diff --git a/poetry.lock b/poetry.lock
index 32ad02b97..91efbc060 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -439,7 +439,7 @@ testing = ["beautifulsoup4", "coverage[toml]", "pytest (>=6,<7)", "pytest-cov",
 name = "packaging"
 version = "22.0"
 description = "Core utilities for Python packages"
-category = "dev"
+category = "main"
 optional = false
 python-versions = ">=3.7"
 
@@ -945,7 +945,7 @@ test = []
 [metadata]
 lock-version = "1.1"
 python-versions = "^3.7"
-content-hash = "6a05ee2efdef9d79f3c1f8283f8c6ada1be53819a998d129fb15e69477019cca"
+content-hash = "20cb0283c8677c189b02f0dd7c1f7d29a5579f11116c68a6031e27d93ca6102c"
 
 [metadata.files]
 alabaster = [
diff --git a/pyproject.toml b/pyproject.toml
index 48f0dcec0..a2b402c6e 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -47,6 +47,7 @@ Changes = "https://github.com/tmux-python/libtmux/blob/master/CHANGES"
 
 [tool.poetry.dependencies]
 python = "^3.7"
+packaging = {version = "*",  python="^3.10.0"}
 
 [tool.poetry.dev-dependencies]
 ### Docs ###
diff --git a/src/libtmux/_compat.py b/src/libtmux/_compat.py
index d7b6bb274..99dced382 100644
--- a/src/libtmux/_compat.py
+++ b/src/libtmux/_compat.py
@@ -31,3 +31,231 @@ def str_from_console(s: t.Union[str, bytes]) -> str:
         return str(s)
     except UnicodeDecodeError:
         return str(s, encoding="utf_8") if isinstance(s, bytes) else s
+
+
+try:
+    import collections
+    import functools
+    import re
+    from typing import Iterator, List, Tuple
+
+    from packaging import version as V
+    from packaging.version import VERSION_PATTERN, Version, _BaseVersion
+
+    ###
+    ### Legacy support for LooseVersion / LegacyVersion, e.g. 2.4-openbsd
+    ### https://github.com/pypa/packaging/blob/21.3/packaging/version.py#L106-L115
+    ### License: BSD, Accessed: Jan 14th, 2022
+    ###
+
+    LegacyCmpKey = Tuple[int, Tuple[str, ...]]
+
+    _legacy_version_component_re = re.compile(r"(\d+ | [a-z]+ | \.| -)", re.VERBOSE)
+    _legacy_version_replacement_map = {
+        "pre": "c",
+        "preview": "c",
+        "-": "final-",
+        "rc": "c",
+        "dev": "@",
+    }
+
+    def _parse_version_parts(s: str) -> Iterator[str]:
+        for part in _legacy_version_component_re.split(s):
+            part = _legacy_version_replacement_map.get(part, part)
+
+            if not part or part == ".":
+                continue
+
+            if part[:1] in "0123456789":
+                # pad for numeric comparison
+                yield part.zfill(8)
+            else:
+                yield "*" + part
+
+        # ensure that alpha/beta/candidate are before final
+        yield "*final"
+
+    def _legacy_cmpkey(version: str) -> LegacyCmpKey:
+        # We hardcode an epoch of -1 here. A PEP 440 version can only have a epoch
+        # greater than or equal to 0. This will effectively put the LegacyVersion,
+        # which uses the defacto standard originally implemented by setuptools,
+        # as before all PEP 440 versions.
+        epoch = -1
+
+        # This scheme is taken from pkg_resources.parse_version setuptools prior to
+        # it's adoption of the packaging library.
+        parts: List[str] = []
+        for part in _parse_version_parts(version.lower()):
+            if part.startswith("*"):
+                # remove "-" before a prerelease tag
+                if part < "*final":
+                    while parts and parts[-1] == "*final-":
+                        parts.pop()
+
+                # remove trailing zeros from each series of numeric parts
+                while parts and parts[-1] == "00000000":
+                    parts.pop()
+
+            parts.append(part)
+
+        return epoch, tuple(parts)
+
+    class LegacyVersion(_BaseVersion):
+        def __init__(self, version: str) -> None:
+            self._version = str(version)
+            self._key = _legacy_cmpkey(self._version)
+
+        def __str__(self) -> str:
+            return self._version
+
+        def __lt__(self, other):
+            if isinstance(other, str):
+                other = LegacyVersion(other)
+            return super().__lt__(other)
+
+        def __eq__(self, other) -> bool:
+            if isinstance(other, str):
+                other = LegacyVersion(other)
+            if not isinstance(other, LegacyVersion):
+                return NotImplemented
+
+            return self._key == other._key
+
+        def __repr__(self) -> str:
+            return "<LegacyVersion({0})>".format(repr(str(self)))
+
+        @property
+        def public(self) -> str:
+            return self._version
+
+        @property
+        def base_version(self) -> str:
+            return self._version
+
+        @property
+        def epoch(self) -> int:
+            return -1
+
