diff --git a/client/devpi/main.py b/client/devpi/main.py
index 952ca29ac..1a4108c0f 100644
--- a/client/devpi/main.py
+++ b/client/devpi/main.py
@@ -3,7 +3,6 @@
 import sys
 import time
 import traceback
-import py
 import argparse
 import shlex
 import shutil
@@ -11,6 +10,7 @@
 import textwrap
 from base64 import b64encode
 from contextlib import closing, contextmanager
+from contextlib import suppress
 from devpi import hookspecs
 from devpi_common.terminal import TerminalWriter
 from devpi_common.types import lazydecorator, cached_property
@@ -18,6 +18,7 @@
 from devpi.use import PersistentCurrent
 from devpi_common.request import new_requests_session
 from devpi import __version__ as client_version
+from pathlib import Path
 from pluggy import HookimplMarker
 from pluggy import PluginManager
 from shutil import rmtree
@@ -70,7 +71,7 @@ class Hub:
     def __init__(self, args, file=None, pm=None):
         self._tw = TerminalWriter(file)
         self.args = args
-        self.cwd = py.path.local()
+        self.cwd = Path()
         self.quiet = False
         self._last_http_stati = []
         self.http = new_requests_session(agent=("client", client_version))
@@ -95,24 +96,24 @@ def set_quiet(self):
 
     @property
     def clientdir(self):
-        return py.path.local(self.args.clientdir)
+        return Path(self.args.clientdir)
 
     @property
     def auth_path(self):
-        return self.clientdir.join("auth.json")
+        return self.clientdir / "auth.json"
 
     @property
     def local_current_path(self):
         venv = self.active_venv()
         if venv is not None:
-            return venv.join('devpi.json')
+            return venv / 'devpi.json'
 
     @property
     def current_path(self):
         local_path = self.local_current_path
         if local_path is not None and local_path.exists():
             return local_path
-        return self.clientdir.join("current.json")
+        return self.clientdir / "current.json"
 
     def require_valid_current_with_index(self):
         current = self.current
@@ -238,17 +239,16 @@ def remove_readonly(func, path, excinfo):
                 else:
                     return
 
-        workdir = py.path.local(
-            mkdtemp(prefix=prefix))
+        workdir = Path(mkdtemp(prefix=prefix))
 
         self.info("using workdir", workdir)
         try:
             yield workdir
         finally:
-            rmtree(workdir.strpath, onerror=remove_readonly)
+            rmtree(workdir, onerror=remove_readonly)
 
     def get_current(self, args_url=None):
-        self.clientdir.ensure(dir=1)
+        self.clientdir.mkdir(parents=True, exist_ok=True)
         current = PersistentCurrent(self.auth_path, self.current_path)
         index_url = getattr(self.args, "index", None)
         if "DEVPI_INDEX" in os.environ:
@@ -307,10 +307,10 @@ def current(self):
         return self.get_current()
 
     def get_existing_file(self, arg):
-        p = py.path.local(arg, expanduser=True)
+        p = Path(arg).expanduser()
         if not p.exists():
             self.fatal("file does not exist: %s" % p)
-        elif not p.isfile():
+        elif not p.is_file():
             self.fatal("is not a file: %s" % p)
         return p
 
@@ -349,11 +349,11 @@ def venv(self):
             else:
                 venvdir = self.current.venvdir or self.active_venv()
             if venvdir:
-                cand = self.cwd.join(venvdir, vbin, abs=True)
-                if not cand.check() and self.venvwrapper_home:
-                    cand = self.venvwrapper_home.join(venvdir, vbin, abs=True)
-                venvdir = cand.dirpath().strpath
-                if not cand.check():
+                cand = self.cwd / venvdir / vbin
+                if not cand.exists() and self.venvwrapper_home:
+                    cand = self.venvwrapper_home / venvdir / vbin
+                venvdir = str(cand.parent)
+                if not cand.exists():
                     if self.current.venvdir:
                         self.fatal(
                             "No virtualenv found at: %r\n"
@@ -376,14 +376,14 @@ def venvwrapper_home(self):
         path = os.environ.get("WORKON_HOME", None)
         if path is None:
             return
-        return py.path.local(path)
+        return Path(path)
 
     def active_venv(self):
         """current activated virtualenv"""
         path = os.environ.get("VIRTUAL_ENV", None)
         if path is None:
             return
-        return py.path.local(path)
+        return Path(path)
 
     def popen_output(self, args, cwd=None, report=True):
         if isinstance(args, str):
@@ -426,15 +426,15 @@ def popen(self, args, cwd=None, dryrun=None, **popen_kwargs):
 
     def report_popen(self, args, cwd=None, extraenv=None):
         base = cwd or self.cwd
-        rel = py.path.local(args[0]).relto(base)
-        if not rel:
-            rel = str(args[0])
+        rel = Path(args[0])
+        with suppress(ValueError):
+            rel = rel.relative_to(base)
         if extraenv is not None:
             envadd = " [%s]" % ",".join(
                 ["%s=%r" % item for item in sorted(extraenv.items())])
         else:
             envadd = ""
-        self.line("--> ", base + "$", rel, " ".join(args[1:]), envadd)
+        self.line(f"--> {base}$ {rel} {' '.join(args[1:])} {envadd}")
 
     def popen_check(self, args, extraenv=None, **kwargs):
         assert args[0], args
diff --git a/client/devpi/push.py b/client/devpi/push.py
index 3816c76ce..e887ac481 100644
--- a/client/devpi/push.py
+++ b/client/devpi/push.py
@@ -1,6 +1,6 @@
-import py
 from devpi_common.metadata import parse_requirement, splitbasename
 from . import pypirc
+from pathlib import Path
 import traceback
 
 
@@ -34,11 +34,11 @@ def parse_target(hub, args):
         posturl = args.target[5:]
         pypirc_path = args.pypirc
         if pypirc_path is None:
-            pypirc_path = py.path.local._gethomedir().join(".pypirc")
+            pypirc_path = Path().home() / ".pypirc"
         else:
-            pypirc_path = py.path.local().join(args.pypirc, abs=True)
-        if not pypirc_path.check():
-            hub.fatal("no pypirc file found at: %s" %(pypirc_path))
+            pypirc_path = Path() / args.pypirc
+        if not pypirc_path.is_file():
+            hub.fatal(f"no pypirc file found at: {pypirc_path}")
         hub.info("using pypirc", pypirc_path)
         auth = pypirc.Auth(pypirc_path)
         try:
diff --git a/client/devpi/pypirc.py b/client/devpi/pypirc.py
index 2594e7b2f..70b78cbf4 100644
--- a/client/devpi/pypirc.py
+++ b/client/devpi/pypirc.py
@@ -1,14 +1,14 @@
 """
 helpers for authenticating against info from .pypirc files.
 """
+from pathlib import Path
 import iniconfig
-import py
 
 
 class Auth:
     def __init__(self, path=None):
         if path is None:
-            path = py.path.local._gethomedir().join(".pypirc")
+            path = Path().home() / ".pypirc"
         self.ini = iniconfig.IniConfig(path)
 
     def get_url_auth(self, secname):
diff --git a/client/devpi/test.py b/client/devpi/test.py
index 4f2ed078f..d6cafb05f 100644
--- a/client/devpi/test.py
+++ b/client/devpi/test.py
@@ -3,6 +3,7 @@
 import hashlib
 import shutil
 from devpi_common.archive import Archive
+from devpi_common.contextlib import chdir
 from devpi_common.metadata import parse_requirement
 import json
 import sys
@@ -10,14 +11,15 @@
 from devpi_common.url import URL
 from devpi_common.metadata import get_sorted_versions
 from devpi_common.viewhelp import ViewLinkStore
+from pathlib import Path
 
 
 class DevIndex:
     def __init__(self, hub, rootdir, current):
-        self.rootdir = rootdir
+        self.rootdir = Path(rootdir)
         self.current = current
         self.hub = hub
-        self.dir_download = self.rootdir.mkdir("downloads")
+        self.dir_download = self.rootdir / "downloads"
 
     def download_and_unpack(self, versioninfo, link):
         basic_auth = self.hub.current.get_basic_auth(link.href)
@@ -43,7 +45,8 @@ def download_and_unpack(self, versioninfo, link):
             assert digest == link.md5, (digest, link.md5)
         basename = URL(url).basename
 
