diff --git a/setup.py b/setup.py
index 6c6a0e57..fbf3b38b 100644
--- a/setup.py
+++ b/setup.py
@@ -20,7 +20,7 @@
 
 install_requires = [
     "pkginfo",
-    "requests >= 2.0",
+    "requests >= 2.3.0",
     "setuptools >= 0.7.0",
 ]
 
diff --git a/twine/commands/upload.py b/twine/commands/upload.py
index a7e57275..5979e628 100644
--- a/twine/commands/upload.py
+++ b/twine/commands/upload.py
@@ -30,6 +30,7 @@
 import pkg_resources
 import requests
 
+import twine.exceptions as exc
 from twine.utils import get_config, get_username, get_password
 from twine.wheel import Wheel
 from twine.wininst import WinInst
@@ -210,11 +211,23 @@ def upload(dists, repository, sign, identity, username, password, comment,
             data=dict((k, v) for k, v in data.items() if v),
             files=filedata,
             auth=(username, password),
+            allow_redirects=False,
         )
         # Bug 28. Try to silence a ResourceWarning by releasing the socket and
         # clearing the connection pool.
         resp.close()
         session.close()
+
+        # Bug 92. If we get a redirect we should abort because something seems
+        # funky. The behaviour is not well defined and redirects being issued
+        # by PyPI should never happen in reality. This should catch malicious
+        # redirects as well.
+        if resp.is_redirect():
+            raise exc.RedirectDetected(
+                ('"{0}" attempted to redirect to "{1}" during upload.'
+                 ' Aborting...').format(config["respository"],
+                                        resp.headers["location"]))
+        # Otherwise, raise an HTTPError based on the status code.
         resp.raise_for_status()
 
 
diff --git a/twine/exceptions.py b/twine/exceptions.py
new file mode 100644
index 00000000..52fa6cbb
--- /dev/null
+++ b/twine/exceptions.py
@@ -0,0 +1,24 @@
+# Copyright 2015 Ian Cordasco
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+# http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+
+class RedirectDetected(Exception):
+    """A redirect was detected that the user needs to resolve.
+
+    In some cases, requests refuses to issue a new POST request after a
+    redirect. In order to prevent a confusing user experience, we raise this
+    exception to allow users to know the index they're uploading to is
+    redirecting them.
+    """
+    pass