diff --git a/Dockerfile b/Dockerfile
index b9ea168de..d7aca784b 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -48,7 +48,7 @@ COPY letsencrypt-apache /opt/letsencrypt/src/letsencrypt-apache/
 COPY letsencrypt-nginx /opt/letsencrypt/src/letsencrypt-nginx/
 
 
-# requirements.txt not installed!
+# py26reqs.txt not installed!
 RUN virtualenv --no-site-packages -p python2 /opt/letsencrypt/venv && \
     /opt/letsencrypt/venv/bin/pip install \
     -e /opt/letsencrypt/src/acme \
diff --git a/Dockerfile-dev b/Dockerfile-dev
index daa8e9af0..028366b2c 100644
--- a/Dockerfile-dev
+++ b/Dockerfile-dev
@@ -32,7 +32,8 @@ RUN /opt/letsencrypt/src/ubuntu.sh && \
 # the above is not likely to change, so by putting it further up the
 # Dockerfile we make sure we cache as much as possible
 
-COPY setup.py README.rst CHANGES.rst MANIFEST.in requirements.txt DISCLAIMER linter_plugin.py tox.cover.sh tox.ini pep8.travis.sh .pep8 .pylintrc /opt/letsencrypt/src/
+# py26reqs.txt not installed!
+COPY setup.py README.rst CHANGES.rst MANIFEST.in DISCLAIMER linter_plugin.py tox.cover.sh tox.ini pep8.travis.sh .pep8 .pylintrc /opt/letsencrypt/src/
 
 # all above files are necessary for setup.py, however, package source
 # code directory has to be copied separately to a subdirectory...
@@ -52,7 +53,6 @@ COPY tests /opt/letsencrypt/src/tests/
 
 RUN virtualenv --no-site-packages -p python2 /opt/letsencrypt/venv && \
     /opt/letsencrypt/venv/bin/pip install \
-    -r /opt/letsencrypt/src/requirements.txt \
     -e /opt/letsencrypt/src/acme \
     -e /opt/letsencrypt/src \
     -e /opt/letsencrypt/src/letsencrypt-apache \
diff --git a/MANIFEST.in b/MANIFEST.in
index fa0d16e0d..5d5b0bed4 100644
--- a/MANIFEST.in
+++ b/MANIFEST.in
@@ -1,4 +1,4 @@
-include requirements.txt
+include py26reqs.txt
 include README.rst
 include CHANGES.rst
 include CONTRIBUTING.md
diff --git a/bootstrap/README b/bootstrap/README
index 6a04ac0ba..89fd8b6ba 100644
--- a/bootstrap/README
+++ b/bootstrap/README
@@ -2,6 +2,6 @@ This directory contains scripts that install necessary OS-specific
 prerequisite dependencies (see docs/using.rst).
 
 General dependencies:
-- git-core: requirements.txt git+https://*
+- git-core: py26reqs.txt git+https://*
 - ca-certificates: communication with demo ACMO server at
-  https://www.letsencrypt-demo.org, requirements.txt git+https://*
+  https://www.letsencrypt-demo.org, py26reqs.txt git+https://*
diff --git a/bootstrap/dev/venv.sh b/bootstrap/dev/venv.sh
index d6cf95bb5..2bd32a89b 100755
--- a/bootstrap/dev/venv.sh
+++ b/bootstrap/dev/venv.sh
@@ -4,7 +4,7 @@
 export VENV_ARGS="--python python2"
 
 ./bootstrap/dev/_venv_common.sh \
-  -r requirements.txt \
+  -r py26reqs.txt \
   -e acme[testing] \
   -e .[dev,docs,testing] \
   -e letsencrypt-apache \
diff --git a/bootstrap/venv.sh b/bootstrap/venv.sh
index 6ca082446..ff1a50c6c 100755
--- a/bootstrap/venv.sh
+++ b/bootstrap/venv.sh
@@ -13,14 +13,14 @@ VENV_PATH=${VENV_PATH:-"$XDG_DATA_HOME/$VENV_NAME"}
 # later steps, causing "ImportError: cannot import name unpack_url"
 if [ ! -d $VENV_PATH ]
 then
-  virtualenv --no-site-packages --python python2 $VENV_PATH
+  virtualenv --no-site-packages --python ${LE_PYTHON:-python2} $VENV_PATH
 fi
 
 . $VENV_PATH/bin/activate
 pip install -U setuptools
 pip install -U pip
 
-pip install -U letsencrypt letsencrypt-apache # letsencrypt-nginx
+pip install -U -r py26reqs.txt letsencrypt letsencrypt-apache # letsencrypt-nginx
 
 echo
 echo "Congratulations, Let's Encrypt has been successfully installed/updated!"
diff --git a/letsencrypt-auto b/letsencrypt-auto
index d163998aa..b695b0450 100755
--- a/letsencrypt-auto
+++ b/letsencrypt-auto
@@ -19,13 +19,53 @@ else
   SUDO=
 fi
 