+    @functools.total_ordering
+    class _VersionCmpMixin:
+        # Credit: @layday
+        # Link: https://github.com/pypa/packaging/issues/465#issuecomment-1013715662
+        def __eq__(self, other: object) -> bool:
+            if isinstance(other, str):
+                other = self.__class__(other)
+            return super().__eq__(other)
+
+        def __lt__(self, other: object) -> bool:
+            if isinstance(other, str):
+                other = self.__class__(other)
+            return super().__lt__(other)
+
+    _Version = collections.namedtuple(
+        "_Version", ["epoch", "release", "dev", "pre", "post", "local", "platform"]
+    )
+
+    def _cmpkey(
+        epoch,  # type: int
+        release,  # type: Tuple[int, ...]
+        pre,  # type: Optional[Tuple[str, int]]
+        post,  # type: Optional[Tuple[str, int]]
+        dev,  # type: Optional[Tuple[str, int]]
+        local,  # type: Optional[Tuple[SubLocalType]]
+        platform,  # type: Optional[Tuple[SubLocalType]]
+    ):
+        return V._cmpkey(epoch, release, pre, post, dev, local) + (
+            tuple(
+                (i, "") if isinstance(i, int) else (V.NegativeInfinity, i)
+                for i in platform
+            )
+        )
+
+    class LegacyVersion(Version):
+        _regex = re.compile
+        _regex = re.compile(
+            r"^\s*"
+            + VERSION_PATTERN
+            + r"(?:(?P<platform>(?:[-_\.][a-z0-9]+)*))?       # platform version"
+            + r"\s*$",
+            re.VERBOSE | re.IGNORECASE,
+        )
+
+        def __init__(self, version):
+            # type: (str) -> None
+
+            # Validate the version and parse it into pieces
+            match = self._regex.search(version)
+            if not match:
+                raise V.InvalidVersion("Invalid version: '{0}'".format(version))
+
+            # Store the parsed out pieces of the version
+            self._version = _Version(
+                epoch=int(match.group("epoch")) if match.group("epoch") else 0,
+                release=tuple(int(i) for i in match.group("release").split(".")),
+                pre=V._parse_letter_version(match.group("pre_l"), match.group("pre_n")),
+                post=V._parse_letter_version(
+                    match.group("post_l"),
+                    match.group("post_n1") or match.group("post_n2"),
+                ),
+                dev=V._parse_letter_version(match.group("dev_l"), match.group("dev_n")),
+                local=V._parse_local_version(match.group("local")),
+                platform=str(match.group("platform"))
+                if match.group("platform")
+                else "",
+            )
+
+            # Generate a key which will be used for sorting
+            self._key = _cmpkey(
+                self._version.epoch,
+                self._version.release,
+                self._version.pre,
+                self._version.post,
+                self._version.dev,
+                self._version.local,
+                self._version.platform,
+            )
+
+        @property
+        def platform(self):
+            # type: () -> Optional[str]
+            if self._version.platform:
+                return ".".join(str(x) for x in self._version.platform)
+            else:
+                return None
+
+        def __str__(self):
+            # type: () -> str
+            parts = []
+
+            # Epoch
+            if self.epoch != 0:
+                parts.append("{0}!".format(self.epoch))
+
+            # Release segment
+            parts.append(".".join(str(x) for x in self.release))
+
+            # Pre-release
+            if self.pre is not None:
+                parts.append("".join(str(x) for x in self.pre))
+
+            # Post-release
+            if self.post is not None:
+                parts.append(".post{0}".format(self.post))
+
+            # Development release
+            if self.dev is not None:
+                parts.append(".dev{0}".format(self.dev))
+
+            # Local version segment
+            if self.local is not None:
+                parts.append("+{0}".format(self.local))
+
+            # Platform version segment
+            if self.platform is not None:
+                parts.append("_{0}".format(self.platform))
+
+            return "".join(parts)
+
+    LooseVersion = LegacyVersion
+except ImportError:
+    from distutils.version import LooseVersion, Version
diff --git a/src/libtmux/common.py b/src/libtmux/common.py
index 430053963..4dc04e140 100644
--- a/src/libtmux/common.py
+++ b/src/libtmux/common.py
@@ -11,7 +11,6 @@
 import subprocess
 import sys
 import typing as t
-from distutils.version import LooseVersion
 from typing import Dict, Generic, KeysView, List, Optional, TypeVar, Union, overload
 
