diff --git a/asdf.sh b/asdf.sh
index a19265c0a..2c0dab70c 100644
--- a/asdf.sh
+++ b/asdf.sh
@@ -59,6 +59,36 @@ fi
 _asdf_bin="$ASDF_DIR/bin"
 _asdf_shims="${ASDF_DATA_DIR:-$HOME/.asdf}/shims"
 
+# If ASDF_FORCE_PREPEND is set, remove any existing instances of asdf from PATH so
+# the prepending done after is always at the frontmost part of the PATH.
+if [ -n "${ASDF_FORCE_PREPEND+x}" ]; then
+  if [ -n "$BASH_VERSION" ] || [ -n "$ZSH_VERSION" ]; then
+    # shellcheck disable=SC3060
+    case ":$PATH:" in
+      *":${_asdf_bin}:"*) PATH=${PATH//$_asdf_bin:/} ;;
+    esac
+    # shellcheck disable=SC3060
+    case ":$PATH:" in
+      *":${_asdf_shims}:"*) PATH=${PATH//$_asdf_shims:/} ;;
+    esac
+  else
+    _path=${PATH}:
+    _new_path=
+    while [ -n "$_path" ]; do
+      _part=${_path%%:*}
+      _path=${_path#*:}
+
+      if [ "$_part" = "$_asdf_bin" ] || [ "$_part" = "$_asdf_shims" ]; then
+        continue
+      fi
+
+      _new_path="$_new_path${_new_path:+:}$_part"
+    done
+    PATH=$_new_path
+    unset -v _path _new_path _part
+  fi
+fi
+
 case ":$PATH:" in
   *":$_asdf_bin:"*) : ;;
   *) PATH="$_asdf_bin:$PATH" ;;
diff --git a/docs/guide/getting-started.md b/docs/guide/getting-started.md
index 38d679c18..06c2839be 100644
--- a/docs/guide/getting-started.md
+++ b/docs/guide/getting-started.md
@@ -51,7 +51,9 @@ We highly recommend using the official `git` method.
 
 ## 3. Install asdf
 
-There are many different combinations of Shells, OSs & Installation methods all of which affect the configuration here. Expand the selection below that best matches your system:
+There are many different combinations of Shells, OSs & Installation methods all of which affect the configuration here. Expand the selection below that best matches your system.
+
+**macOS users, be sure to read the warning about `path_helper` at the end of this section.**
 
 ::: details Bash & Git
 
@@ -359,6 +361,10 @@ export ASDF_DIR="/opt/asdf-vm"
 
 `asdf` scripts need to be sourced **after** you have set your `$PATH` and **after** you have sourced your framework (oh-my-zsh etc).
 
+::: warning
+On macOS, starting a Bash or Zsh shell automatically calls a utility called `path_helper`. `path_helper` has poor logic and rearranges items in `PATH` (and `MANPATH`) in a bad way. To workaround this, set the `ASDF_FORCE_PREPEND` variable before sourcing `asdf`, like so: `ASDF_FORCE_PREPEND= . "<path-to-asdf-directory>/asdf.sh"`.
+:::
+
 Restart your shell so that `PATH` changes take effect. Opening a new terminal tab will usually do it.
 
 ## Core Installation Complete!