-        path_archive = self.dir_download.join(basename)
+        self.dir_download.mkdir(exist_ok=True)
+        path_archive = self.dir_download / basename
         with path_archive.open("wb") as f:
             f.write(content)
         pkg = UnpackedPackage(
@@ -64,7 +67,7 @@ def get_matching_versioninfo(self, pkgname, indexname):
             return ViewLinkStore(projurl, r.result[version])
 
     def runtox(self, link, pkg, sdist_pkg=None, upload_tox_results=True):
-        jsonreport = pkg.rootdir.join("toxreport.json")
+        jsonreport = pkg.rootdir / "toxreport.json"
         path_archive = pkg.path_archive
         tox_path = self.hub.current.getvenvbin(
             "tox", venvdir=self.hub.venv, glob=True)
@@ -94,7 +97,7 @@ def runtox(self, link, pkg, sdist_pkg=None, upload_tox_results=True):
         toxcmd.extend(self.get_tox_args(unpack_path=sdist_pkg.path_unpacked))
 
         ret = 0
-        with sdist_pkg.path_unpacked.as_cwd():
+        with chdir(sdist_pkg.path_unpacked):
             try:
                 self.hub.popen_check(
                     toxcmd,
@@ -115,6 +118,7 @@ def runtox(self, link, pkg, sdist_pkg=None, upload_tox_results=True):
         return 0
 
     def get_tox_args(self, unpack_path):
+        assert isinstance(unpack_path, Path)
         hub = self.hub
         args = self.hub.args
         toxargs = []
@@ -122,8 +126,8 @@ def get_tox_args(self, unpack_path):
             toxargs.append("-e" + args.toxenv)
         if args.toxini:
             ini = hub.get_existing_file(args.toxini)
-        elif unpack_path.join("tox.ini").exists():
-            ini = hub.get_existing_file(unpack_path.join("tox.ini"))
+        elif unpack_path.joinpath("tox.ini").is_file():
+            ini = hub.get_existing_file(unpack_path / "tox.ini")
         elif args.fallback_ini:
             ini = hub.get_existing_file(args.fallback_ini)
         else:
@@ -148,12 +152,12 @@ def __init__(self, hub, rootdir, path_archive, versioninfo, link):
         self.hub = hub
         basename = link.basename
         if basename.endswith(".whl"):
-            rootdir = rootdir.join(basename)
+            rootdir = rootdir / basename
         elif basename.endswith((".tar.gz", ".tgz")):
-            rootdir = rootdir.join("targz")
+            rootdir = rootdir / "targz"
         elif basename.endswith(".zip"):
-            rootdir = rootdir.join("zip")
-        assert not rootdir.check(), rootdir
+            rootdir = rootdir / "zip"
+        assert not rootdir.exists(), rootdir
         self.rootdir = rootdir
         self.path_archive = path_archive
         self.versioninfo = versioninfo
@@ -168,13 +172,13 @@ def unpack(self):
         if self.link.basename.endswith(".whl"):
             inpkgdir = self.rootdir
         else:
-            inpkgdir = self.rootdir.join("%s-%s" %(pkgname, version))
-            if not inpkgdir.check():
+            inpkgdir = self.rootdir / f"{pkgname}-{version}"
+            if not inpkgdir.exists():
                 # sometimes dashes are replaced by underscores,
                 # for example the source releases of argon2_cffi
-                inpkgdir = self.rootdir.join(
-                    "%s-%s" % (pkgname.replace('-', '_'), version))
-        if not inpkgdir.check():
+                inpkgdir = self.rootdir.joinpath(
+                    f"{pkgname.replace('-', '_')}-{version}")
+        if not inpkgdir.exists():
             self.hub.fatal("Couldn't find unpacked package in", inpkgdir)
         self.path_unpacked = inpkgdir
 
diff --git a/client/devpi/upload.py b/client/devpi/upload.py
index 80697ecd5..b22478a6d 100644
--- a/client/devpi/upload.py
+++ b/client/devpi/upload.py
@@ -1,7 +1,6 @@
 import iniconfig
 import os
 import sys
-import py
 import re
 import shutil
 import zipfile
@@ -13,8 +12,11 @@
 from devpi_common.metadata import splitext_archive
 from devpi_common.archive import Archive
 from devpi_common.archive import zip_dir
+from devpi_common.contextlib import chdir
 from devpi_common.types import CompareMixin
 from .main import HTTPReply, set_devpi_auth_header
+from pathlib import Path
+from shutil import rmtree
 
 
 def main(hub, args):
@@ -71,10 +73,10 @@ def filter_latest(path_pkginfo):
 def main_fromfiles(hub, args):
     paths = []
     for p in args.path:
-        p = py.path.local(os.path.expanduser(p))
-        if not p.check():
+        p = Path(p).expanduser()
+        if not p.exists():
             hub.fatal("path does not exist: %s" % p)
-        if p.isdir() and not args.fromdir:
+        if p.is_dir() and not args.fromdir:
             hub.fatal("%s: is a directory but --from-dir not specified" % p)
         paths.append(p)
 
@@ -102,7 +104,7 @@ def do_upload_paths(self, paths):
                 pkginfo = get_pkginfo(archivepath)
                 if pkginfo is None or pkginfo.name is None:
                     hub.error("%s: does not contain PKGINFO, skipping" %
-                              archivepath.basename)
+                              archivepath.name)
                     continue
                 if isinstance(pkginfo, DocZipMeta):
                     doczip2pkginfo[archivepath] = pkginfo
@@ -122,15 +124,15 @@ def upload_doc(self, path, pkginfo):
         with self.hub.workdir() as tmp:
             if pkginfo.needs_repackage:
                 if version is None:
-                    fn = tmp.join('%s.doc.zip' % name)
+                    fn = tmp / f'{name}.doc.zip'
                 else:
-                    fn = tmp.join('%s-%s.doc.zip' % (name, version))
-                with zipfile.ZipFile(fn.strpath, "w") as z:
+                    fn = tmp / f'{name}-{version}.doc.zip'
+                with zipfile.ZipFile(str(fn), "w") as z:
                     with Archive(path) as archive:
                         for aname in archive.namelist():
                             z.writestr(aname, archive.read(aname))
                 self.hub.info(
-                    "repackaged %s to %s" % (path.basename, fn.basename))
+                    "repackaged %s to %s" % (path.name, fn.name))
                 path = fn
             self.post(
                 "doc_upload", path,
@@ -149,11 +151,11 @@ def post(self, action, path, meta):
             auth = (auth[0], hub.derive_token(auth[1], meta['name']))
             set_devpi_auth_header(headers, auth)
         if path:
-            files = {"content": (path.basename, path.open("rb"))}
+            files = {"content": (path.name, path.open("rb"))}
         else:
             files = None
         if path:
-            msg = "%s of %s to %s" %(action, path.basename, self.pypisubmit)
+            msg = f"{action} of {path.name} to {self.pypisubmit}"
         else:
             msg = "%s %s-%s to %s" %(action, meta["name"], meta["version"],
                                      self.pypisubmit)
@@ -187,7 +189,7 @@ def upload_release_file(self, path, pkginfo):
         meta = {}
         for attr in pkginfo:
             meta[attr] = getattr(pkginfo, attr)
-        pyver = get_pyversion_filetype(path.basename)
+        pyver = get_pyversion_filetype(path.name)
         meta["pyversion"], meta["filetype"] = pyver
         self.post("file_upload", path, meta=meta)
 
@@ -196,14 +198,14 @@ def upload_release_file(self, path, pkginfo):
 
 
 def get_archive_files(path):
-    if path.isfile():
+    if path.is_file():
         yield path
         return
-    for x in path.visit():
-        if not x.check(file=1):
+    for x in path.rglob("*"):
+        if not x.is_file():
             continue
         for name in ALLOWED_ARCHIVE_EXTS:
-            if x.basename.endswith(name):
+            if x.name.endswith(name):
                 yield x
 
 
@@ -269,7 +271,7 @@ def __repr__(self):
 
 
 def get_pkginfo(archivepath):
-    info = get_name_version_doczip(archivepath.basename)
+    info = get_name_version_doczip(archivepath.name)
     if info is not None:
         return DocZipMeta(*info)
 
