diff --git a/tests/letstest/scripts/test_leauto_upgrades.sh b/tests/letstest/scripts/test_leauto_upgrades.sh
index e08a0710c..ddcca39cf 100755
--- a/tests/letstest/scripts/test_leauto_upgrades.sh
+++ b/tests/letstest/scripts/test_leauto_upgrades.sh
@@ -79,12 +79,11 @@ if [ $(python -V 2>&1 | cut -d" " -f 2 | cut -d. -f1,2 | sed 's/\.//') -eq 26 ];
         echo "Certbot shouldn't have updated to a new version!"
         exit 1
     fi
-    if [ -d "/opt/eff.org" ]; then
-        echo "New directory shouldn't have been created!"
-        exit 1
-    fi
-    # Create a 2nd venv at the new path to ensure we properly handle this case
-    export VENV_PATH="/opt/eff.org/certbot/venv"
+    # Create a 2nd venv at the old path to ensure we properly handle the (unlikely) case of two separate virtual environments below.
+    HOME=${HOME:-~root}
+    XDG_DATA_HOME=${XDG_DATA_HOME:-~/.local/share}
+    OLD_VENV_PATH="$XDG_DATA_HOME/letsencrypt"
+    export VENV_PATH="$OLD_VENV_PATH"
     if ! sudo -E ./letsencrypt-auto -v --debug --version --no-self-upgrade 2>&1 | tail -n1 | grep "^certbot $INITIAL_VERSION$" ; then
         echo second installation appeared to fail
         exit 1
@@ -117,11 +116,10 @@ if [ "$RUN_PYTHON3_TESTS" = 1 ]; then
         echo "Python3 wasn't used in venv!"
         exit 1
     fi
+
+    if [ "$(tools/readlink.py $OLD_VENV_PATH)" != "/opt/eff.org/certbot/venv" ]; then
+        echo symlink from old venv path not properly created!
+        exit 1
+    fi
 fi
 echo upgrade appeared to be successful
-
-if [ "$(tools/readlink.py ${XDG_DATA_HOME:-~/.local/share}/letsencrypt)" != "/opt/eff.org/certbot/venv" ]; then
-    echo symlink from old venv path not properly created!
-    exit 1
-fi
-echo symlink properly created
diff --git a/tests/letstest/scripts/test_letsencrypt_auto_certonly_standalone.sh b/tests/letstest/scripts/test_letsencrypt_auto_certonly_standalone.sh
index 081ff3829..901d01e4a 100755
--- a/tests/letstest/scripts/test_letsencrypt_auto_certonly_standalone.sh
+++ b/tests/letstest/scripts/test_letsencrypt_auto_certonly_standalone.sh
@@ -11,12 +11,26 @@ set -eo pipefail
 cd letsencrypt
 export PATH="$PWD/letsencrypt-auto-source:$PATH"
 letsencrypt-auto --os-packages-only --debug --version
+
+# Create a venv-like layout at the old virtual environment path to test that a
+# symlink is properly created when letsencrypt-auto runs.
+HOME=${HOME:-~root}
+XDG_DATA_HOME=${XDG_DATA_HOME:-~/.local/share}
+OLD_VENV_BIN="$XDG_DATA_HOME/letsencrypt/bin"
+mkdir -p "$OLD_VENV_BIN"
+touch "$OLD_VENV_BIN/letsencrypt"
+
 letsencrypt-auto certonly --no-self-upgrade -v --standalone --debug \
                    --text --agree-dev-preview --agree-tos \
                    --renew-by-default --redirect \
                    --register-unsafely-without-email \
                    --domain $PUBLIC_HOSTNAME --server $BOULDER_URL
 
+if [ "$(tools/readlink.py ${XDG_DATA_HOME:-~/.local/share}/letsencrypt)" != "/opt/eff.org/certbot/venv" ]; then
+    echo symlink from old venv path not properly created!
+    exit 1
+fi
+
 if ! letsencrypt-auto --help --no-self-upgrade | grep -F "letsencrypt-auto [SUBCOMMAND]"; then
     echo "letsencrypt-auto not included in help output!"
     exit 1