diff --git a/asdf.sh b/asdf.sh
index aadb43f3..1f8d2b56 100644
--- a/asdf.sh
+++ b/asdf.sh
@@ -59,6 +59,60 @@ fi
 _asdf_bin="$ASDF_DIR/bin"
 _asdf_shims="${ASDF_DATA_DIR:-$HOME/.asdf}/shims"
 
+_asdf_should_prepend=no
+if [ -n "${ASDF_FORCE_PREPEND+x}" ]; then
+  _asdf_should_prepend=$ASDF_FORCE_PREPEND
+else
+  # If ASDF_FORCE_PREPEND is not set, then prepend by default on macOS
+  # to workaround `path_helper`.
+  if [ -n "$BASH_VERSION" ] || [ -n "$ZSH_VERSION" ]; then
+    # shellcheck disable=SC3028
+    case $OSTYPE in
+      darwin*) _asdf_should_prepend=yes ;;
+    esac
+  else
+    if ! _asdf_output=$(uname); then
+      printf "%s\n" "asdf: Error: Failed to execute 'uname'" >&2
+      return 1
+    fi
+    if [ "$_asdf_output" = 'Darwin' ]; then
+      _asdf_should_prepend=yes
+    fi
+    unset -v _asdf_output
+  fi
+fi
+
+# If prepending is enabled, remove any existing instances of asdf from PATH so
+# the prepending done after is always at the frontmost part of the PATH.
+if [ "$_asdf_should_prepend" = 'yes' ]; 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
+unset -v _asdf_should_prepend
+
 case ":$PATH:" in
   *":$_asdf_bin:"*) : ;;
   *) PATH="$_asdf_bin:$PATH" ;;
diff --git a/docs/guide/getting-started.md b/docs/guide/getting-started.md
index 38d679c1..f6e91b93 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` can rearrange items in `PATH` (and `MANPATH`), causing inconsistent behavior for tools that require specific ordering. To workaround this, `asdf` on macOS defaults to forcily adding its `PATH`-entries to the front (taking highest priority). This is controllable with the `ASDF_FORCE_PREPEND` variable.`.
+:::
+
 Restart your shell so that `PATH` changes take effect. Opening a new terminal tab will usually do it.
 
 ## Core Installation Complete!
diff --git a/docs/manage/configuration.md b/docs/manage/configuration.md
index 225a49c4..1ec7d83e 100644
--- a/docs/manage/configuration.md
+++ b/docs/manage/configuration.md
@@ -188,6 +188,15 @@ Number of cores to use when compiling the source code. If set, this value takes
 - If Unset: the asdf config `concurrency` value is used.
 - Usage: `export ASDF_CONCURRENCY=32`
 
+### `ASDF_FORCE_PREPEND`
+
+Whether or not to prepend the `asdf` shims and path directories to the front-most (highest-priority) part of the `PATH`.
+
+- If Unset: On macOS, defaults to `yes`; but on other systems, defaults to `no`
+- If `yes`: Force `asdf` directories to the front of the `PATH`
+- If set to any string _other_ than `yes`: Do _not_ force `asdf` directories to the front of the `PATH`
+- Usage: `ASDF_FORCE_PREPEND=no . "<path-to-asdf-directory>/asdf.sh"`
+
 ## Full Configuration Example
 
 Following a simple asdf setup with: