diff --git a/examples/pyo3-pytests/src/lib.rs b/examples/pyo3-pytests/src/lib.rs
index 0dea9c03679..ed0b818038d 100644
--- a/examples/pyo3-pytests/src/lib.rs
+++ b/examples/pyo3-pytests/src/lib.rs
@@ -8,6 +8,7 @@ pub mod dict_iter;
 pub mod misc;
 pub mod objstore;
 pub mod othermod;
+pub mod path;
 pub mod pyclass_iter;
 pub mod subclassing;
 
@@ -17,6 +18,7 @@ use dict_iter::*;
 use misc::*;
 use objstore::*;
 use othermod::*;
+use path::*;
 use pyclass_iter::*;
 use subclassing::*;
 
@@ -28,6 +30,7 @@ fn pyo3_pytests(py: Python, m: &PyModule) -> PyResult<()> {
     m.add_wrapped(wrap_pymodule!(misc))?;
     m.add_wrapped(wrap_pymodule!(objstore))?;
     m.add_wrapped(wrap_pymodule!(othermod))?;
+    m.add_wrapped(wrap_pymodule!(path))?;
     m.add_wrapped(wrap_pymodule!(pyclass_iter))?;
     m.add_wrapped(wrap_pymodule!(subclassing))?;
 
@@ -42,6 +45,7 @@ fn pyo3_pytests(py: Python, m: &PyModule) -> PyResult<()> {
     sys_modules.set_item("pyo3_pytests.misc", m.getattr("misc")?)?;
     sys_modules.set_item("pyo3_pytests.objstore", m.getattr("objstore")?)?;
     sys_modules.set_item("pyo3_pytests.othermod", m.getattr("othermod")?)?;
+    sys_modules.set_item("pyo3_pytests.path", m.getattr("path")?)?;
     sys_modules.set_item("pyo3_pytests.pyclass_iter", m.getattr("pyclass_iter")?)?;
     sys_modules.set_item("pyo3_pytests.subclassing", m.getattr("subclassing")?)?;
 
diff --git a/examples/pyo3-pytests/src/path.rs b/examples/pyo3-pytests/src/path.rs
new file mode 100644
index 00000000000..d3214aa0c91
--- /dev/null
+++ b/examples/pyo3-pytests/src/path.rs
@@ -0,0 +1,21 @@
+use pyo3::prelude::*;
+use pyo3::wrap_pyfunction;
+use std::path::{Path, PathBuf};
+
+#[pyfunction]
+fn make_path() -> PathBuf {
+    Path::new("/root").to_owned()
+}
+
+#[pyfunction]
+fn take_pathbuf(path: PathBuf) -> PathBuf {
+    path
+}
+
+#[pymodule]
+fn path(_py: Python<'_>, m: &PyModule) -> PyResult<()> {
+    m.add_function(wrap_pyfunction!(make_path, m)?)?;
+    m.add_function(wrap_pyfunction!(take_pathbuf, m)?)?;
+
+    Ok(())
+}
diff --git a/examples/pyo3-pytests/tests/test_path.py b/examples/pyo3-pytests/tests/test_path.py
new file mode 100644
index 00000000000..07c4cb3504f
--- /dev/null
+++ b/examples/pyo3-pytests/tests/test_path.py
@@ -0,0 +1,18 @@
+import pathlib
+
+import pyo3_pytests.path as rpath
+
+
+def test_make_path():
+    p = rpath.make_path()
+    assert p == "/root"
+
+
+def test_take_pathbuf():
+    p = "/root"
+    assert rpath.take_pathbuf(p) == p
+
+
+def test_take_pathlib():
+    p = pathlib.Path("/root")
+    assert rpath.take_pathbuf(p) == str(p)
diff --git a/src/conversions/osstr.rs b/src/conversions/osstr.rs
index 466a4417b86..fefe8daf3f2 100644
--- a/src/conversions/osstr.rs
+++ b/src/conversions/osstr.rs
@@ -58,7 +58,22 @@ impl ToPyObject for OsStr {
 
 impl FromPyObject<'_> for OsString {
     fn extract(ob: &PyAny) -> PyResult<Self> {
-        let pystring = <PyString as PyTryFrom>::try_from(ob)?; // Cast PyAny to PyString
+        let pystring = match <PyString as PyTryFrom>::try_from(ob) {
+            // Cast PyAny to PyString
+            Ok(s) => s,
+            Err(err) => {
+                let py = ob.py();
+                let pathlib = py.import("pathlib")?;
+                let pathlib_path = pathlib.getattr("Path")?;
+                // FIXME: right way to get the type object of pathlib.Path?
+                let path_instance = pathlib_path.call0()?;
+                if path_instance.get_type().is_instance(ob)? {
+                    ob.call_method0("__str__")?
+                } else {
+                    return Err(err.into());
+                }
+            }
+        };
 
         #[cfg(not(windows))]
         {