@@ -296,6 +298,7 @@ def find_parent_subpath(startpath, relpath, raising=True):
 
 class Checkout:
     def __init__(self, hub, args, setupdir, hasvcs=None, setupdir_only=None):
+        setupdir = Path(setupdir)
         self.hub = hub
         self.args = args
         self.cm_ui = None
@@ -304,7 +307,7 @@ def __init__(self, hub, args, setupdir, hasvcs=None, setupdir_only=None):
         hasvcs = not hasvcs and not args.novcs
         setupdir_only = bool(setupdir_only or args.setupdironly)
         if hasvcs:
-            with setupdir.as_cwd():
+            with chdir(setupdir):
                 try:
                     if self.cm_ui:
                         hasvcs = check_manifest.detect_vcs(self.cm_ui).metadata_name
@@ -315,10 +318,10 @@ def __init__(self, hub, args, setupdir, hasvcs=None, setupdir_only=None):
                 else:
                     if hasvcs not in (".hg", ".git") or setupdir_only:
                         # XXX for e.g. svn we don't do copying
-                        self.rootpath = setupdir
+                        self.rootpath = Path(setupdir)
                     else:
-                        for p in setupdir.parts(reverse=True):
-                            if p.join(hasvcs).exists():
+                        for p in (setupdir, *setupdir.parents):
+                            if p.joinpath(hasvcs).exists():
                                 self.rootpath = p
                                 break
                         else:
@@ -328,37 +331,34 @@ def __init__(self, hub, args, setupdir, hasvcs=None, setupdir_only=None):
         self.setupdir_only = setupdir_only
 
     def export(self, basetemp):
+        assert isinstance(basetemp, Path)
         if not self.hasvcs:
             return Exported(self.hub, self.args, self.setupdir, self.setupdir)
-        with self.rootpath.as_cwd():
+        with chdir(self.rootpath):
             if self.cm_ui:
                 files = check_manifest.get_vcs_files(self.cm_ui)
             else:
                 files = check_manifest.get_vcs_files()
-        newrepo = basetemp.join(self.rootpath.basename)
+        newrepo = basetemp / self.rootpath.name
         for fn in files:
-            source = self.rootpath.join(fn)
-            if source.islink():
-                dest = newrepo.join(fn)
-                dest.dirpath().ensure(dir=1)
-                dest.mksymlinkto(source.readlink(), absolute=True)
-            elif source.isfile():
-                dest = newrepo.join(fn)
-                dest.dirpath().ensure(dir=1)
-                source.copy(dest, mode=True)
+            source = self.rootpath / fn
+            dest = newrepo / fn
+            dest.parent.mkdir(parents=True, exist_ok=True)
+            shutil.copy2(source, dest, follow_symlinks=False)
         self.hub.debug("copied", len(files), "files to", newrepo)
 
         if self.hasvcs not in (".git", ".hg") or self.setupdir_only:
             self.hub.warn("not copying vcs repository metadata for", self.hasvcs)
         else:
-            srcrepo = self.rootpath.join(self.hasvcs)
+            srcrepo = self.rootpath / self.hasvcs
             assert srcrepo.exists(), srcrepo
-            destrepo = newrepo.join(self.hasvcs)
-            self.rootpath.join(self.hasvcs).copy(destrepo, mode=True)
+            destrepo = newrepo / self.hasvcs
+            source = self.rootpath / self.hasvcs
+            shutil.copytree(srcrepo, destrepo)
             self.hub.info("copied repo", srcrepo, "to", destrepo)
         self.hub.debug(
             "%s-exported project to %s -> new CWD" % (self.hasvcs, newrepo))
-        setupdir_newrepo = newrepo.join(self.setupdir.relto(self.rootpath))
+        setupdir_newrepo = newrepo / self.setupdir.relative_to(self.rootpath)
         return Exported(self.hub, self.args, setupdir_newrepo, self.setupdir)
 
 
@@ -368,7 +368,7 @@ def __init__(self, hub, args, rootpath, origrepo):
         self.args = args
         self.rootpath = rootpath
         self.origrepo = origrepo
-        self.target_distdir = origrepo.join("dist")
+        self.target_distdir = origrepo / "dist"
 
     @property
     def python(self):
@@ -394,7 +394,7 @@ def __str__(self):
 
     def setup_name_and_version(self):
         metadata = build.util.project_wheel_metadata(
-            self.rootpath.strpath, False
+            str(self.rootpath), False
         )
         name = metadata["name"]
         version = metadata["version"]
@@ -402,9 +402,9 @@ def setup_name_and_version(self):
         return name, version
 
     def prepare(self):
-        if self.target_distdir.check():
+        if self.target_distdir.is_dir():
             self.hub.line("pre-build: cleaning %s" % self.target_distdir)
-            self.target_distdir.remove()
+            rmtree(self.target_distdir)
         self.target_distdir.mkdir()
 
     @staticmethod
@@ -498,10 +498,10 @@ def setup_build(self, default_formats=None):
 
         archives = []
         for cmd in cmds:
-            distdir = self.rootpath.join("dist")
+            distdir = self.rootpath / "dist"
             if self.rootpath != self.origrepo:
                 if distdir.exists():
-                    distdir.remove()
+                    rmtree(distdir)
 
             if self.args.verbose:
                 ret = self.hub.popen_check(cmd, cwd=self.rootpath)
@@ -511,9 +511,9 @@ def setup_build(self, default_formats=None):
             if ret is None:  # dryrun
                 continue
 
-            for x in distdir.listdir():  # usually just one
-                target = self.target_distdir.join(x.basename)
-                x.move(target)
+            for x in distdir.iterdir():  # usually just one
+                target = self.target_distdir / x.name
+                x.rename(target)
                 archives.append(target)
                 self.log_build(target)
 
@@ -521,19 +521,19 @@ def setup_build(self, default_formats=None):
 
     def setup_build_docs(self):
         name, version = self.setup_name_and_version()
-        build = self.rootpath.join("build")
+        build = self.rootpath / "build"
         if build.exists():
-            build.remove()
+            rmtree(build)
         for guess in ("doc", "docs", "source"):
-            docs = self.rootpath.join(guess)
-            if docs.isdir():
-                if docs.join("conf.py").exists():
+            docs = self.rootpath / guess
+            if docs.is_dir():
+                if docs.joinpath("conf.py").is_file():
+                    break
+                source = docs / "source"
+                if source.is_dir() and source.joinpath("conf.py").is_file():
+                    build = docs / "build"
+                    docs = source
                     break
-                else:
-                    source = docs.join("source")
-                    if source.isdir() and source.join("conf.py").exists():
-                        build, docs = docs.join("build"), source
-                        break
         cmd = ["sphinx-build", "-E", docs, build]
         if self.args.verbose:
             ret = self.hub.popen_check(cmd, cwd=self.rootpath)
@@ -541,13 +541,13 @@ def setup_build_docs(self):
             ret = self.hub.popen_output(cmd, cwd=self.rootpath)
         if ret is None:
             return
-        p = self.target_distdir.join("%s-%s.doc.zip" %(name, version))
+        p = self.target_distdir / f"{name}-{version}.doc.zip"
         zip_dir(build, p)
         self.log_build(p, "[sphinx docs]")
         return p
 
     def log_build(self, path, suffix=None):
-        kb = path.size() / 1000
+        kb = path.stat().st_size // 1000
         if suffix:
             self.hub.line("built: %s %s %skb" % (path, suffix, kb))
         else:
@@ -590,8 +590,8 @@ def get(self, key):
 
 
 def read_setupcfg(hub, path):
-    setup_cfg = path.join("setup.cfg")
-    if setup_cfg.exists():
+    setup_cfg = Path(path) / "setup.cfg"
+    if setup_cfg.is_file():
         cfg = iniconfig.IniConfig(setup_cfg)
         if 'devpi:upload' in cfg.sections:
             hub.line("detected devpi:upload section in %s" % setup_cfg, bold=True)
diff --git a/client/devpi/use.py b/client/devpi/use.py
index 9211dab2e..e2f33ae4a 100644
--- a/client/devpi/use.py
+++ b/client/devpi/use.py
@@ -4,13 +4,14 @@
 import itertools
 import os
 import sys
-import py
 import re
 import json
 import shutil
 
 from devpi_common.types import cached_property
 from devpi_common.url import URL
+from pathlib import Path
+
 
