From a7483ccd8dc4c0a93bace88f4c5263cb68da08b7 Mon Sep 17 00:00:00 2001
From: Viswa Marepalli <reachvishm@gmail.com>
Date: Tue, 27 Oct 2026 21:40:07 +0000
Subject: [PATCH] Bind ssl lazily after no_ssl so boto3 imports

no_ssl makes `import ssl` fail while urllib3.util.ssl_ and similar modules
load, and their fallback code can leave the name `ssl` unbound. botocore does
`from urllib3.util.ssl_ import ssl`, so importing boto3 failed. After no_ssl,
add a module __getattr__ that imports ssl on first access.

Ported from cloudflare/workers-py#292 (f3e7851).

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
---
 workers/src/_crosswind_patches/entropy.py    | 40 +++++++++++++++++---
 workers/tests/e2e/entropy/src/boto3_entry.py | 10 +++++
 workers/tests/e2e/test_entropy_e2e.py        | 22 +++++++++++
 3 files changed, 67 insertions(+), 5 deletions(-)
 create mode 100644 workers/tests/e2e/entropy/src/boto3_entry.py

diff --git a/workers/src/_crosswind_patches/entropy.py b/workers/src/_crosswind_patches/entropy.py
index df87953..cd5e8ed 100644
--- a/workers/src/_crosswind_patches/entropy.py
+++ b/workers/src/_crosswind_patches/entropy.py
@@ -159,13 +159,42 @@ def find_spec(
         return None
 
 
+def add_lazy_ssl_attribute(module: ModuleType) -> None:
+    """
+    When `import ssl` fails inside a module, its fallback code can leave the name
+    `ssl` unbound. Other packages may still import it from there, for example
+    botocore does `from urllib3.util.ssl_ import ssl`. Bind it lazily on first
+    access.
+
+    TODO: Drop this when https://github.com/boto/botocore/pull/3640 is merged.
+    """
+    if "ssl" in module.__dict__:
+        return
+
+    orig_getattr = module.__dict__.get("__getattr__")
+
+    def lazy_getattr(name: str):
+        if name == "ssl":
+            import ssl
+
+            setattr(module, "ssl", ssl)  # noqa: B010
+            return ssl
+        if orig_getattr is not None:
+            return orig_getattr(name)
+        raise AttributeError(f"module {module.__name__!r} has no attribute {name!r}")
+
+    # setattr, because ty only sees the declared ModuleType attributes.
+    setattr(module, "__getattr__", lazy_getattr)  # noqa: B010
+
+
 @contextmanager
-def no_ssl():
+def no_ssl(module: ModuleType):
     """
     Various packages will call ssl.create_default_context() at top level which uses
     entropy if they can import ssl. By temporarily making importing ssl raise an
     import error, we exercise the workaround code and so avoid the entropy calls.
-    After, we put the ssl module back to the normal value.
+    After, we put the ssl module back to the normal value and make `module.ssl`
+    available again in case the workaround code left it unbound.
     """
     try:
         f = NoSslFinder()
@@ -176,26 +205,27 @@ def no_ssl():
         sys.meta_path.remove(f)
         if ssl:
             sys.modules["ssl"] = ssl
+    add_lazy_ssl_attribute(module)
 
 
 @register_exec_patch("aiohttp.connector")
 @contextmanager
 def aiohttp_connector_context(module):
-    with no_ssl():
+    with no_ssl(module):
         yield
 
 
 @register_exec_patch("requests.adapters")
 @contextmanager
 def requests_adapters_context(module):
-    with no_ssl():
+    with no_ssl(module):
         yield
 
 
 @register_exec_patch("urllib3.util.ssl_")
 @contextmanager
 def urllib3_util_ssl__context(module):
-    with no_ssl():
+    with no_ssl(module):
         yield
 
 
diff --git a/workers/tests/e2e/entropy/src/boto3_entry.py b/workers/tests/e2e/entropy/src/boto3_entry.py
new file mode 100644
index 0000000..2329451
--- /dev/null
+++ b/workers/tests/e2e/entropy/src/boto3_entry.py
@@ -0,0 +1,10 @@
+# botocore does `from urllib3.util.ssl_ import ssl`, but crosswind imports
+# urllib3.util.ssl_ without ssl to avoid entropy calls, which leaves it unbound.
+import boto3
+
+from workers import Response, WorkerEntrypoint
+
+
+class Default(WorkerEntrypoint):
+    async def fetch(self, request):
+        return Response(boto3.__name__)
diff --git a/workers/tests/e2e/test_entropy_e2e.py b/workers/tests/e2e/test_entropy_e2e.py
index 5bf99ad..247fc1e 100644
--- a/workers/tests/e2e/test_entropy_e2e.py
+++ b/workers/tests/e2e/test_entropy_e2e.py
@@ -23,3 +23,25 @@ def test_numpy_and_pydantic_import_at_top_level(
     name, value = body.split(" ")
     assert name == "ok"
     assert 0 <= float(value) < 1
+
+
+@TARGETS
+def test_boto3_import_at_top_level(tmp_path: Path, date: str, version: str) -> None:
+    # Before 3.14 the flag hands patching to crosswind's .pth hook, as in
+    # test_fastapi_app_answers.
+    flags = ["python_process_pth_files"] if version != "3.14" else []
+    make_project(
+        tmp_path,
+        Path(__file__).parent / "entropy",
+        {
+            "main": "src/boto3_entry.py",
+            "compatibility_date": date,
+            "compatibility_flags": ["python_workers", *flags],
+        },
+        ("boto3",),
+    )
+
+    with wynd_dev(tmp_path) as server:
+        _, body = server.get("/")
+
+    assert body == "boto3"