diff --git a/tests/test_upload.py b/tests/test_upload.py
index 42939f93..b30fe583 100644
--- a/tests/test_upload.py
+++ b/tests/test_upload.py
@@ -18,6 +18,7 @@
 from twine import cli
 from twine import exceptions
 from twine import package as package_file
+from twine import utils
 from twine.commands import upload
 
 from . import helpers
@@ -72,6 +73,31 @@ def test_successs_prints_release_urls(upload_settings, stub_repository, capsys):
     assert captured.out.count(NEW_RELEASE_URL) == 1
 
 
+def test_successs_prints_uploaded_package_names_if_verbose(upload_settings, capsys):
+    """Print the path and file size of each distribution attempting to be uploaded."""
+    dists_to_upload = [
+        helpers.WHEEL_FIXTURE,
+        helpers.SDIST_FIXTURE,
+        helpers.NEW_SDIST_FIXTURE,
+        helpers.NEW_WHEEL_FIXTURE,
+    ]
+
+    sizes_of_dists_to_upload = [utils.get_file_size(dist) for dist in dists_to_upload]
+
+    upload_settings.verbose = True
+
+    result = upload.upload(upload_settings, dists_to_upload)
+
+    assert result is None
+
+    captured = capsys.readouterr()
+
+    for dist_to_upload in dists_to_upload:
+        assert captured.out.count(dist_to_upload) == 1
+    for size_of_dist_to_upload in sizes_of_dists_to_upload:
+        assert captured.out.count(size_of_dist_to_upload) == 1
+
+
 def test_success_with_pre_signed_distribution(upload_settings, stub_repository):
     """Adds GPG signature provided by user to uploaded package."""
     # Upload a pre-signed distribution
diff --git a/tests/test_utils.py b/tests/test_utils.py
index 55d96706..b8ae34ca 100644
--- a/tests/test_utils.py
+++ b/tests/test_utils.py
@@ -313,3 +313,19 @@ def test_check_status_code_for_missing_status_code(capsys, repo_url):
 
     captured = capsys.readouterr()
     assert captured.out == "NOTE: Try --verbose to see response content.\n"
+
+
+@pytest.mark.parametrize(
+    ("filename, expected"),
+    [
+        (helpers.WHEEL_FIXTURE, "15.4 KB"),
+        (helpers.SDIST_FIXTURE, "20.8 KB"),
+        (helpers.NEW_SDIST_FIXTURE, "26.1 KB"),
+        (helpers.NEW_WHEEL_FIXTURE, "21.9 KB"),
+    ],
+)
+def test_get_file_size(filename, expected):
+    """Compare the size of a file to the expected value."""
+    file_size = utils.get_file_size(filename)
+
+    assert file_size == expected
diff --git a/twine/commands/upload.py b/twine/commands/upload.py
index a37e8bd0..ef7ff67f 100644
--- a/twine/commands/upload.py
+++ b/twine/commands/upload.py
@@ -60,6 +60,11 @@ def upload(upload_settings: settings.Settings, dists: List[str]) -> None:
     repository_url = cast(str, upload_settings.repository_config["repository"])
 
     print(f"Uploading distributions to {repository_url}")
+    if upload_settings.verbose:
+        for filename in uploads:
+            file_size = utils.get_file_size(filename)
+            print(f"  {filename} ({file_size})")
+        print("\n")
 
     repository = upload_settings.create_repository()
     uploaded_packages = []
diff --git a/twine/utils.py b/twine/utils.py
index f49360de..d859904e 100644
--- a/twine/utils.py
+++ b/twine/utils.py
@@ -159,6 +159,18 @@ def normalize_repository_url(url: str) -> str:
     return urlunparse(parsed)
 
 
+def get_file_size(filename: str) -> str:
+    """Return the size of a file, in KB if < .1 MB."""
+    file_size = os.path.getsize(filename) / 1024
+    size_unit = "KB"
+
+    if file_size > 1024:
+        file_size = file_size / 1024
+        size_unit = "MB"
+
+    return f"{file_size:.1f} {size_unit}"
+
+
 def check_status_code(response: requests.Response, verbose: bool) -> None:
     """Generate a helpful message based on the response from the repository.