diff --git a/CHANGES/plugin_api/5559.feature b/CHANGES/plugin_api/5559.feature
new file mode 100644
index 00000000000..5bc72255da3
--- /dev/null
+++ b/CHANGES/plugin_api/5559.feature
@@ -0,0 +1,3 @@
+Added artifact path overlap checks for repo versions and publications. Plugin writers should call
+``validate_version_paths()`` or ``validate_publication_paths()`` during the finalize step when
+creating RepositoryVersions or Publications (respectively).
diff --git a/doc_requirements.txt b/doc_requirements.txt
index c60b55d1c89..0a60a2d768a 100644
--- a/doc_requirements.txt
+++ b/doc_requirements.txt
@@ -11,6 +11,7 @@ drf-yasg
 dynaconf
 plantuml
 pyyaml
+pygtrie
 rq
 sphinx
 sphinx-rtd-theme
diff --git a/pulpcore/app/files.py b/pulpcore/app/files.py
index ba284174e59..4662a1cb6c3 100644
--- a/pulpcore/app/files.py
+++ b/pulpcore/app/files.py
@@ -1,8 +1,10 @@
 import hashlib
 import os
+from gettext import gettext as _
 
 from django.core.files.uploadedfile import TemporaryUploadedFile
 from django.core.files.uploadhandler import TemporaryFileUploadHandler
+from pygtrie import StringTrie
 
 
 class PulpTemporaryUploadedFile(TemporaryUploadedFile):
@@ -90,3 +92,41 @@ def __init__(self, file, name=None):
         if name is None:
             name = getattr(file, 'name', None)
         self.name = name
+
+
+def validate_file_paths(paths):
+    """
+    Check for valid POSIX paths (ie ones that aren't duplicated and don't overlap).
+
+    Overlapping paths are where one path terminates inside another (e.g. a/b and a/b/c).
+
+    This function will raise an exception at the first dupe or overlap it detects. We use a trie (or
+    prefix tree) to keep track of which paths we've already seen.
+
+    Args:
+        paths (list): A list of strings each representing a relative path
+
+    Raises:
+        ValueError: If any path overlaps another
+    """
+    overlap_error = _("The path for file '{path}' overlaps: {conflicts}")
+
+    path_trie = StringTrie(separator="/")
+    for path in paths:
+        if path_trie.has_key(path):
+            # path duplicates a path already in the trie
+            raise ValueError(_("Path is duplicated: {path}").format(path=path))
+
+        if path_trie.has_subtrie(path):
+            # overlap where path is 'a/b' and trie has 'a/b/c'
+            conflicts = [item[0] for item in path_trie.items(prefix=path)]
+            raise ValueError(overlap_error.format(path=path, conflicts=(", ").join(conflicts)))
+
+        prefixes = list(path_trie.prefixes(path))
+        if prefixes:
+            # overlap where path is 'a/b/c' and trie has 'a/b'
+            conflicts = [prefix.key for prefix in prefixes]
+            raise ValueError(overlap_error.format(path=path, conflicts=(", ").join(conflicts)))
+
+        # if there are no overlaps, add it to our trie and continue
+        path_trie[path] = True
diff --git a/pulpcore/plugin/publication_utils.py b/pulpcore/plugin/publication_utils.py
new file mode 100644
index 00000000000..8e3bbcad17c
--- /dev/null
+++ b/pulpcore/plugin/publication_utils.py
@@ -0,0 +1,22 @@
+from pulpcore.app.models import ContentArtifact
+from pulpcore.app.files import validate_file_paths
+
+
+def validate_publication_paths(publication):
+    """
+    Validate artifact relative paths for dupes or overlap (e.g. a/b and a/b/c).
+
+    Raises:
+        ValueError: If two artifact relative paths are dupes or overlap
+    """
+    paths = list(publication.published_artifact.values_list("relative_path", flat=True))
+
+    if publication.pass_through:
+        paths += ContentArtifact.objects. \
+            filter(content__pk__in=publication.repository_version.content). \
+            values_list("relative_path", flat=True)
+
+    try:
+        validate_file_paths(paths)
+    except ValueError as e:
+        raise ValueError(_("Cannot create publication. {err}.").format(err=e))
diff --git a/pulpcore/plugin/repo_version_utils.py b/pulpcore/plugin/repo_version_utils.py
index 1736c69fb3f..494355f0db5 100644
--- a/pulpcore/plugin/repo_version_utils.py
+++ b/pulpcore/plugin/repo_version_utils.py
@@ -4,6 +4,9 @@
 
 from django.db.models import Q
 
+from pulpcore.app.models import ContentArtifact
+from pulpcore.app.files import validate_file_paths
+
 
 _logger = logging.getLogger(__name__)
 
@@ -41,3 +44,20 @@ def remove_duplicates(repository_version):
         _logger.debug(_("Removing duplicates for type: {}".format(model)))
         qs = model.objects.filter(query_for_repo_duplicates_by_type[model])
         repository_version.remove_content(qs)
+
+
+def validate_version_paths(version):
+    """
+    Validate artifact relative paths for dupes or overlap (e.g. a/b and a/b/c).
+
+    Raises:
+        ValueError: If two artifact relative paths overlap
+    """
+    paths = ContentArtifact.objects. \
+        filter(content__pk__in=version.content). \
+        values_list("relative_path", flat=True)
+
+    try:
+        validate_file_paths(paths)
+    except ValueError as e:
+        raise ValueError(_("Cannot create repository version. {err}.").format(err=e))
diff --git a/pulpcore/tests/unit/test_files.py b/pulpcore/tests/unit/test_files.py
new file mode 100644
index 00000000000..c76239d6d00
--- /dev/null
+++ b/pulpcore/tests/unit/test_files.py
@@ -0,0 +1,36 @@
+from unittest import TestCase
+
+from pulpcore.app.files import validate_file_paths
+
+
+class TestValidateFilePaths(TestCase):
+    def test_valid_paths(self):
+        """
+        Test for valid paths.
+        """
+        paths = ['a/b', 'a/c/b', 'PULP_MANIFEST', 'b']
+        validate_file_paths(paths)
+
+    def test_dupes(self):
+        """
+        Test for two duplicate paths.
+        """
+        paths = ['a/b', 'PULP_MANIFEST', 'PULP_MANIFEST']
+        with self.assertRaisesRegex(ValueError, "Path is duplicated: PULP_MANIFEST"):
+            validate_file_paths(paths)
+
+    def test_overlaps(self):
+        """
+        Test for overlapping paths.
+        """
+        paths = ['a/b', 'a/b/c']
+        with self.assertRaises(ValueError):
+            validate_file_paths(paths)
+
+        paths = ['a/b/c', 'a/b']
+        with self.assertRaises(ValueError):
+            validate_file_paths(paths)
+
+        paths = ['b/c', 'a/b', 'b']
+        with self.assertRaises(ValueError):
+            validate_file_paths(paths)
diff --git a/setup.py b/setup.py
index 59b7cf57c47..fbb2fb88d31 100644
--- a/setup.py
+++ b/setup.py
@@ -22,6 +22,7 @@
     'setuptools>=39.2.0,<42.1.0',
     'dynaconf>=2.2,<2.3',
     'whitenoise~=4.1.3',
+    'pygtrie~=2.3.2',
 ]
 
 setup(