diff --git a/letsencrypt-auto-source/letsencrypt-auto b/letsencrypt-auto-source/letsencrypt-auto
index ce469a56a..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
@@ -484,28 +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
@@ -1643,18 +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.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 1ff07253e..381759a5c 100644
--- a/letsencrypt-auto-source/pieces/letsencrypt-auto-requirements.txt
+++ b/letsencrypt-auto-source/pieces/letsencrypt-auto-requirements.txt
@@ -35,28 +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
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