-for arg in "$@" ; do 
+for arg in "$@" ; 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" = "--debug" ] ; then
+    DEBUG=1
   fi
 done
 
+ExperimentalBootstrap() {
+  # Arguments: Platform name, boostrap script name, SUDO command (iff needed)
+  if [ "$DEBUG" = 1 ] ; then
+    if [ "$2" != "" ]  ; then
+      echo "Bootstrapping dependencies for $1..."
+      "$3" "$BOOTSTRAP/$2"
+    fi
+  else
+    echo "WARNING: $1 support is very experimental at present..."
+    echo "if you would like to work on improving it, please ensure you have backups"
+    echo "and then run this script again with the --debug flag!"
+    exit 1
+  fi
+}
+
+
+DeterminePythonVersion() {
+  if which python2 > /dev/null ; then
+    export LE_PYTHON=${LE_PYTHON:-python2}
+  elif which python2.7 > /dev/null ; then
+    export LE_PYTHON=${LE_PYTHON:-python2.7}
+  elif which python > /dev/null ; then
+    export LE_PYTHON=${LE_PYTHON:-python}
+  else
+    echo "Cannot find any Pythons... please install one!"
+  fi
+
+  PYVER=`$LE_PYTHON --version 2>&1 | cut -d" " -f 2 | cut -d. -f1,2 | sed 's/\.//'`
+  if [ $PYVER -eq 26 ] ; then
+    ExperimentalBootstrap "Python 2.6"
+  elif [ $PYVER -lt 26 ] ; then
+    echo "You have an ancient version of Python entombed in your operating system..."
+    echo "This isn't going to work."
+    exit 1
+  fi
+}
+
+
 # virtualenv call is not idempotent: it overwrites pip upgraded in
 # later steps, causing "ImportError: cannot import name unpack_url"
 if [ ! -d $VENV_PATH ]
@@ -35,28 +75,24 @@ then
     echo "Cannot find the letsencrypt bootstrap scripts in $BOOTSTRAP"
     exit 1
   fi
+
   if [ -f /etc/debian_version ] ; then
     echo "Bootstrapping dependencies for Debian-based OSes..."
     $SUDO $BOOTSTRAP/_deb_common.sh
+  elif [ -f /etc/redhat-release ] ; then
+    echo "Bootstrapping dependencies for RedHat-based OSes..."
+    $SUDO $BOOTSTRAP/_rpm_common.sh
   elif [ -f /etc/arch-release ] ; then
     echo "Bootstrapping dependencies for Archlinux..."
     $SUDO $BOOTSTRAP/archlinux.sh
   elif [ -f /etc/manjaro-release ] ; then
-    echo "Bootstrapping dependencies for Manjaro Linux..."
-    $SUDO $BOOTSTRAP/manjaro.sh
-  elif [ -f /etc/redhat-release ] ; then
-    echo "Bootstrapping dependencies for RedHat-based OSes..."
-    $SUDO $BOOTSTRAP/_rpm_common.sh
+    ExperimentalBootstrap "Manjaro Linux" majaro.sh "$SUDO"
   elif [ -f /etc/gentoo-release ] ; then
-    echo "Bootstrapping dependencies for Gentoo-based OSes..."
-    $SUDO $BOOTSTRAP/_gentoo_common.sh
+    ExperimentalBootstrap "Gentoo" _gentoo_common.sh "$SUDO"
   elif uname | grep -iq FreeBSD ; then
-    echo "Bootstrapping dependencies for FreeBSD..."
-    $SUDO $BOOTSTRAP/freebsd.sh
+    ExperimentalBootstrap "FreeBSD" freebsd.sh "$SUDO"
   elif uname | grep -iq Darwin ; then
-    echo "Bootstrapping dependencies for Mac OS X..."
-    echo "WARNING: Mac support is very experimental at present..."
-    $BOOTSTRAP/mac.sh
+    ExperimentalBootstrap "Mac OS X" mac.sh
   else
     echo "Sorry, I don't know how to bootstrap Let's Encrypt on your operating system!"
     echo
@@ -65,24 +101,28 @@ then
     echo "for more info"
   fi
 
