diff --git a/changelog/815.feature.rst b/changelog/815.feature.rst
new file mode 100644
index 00000000..aa819df6
--- /dev/null
+++ b/changelog/815.feature.rst
@@ -0,0 +1 @@
+Show more helpful messages for invalid passwords.
diff --git a/docs/index.rst b/docs/index.rst
index 9b2ae695..ead6d7d8 100644
--- a/docs/index.rst
+++ b/docs/index.rst
@@ -88,6 +88,20 @@ Using Twine
 
 4. Done!
 
+.. _entering-credentials:
+
+.. note::
+
+   Like many other command line tools, Twine does not show any characters when
+   you enter your password.
+
+   If you're using Windows and trying to paste your username, password, or
+   token in the Command Prompt or PowerShell, ``Ctrl-V`` and ``Shift+Insert``
+   won't work. Instead, you can use "Edit > Paste" from the window menu, or
+   enable "Use Ctrl+Shift+C/V as Copy/Paste" in "Properties". This is a
+   `known issue <https://bugs.python.org/issue37426>`_ with Python's
+   ``getpass`` module.
+
 More documentation on using Twine to upload packages to PyPI is in
 the `Python Packaging User Guide`_.
 
diff --git a/tests/test_auth.py b/tests/test_auth.py
index c8e470d5..7e59b2b8 100644
--- a/tests/test_auth.py
+++ b/tests/test_auth.py
@@ -1,3 +1,4 @@
+import getpass
 import logging
 
 import pytest
@@ -202,3 +203,26 @@ def test_logs_config_values(config, caplog):
         "username set from config file",
         "password set from config file",
     ]
+
+
+@pytest.mark.parametrize(
+    "password, warning",
+    [
+        ("", "Your password is empty"),
+        ("\x16", "Your password contains control characters"),
+        ("entered\x16pw", "Your password contains control characters"),
+    ],
+)
+def test_warns_for_empty_password(
+    password,
+    warning,
+    monkeypatch,
+    entered_username,
+    config,
+    caplog,
+):
+    monkeypatch.setattr(getpass, "getpass", lambda prompt: password)
+
+    assert auth.Resolver(config, auth.CredentialInput()).password == password
+
+    assert caplog.messages[0].startswith(f"  {warning}")
diff --git a/twine/utils.py b/twine/utils.py
index 6256ee0a..0aa5c75a 100644
--- a/twine/utils.py
+++ b/twine/utils.py
@@ -18,6 +18,7 @@
 import logging
 import os
 import os.path
+import unicodedata
 from typing import Any, Callable, DefaultDict, Dict, Optional, Sequence, Union
 from urllib.parse import urlparse
 from urllib.parse import urlunparse
@@ -240,11 +241,31 @@ def get_userpass_value(
     if cli_value is not None:
         logger.info(f"{key} set by command options")
         return cli_value
+
     elif config.get(key) is not None:
         logger.info(f"{key} set from config file")
         return config[key]
+
     elif prompt_strategy:
-        return prompt_strategy()
+        warning = ""
+        value = prompt_strategy()
+
+        if not value:
+            warning = f"Your {key} is empty"
+        elif any(unicodedata.category(c).startswith("C") for c in value):
+            # See https://www.unicode.org/reports/tr44/#General_Category_Values
+            # Most common case is "\x16" when pasting in Windows Command Prompt
+            warning = f"Your {key} contains control characters"
+
+        if warning:
+            logger.warning(f"  {warning}. Did you enter it correctly?")
+            logger.warning(
+                "  See https://twine.readthedocs.io/#entering-credentials "
+                "for more information."
+            )
+
+        return value
+
     else:
         return None