 if sys.platform == "win32":
     vbin = "Scripts"
@@ -357,7 +358,7 @@ def getvenvbin(self, name, venvdir=None, glob=True):
         if venvdir is None:
             venvdir = self.venvdir
         if venvdir:
-            bindir = py.path.local(venvdir).join(vbin)
+            bindir = Path(venvdir) / vbin
             return shutil.which(name, path=str(bindir))
         if glob:
             return shutil.which(name)
@@ -403,9 +404,10 @@ def get_simpleproject_url(self, name, indexname=None):
 def _load_json(path, dest):
     if path is None:
         return
-    if not path.check():
+    path = Path(path)
+    if not path.is_file():
         return
-    raw = path.read().strip()
+    raw = path.read_text().strip()
     if not raw:
         return
     data = json.loads(raw)
@@ -425,19 +427,20 @@ def __init__(self, auth_path, current_path):
         _load_json(self.current_path, self._currentdict)
 
     def exists(self):
-        return self.current_path and self.current_path.check()
+        return self.current_path and self.current_path.is_file()
 
     def _persist(self, data, path, force_write=False):
         if path is None:
             return
+        path = Path(path)
         try:
-            olddata = json.loads(path.read())
+            olddata = json.loads(path.read_text())
         except Exception:
             olddata = {}
         if force_write or data != olddata:
             oldumask = os.umask(7 * 8 + 7)
             try:
-                path.write(
+                path.write_text(
                     json.dumps(data, indent=2, sort_keys=True))
             finally:
                 os.umask(oldumask)
@@ -475,7 +478,7 @@ def main(hub, args=None):
         if not hub.local_current_path.exists():
             current = hub.current
             hub.info("Creating local configuration at %s" % hub.local_current_path)
-            hub.local_current_path.ensure()
+            hub.local_current_path.touch()
             current = current.switch_to_local(
                 hub, current.index, hub.local_current_path)
             # now store existing data in new location
@@ -485,7 +488,7 @@ def main(hub, args=None):
     if args.delete:
         if not hub.current.exists():
             hub.error_and_out("NO configuration found")
-        hub.current.current_path.remove()
+        hub.current.current_path.unlink()
         hub.info("REMOVED configuration at", hub.current.current_path)
         return
     if current.exists():
@@ -625,16 +628,18 @@ def __init__(self, path=None):
         if path is None:
             path = self.default_location
         self.screen_name = str(path)
-        self.path = py.path.local(path, expanduser=True)
-        self.backup_path = self.path + "-bak"
+        self.path = Path(path).expanduser()
+        self.backup_path = self.path.with_name(self.path.name + "-bak")
 
     def exists(self):
         return self.path.exists()
 
     @property
     def indexserver(self):
-        if self.path.exists():
-            for line in self.path.readlines(cr=0):
+        if not self.path.exists():
+            return
+        with self.path.open() as f:
+            for line in f:
                 m = self.regex.match(line)
                 if m:
                     return m.group(2)
@@ -644,20 +649,22 @@ def write_default(self, indexserver):
             raise ValueError("config file already exists")
         content = "\n".join([self.section_name,
                              "%s = %s\n" % (self.config_name, indexserver)])
-        self.path.ensure().write(content)
+        self.path.parent.mkdir(parents=True, exist_ok=True)
+        self.path.write_text(content)
 
     def write_indexserver(self, indexserver):
         self.ensure_backup_file()
         if not self.path.exists():
             self.write_default(indexserver)
+            return
+        if self.indexserver:
+            section = None
         else:
-            if self.indexserver:
-                section = None
-            else:
-                section = self.section_name
-            newlines = []
-            found = False
-            for line in self.path.readlines(cr=1):
+            section = self.section_name
+        newlines = []
+        found = False
+        with self.path.open() as f:
+            for line in f:
                 if not section:
                     m = self.regex.match(line)
                     if m:
@@ -670,19 +677,20 @@ def write_indexserver(self, indexserver):
             if not found:
                 newlines.append(self.section_name + "\n")
                 newlines.append("%s = %s\n" %(self.config_name, indexserver))
-            self.path.write("".join(newlines))
+        self.path.write_text("".join(newlines))
 
     def ensure_backup_file(self):
         if self.path.exists() and not self.backup_path.exists():
-            self.path.copy(self.backup_path)
+            self.backup_path.write_text(self.path.read_text())
+            shutil.copyfile(self.path, self.backup_path)
 
 
 class DistutilsCfg(BaseCfg):
     section_name = "[easy_install]"
-    default_location = py.path.local(
+    default_location = Path(
         "~/.pydistutils.cfg"
         if sys.platform != "win32"
-        else "~/pydistutils.cfg", expanduser=True)
+        else "~/pydistutils.cfg").expanduser()
 
 
 class PipCfg(BaseCfg):
@@ -703,20 +711,20 @@ def appdirs(self):
 
     @property
     def legacy_location(self):
-        confdir = py.path.local(
-            "~/.pip" if sys.platform != "win32" else "~/pip",
-            expanduser=True)
-        return confdir.join(self.pip_conf_name)
+        confdir = Path(
+            "~/.pip" if sys.platform != "win32" else "~/pip").expanduser()
+        return confdir / self.pip_conf_name
 
     @property
     def new_location(self):
-        return py.path.local(
-            self.appdirs.user_config_dir("pip")).join(self.pip_conf_name)
+        return Path(
+            self.appdirs.user_config_dir("pip")) / self.pip_conf_name
 
     @property
     def default_location(self):
         if self.venv:
-            default_location = py.path.local(self.venv, expanduser=True).join(self.pip_conf_name)
+            default_location = Path(
+                self.venv).expanduser() / self.pip_conf_name
         elif 'PIP_CONFIG_FILE' in os.environ:
             default_location = os.environ.get('PIP_CONFIG_FILE')
         elif self.legacy_location.exists():
@@ -737,20 +745,21 @@ def write_searchindexserver(self, searchindexserver):
         newlines = []
         found = False
         insection = False
-        for line in self.path.readlines(cr=1):
-            if insection:
-                if line.strip().startswith('['):
-                    insection = False
-            if section in line.lower() and not insection:
-                insection = True
-            if insection and re.match(r'index\s*=.*', line):
-                line = "index = %s\n" % searchindexserver
-                found = True
-            newlines.append(line)
+        with self.path.open() as f:
+            for line in f:
+                if insection:
+                    if line.strip().startswith('['):
+                        insection = False
+                if section in line.lower() and not insection:
+                    insection = True
+                if insection and re.match(r'index\s*=.*', line):
+                    line = "index = %s\n" % searchindexserver
+                    found = True
+                newlines.append(line)
         if not found:
             newlines.append(section + "\n")
             newlines.append("index = %s\n" % searchindexserver)
-        self.path.write("".join(newlines))
+        self.path.write_text("".join(newlines))
 
     def write_trustedhost(self, indexserver):
         self.ensure_backup_file()
@@ -761,22 +770,23 @@ def write_trustedhost(self, indexserver):
         insection = False
         indexserver = URL(indexserver)
         trustedhost = "trusted-host = %s\n" % indexserver.hostname
-        for line in self.path.readlines(cr=1):
-            if insection:
-                if line.strip().startswith('['):
-                    if not found:
-                        newlines.append(trustedhost)
-                        found = True
-                    insection = False
-            if not found and self.section_name in line.lower() and not insection:
-                insection = True
-            if not found and insection and re.match(r'trusted-host\s*=\s*%s' % indexserver.hostname, line):
-                found = True
-            newlines.append(line)
+        with self.path.open() as f:
+            for line in f:
+                if insection:
+                    if line.strip().startswith('['):
+                        if not found:
+                            newlines.append(trustedhost)
+                            found = True
+                        insection = False
+                if not found and self.section_name in line.lower() and not insection:
+                    insection = True
+                if not found and insection and re.match(r'trusted-host\s*=\s*%s' % indexserver.hostname, line):
+                    found = True
+                newlines.append(line)
         if not found:
             newlines.append(self.section_name + "\n")
             newlines.append(trustedhost)
-        self.path.write("".join(newlines))
+        self.path.write_text("".join(newlines))
 
     def clear_trustedhost(self, indexserver):
         self.ensure_backup_file()
@@ -784,18 +794,18 @@ def clear_trustedhost(self, indexserver):
             return
         newlines = []
         indexserver = URL(indexserver)
-        for line in self.path.readlines(cr=1):
-            if not re.match(r'trusted-host\s*=\s*%s' % indexserver.hostname, line):
-                newlines.append(line)
-        self.path.write("".join(newlines))
+        with self.path.open() as f:
+            for line in f:
+                if not re.match(r'trusted-host\s*=\s*%s' % indexserver.hostname, line):
+                    newlines.append(line)
+        self.path.write_text("".join(newlines))
 
