diff --git a/AUTHORS b/AUTHORS
index e8b0afb1..deb63c10 100644
--- a/AUTHORS
+++ b/AUTHORS
@@ -17,3 +17,4 @@ Jens Diemer <github@jensdiemer.de> (http://jensdiemer.de/)
 Andrew Watts <andrewwatts@gmail.com>
 Anna Martelli Ravenscroft <annaraven@gmail.com>
 Sumana Harihareswara <sh@changeset.nyc>
+Dustin Ingram <di@di.codes> (https://di.codes)
diff --git a/docs/changelog.rst b/docs/changelog.rst
index 35cae6df..6b8c1234 100644
--- a/docs/changelog.rst
+++ b/docs/changelog.rst
@@ -4,6 +4,8 @@
 Changelog
 =========
 
+* :feature:`319` Support Metadata 2.1 (`PEP 566
+  <https://www.python.org/dev/peps/pep-0566/>`_).
 * :support:`318` `Update PyPI URLs
   <https://packaging.python.org/guides/migrating-to-pypi-org/>`_.
 * :release:`1.10.0 <2018-03-07>`
diff --git a/setup.cfg b/setup.cfg
index 59a6ebbb..c308f888 100644
--- a/setup.cfg
+++ b/setup.cfg
@@ -11,7 +11,7 @@ requires-dist =
     tqdm >= 4.14
     requests >= 2.5.0, != 2.15, != 2.16
     requests-toolbelt >= 0.8.0
-    pkginfo >= 1.0
+    pkginfo >= 1.4.2
     setuptools >= 0.7.0
     argparse; python_version == '2.6'
     pyblake2; extra == 'with-blake2' and python_version < '3.6'
diff --git a/setup.py b/setup.py
index b01b0039..32b75118 100644
--- a/setup.py
+++ b/setup.py
@@ -20,7 +20,7 @@
 
 install_requires = [
     "tqdm >= 4.14",
-    "pkginfo >= 1.0",
+    "pkginfo >= 1.4.2",
     "requests >= 2.5.0, != 2.15, != 2.16",
     "requests-toolbelt >= 0.8.0",
     "setuptools >= 0.7.0",
diff --git a/tests/test_package.py b/tests/test_package.py
index d28eec1e..f3624d6f 100644
--- a/tests/test_package.py
+++ b/tests/test_package.py
@@ -15,6 +15,7 @@
 from twine import package
 
 import pretend
+import pytest
 
 
 def test_sign_file(monkeypatch):
@@ -70,3 +71,95 @@ def test_package_signed_name_is_correct():
 
     assert pkg.signed_basefilename == "deprecated-pypirc.asc"
     assert pkg.signed_filename == (filename + '.asc')
+
+
+@pytest.mark.parametrize('gpg_signature', [
+    (None),
+    (pretend.stub()),
+])
+def test_metadata_dictionary(gpg_signature):
+    meta = pretend.stub(
+        name='whatever',
+        version=pretend.stub(),
+        metadata_version=pretend.stub(),
+        summary=pretend.stub(),
+        home_page=pretend.stub(),
+        author=pretend.stub(),
+        author_email=pretend.stub(),
+        maintainer=pretend.stub(),
+        maintainer_email=pretend.stub(),
+        license=pretend.stub(),
+        description=pretend.stub(),
+        keywords=pretend.stub(),
+        platforms=pretend.stub(),
+        classifiers=pretend.stub(),
+        download_url=pretend.stub(),
+        supported_platforms=pretend.stub(),
+        provides=pretend.stub(),
+        requires=pretend.stub(),
+        obsoletes=pretend.stub(),
+        project_urls=pretend.stub(),
+        provides_dist=pretend.stub(),
+        obsoletes_dist=pretend.stub(),
+        requires_dist=pretend.stub(),
+        requires_external=pretend.stub(),
+        requires_python=pretend.stub(),
+        provides_extras=pretend.stub(),
+        description_content_type=pretend.stub(),
+    )
+
+    pkg = package.PackageFile(
+        filename='tests/fixtures/twine-1.5.0-py2.py3-none-any.whl',
+        comment=pretend.stub(),
+        metadata=meta,
+        python_version=pretend.stub(),
+        filetype=pretend.stub(),
+    )
+    pkg.gpg_signature = gpg_signature
+
+    result = pkg.metadata_dictionary()
+
+    # identify release
+    assert result['name'] == pkg.safe_name
+    assert result['version'] == meta.version
+
+    # file content
+    assert result['filetype'] == pkg.filetype
+    assert result['pyversion'] == pkg.python_version
+
+    # additional meta-data
+    assert result['metadata_version'] == meta.metadata_version
+    assert result['summary'] == meta.summary
+    assert result['home_page'] == meta.home_page
+    assert result['author'] == meta.author
+    assert result['author_email'] == meta.author_email
+    assert result['maintainer'] == meta.maintainer
+    assert result['maintainer_email'] == meta.maintainer_email
+    assert result['license'] == meta.license
+    assert result['description'] == meta.description
+    assert result['keywords'] == meta.keywords
+    assert result['platform'] == meta.platforms
+    assert result['classifiers'] == meta.classifiers
+    assert result['download_url'] == meta.download_url
+    assert result['supported_platform'] == meta.supported_platforms
+    assert result['comment'] == pkg.comment
+
+    # PEP 314
+    assert result['provides'] == meta.provides
+    assert result['requires'] == meta.requires
+    assert result['obsoletes'] == meta.obsoletes
+
+    # Metadata 1.2
+    assert result['project_urls'] == meta.project_urls
+    assert result['provides_dist'] == meta.provides_dist
+    assert result['obsoletes_dist'] == meta.obsoletes_dist
+    assert result['requires_dist'] == meta.requires_dist
+    assert result['requires_external'] == meta.requires_external
+    assert result['requires_python'] == meta.requires_python
+
+    # Metadata 2.1
+    assert result['provides_extras'] == meta.provides_extras
+    assert result['description_content_type'] == meta.description_content_type
+
+    # GPG signature
+    assert result.get('gpg_signature') == gpg_signature
diff --git a/twine/package.py b/twine/package.py
index 8d283949..744b9eeb 100644
--- a/twine/package.py
+++ b/twine/package.py
@@ -148,6 +148,10 @@ def metadata_dictionary(self):
             "requires_dist": meta.requires_dist,
             "requires_external": meta.requires_external,
             "requires_python": meta.requires_python,
+
+            # Metadata 2.1
+            "provides_extras": meta.provides_extras,
+            "description_content_type": meta.description_content_type,
         }
 
         if self.gpg_signature is not None: