
     def tearDown(self):
         sys.stdout = self.old_stdout
diff --git a/letsencrypt/tests/testdata/sample-renewal-ancient.conf b/letsencrypt/tests/testdata/sample-renewal-ancient.conf
old mode 100755
new mode 100644
diff --git a/letsencrypt/tests/testdata/sample-renewal.conf b/letsencrypt/tests/testdata/sample-renewal.conf
old mode 100755
new mode 100644
index 16778303a..d6ebbd845
--- a/letsencrypt/tests/testdata/sample-renewal.conf
+++ b/letsencrypt/tests/testdata/sample-renewal.conf
@@ -2,7 +2,7 @@ cert = MAGICDIR/live/sample-renewal/cert.pem
 privkey = MAGICDIR/live/sample-renewal/privkey.pem
 chain = MAGICDIR/live/sample-renewal/chain.pem
 fullchain = MAGICDIR/live/sample-renewal/fullchain.pem
-renew_before_expiry = 1 year
+renew_before_expiry = 4 years
 
 # Options and defaults used in the renewal process
 [renewalparams]
diff --git a/letshelp-letsencrypt/letshelp_letsencrypt/apache.py b/letshelp-letsencrypt/letshelp_letsencrypt/apache.py
index ac4e9b831..d7cb05b70 100755
--- a/letshelp-letsencrypt/letshelp_letsencrypt/apache.py
+++ b/letshelp-letsencrypt/letshelp_letsencrypt/apache.py
@@ -1,5 +1,8 @@
 #!/usr/bin/env python
 """Let's Encrypt Apache configuration submission script"""
+
+from __future__ import print_function
+
 import argparse
 import atexit
 import contextlib
@@ -48,20 +51,20 @@ def make_and_verify_selection(server_root, temp_dir):
     """
     copied_files, copied_dirs = copy_config(server_root, temp_dir)
 
-    print textwrap.fill("A secure copy of the files that have been selected "
+    print(textwrap.fill("A secure copy of the files that have been selected "
                         "for submission has been created under {0}. All "
                         "comments have been removed and the files are only "
                         "accessible by the current user. A list of the files "
                         "that have been included is shown below. Please make "
                         "sure that this selection does not contain private "
                         "keys, passwords, or any other sensitive "
-                        "information.".format(temp_dir))
-    print "\nFiles:"
+                        "information.".format(temp_dir)))
+    print("\nFiles:")
     for copied_file in copied_files:
-        print copied_file
-    print "Directories (including all contained files):"
+        print(copied_file)
+    print("Directories (including all contained files):")
     for copied_dir in copied_dirs:
-        print copied_dir
+        print(copied_dir)
 
     sys.stdout.write("\nIs it safe to submit these files? ")
     while True:
diff --git a/setup.py b/setup.py
index cbf0ff89d..b187e6fdb 100644
--- a/setup.py
+++ b/setup.py
@@ -45,7 +45,9 @@ install_requires = [
     'pyrfc3339',
     'python2-pythondialog>=3.2.2rc1',  # Debian squeeze support, cf. #280
     'pytz',
-    'setuptools',  # pkg_resources
+    # For pkg_resources. >=1.0 so pip resolves it to a version cryptography
+    # will tolerate; see #2599:
+    'setuptools>=1.0',
     'six',
     'zope.component',
     'zope.interface',
diff --git a/tests/boulder-integration.sh b/tests/boulder-integration.sh
index 32c292e90..77e866b52 100755
--- a/tests/boulder-integration.sh
+++ b/tests/boulder-integration.sh
@@ -68,7 +68,7 @@ common renew
 CheckCertCount 2
 
 # This will renew because the expiry is less than 10 years from now
-sed -i "4arenew_before_expiry = 10 years" "$root/conf/renewal/le.wtf.conf"
+sed -i "4arenew_before_expiry = 4 years" "$root/conf/renewal/le.wtf.conf"
 common_no_force_renew renew --rsa-key-size 2048
 CheckCertCount 3
 
diff --git a/tools/eff-pubkey.pem b/tools/eff-pubkey.pem
new file mode 100644
index 000000000..fe6c2f5bb
--- /dev/null
+++ b/tools/eff-pubkey.pem
@@ -0,0 +1,9 @@
+-----BEGIN PUBLIC KEY-----
+MIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEA6MR8W/galdxnpGqBsYbq
+OzQb2eyW15YFjDDEMI0ZOzt8f504obNs920lDnpPD2/KqgsfjOgw2K7xWDJIj/18
+xUvWPk3LDkrnokNiRkA3KOx3W6fHycKL+zID7zy+xZYBuh2fLyQtWV1VGQ45iNRp
+9+Zo7rH86cdfgkdnWTlNSHyTLW9NbXvyv/E12bppPcEvgCTAQXgnDVJ0/sqmeiij
+n9tTFh03aM+R2V/21h8aTraAS24qiPCz6gkmYGC8yr6mglcnNoYbsLNYZ69zF1XH
+cXPduCPdPdfLlzVlKK1/U7hkA28eG3BIAMh6uJYBRJTpiGgaGdPd7YekUB8S6cy+
+CQIDAQAB
+-----END PUBLIC KEY-----
diff --git a/tools/release.sh b/tools/release.sh
index 02e3d00b8..00c986534 100755
--- a/tools/release.sh
+++ b/tools/release.sh
@@ -161,6 +161,23 @@ for module in letsencrypt $subpkgs_modules ; do
 done
 deactivate
 
+# pin peep hashes of the things we just built
+for pkg in acme letsencrypt letsencrypt-apache ; do
+    echo
+    letsencrypt-auto-source/pieces/peep.py hash dist."$version/$pkg"/*.{whl,gz}
+    echo $pkg==$version
+done > /tmp/hashes.$$
+
+if ! wc -l /tmp/hashes.$$ | grep -qE "^\s*12 " ; then
+    echo Unexpected peep hash output
+    exit 1
+fi
+
+# perform hideous surgery on requirements.txt...
+head -n -12 letsencrypt-auto-source/pieces/letsencrypt-auto-requirements.txt > /tmp/req.$$
+cat /tmp/hashes.$$ >> /tmp/req.$$
+cp /tmp/req.$$ letsencrypt-auto-source/pieces/letsencrypt-auto-requirements.txt
+
 # ensure we have the latest built version of leauto
 letsencrypt-auto-source/build.py
 
@@ -199,6 +216,8 @@ echo twine upload "$root/dist.$version/*/*"
 
 if [ "$RELEASE_BRANCH" = candidate-"$version" ] ; then
     SetVersion "$nextversion".dev0
+    letsencrypt-auto-source/build.py
+    git add letsencrypt-auto-source/letsencrypt-auto
     git diff
     git commit -m "Bump version to $nextversion"
 fi
diff --git a/tox.ini b/tox.ini
index 57359cd86..6af9610e3 100644
--- a/tox.ini
+++ b/tox.ini
@@ -91,4 +91,4 @@ commands =
     docker run --rm -t -i lea
 whitelist_externals =
     docker
-passenv = DOCKER_*
\ No newline at end of file
+passenv = DOCKER_*