diff --git a/Lib/test/test_zipfile.py b/Lib/test/test_zipfile.py
index 33602cff55c..1bef5750a15 100644
--- a/Lib/test/test_zipfile.py
+++ b/Lib/test/test_zipfile.py
@@ -646,7 +646,7 @@ def test_write_filtered_python_package(self):
             self.assertTrue('SyntaxError' not in reportStr)
 
             # then check that the filter works on individual files
-            with captured_stdout() as reportSIO:
+            with captured_stdout() as reportSIO, self.assertWarns(UserWarning):
                 zipfp.writepy(packagedir, filterfunc=lambda fn:
                                                      'bad' not in fn)
             reportStr = reportSIO.getvalue()
@@ -896,7 +896,9 @@ def test_open_via_zip_info(self):
         # Create the ZIP archive
         with zipfile.ZipFile(TESTFN2, "w", zipfile.ZIP_STORED) as zipfp:
             zipfp.writestr("name", "foo")
-            zipfp.writestr("name", "bar")
+            with self.assertWarns(UserWarning):
+                zipfp.writestr("name", "bar")
+            self.assertEqual(zipfp.namelist(), ["name"] * 2)
 
         with zipfile.ZipFile(TESTFN2, "r") as zipfp:
             infos = zipfp.infolist()
@@ -1213,7 +1215,8 @@ def test_comments(self):
 
         # check a comment that is too long is truncated
         with zipfile.ZipFile(TESTFN, mode="w") as zipf:
-            zipf.comment = comment2 + b'oops'
+            with self.assertWarns(UserWarning):
+                zipf.comment = comment2 + b'oops'
             zipf.writestr("foo.txt", "O, for a Muse of Fire!")
         with zipfile.ZipFile(TESTFN, mode="r") as zipfr:
             self.assertEqual(zipfr.comment, comment2)
diff --git a/Lib/zipfile.py b/Lib/zipfile.py
index 12c1754d714..7b6bd5f8091 100644
--- a/Lib/zipfile.py
+++ b/Lib/zipfile.py
@@ -1104,10 +1104,10 @@ def comment(self, comment):
         if not isinstance(comment, bytes):
             raise TypeError("comment: expected bytes, got %s" % type(comment))
         # check for valid comment length
-        if len(comment) >= ZIP_MAX_COMMENT:
-            if self.debug:
-                print('Archive comment is too long; truncating to %d bytes'
-                      % ZIP_MAX_COMMENT)
+        if len(comment) > ZIP_MAX_COMMENT:
+            import warnings
+            warnings.warn('Archive comment is too long; truncating to %d bytes'
+                          % ZIP_MAX_COMMENT, stacklevel=2)
             comment = comment[:ZIP_MAX_COMMENT]
         self._comment = comment
         self._didModify = True
@@ -1296,8 +1296,8 @@ def _extract_member(self, member, targetpath, pwd):
     def _writecheck(self, zinfo):
         """Check for errors before writing a file to the archive."""
         if zinfo.filename in self.NameToInfo:
-            if self.debug:      # Warning for duplicate names
-                print("Duplicate name:", zinfo.filename)
+            import warnings
+            warnings.warn('Duplicate name: %r' % zinfo.filename, stacklevel=3)
         if self.mode not in ("w", "a"):
             raise RuntimeError('write() requires mode "w" or "a"')
         if not self.fp:
diff --git a/Misc/NEWS b/Misc/NEWS
index 19e2a6e9f1f..66d65f084f7 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -25,6 +25,9 @@ Core and Builtins
 Library
 -------
 
+- Issue #20262: Warnings are raised now when duplicate names are added in the
+  ZIP file or too long ZIP file comment is truncated.
+
 - Issue #20165: The unittest module no longer considers tests marked with
   @expectedFailure successful if they pass.