diff --git a/compiler/python_archive.py b/compiler/python_archive.py
index 3dfdba0..822c9de 100755
--- a/compiler/python_archive.py
+++ b/compiler/python_archive.py
@@ -50,6 +50,27 @@
 # End boilerplate
 """
 
+# Boilerplate must be after the last __future__ import.  See
+# https://docs.python.org/2/reference/simple_stmts.html#future
+_boilerplate_insertion_regex = re.compile('''(?sx)
+(?P<before>
+    (
+        (
+            ([#][^\\r\\n]*) | # comment
+            (\\s*) | # whitespace
+            (from\\s+__future__\\s+import\\s+[^\\r\\n]+) | # future import
+            ('[^'].*?') | # module doc comment form 1
+            ("[^"].*?") | # module doc comment form 2
+            (\'\'\'.*?(\'\'\')) | # module doc comment form 3
+            (""".*?""") # module doc comment form 4
+        )
+        [\\r\\n]+ # end of line(s) for Mac, Unix and/or Windows
+    )*
+)
+# Boilerplate is inserted here
+(?P<after>.*)
+''')
+
 # Fully qualified names of subpar packages
 _subpar_package = 'subpar'
 _compiler_package = _subpar_package + '.compiler'
@@ -159,25 +180,23 @@ def generate_main(self, main_filename, boilerplate_contents):
         # Read main source file, in unknown encoding.  We use latin-1
         # here, but any single-byte encoding that doesn't raise errors
         # would work.
-        output_lines = []
         with io.open(main_filename, 'rt', encoding='latin-1') as main_file:
-            output_lines = list(main_file)
+            original_content = main_file.read()
 
         # Find a good place to insert the boilerplate, which is the
-        # first line that is not a comment, blank line, or future
-        # import.
-        skip_regex = re.compile(
-            '''(#.*)|(\\s+)|(from\\s+__future__\\s+import)''')
-        idx = 0
-        while idx < len(output_lines):
-            if not skip_regex.match(output_lines[idx]):
-                break
-            idx += 1
+        # first line that is not a comment, blank line, doc comment,
+        # or future import.
+        match = re.match(_boilerplate_insertion_regex, original_content)
+        assert match, original_content
+        assert (len(match.group('before')) + len(match.group('after'))) == \
+                len(original_content), (match, original_content)
+        new_content = (match.group('before') +
+                       boilerplate_contents +
+                       match.group('after'))
 
         # Insert boilerplate (might be beginning, middle or end)
-        output_lines[idx:idx] = [boilerplate_contents]
-        contents = ''.join(output_lines).encode('latin-1')
-        return stored_resource.StoredContent('__main__.py', contents)
+        encoded_content = new_content.encode('latin-1')
+        return stored_resource.StoredContent('__main__.py', encoded_content)
 
     def scan_manifest(self, manifest):
         """Return a dict of StoredResources based on an input manifest.
diff --git a/compiler/python_archive_test.py b/compiler/python_archive_test.py
index 17d5049..e11c941 100644
--- a/compiler/python_archive_test.py
+++ b/compiler/python_archive_test.py
@@ -140,6 +140,15 @@ def test_generate_main(self):
             # Future import
             (b'from __future__ import print_function\n',
              b'from __future__ import print_function\nBOILERPLATE\n'),
+            # Module docstrings
+            (b"'Single-quote Module docstring'\n",
+             b"'Single-quote Module docstring'\nBOILERPLATE\n"),
+            (b'"Double-quote Module docstring"\n',
+             b'"Double-quote Module docstring"\nBOILERPLATE\n'),
+            (b"'''Triple-single-quote module \"'\n\n docstring'''\n",
+             b"'''Triple-single-quote module \"'\n\n docstring'''\nBOILERPLATE\n"),
+            (b'"""Triple-double-quote module "\'\n\n docstring"""\n',
+             b'"""Triple-double-quote module "\'\n\n docstring"""\nBOILERPLATE\n'),
         ]
         for main_content, expected in cases:
             with test_utils.temp_file(main_content) as main_file:
diff --git a/tests/BUILD b/tests/BUILD
index a87f306..0e72f9d 100644
--- a/tests/BUILD
+++ b/tests/BUILD
@@ -76,9 +76,9 @@ par_binary(
 )
 
 par_binary(
-    name = "package_g/g",
-    srcs = ["package_g/g.py"],
-    main = "package_g/g.py",
+    name = "package_boilerplate/main",
+    srcs = ["package_boilerplate/main.py"],
+    main = "package_boilerplate/main.py",
     srcs_version = "PY2AND3",
 )
 
