diff --git a/plugins/python/README.md b/plugins/python/README.md
index ca424ea55..2727e81cd 100644
--- a/plugins/python/README.md
+++ b/plugins/python/README.md
@@ -34,6 +34,7 @@ virtual environments:
   `<venv-name>/bin/activate`, and automatically deactivate it when navigating out of it (keeps venv activated
   in subdirectories).
   - To enable the feature, set `PYTHON_AUTO_VRUN=true` before sourcing oh-my-zsh.
+  - To also search parent directories (useful for monorepos), set `PYTHON_AUTO_VRUN_RECURSIVE=true` as well.
   - The plugin activates the first existing virtual environment, in order, appearing in `$PYTHON_VENV_NAMES`.
     The default virtual environment name is `venv`. To use a different name, set
     `PYTHON_VENV_NAME=<venv-name>`. For example: `PYTHON_VENV_NAME=".venv"`
diff --git a/plugins/python/python.plugin.zsh b/plugins/python/python.plugin.zsh
index 2b139ddf0..b2ca11f2f 100644
--- a/plugins/python/python.plugin.zsh
+++ b/plugins/python/python.plugin.zsh
@@ -113,8 +113,21 @@ if [[ "$PYTHON_AUTO_VRUN" == "true" ]]; then
         # make sure we're not in a venv already
         (( $+functions[deactivate] )) && deactivate > /dev/null 2>&1
         source $file > /dev/null 2>&1
-        break
+        return
       done
+
+      # Search parent directories if recursive mode is enabled
+      if [[ "$PYTHON_AUTO_VRUN_RECURSIVE" == "true" ]]; then
+        local search_dir="$PWD:h"
+        while [[ "$search_dir" != "/" && "$search_dir" != "." ]]; do
+          for file in "${search_dir}/"${^PYTHON_VENV_NAMES[@]}"/bin/activate"(N.); do
+            (( $+functions[deactivate] )) && deactivate > /dev/null 2>&1
+            source $file > /dev/null 2>&1
+            return
+          done
+          search_dir="${search_dir:h}"
+        done
+      fi
     fi
   }
   add-zsh-hook chpwd auto_vrun