+  DeterminePythonVersion
   echo "Creating virtual environment..."
   if [ "$VERBOSE" = 1 ] ; then
-    virtualenv --no-site-packages --python python2 $VENV_PATH
+    virtualenv --no-site-packages --python $LE_PYTHON $VENV_PATH
   else
-    virtualenv --no-site-packages --python python2 $VENV_PATH > /dev/null
+    virtualenv --no-site-packages --python $LE_PYTHON $VENV_PATH > /dev/null
   fi
+else
+  DeterminePythonVersion
 fi
 
+
 printf "Updating letsencrypt and virtual environment dependencies..."
 if [ "$VERBOSE" = 1 ]  ; then
   echo
   $VENV_BIN/pip install -U setuptools
   $VENV_BIN/pip install -U pip
-  $VENV_BIN/pip install -U letsencrypt letsencrypt-apache 
+  $VENV_BIN/pip install -r py26reqs.txt -U letsencrypt letsencrypt-apache
   # nginx is buggy / disabled for now, but upgrade it if the user has
   # installed it manually
   if $VENV_BIN/pip freeze | grep -q letsencrypt-nginx ; then
-    $VENV_BIN/pip install -U letsencrypt letsencrypt-nginx 
+    $VENV_BIN/pip install -U letsencrypt letsencrypt-nginx
   fi
 else
   $VENV_BIN/pip install -U setuptools > /dev/null
@@ -90,6 +130,8 @@ else
   $VENV_BIN/pip install -U pip > /dev/null
   printf .
   # nginx is buggy / disabled for now...
+  $VENV_BIN/pip install -r py26reqs.txt
+  printf .
   $VENV_BIN/pip install -U letsencrypt > /dev/null
   printf .
   $VENV_BIN/pip install -U letsencrypt-apache > /dev/null
diff --git a/letsencrypt/cli.py b/letsencrypt/cli.py
index 9f532f002..5757783cd 100644
--- a/letsencrypt/cli.py
+++ b/letsencrypt/cli.py
@@ -843,7 +843,8 @@ def prepare_and_parse_args(plugins, args):
         "really know what you're doing!")
     helpful.add(
         "testing", "--debug", action="store_true",
-        help="Show tracebacks if the program exits abnormally")
+        help="Show tracebacks in case of errors, and allow letsencrypt-auto "
+             "execution on experimental platforms")
     helpful.add(
         "testing", "--no-verify-ssl", action="store_true",
         help=config_help("no_verify_ssl"),
diff --git a/py26reqs.txt b/py26reqs.txt
new file mode 100644
index 000000000..a94b22c0c
--- /dev/null
+++ b/py26reqs.txt
@@ -0,0 +1,2 @@
+# https://github.com/bw2/ConfigArgParse/issues/17
+git+https://github.com/kuba/ConfigArgParse.git@python2.6-0.9.3#egg=ConfigArgParse
diff --git a/requirements.txt b/requirements.txt
deleted file mode 100644
index 972e87eaf..000000000
--- a/requirements.txt
+++ /dev/null
@@ -1,2 +0,0 @@
-# https://github.com/bw2/ConfigArgParse/issues/17
-git+https://github.com/kuba/ConfigArgParse.git@python2.6#egg=ConfigArgParse
diff --git a/tox.ini b/tox.ini
index 8ea3e518f..9988d8d1f 100644
--- a/tox.ini
+++ b/tox.ini
@@ -17,7 +17,7 @@ envlist = py26,py27,py33,py34,cover,lint
 commands =
     pip install -e acme[testing]
     nosetests -v acme
-    pip install -r requirements.txt -e .[testing]
+    pip install -r py26reqs.txt -e .[testing]
     nosetests -v letsencrypt
     pip install -e letsencrypt-apache
     nosetests -v letsencrypt_apache
@@ -44,7 +44,7 @@ commands =
 [testenv:cover]
 basepython = python2.7
 commands =
-    pip install -r requirements.txt -e acme -e .[testing] -e letsencrypt-apache -e letsencrypt-nginx -e letshelp-letsencrypt
+    pip install -e acme -e .[testing] -e letsencrypt-apache -e letsencrypt-nginx -e letshelp-letsencrypt
     ./tox.cover.sh
 
 [testenv:lint]
@@ -54,7 +54,7 @@ basepython = python2.7
 # duplicate code checking; if one of the commands fails, others will
 # continue, but tox return code will reflect previous error
 commands =
-    pip install -r requirements.txt -e acme -e .[dev] -e letsencrypt-apache -e letsencrypt-nginx -e letsencrypt-compatibility-test -e letshelp-letsencrypt
+    pip install -e acme -e .[dev] -e letsencrypt-apache -e letsencrypt-nginx -e letsencrypt-compatibility-test -e letshelp-letsencrypt
     ./pep8.travis.sh
     pylint --rcfile=.pylintrc letsencrypt
     pylint --rcfile=.pylintrc acme/acme