@@ -179,7 +179,7 @@ par_binary(
         "tests/package_import_roots/import_roots",
     ),
     ("indirect_dependency", "//tests:package_c/c", "tests/package_c/c"),
-    ("main_boilerplate", "//tests:package_g/g", "tests/package_g/g"),
+    ("main_boilerplate", "//tests:package_boilerplate/main", "tests/package_boilerplate/main"),
     ("pkg_resources", "//tests:package_pkg_resources/main", "tests/package_pkg_resources/main"),
     ("shadow", "//tests:package_shadow/main", "tests/package_shadow/main"),
     ("version", "//tests:package_f/f", "tests/package_f/f"),
diff --git a/tests/package_g/g.py b/tests/package_boilerplate/main.py
similarity index 87%
rename from tests/package_g/g.py
rename to tests/package_boilerplate/main.py
index 2006319..03ef2d6 100755
--- a/tests/package_g/g.py
+++ b/tests/package_boilerplate/main.py
@@ -1,14 +1,16 @@
 #!/usr/bin/env python3
 # -*- coding: latin-1
 
-# Test __future__ imports
-from __future__ import print_function
-
-"""Integration test program G for Subpar.
+# Test module docstring before boilerplate insertion
+"""Integration test program for Subpar.
 
 Test bootstrap interaction with __future__ imports and source file encodings.
 """
 
+# Test __future__ imports
+from __future__ import print_function
+
+
 # Test the source file encoding specification above.  See PEP 263 for
 # details.  In the line below, this source file contains a byte
 # sequence that is valid latin-1 but not valid utf-8.  Specifically,
diff --git a/tests/package_boilerplate/main_PY2_filelist.txt b/tests/package_boilerplate/main_PY2_filelist.txt
new file mode 100644
index 0000000..0b93076
--- /dev/null
+++ b/tests/package_boilerplate/main_PY2_filelist.txt
@@ -0,0 +1,8 @@
+__main__.py
+subpar/__init__.py
+subpar/runtime/__init__.py
+subpar/runtime/support.py
+subpar/tests/__init__.py
+subpar/tests/package_boilerplate/__init__.py
+subpar/tests/package_boilerplate/main
+subpar/tests/package_boilerplate/main.py
diff --git a/tests/package_boilerplate/main_PY3_filelist.txt b/tests/package_boilerplate/main_PY3_filelist.txt
new file mode 100644
index 0000000..0b93076
--- /dev/null
+++ b/tests/package_boilerplate/main_PY3_filelist.txt
@@ -0,0 +1,8 @@
+__main__.py
+subpar/__init__.py
+subpar/runtime/__init__.py
+subpar/runtime/support.py
+subpar/tests/__init__.py
+subpar/tests/package_boilerplate/__init__.py
+subpar/tests/package_boilerplate/main
+subpar/tests/package_boilerplate/main.py
diff --git a/tests/package_g/g_PY2_filelist.txt b/tests/package_g/g_PY2_filelist.txt
deleted file mode 100644
index b58fe85..0000000
--- a/tests/package_g/g_PY2_filelist.txt
+++ /dev/null
@@ -1,8 +0,0 @@
-__main__.py
-subpar/__init__.py
-subpar/runtime/__init__.py
-subpar/runtime/support.py
-subpar/tests/__init__.py
-subpar/tests/package_g/__init__.py
-subpar/tests/package_g/g
-subpar/tests/package_g/g.py
diff --git a/tests/package_g/g_PY3_filelist.txt b/tests/package_g/g_PY3_filelist.txt
deleted file mode 100644
index b58fe85..0000000
--- a/tests/package_g/g_PY3_filelist.txt
+++ /dev/null
@@ -1,8 +0,0 @@
-__main__.py
-subpar/__init__.py
-subpar/runtime/__init__.py
-subpar/runtime/support.py
-subpar/tests/__init__.py
-subpar/tests/package_g/__init__.py
-subpar/tests/package_g/g
-subpar/tests/package_g/g.py