 
 class BuildoutCfg(BaseCfg):
     section_name = "[buildout]"
     config_name = "index"
     regex = re.compile(r"(index)\s*=\s*(.*)")
-    default_location = py.path.local(
-        "~/.buildout/default.cfg", expanduser=True)
+    default_location = Path("~/.buildout/default.cfg").expanduser()
 
 
 class KeyValues(list):
diff --git a/client/news/pylib.removal b/client/news/pylib.removal
new file mode 100644
index 000000000..d341f9cb6
--- /dev/null
+++ b/client/news/pylib.removal
@@ -0,0 +1,2 @@
+Removed dependency on py package.
+Plugins which expect py.path.local need to be adjusted to work with pathlib.Path.
\ No newline at end of file
diff --git a/client/pyproject.toml b/client/pyproject.toml
index 0067c778e..e302cb0ea 100644
--- a/client/pyproject.toml
+++ b/client/pyproject.toml
@@ -16,7 +16,6 @@ dependencies = [
     "pkginfo>=1.4.2",
     "platformdirs",
     "pluggy>=0.6.0,<2.0",
-    "py>=1.4.31",
 ]
 requires-python = ">=3.7"
 maintainers = [
diff --git a/client/testing/conftest.py b/client/testing/conftest.py
index 7c7ebb32f..bb8c0afab 100644
--- a/client/testing/conftest.py
+++ b/client/testing/conftest.py
@@ -1,13 +1,14 @@
 from _pytest import capture
 from contextlib import closing
+from devpi_common.contextlib import chdir
 from devpi_common.metadata import parse_version
 from io import StringIO
+from pathlib import Path
 import codecs
 import os
 import pytest
 import socket
 import textwrap
-import py
 import shutil
 import sys
 import json
@@ -246,7 +247,6 @@ def devpi(cmd_devpi, devpi_username, url_of_liveserver):
 
 
 def _path_parts(path):
-    path = path and str(path)  # py.path.local support
     parts = []
     while path:
         folder, name = os.path.split(path)
@@ -259,13 +259,6 @@ def _path_parts(path):
     return parts
 
 
-def _path_join(base, *args):
-    # workaround for a py.path.local bug on Windows (`path.join('/x', abs=1)`
-    # should be py.path.local('X:\\x') where `X` is the current drive, when in
-    # fact it comes out as py.path.local('\\x'))
-    return py.path.local(base.join(*args, abs=1))
-
-
 def _filedefs_contains(base, filedefs, path):
     """
     whether `filedefs` defines a file/folder with the given `path`
@@ -277,10 +270,10 @@ def _filedefs_contains(base, filedefs, path):
 
     """
     unknown = object()
-    base = py.path.local(base)
-    path = _path_join(base, path)
+    base = Path(base)
+    path = base / path
 
-    path_rel_parts = _path_parts(path.relto(base))
+    path_rel_parts = _path_parts(path.relative_to(base))
     for part in path_rel_parts:
         if not isinstance(filedefs, dict):
             return False
@@ -338,7 +331,7 @@ def initproj_(nameversion, filedefs=None, src_root=".", kind="setup.py"):
         else:
             name, version = nameversion
         base = tmpdir.join(name)
-        src_root_path = _path_join(base, src_root)
+        src_root_path = base / src_root
         assert base == src_root_path or src_root_path.relto(
             base
         ), "`src_root` must be the constructed project folder or its direct or indirect subfolder"
@@ -601,8 +594,8 @@ def runproc():
 def runprocess(tmpdir, cmdargs):
     from _pytest.pytester import RunResult
     cmdargs = [str(x) for x in cmdargs]
-    p1 = tmpdir.join("stdout")
-    print_info("running", cmdargs, "curdir=", py.path.local())
+    p1 = Path(tmpdir) / "stdout"
+    print_info("running", cmdargs, "curdir=", Path())
     with codecs.open(str(p1), "w", encoding="utf8") as f1:
         now = time.time()
         popen = subprocess.Popen(
@@ -639,9 +632,9 @@ def do_create_venv():
         # we need to change directory, otherwise the path will become
         # too long on windows
         venvinstalldir.ensure_dir()
-        os.chdir(venvinstalldir.strpath)
+        os.chdir(venvinstalldir)
         subprocess.check_call([
-            "virtualenv", "--never-download", venvdir.strpath])
+            "virtualenv", "--never-download", str(venvdir)])
         # activate
         if sys.platform == "win32":
             bindir = "Scripts"
@@ -687,7 +680,7 @@ def mkhub(arglist):
             arglist.append("--clientdir=%s" % tmp)
         pm = get_pluginmanager()
         args = parse_args(["devpi_"] + arglist, pm)
-        with tmp.as_cwd():
+        with chdir(tmp):
             return Hub(args)
     return mkhub
 
diff --git a/client/testing/test_list_remove.py b/client/testing/test_list_remove.py
index 514269596..e7d7b49af 100644
--- a/client/testing/test_list_remove.py
+++ b/client/testing/test_list_remove.py
@@ -6,7 +6,7 @@
 from devpi.list_remove import out_index
 from devpi.list_remove import out_project
 from devpi.list_remove import show_commands
-import py
+from pathlib import Path
 import pytest
 
 
@@ -108,7 +108,7 @@ def test_all(self, initproj, devpi, out_devpi):
         initproj("hello-1.0", {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         devpi("upload", "--no-isolation", "--formats", "sdist.zip")
         devpi("upload", "--no-isolation", "--formats", "sdist.zip,bdist_dumb")
         initproj("hello-1.1", {"doc": {
@@ -142,7 +142,7 @@ def test_remove_file(self, initproj, devpi, out_devpi, server_version, url_of_li
         initproj("hello-1.0", {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         devpi("upload", "--no-isolation", "--formats", "sdist.zip")
         devpi("upload", "--no-isolation", "--formats", "sdist.zip,bdist_dumb")
         initproj("hello-1.1", {"doc": {
@@ -168,7 +168,7 @@ def test_all_index_option(self, initproj, devpi, out_devpi, other_index):
         initproj("hello-1.0", {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         devpi("upload", "--no-isolation", "--formats", "sdist.zip")
         devpi("upload", "--no-isolation", "--formats", "sdist.zip,bdist_dumb")
         initproj("hello-1.1", {"doc": {
@@ -211,7 +211,7 @@ def test_delete_version_with_inheritance(self, initproj, devpi, out_devpi):
         initproj("dddttt-0.666", {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         devpi("upload", "--no-isolation", "--formats", "sdist.zip")
         out = out_devpi("list", "dddttt", "--all")
         out.stdout.fnmatch_lines_random("*/dev/*/dddttt-0.666.zip")
@@ -226,7 +226,7 @@ def test_delete_version_range_with_inheritance(self, initproj, devpi, out_devpi)
         initproj("dddttt-0.666", {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         devpi("upload", "--no-isolation", "--formats", "sdist.zip")
         # remember username
         out = out_devpi("use")
@@ -237,13 +237,13 @@ def test_delete_version_range_with_inheritance(self, initproj, devpi, out_devpi)
         initproj("dddttt-1.0", {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         devpi("upload", "--no-isolation", "--formats", "sdist.zip")
         # upload 2.0 to dev2 index
         initproj("dddttt-2.0", {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         devpi("upload", "--no-isolation", "--formats", "sdist.zip")
 
         out = out_devpi("list", "dddttt", "--all")
@@ -267,7 +267,7 @@ def test_delete_project_with_inheritance(self, initproj, devpi, out_devpi, simpy
         initproj("dddttt-0.666", {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         devpi("upload", "--no-isolation", "--formats", "sdist.zip")
         out = out_devpi("list", "dddttt", "--all")
         out.stdout.fnmatch_lines_random("*/dev/*/dddttt-0.666.zip")
@@ -285,7 +285,7 @@ def test_delete_file_non_volatile(self, initproj, devpi, out_devpi, server_versi
         initproj("dddttt-0.666", {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         devpi("upload", "--no-isolation", "--formats", "sdist.zip")
         out = out_devpi("list", "dddttt", "--all")
         out.stdout.fnmatch_lines_random("*/dev/*/dddttt-0.666.zip")
@@ -305,7 +305,7 @@ def test_delete_project_non_volatile(self, initproj, devpi, out_devpi, server_ve
         initproj("dddttt-0.666", {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         devpi("upload", "--no-isolation", "--formats", "sdist.zip")
         out = out_devpi("list", "dddttt", "--all")
         out.stdout.fnmatch_lines_random("*/dev/*/dddttt-0.666.zip")
diff --git a/client/testing/test_test.py b/client/testing/test_test.py
index 35b0392e5..4541ee682 100644
--- a/client/testing/test_test.py
+++ b/client/testing/test_test.py
@@ -1,6 +1,5 @@
 import os
 import subprocess
-import py
 import pytest
 import sys
 from devpi_common.viewhelp import ViewLinkStore
@@ -8,6 +7,7 @@
 from devpi.test import find_sdist_and_wheels
 from devpi.test import prepare_toxrun_args
 from devpi.test import post_tox_json_report
+from pathlib import Path
 
