diff --git a/letsencrypt-auto-source/letsencrypt-auto b/letsencrypt-auto-source/letsencrypt-auto
index 0ad089acd..b86517bb6 100755
--- a/letsencrypt-auto-source/letsencrypt-auto
+++ b/letsencrypt-auto-source/letsencrypt-auto
@@ -897,7 +897,11 @@ TempDir() {
   mktemp -d 2>/dev/null || mktemp -d -t 'le'  # Linux || macOS
 }
 
-
+# Returns 0 if a letsencrypt installation exists at $OLD_VENV_PATH, otherwise,
+# returns a non-zero number.
+OldVenvExists() {
+    [ -n "$OLD_VENV_PATH" -a -f "$OLD_VENV_PATH/bin/letsencrypt" ]
+}
 
 if [ "$1" = "--le-auto-phase2" ]; then
   # Phase 2: Create venv, install LE, and run.
@@ -910,13 +914,21 @@ if [ "$1" = "--le-auto-phase2" ]; then
   fi
 
   INSTALLED_VERSION="none"
-  if [ -d "$VENV_PATH" ]; then
+  if [ -d "$VENV_PATH" ] || OldVenvExists; then
     # If the selected Bootstrap function isn't a noop and it differs from the
     # previously used version
     if [ -n "$BOOTSTRAP_VERSION" -a "$BOOTSTRAP_VERSION" != "$PREV_BOOTSTRAP_VERSION" ]; then
       # if non-interactive mode or stdin and stdout are connected to a terminal
       if [ \( "$NONINTERACTIVE" = 1 \) -o \( \( -t 0 \) -a \( -t 1 \) \) ]; then
-        rm -rf "$VENV_PATH"
+        if [ -d "$VENV_PATH" ]; then
+          rm -rf "$VENV_PATH"
+        fi
+        # In the case the old venv was just a symlink to the new one,
+        # OldVenvExists is now false because we deleted the venv at VENV_PATH.
+        if OldVenvExists; then
+          rm -rf "$OLD_VENV_PATH"
+          ln -s "$VENV_PATH" "$OLD_VENV_PATH"
+        fi
         RerunWithArgs "$@"
       else
         error "Skipping upgrade because new OS dependencies may need to be installed."
@@ -926,6 +938,10 @@ if [ "$1" = "--le-auto-phase2" ]; then
         error "install any required packages."
         # Set INSTALLED_VERSION to be the same so we don't update the venv
         INSTALLED_VERSION="$LE_AUTO_VERSION"
+        # Continue to use OLD_VENV_PATH if the new venv doesn't exist
+        if [ ! -d "$VENV_PATH" ]; then
+          VENV_BIN="$OLD_VENV_PATH/bin"
+        fi
       fi
     elif [ -f "$VENV_BIN/letsencrypt" ]; then
       # --version output ran through grep due to python-cryptography DeprecationWarnings
@@ -1418,7 +1434,7 @@ else
   export PHASE_1_VERSION="$LE_AUTO_VERSION"
 
   if [ ! -f "$VENV_BIN/letsencrypt" ]; then
-    if [ -z "$OLD_VENV_PATH" -o ! -f "$OLD_VENV_PATH/bin/letsencrypt" ]; then
+    if ! OldVenvExists; then
       if [ "$HELP" = 1 ]; then
         echo "$USAGE"
         exit 0
diff --git a/letsencrypt-auto-source/letsencrypt-auto.template b/letsencrypt-auto-source/letsencrypt-auto.template
index 5b8b1c164..96e5c2db0 100755
--- a/letsencrypt-auto-source/letsencrypt-auto.template
+++ b/letsencrypt-auto-source/letsencrypt-auto.template
@@ -436,7 +436,11 @@ TempDir() {
   mktemp -d 2>/dev/null || mktemp -d -t 'le'  # Linux || macOS
 }
 
-
+# Returns 0 if a letsencrypt installation exists at $OLD_VENV_PATH, otherwise,
+# returns a non-zero number.
+OldVenvExists() {
+    [ -n "$OLD_VENV_PATH" -a -f "$OLD_VENV_PATH/bin/letsencrypt" ]
+}
 
 if [ "$1" = "--le-auto-phase2" ]; then
   # Phase 2: Create venv, install LE, and run.
@@ -449,13 +453,21 @@ if [ "$1" = "--le-auto-phase2" ]; then
   fi
 
