diff --git a/ops/model.py b/ops/model.py
index 7d24ec5ca..3458c77c7 100644
--- a/ops/model.py
+++ b/ops/model.py
@@ -2093,7 +2093,7 @@ def push_path(self,
 
         def local_list(source_path: Path) -> List[pebble.FileInfo]:
             paths = source_path.iterdir() if source_path.is_dir() else [source_path]
-            files = [self._build_fileinfo(source_path / f) for f in paths]
+            files = [self._build_fileinfo(f) for f in paths]
             return files
 
         errors: List[Tuple[str, Exception]] = []
@@ -2256,7 +2256,7 @@ def _build_destpath(
         # /src --> /dst/src
         file_path, source_path, dest_dir = Path(file_path), Path(source_path), Path(dest_dir)
         prefix = str(source_path.parent)
-        if os.path.commonprefix([prefix, str(file_path)]) != prefix:
+        if prefix != '.' and os.path.commonprefix([prefix, str(file_path)]) != prefix:
             raise RuntimeError(
                 f'file "{file_path}" does not have specified prefix "{prefix}"')
         path_suffix = os.path.relpath(str(file_path), prefix)
diff --git a/test/test_model.py b/test/test_model.py
index 7b7344a94..97b0c9ca4 100755
--- a/test/test_model.py
+++ b/test/test_model.py
@@ -1174,6 +1174,64 @@ def test_recursive_push_and_pull(case):
         assert c.exists(fpath), f'pull_path failed: file {fpath} missing at destination'
 
 
+@pytest.mark.parametrize('case', [
+    PushPullCase(
+        name='push directory without trailing slash',
+        path='foo',
+        dst='/baz',
+        files=['foo/bar/baz.txt', 'foo/foobar.txt'],
+        want={'/baz/foo/foobar.txt', '/baz/foo/bar/baz.txt'},
+    ),
+    PushPullCase(
+        name='push directory with trailing slash',
+        path='foo/',
+        dst='/baz',
+        files=['foo/bar/baz.txt', 'foo/foobar.txt'],
+        want={'/baz/foo/foobar.txt', '/baz/foo/bar/baz.txt'},
+    ),
+    PushPullCase(
+        name='push directory relative pathing',
+        path='./foo',
+        dst='/baz',
+        files=['foo/bar/baz.txt', 'foo/foobar.txt'],
+        want={'/baz/foo/foobar.txt', '/baz/foo/bar/baz.txt'},
+    ),
+])
+def test_push_path_relative(case):
+    harness = ops.testing.Harness(ops.CharmBase, meta='''
+        name: test-app
+        containers:
+          foo:
+            resource: foo-image
+        ''')
+    harness.begin()
+    harness.set_can_connect('foo', True)
+    container = harness.model.unit.containers['foo']
+
+    with tempfile.TemporaryDirectory() as tmpdir:
+        cwd = os.getcwd()
+        # change working directory to enable relative pathing for testing
+        os.chdir(tmpdir)
+        try:
+            # create test files under temporary test directory
+            tmp = pathlib.Path(tmpdir)
+            for testfile in case.files:
+                testfile_path = pathlib.Path(tmp / testfile)
+                testfile_path.parent.mkdir(parents=True, exist_ok=True)
+                testfile_path.touch(exist_ok=True)
+                testfile_path.write_text("test", encoding="utf-8")
+
+            # push path under test to container
+            container.push_path(case.path, case.dst)
+
+            # test
+            for want_path in case.want:
+                content = container.pull(want_path).read()
+                assert content == 'test'
+        finally:
+            os.chdir(cwd)
+
+
 class TestApplication(unittest.TestCase):
 
     def setUp(self):