 
 def test_post_tox_json_report(loghub, mock_http_api):
@@ -49,7 +49,7 @@ def test_passthrough_args_toxargs(makehub, tmpdir, pseudo_current):
     hub = makehub(["test", "--tox-args", "-- -x", "somepkg"])
     index = DevIndex(hub, tmpdir, pseudo_current)
     tmpdir.ensure("tox.ini")
-    args = index.get_tox_args(unpack_path=tmpdir)
+    args = index.get_tox_args(unpack_path=Path(tmpdir.strpath))
     assert args[-2:] == ["--", "-x"]
 
 
@@ -147,7 +147,7 @@ def test_toxini(makehub, tmpdir, pseudo_current):
     hub = makehub(["test", "-c", toxini, "somepkg"])
     index = DevIndex(hub, tmpdir, pseudo_current)
     tmpdir.ensure("tox.ini")
-    args = index.get_tox_args(unpack_path=tmpdir)
+    args = index.get_tox_args(unpack_path=Path(tmpdir.strpath))
     assert contains_sublist(args, ["-c", str(toxini)])
 
 
@@ -155,7 +155,7 @@ def test_passthrough_args_env(makehub, tmpdir, pseudo_current):
     hub = makehub(["test", "-epy27", "somepkg"])
     index = DevIndex(hub, tmpdir, pseudo_current)
     tmpdir.ensure("tox.ini")
-    args = index.get_tox_args(unpack_path=tmpdir)
+    args = index.get_tox_args(unpack_path=Path(tmpdir.strpath))
     assert contains_sublist(args, ["-epy27"])
 
 
@@ -163,10 +163,10 @@ def test_fallback_ini(makehub, tmpdir, pseudo_current):
     p = tmpdir.ensure("mytox.ini")
     hub = makehub(["test", "--fallback-ini", str(p), "somepkg"])
     index = DevIndex(hub, tmpdir, pseudo_current)
-    args = index.get_tox_args(unpack_path=tmpdir)
+    args = index.get_tox_args(unpack_path=Path(tmpdir.strpath))
     assert contains_sublist(args, ["-c", str(p)])
     p2 = tmpdir.ensure("tox.ini")
-    args = index.get_tox_args(unpack_path=tmpdir)
+    args = index.get_tox_args(unpack_path=Path(tmpdir.strpath))
     assert contains_sublist(args, ["-c", str(p2)])
 
 
@@ -243,16 +243,17 @@ def test_prepare_toxrun_args(self, loghub, pseudo_current, tmpdir, reqmock, init
         initproj("prep1-1.0", filedefs={})
         subprocess.check_call(["python", "setup.py", "sdist", "--formats=gztar,zip"])
         subprocess.check_call(["python", "setup.py", "bdist_wheel", "--universal"])
-        for p in py.path.local("dist").listdir():
-            reqmock.mockresponse("http://b/" + p.basename, code=200, method="GET",
-                                 data=p.read("rb"))
+        for p in Path("dist").iterdir():
+            reqmock.mockresponse(
+                f"http://b/{p.name}",
+                code=200, data=p.read_bytes(), method="GET")
         toxrunargs = prepare_toxrun_args(dev_index, vl, sdist_links, wheel_links)
         assert len(toxrunargs) == 3
         sdist1, sdist2, wheel1 = toxrunargs
         assert sdist1[0].basename == "prep1-1.0.tar.gz"
-        assert sdist1[1].path_unpacked.strpath.endswith("targz" + os.sep + "prep1-1.0")
+        assert str(sdist1[1].path_unpacked).endswith("targz" + os.sep + "prep1-1.0")
         assert sdist2[0].basename == "prep1-1.0.zip"
-        assert sdist2[1].path_unpacked.strpath.endswith("zip" + os.sep + "prep1-1.0")
+        assert str(sdist2[1].path_unpacked).endswith("zip" + os.sep + "prep1-1.0")
         assert wheel1[0].basename == "prep1-1.0-py2.py3-none-any.whl"
         assert str(wheel1[1].path_unpacked).endswith(wheel1[0].basename)
 
@@ -273,16 +274,17 @@ def test_prepare_toxrun_args2(self, loghub, pseudo_current, tmpdir, reqmock, ini
         initproj("prep_under-1.0", filedefs={})
         subprocess.check_call(["python", "setup.py", "sdist", "--formats=gztar,zip"])
         subprocess.check_call(["python", "setup.py", "bdist_wheel", "--universal"])
-        for p in py.path.local("dist").listdir():
-            reqmock.mockresponse("http://b/" + p.basename, code=200, method="GET",
-                                 data=p.read("rb"))
+        for p in Path("dist").iterdir():
+            reqmock.mockresponse(
+                f"http://b/{p.name}",
+                code=200, data=p.read_bytes(), method="GET")
         toxrunargs = prepare_toxrun_args(dev_index, vl, sdist_links, wheel_links)
         assert len(toxrunargs) == 3
         sdist1, sdist2, wheel1 = toxrunargs
         assert sdist1[0].basename == "prep_under-1.0.tar.gz"
-        assert sdist1[1].path_unpacked.strpath.endswith("targz" + os.sep + "prep_under-1.0")
+        assert str(sdist1[1].path_unpacked).endswith("targz" + os.sep + "prep_under-1.0")
         assert sdist2[0].basename == "prep_under-1.0.zip"
-        assert sdist2[1].path_unpacked.strpath.endswith("zip" + os.sep + "prep_under-1.0")
+        assert str(sdist2[1].path_unpacked).endswith("zip" + os.sep + "prep_under-1.0")
         assert wheel1[0].basename == "prep_under-1.0-py2.py3-none-any.whl"
         assert str(wheel1[1].path_unpacked).endswith(wheel1[0].basename)
 
@@ -302,9 +304,10 @@ def test_prepare_toxrun_args_select(self, loghub, pseudo_current, tmpdir, reqmoc
         initproj("prep_under-1.0", filedefs={})
         subprocess.check_call(["python", "setup.py", "sdist", "--formats=gztar"])
         subprocess.check_call(["python", "setup.py", "bdist_wheel"])
-        for p in py.path.local("dist").listdir():
-            reqmock.mockresponse("http://b/" + p.basename, code=200, method="GET",
-                                 data=p.read("rb"))
+        for p in Path("dist").iterdir():
+            reqmock.mockresponse(
+                f"http://b/{p.name}",
+                code=200, data=p.read_bytes(), method="GET")
         toxrunargs = prepare_toxrun_args(
             dev_index, vl, sdist_links, wheel_links, select=pyver)
         assert len(toxrunargs) == 1
@@ -339,8 +342,8 @@ def test_wheels_only_download_selected(self, loghub, monkeypatch, pseudo_current
             select="(?:.*39)(?:.*linux)(?:.*whl)")
         ((wheel_link, wheel, wheel_sdist),) = toxrunargs
         assert wheel_link.basename == "prep_under-1.0-cp39-cp39-manylinux_2_17_x86_64.manylinux2014_x86_64.whl"
-        assert wheel.path_archive.basename == "prep_under-1.0-cp39-cp39-manylinux_2_17_x86_64.manylinux2014_x86_64.whl"
-        assert wheel_sdist.path_archive.basename == "prep_under-1.0.tar.gz"
+        assert wheel.path_archive.name == "prep_under-1.0-cp39-cp39-manylinux_2_17_x86_64.manylinux2014_x86_64.whl"
+        assert wheel_sdist.path_archive.name == "prep_under-1.0.tar.gz"
 
     def test_wheels_and_sdist(self, out_devpi, create_and_upload):
         create_and_upload("exa-1.0", filedefs={
diff --git a/client/testing/test_upload.py b/client/testing/test_upload.py
index 1c21271f7..b6e69003b 100644
--- a/client/testing/test_upload.py
+++ b/client/testing/test_upload.py
@@ -1,7 +1,6 @@
 import json
 import os
 import stat
-import py
 import pytest
 import re
 import shutil
@@ -13,7 +12,9 @@
 from devpi.upload import get_pkginfo
 from devpi.upload import main
 from devpi.upload import read_setupcfg
+from devpi_common.contextlib import chdir
 from io import BytesIO
+from pathlib import Path
 from textwrap import dedent
 from devpi_common.metadata import splitbasename
 from devpi_common.viewhelp import ViewLinkStore
@@ -22,7 +23,7 @@
 