   INSTALLED_VERSION="none"
-  if [ -d "$VENV_PATH" ]; then
+  if [ -d "$VENV_PATH" ] || OldVenvExists; then
     # If the selected Bootstrap function isn't a noop and it differs from the
     # previously used version
     if [ -n "$BOOTSTRAP_VERSION" -a "$BOOTSTRAP_VERSION" != "$PREV_BOOTSTRAP_VERSION" ]; then
       # if non-interactive mode or stdin and stdout are connected to a terminal
       if [ \( "$NONINTERACTIVE" = 1 \) -o \( \( -t 0 \) -a \( -t 1 \) \) ]; then
-        rm -rf "$VENV_PATH"
+        if [ -d "$VENV_PATH" ]; then
+          rm -rf "$VENV_PATH"
+        fi
+        # In the case the old venv was just a symlink to the new one,
+        # OldVenvExists is now false because we deleted the venv at VENV_PATH.
+        if OldVenvExists; then
+          rm -rf "$OLD_VENV_PATH"
+          ln -s "$VENV_PATH" "$OLD_VENV_PATH"
+        fi
         RerunWithArgs "$@"
       else
         error "Skipping upgrade because new OS dependencies may need to be installed."
@@ -465,6 +477,10 @@ if [ "$1" = "--le-auto-phase2" ]; then
         error "install any required packages."
         # Set INSTALLED_VERSION to be the same so we don't update the venv
         INSTALLED_VERSION="$LE_AUTO_VERSION"
+        # Continue to use OLD_VENV_PATH if the new venv doesn't exist
+        if [ ! -d "$VENV_PATH" ]; then
+          VENV_BIN="$OLD_VENV_PATH/bin"
+        fi
       fi
     elif [ -f "$VENV_BIN/letsencrypt" ]; then
       # --version output ran through grep due to python-cryptography DeprecationWarnings
@@ -577,7 +593,7 @@ else
   export PHASE_1_VERSION="$LE_AUTO_VERSION"
 
   if [ ! -f "$VENV_BIN/letsencrypt" ]; then
-    if [ -z "$OLD_VENV_PATH" -o ! -f "$OLD_VENV_PATH/bin/letsencrypt" ]; then
+    if ! OldVenvExists; then
       if [ "$HELP" = 1 ]; then
         echo "$USAGE"
         exit 0
diff --git a/tests/letstest/scripts/test_leauto_upgrades.sh b/tests/letstest/scripts/test_leauto_upgrades.sh
index a83cbd826..51472f2e6 100755
--- a/tests/letstest/scripts/test_leauto_upgrades.sh
+++ b/tests/letstest/scripts/test_leauto_upgrades.sh
@@ -64,10 +64,45 @@ iQIDAQAB
 -----END PUBLIC KEY-----
 "
 
-if ! ./letsencrypt-auto -v --debug --version || ! diff letsencrypt-auto letsencrypt-auto-source/letsencrypt-auto ; then
+if [ $(python -V 2>&1 | cut -d" " -f 2 | cut -d. -f1,2 | sed 's/\.//') -eq 26 ]; then
+    if command -v python3; then
+        echo "Didn't expect Python 3 to be installed!"
+        exit 1
+    fi
+    cp letsencrypt-auto cb-auto
+    if ! ./cb-auto -v --debug --version 2>&1 | grep 0.5.0 ; then
+        echo "Certbot shouldn't have updated to a new version!"
+        exit 1
+    fi
+    if [ -d "/opt/eff.org" ]; then
+        echo "New directory shouldn't have been created!"
+        exit 1
+    fi
+    # Create a 2nd venv at the new path to ensure we properly handle this case
+    export VENV_PATH="/opt/eff.org/certbot/venv"
+    if ! sudo -E ./letsencrypt-auto -v --debug --version --no-self-upgrade 2>&1 | grep 0.5.0 ; then
+        echo second installation appeared to fail
+        exit 1
+    fi
+    unset VENV_PATH
+    EXPECTED_VERSION=$(grep -m1 LE_AUTO_VERSION certbot-auto | cut -d\" -f2)
+    if ! ./cb-auto -v --debug --version -n 2>&1 | grep "$EXPECTED_VERSION" ; then
+        echo "Certbot didn't upgrade as expected!"
+        exit 1
+    fi
+    if ! command -v python3; then
+        echo "Python3 wasn't properly installed"
+        exit 1
+    fi
+    if [ "$(/opt/eff.org/certbot/venv/bin/python -V 2>&1 | cut -d" " -f 2 | cut -d. -f1)" != 3 ]; then
+        echo "Python3 wasn't used in venv!"
+        exit 1
+    fi
+elif ! ./letsencrypt-auto -v --debug --version || ! diff letsencrypt-auto letsencrypt-auto-source/letsencrypt-auto ; then
     echo upgrade appeared to fail
     exit 1
 fi
+
 echo upgrade appeared to be successful
 
 if [ "$(tools/readlink.py ${XDG_DATA_HOME:-~/.local/share}/letsencrypt)" != "/opt/eff.org/certbot/venv" ]; then