diff --git a/setup.cfg b/setup.cfg
index 797f33e..1e54bd9 100644
--- a/setup.cfg
+++ b/setup.cfg
@@ -8,7 +8,7 @@ url = https://github.com/asottile/setup-cfg-fmt
 author = Anthony Sottile
 author_email = asottile@umich.edu
 license = MIT
-license_file = LICENSE
+license_files = LICENSE
 classifiers =
     License :: OSI Approved :: MIT License
     Programming Language :: Python :: 3
diff --git a/setup_cfg_fmt.py b/setup_cfg_fmt.py
index b246418..85956f3 100644
--- a/setup_cfg_fmt.py
+++ b/setup_cfg_fmt.py
@@ -96,14 +96,16 @@ def cb(match: Match[str]) -> str:
     return GLOB_PART.sub(cb, s)
 
 
-def _first_file(setup_cfg: str, prefix: str) -> Optional[str]:
+def _all_files(setup_cfg: str, prefix: str) -> Optional[List[str]]:
+    filenames = []
     prefix = _case_insensitive_glob(prefix)
     path = _adjacent_filename(setup_cfg, prefix)
     for filename in sorted(glob.iglob(f'{path}*')):
         if os.path.isfile(filename):
-            return filename
-    else:
+            filenames.append(filename)
+    if not filenames:
         return None
+    return filenames
 
 
 def _py3_excluded(min_py3_version: Tuple[int, int]) -> Set[Tuple[int, int]]:
@@ -365,12 +367,12 @@ def format_file(
     cfg['metadata']['name'] = cfg['metadata']['name'].replace('-', '_')
 
     # if README.md exists, set `long_description` + content type
-    readme = _first_file(filename, 'readme')
-    if readme is not None:
-        long_description = f'file: {os.path.basename(readme)}'
+    readmes = _all_files(filename, 'readme')
+    if readmes is not None:
+        long_description = f'file: {", ".join([os.path.basename(r) for r in readmes])}'
         cfg['metadata']['long_description'] = long_description
 
-        tags = identify.tags_from_filename(readme)
+        tags = identify.tags_from_filename(readmes[0])
         if 'markdown' in tags:
             cfg['metadata']['long_description_content_type'] = 'text/markdown'
         elif 'rst' in tags:
@@ -379,18 +381,20 @@ def format_file(
             cfg['metadata']['long_description_content_type'] = 'text/plain'
 
     # set license fields if a license exists
-    license_filename = _first_file(filename, 'licen[sc]e')
-    if license_filename is not None:
-        cfg['metadata']['license_file'] = os.path.basename(license_filename)
-
-        license_id = identify.license_id(license_filename)
-        if license_id is not None:
-            cfg['metadata']['license'] = license_id
-
-        if license_id in LICENSE_TO_CLASSIFIER:
+    license_filenames = _all_files(filename, 'licen[sc]e')
+    if license_filenames is not None:
+        cfg['metadata']['license_files'] = "\n   ".join([os.path.basename(f) for f in license_filenames])
+        license_ids = [identify.license_id(i) for i in license_filenames]
+        license_ids = [i for i in license_ids if i is not None]
+        if len(license_ids) > 1:
+            raise RuntimeError(f"There is more than one license: {license_ids}")
+        if license_ids:
+            cfg['metadata']['license'] = license_ids[0]
+
+        if license_ids and license_ids[0] in LICENSE_TO_CLASSIFIER:
             cfg['metadata']['classifiers'] = (
                 cfg['metadata'].get('classifiers', '').rstrip() +
-                f'\n{LICENSE_TO_CLASSIFIER[license_id]}'
+                f'\n{LICENSE_TO_CLASSIFIER[license_ids[0]]}'
             )
 
     requires = _python_requires(filename, min_py3_version=min_py3_version)
diff --git a/tests/setup_cfg_fmt_test.py b/tests/setup_cfg_fmt_test.py
index 05a7b8d..549fb4a 100644
--- a/tests/setup_cfg_fmt_test.py
+++ b/tests/setup_cfg_fmt_test.py
@@ -328,7 +328,7 @@ def test_sets_license_file_if_license_exists(filename, tmpdir):
         f'[metadata]\n'
         f'name = pkg\n'
         f'version = 1.0\n'
-        f'license_file = {filename}\n'
+        f'license_files = {filename}\n'
     )
 
 
@@ -356,7 +356,7 @@ def test_rewrite_sets_license_type_and_classifier(tmpdir):
         'name = pkg\n'
         'version = 1.0\n'
         'license = MIT\n'
-        'license_file = LICENSE\n'
+        'license_files = LICENSE\n'
         'classifiers =\n'
         '    License :: OSI Approved :: MIT License\n'
     )
@@ -399,7 +399,7 @@ def test_rewrite_identifies_license(tmpdir):
         'name = pkg\n'
         'version = 1.0\n'
         'license = Zlib\n'
-        'license_file = LICENSE\n'
+        'license_files = LICENSE\n'
         'classifiers =\n'
         '    License :: OSI Approved :: zlib/libpng License\n'
     )