 @pytest.fixture
 def datadir():
-    return py.path.local(__file__).dirpath("data")
+    return Path(__file__).parent / "data"
 
 
 def runproc(cmd):
@@ -78,7 +79,7 @@ def repo(self, request, setupdir_rel, tmpdir_factory):
         if request.param == "hg":
             if not shutil.which("hg"):
                 pytest.skip("'hg' command not found")
-            with repo.as_cwd():
+            with chdir(repo):
                 runproc("hg init")
                 runproc("hg add {0}/file {0}/link {0}/setup.py".format(setupdir_rel))
                 runproc("hg add {0}/file {0}/{1}".format(setupdir_rel,
@@ -87,7 +88,7 @@ def repo(self, request, setupdir_rel, tmpdir_factory):
             return repo
         if not shutil.which("git"):
             pytest.skip("'git' command not found")
-        with repo.as_cwd():
+        with chdir(repo):
             runproc("git init")
             runproc("git config user.email 'you@example.com'")
             runproc("git config user.name 'you'")
@@ -100,57 +101,56 @@ def repo(self, request, setupdir_rel, tmpdir_factory):
     def test_vcs_export(self, uploadhub, repo, setupdir, tmpdir):
         checkout = Checkout(uploadhub, uploadhub.args, setupdir)
         assert checkout.rootpath == repo
-        newrepo = tmpdir.mkdir("newrepo")
+        newrepo = Path(tmpdir.mkdir("newrepo").strpath)
         result = checkout.export(newrepo)
-        assert result.rootpath.join("file").check()
-        assert result.rootpath.join("link").check()
+        assert result.rootpath.joinpath("file").exists()
+        assert result.rootpath.joinpath("link").exists()
         if not sys.platform.startswith("win"):
-            assert result.rootpath.join("link").readlink() == ".."
-        assert result.rootpath == newrepo.join(repo.basename).join(
-            repo.bestrelpath(setupdir))
+            assert os.readlink(result.rootpath / "link") == ".."
+        assert result.rootpath == newrepo / repo.basename / repo.bestrelpath(setupdir)
         # ensure we also copied repo meta info
         if repo.join(".hg").exists():
-            assert newrepo.join(repo.basename).join(".hg").listdir()
+            assert list(newrepo.joinpath(repo.basename, ".hg").iterdir())
         else:
-            assert newrepo.join(repo.basename).join(".git").listdir()
+            assert list(newrepo.joinpath(repo.basename, ".git").iterdir())
         with uploadhub.workdir() as uploadbase:
             checkout.export(uploadbase)
-            readonly = uploadbase.join("readonly")
-            readonly.write("foo")
+            readonly = uploadbase / "readonly"
+            readonly.write_text("foo")
             ro_bits = stat.S_IRUSR | stat.S_IRGRP | stat.S_IROTH
             os.chmod(str(readonly), ro_bits)
-        assert readonly.check() is False
-        assert uploadbase.check() is False
+        assert not readonly.exists()
+        assert not uploadbase.exists()
 
     def test_vcs_export_setupdironly(self, uploadhub, setupdir, tmpdir, monkeypatch):
         monkeypatch.setattr(uploadhub.args, "setupdironly", True)
         checkout = Checkout(uploadhub, uploadhub.args, setupdir)
         assert checkout.rootpath == setupdir
-        newrepo = tmpdir.mkdir("newrepo")
+        newrepo = Path(tmpdir.mkdir("newrepo").strpath)
         result = checkout.export(newrepo)
-        assert result.rootpath.join("file").check()
-        assert result.rootpath.join("link").check()
-        p = result.rootpath.join("setup.py")
+        assert result.rootpath.joinpath("file").exists()
+        assert result.rootpath.joinpath("link").exists()
+        p = result.rootpath / "setup.py"
         assert p.exists()
         if not sys.platform.startswith("win"):
-            assert p.stat().mode & int("0777", 8) == int("0777", 8)
-            assert result.rootpath.join("link").readlink() == '..'
-        assert result.rootpath == newrepo.join(setupdir.basename)
+            assert p.stat().st_mode & int("0777", 8) == int("0777", 8)
+            assert os.readlink(result.rootpath / "link") == '..'
+        assert result.rootpath == newrepo / setupdir.basename
 
     def test_vcs_export_disabled(self, uploadhub, setupdir, tmpdir, monkeypatch):
         monkeypatch.setattr(uploadhub.args, "novcs", True)
         checkout = Checkout(uploadhub, uploadhub.args, setupdir)
         assert not checkout.hasvcs
-        exported = checkout.export(tmpdir)
+        exported = checkout.export(Path(tmpdir.strpath))
         assert exported.rootpath == checkout.setupdir
 
     def test_vcs_export_verify_setup(self, uploadhub, setupdir, tmpdir):
         subdir = setupdir.mkdir("subdir")
         subdir.ensure("setup.py")
         checkout = Checkout(uploadhub, uploadhub.args, subdir)
-        wc = tmpdir.mkdir("wc")
+        wc = Path(tmpdir.mkdir("wc").strpath)
         exported = checkout.export(wc)
-        assert not exported.rootpath.join("setup.py").check()
+        assert not exported.rootpath.joinpath("setup.py").exists()
 
     def test_export_attributes(self, uploadhub, setupdir, tmpdir):
         checkout = Checkout(uploadhub, uploadhub.args, setupdir)
@@ -160,7 +160,7 @@ def test_export_attributes(self, uploadhub, setupdir, tmpdir):
             print("* foo, bar")
             setup(name="xyz", version="1.2.3")
         """))
-        exported = checkout.export(tmpdir)
+        exported = checkout.export(Path(tmpdir.strpath))
         name, version = exported.setup_name_and_version()
         assert name == "xyz"
         assert version == "1.2.3"
@@ -171,7 +171,7 @@ def test_setup_build_docs(self, uploadhub, setupdir, tmpdir):
             from setuptools import setup
             setup(name="xyz", version="1.2.3")
         """))
-        exported = checkout.export(tmpdir)
+        exported = checkout.export(Path(tmpdir.strpath))
         assert exported.rootpath != exported.origrepo
         # we have to mock a bit unfortunately
         # to find out if the sphinx building popen command
@@ -254,8 +254,8 @@ class args:
         withdocs = None
 
     initproj("pkg-1.0")
-    tmpdir = py.path.local()
-    certpath = tmpdir.join("cert.key").strpath
+    tmpdir = Path()
+    certpath = str(tmpdir / "cert.key")
     uploadhub.cwd = tmpdir
     uploadhub.http = Session()
     uploadhub.current.reconfigure(dict(
@@ -307,8 +307,7 @@ def send(req, **kw):
         return Response()
 
     initproj("pkg-1.0")
-    tmpdir = py.path.local()
-    uploadhub.cwd = tmpdir
+    uploadhub.cwd = Path()
     uploadhub.current.reconfigure(dict(
         index="http://devpi/foo/bar",
         login="http://devpi/+login",
@@ -365,8 +364,7 @@ class args:
     token = pypitoken.token.Token.load(passwd)
     assert pypitoken.ProjectNamesRestriction(
         project_names=["pkg"]) not in token.restrictions
-    tmpdir = py.path.local()
-    uploadhub.cwd = tmpdir
+    uploadhub.cwd = Path()
     uploadhub.http = Session()
     uploadhub.current.reconfigure(dict(
         index="http://devpi/foo/bar",
@@ -401,7 +399,7 @@ def projname_version(self, projname_version_project):
         return projname_version_project[0]
 
     def test_plain_dry_run(self, devpi, out_devpi, projname_version):
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         out = out_devpi("upload", "--no-isolation", "--dry-run")
         assert out.ret == 0
         out.stdout.fnmatch_lines("""
@@ -629,7 +627,7 @@ def test_upload_to_mirror(
             "conf.py": "#nothing",
             "contents.rst": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
 
