diff --git a/jaraco/develop/add-project.py b/jaraco/develop/add-project.py
index 247c665..397874d 100644
--- a/jaraco/develop/add-project.py
+++ b/jaraco/develop/add-project.py
@@ -4,8 +4,10 @@
 
 import operator
 import subprocess
+from typing_extensions import Annotated
 
 import path
+import typer
 
 import jaraco.text
 from jaraco.ui.main import main
@@ -19,7 +21,10 @@ def add_newlines(lines):
 
 
 @main
-def run(name: str, target: path.Path = path.Path()):
+def run(
+    name: str,
+    target: Annotated[path.Path, typer.Option(parser=path.Path)] = path.Path(),
+):
     repo, path = git.projects_repo()
     project = git.Project.parse(name)
     with git.temp_checkout(repo, quiet=True):
diff --git a/jaraco/develop/checkout-all.py b/jaraco/develop/checkout-all.py
index 00e155d..68b0a93 100644
--- a/jaraco/develop/checkout-all.py
+++ b/jaraco/develop/checkout-all.py
@@ -1,14 +1,17 @@
 import functools
+from typing_extensions import Annotated
 
 import path
+import typer
 from more_itertools import consume
 
+
 from jaraco.ui.main import main
 
 from . import git
 
 
 @main
-def run(target: path.Path = path.Path()):
+def run(target: Annotated[path.Path, typer.Argument(parser=path.Path)] = path.Path()):
     checkout = functools.partial(git.checkout_missing, root=target)
     consume(map(checkout, git.projects()))
diff --git a/newsfragments/+dc04d32d.bugfix.rst b/newsfragments/+dc04d32d.bugfix.rst
new file mode 100644
index 0000000..cc1abbe
--- /dev/null
+++ b/newsfragments/+dc04d32d.bugfix.rst
@@ -0,0 +1 @@
+Fix usage when soliciting a path.Path, which typer doesn't support.
\ No newline at end of file