 from . import exc
@@ -25,6 +24,9 @@
     from libtmux.window import Window
 
 
+from . import exc
+from ._compat import LooseVersion, console_to_str, str_from_console
+
 logger = logging.getLogger(__name__)
 
 
@@ -273,7 +275,7 @@ def __init__(self, *args: t.Any, **kwargs: t.Any) -> None:
 
 # class TmuxMappingObject(t.Mapping[str, t.Union[str,int,bool]]):
 class TmuxMappingObject(t.Mapping[t.Any, t.Any]):
-    r"""Base: :py:class:`MutableMapping`.
+    r"""Base: :py:class:`typing.Mapping`.
 
     Convenience container. Base class for :class:`Pane`, :class:`Window`,
     :class:`Session` and :class:`Server`.
diff --git a/tests/test_common.py b/tests/test_common.py
index d09d21e84..00524fb51 100644
--- a/tests/test_common.py
+++ b/tests/test_common.py
@@ -3,12 +3,12 @@
 import re
 import sys
 import typing as t
-from distutils.version import LooseVersion
 from typing import Optional
 
 import pytest
 
 import libtmux
+from libtmux._compat import LooseVersion
 from libtmux.common import (
     TMUX_MAX_VERSION,
     TMUX_MIN_VERSION,
@@ -43,7 +43,7 @@ def mock_tmux_cmd(*args: t.Any, **kwargs: t.Any) -> Hi:
     assert has_gte_version(TMUX_MIN_VERSION)
     assert has_gt_version(TMUX_MAX_VERSION), "Greater than the max-supported version"
     assert (
-        "%s-master" % TMUX_MAX_VERSION == get_version()
+        LooseVersion("%s-master" % TMUX_MAX_VERSION) == get_version()
     ), "Is the latest supported version with -master appended"
 
 
@@ -63,6 +63,7 @@ def mock_tmux_cmd(*args: t.Any, **kwargs: t.Any) -> Hi:
     assert has_gte_version(TMUX_MIN_VERSION)
     assert has_gt_version(TMUX_MAX_VERSION), "Greater than the max-supported version"
     assert TMUX_NEXT_VERSION == get_version()
+    assert LooseVersion("2.9") == get_version()
 
 
 def test_get_version_openbsd(monkeypatch: pytest.MonkeyPatch) -> None:
@@ -78,7 +79,7 @@ def mock_tmux_cmd(*args: t.Any, **kwargs: t.Any) -> Hi:
     assert has_gte_version(TMUX_MIN_VERSION)
     assert has_gt_version(TMUX_MAX_VERSION), "Greater than the max-supported version"
     assert (
-        "%s-openbsd" % TMUX_MAX_VERSION == get_version()
+        LooseVersion("%s-openbsd" % TMUX_MAX_VERSION) == get_version()
     ), "Is the latest supported version with -openbsd appended"