         # use mirror
         out = out_devpi("use", "root/pypi")
@@ -645,7 +643,7 @@ def test_index_option(
             "conf.py": "#nothing",
             "contents.rst": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         # remember username
         out = out_devpi("use")
         user = re.search(r'\(logged in as (.+?)\)', out.stdout.str()).group(1)
@@ -665,7 +663,7 @@ def test_index_option_with_environment_relative(
             "conf.py": "#nothing",
             "contents.rst": "",
             "index.html": "<html/>"}})
-        assert py.path.local("setup.py").check()
+        assert Path("setup.py").is_file()
         # remember username
         out = out_devpi("use")
         user = re.search(r'\(logged in as (.+?)\)', out.stdout.str()).group(1)
@@ -696,12 +694,12 @@ def test_fromdir(self, initproj, devpi, out_devpi, runproc):
         initproj("hello-1.1", {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        tmpdir = py.path.local()
+        tmpdir = Path()
         runproc(tmpdir, "python setup.py sdist --format=zip".split())
         initproj("hello-1.2")
         runproc(tmpdir, "python setup.py sdist --format=zip".split())
-        dist = tmpdir.join("dist")
-        assert len(dist.listdir()) == 2
+        dist = tmpdir / "dist"
+        assert len(list(dist.iterdir())) == 2
         hub = devpi("upload", "--no-isolation", "--from-dir", dist)
         for ver in ("1.1", '1.2'):
             url = hub.current.get_index_url().url + "hello/%s/" % ver
@@ -724,12 +722,12 @@ def test_frompath(self, initproj, devpi, name_version, out_devpi, path, runproc)
         initproj(name_version, {"doc": {
             "conf.py": "",
             "index.html": "<html/>"}})
-        tmpdir = py.path.local()
+        tmpdir = Path()
         runproc(tmpdir, "python setup.py sdist --format=zip".split())
-        dist = tmpdir.join("dist")
-        zip_dir(tmpdir.join('doc'), dist.join("%s.doc.zip" % name_version_str))
-        assert len(dist.listdir()) == 2
-        (p, dp) = sorted(dist.listdir(), key=lambda x: '.doc.zip' in x.basename)
+        dist = tmpdir / "dist"
+        zip_dir(tmpdir / 'doc', dist / f"{name_version_str}.doc.zip")
+        assert len(list(dist.iterdir())) == 2
+        (p, dp) = sorted(dist.iterdir(), key=lambda x: '.doc.zip' in x.name)
         hub = devpi("upload", "--no-isolation", p, dp)
         url = hub.current.get_index_url().url + path
         out = out_devpi("getjson", url)
@@ -742,8 +740,8 @@ def test_frompath(self, initproj, devpi, name_version, out_devpi, path, runproc)
 
     def test_cli_sdist_precedence(self, initproj, devpi, out_devpi):
         initproj("pkg-1.0")
-        tmpdir = py.path.local()
-        tmpdir.join("setup.cfg").write(dedent("""
+        tmpdir = Path()
+        tmpdir.joinpath("setup.cfg").write_text(dedent("""
             [devpi:upload]
             formats=bdist_wheel,sdist.zip"""))
         hub = devpi("upload", "--sdist", "--no-isolation")
@@ -756,8 +754,8 @@ def test_cli_sdist_precedence(self, initproj, devpi, out_devpi):
 
     def test_cli_wheel_precedence(self, initproj, devpi, out_devpi):
         initproj("pkg-1.0")
-        tmpdir = py.path.local()
-        tmpdir.join("setup.cfg").write(dedent("""
+        tmpdir = Path()
+        tmpdir.joinpath("setup.cfg").write_text(dedent("""
             [devpi:upload]
             formats=bdist_wheel,sdist.zip"""))
         hub = devpi("upload", "--wheel", "--no-isolation")
@@ -772,10 +770,10 @@ def test_cli_wheel_precedence(self, initproj, devpi, out_devpi):
 
 
 def test_getpkginfo(datadir):
-    info = get_pkginfo(datadir.join("dddttt-0.1.dev45-py27-none-any.whl"))
+    info = get_pkginfo(datadir / "dddttt-0.1.dev45-py27-none-any.whl")
     assert info.name == "dddttt"
     assert info.metadata_version == "2.0"
-    info = get_pkginfo(datadir.join("ddd-1.0.doc.zip"))
+    info = get_pkginfo(datadir / "ddd-1.0.doc.zip")
     assert info.name == "ddd"
     assert info.version == "1.0"
 
diff --git a/client/testing/test_use.py b/client/testing/test_use.py
index aca4dd326..b00e20d48 100644
--- a/client/testing/test_use.py
+++ b/client/testing/test_use.py
@@ -83,15 +83,16 @@ def test_local_config(self, capfd, cmd_devpi, create_venv, mock_http_api, monkey
         hub = cmd_devpi("use", "http://devpi/foo/bar")
         (out, err) = capfd.readouterr()
         current_path = hub.current_path
-        assert current_path.strpath.endswith('client/current.json')
+        assert current_path.name == 'current.json'
+        assert current_path.parent.name == 'client'
         local_current_path = hub.local_current_path
-        assert venvdir.strpath in local_current_path.strpath
-        assert local_current_path.strpath.endswith('devpi.json')
+        assert venvdir.strpath in str(local_current_path)
+        assert local_current_path.name == 'devpi.json'
         assert not local_current_path.exists()
         assert venvdir.strpath in out
         hub = cmd_devpi("use", "--local")
         (out, err) = capfd.readouterr()
-        assert hub.current_path.strpath == local_current_path.strpath
+        assert str(hub.current_path) == str(local_current_path)
         assert local_current_path.exists()
         mock_http_api.set(
             "http://devpi/foo/ham/+api", 200, result=dict(
@@ -111,7 +112,7 @@ def test_local_config(self, capfd, cmd_devpi, create_venv, mock_http_api, monkey
         hub = cmd_devpi("use")
         (out, err) = capfd.readouterr()
         assert 'current devpi index: http://devpi/foo/ham' in out
-        local_current_path.remove()
+        local_current_path.unlink()
         hub = cmd_devpi("use")
         (out, err) = capfd.readouterr()
         assert 'current devpi index: http://devpi/foo/bar' in out
@@ -123,7 +124,8 @@ def test_local_config_no_auth_key(self, cmd_devpi, create_venv, monkeypatch):
         monkeypatch.setenv("VIRTUAL_ENV", venvdir.strpath)
         hub = cmd_devpi("use")
         current_path = hub.current_path
-        assert current_path.strpath.endswith('client/current.json')
+        assert current_path.name == 'current.json'
+        assert current_path.parent.name == 'client'
         local_current_path = hub.local_current_path
         assert not local_current_path.exists()
         with current_path.open("w") as f:
@@ -681,7 +683,7 @@ def test_main_setcfg(self, scheme, basic_auth, capfd, mock_http_api, cmd_devpi,
             assert basic_auth not in out
             assert ':****@' in out
         assert PipCfg().default_location.exists()
-        content = PipCfg().default_location.read()
+        content = PipCfg().default_location.read_text()
         assert len(
             re.findall(r"index_url\s*=\s*%s://%sworld/simple" % (
                 scheme, basic_auth), content)) == 1
@@ -709,7 +711,7 @@ def test_main_setcfg(self, scheme, basic_auth, capfd, mock_http_api, cmd_devpi,
         cmd_devpi(
             "use", "--set-cfg", "--pip-set-trusted=yes", "%s://%sworld" % (
                 scheme, basic_auth))
-        content = PipCfg().default_location.read()
+        content = PipCfg().default_location.read_text()
         assert len(
             re.findall(r"trusted-host\s*=\s*world", content)) == 1
         hub = cmd_devpi("use", "--always-set-cfg=yes", "--pip-set-trusted=yes")
diff --git a/client/tox.ini b/client/tox.ini
index a31e0751f..8a676cf3e 100644
--- a/client/tox.ini
+++ b/client/tox.ini
@@ -20,7 +20,6 @@ deps =
        pypitoken
        importlib.metadata;python_version<"3.8"
        mock
-       py!=1.4.32
        sphinx
        webtest
        wheel