I noticed the depending crypto module was changed since commit 948cccf. The project was deployed with GAE release 1.9.32 and gcloud-python 0.9.0.

Here are some context info according to your recent comments:

1. How do you vendor in gcloud-python for App Engine?
   As described in GAE documentation: https://cloud.google.com/appengine/docs/python/tools/libraries27#vendoring

2. Which services / gcloud-python subpackages do you use? (I'm curious which imports / import paths your code has been using.)
   I am generating signed url for an object in Google Cloud Storage. Here's the partial stacktrace:

   Traceback (most recent call last):
   ---- omitted for simple trace) ----
   from ext import cloudstorage as storage
   File "/base/data/home/apps/sjackend-0/1.390622100755930629/ext/cloudstorage.py", line 8, in
   from gcloud import (
   File "/base/data/home/apps/sjackend-0/1.390622100755930629/lib/gcloud/storage/init.py", line 43, in
   from gcloud.storage.blob import Blob
   File "/base/data/home/apps/sjackend-0/1.390622100755930629/lib/gcloud/storage/blob.py", line 28, in
   from gcloud.credentials import generate_signed_url
   File "/base/data/home/apps/sjackend-0/1.390622100755930629/lib/gcloud/credentials.py", line 22, in
   from OpenSSL import crypto
   File "/base/data/home/apps/sjackend-0/1.390622100755930629/lib/OpenSSL/init.py", line 8, in
   from OpenSSL import rand, crypto, SSL
   File "/base/data/home/apps/sjackend-0/1.390622100755930629/lib/OpenSSL/rand.py", line 11, in
   from OpenSSL._util import (
   File "/base/data/home/apps/sjackend-0/1.390622100755930629/lib/OpenSSL/_util.py", line 6, in
   from cryptography.hazmat.bindings.openssl.binding import Binding
   File "/base/data/home/apps/sjackend-0/1.390622100755930629/lib/cryptography/hazmat/bindings/openssl/binding.py", line 14, in
   from cryptography.hazmat.bindings._openssl import ffi, lib
   ImportError: dynamic module does not define init function (init_openssl)

I guess this is caused by the inherent inflexibility with runtime environment in GAE, and affects #1009 which seems to conflict with this issue.