diff --git a/poetry/core/version/pep440/parser.py b/poetry/core/version/pep440/parser.py
index 5fb357094..a10a0df4c 100644
--- a/poetry/core/version/pep440/parser.py
+++ b/poetry/core/version/pep440/parser.py
@@ -56,7 +56,7 @@ def _get_local(cls, match: Optional[Match[AnyStr]]) -> Optional[LocalSegmentType
             return None
 
         return tuple(
-            part.lower() if not part.isdigit() else int(part)
+            part.lower() if not part.isdigit() or part.startswith("0") else int(part)
             for part in cls._local_version_separators.split(match.group("local"))
         )
 
diff --git a/poetry/core/version/pep440/version.py b/poetry/core/version/pep440/version.py
index d46a93822..5450c2034 100644
--- a/poetry/core/version/pep440/version.py
+++ b/poetry/core/version/pep440/version.py
@@ -81,7 +81,9 @@ def _make_compare_key(self):
             # - Shorter versions sort before longer versions when the prefixes
             #   match exactly
             _local = tuple(
-                (i, "") if isinstance(i, int) else (-math.inf, i) for i in self.local
+                # We typecast strings that are integers so that they can be compared
+                (int(i), "") if isinstance(i, int) or i.isdigit() else (-math.inf, i)
+                for i in self.local
             )
         return self.epoch, self.release, _pre, _post, _dev, _local
 
diff --git a/tests/version/test_version_pep440.py b/tests/version/test_version_pep440.py
index 11b873dac..dd2d3c115 100644
--- a/tests/version/test_version_pep440.py
+++ b/tests/version/test_version_pep440.py
@@ -150,12 +150,19 @@ def test_pep440_release_tag_next(phase):
             "1.2.3.rc1",
             PEP440Version(release=Release.from_parts(1, 2, 3), pre=ReleaseTag("rc", 1)),
         ),
+        (
+            "2.2.0dev0+build.05669607",
+            PEP440Version(
+                release=Release.from_parts(2, 2, 0),
+                dev=ReleaseTag("dev", 0),
+                local=("build", "05669607")
+            ),
+        ),
     ],
 )
 def test_pep440_parse_text(text, result):
     assert PEP440Version.parse(text) == result
 
-
 @pytest.mark.parametrize(
     "text", ["1.2.3.dev1-1" "example-1" "1.2.3-random1" "1.2.3-1-1"]
 )