diff --git a/pex/crawler.py b/pex/crawler.py
index ee89d7fee..e0be8f5cb 100644
--- a/pex/crawler.py
+++ b/pex/crawler.py
@@ -95,6 +95,7 @@ def crawl_local(cls, link):
   @classmethod
   def crawl_remote(cls, context, link):
     try:
+      link = context.resolve(link)
       content = context.content(link)
     except context.Error as e:
       TRACER.log('Failed to read %s: %s' % (link.url, e), V=1)
diff --git a/pex/http.py b/pex/http.py
index 6396ff8c3..a1e68419f 100644
--- a/pex/http.py
+++ b/pex/http.py
@@ -119,6 +119,13 @@ def fetch(self, link, into=None):
     os.rename(target_tmp, target)
     return target
 
+  def resolve(self, link):
+    """Resolves final link throught all the redirections.
+
+    :param link: The :class:`Link` to open.
+    """
+    return link
+
 
 class UrllibContext(Context):
   """Default Python standard library Context."""
@@ -134,6 +141,12 @@ def content(self, link):
       encoding = message_from_string(str(fp.headers)).get_content_charset(self.DEFAULT_ENCODING)
       return fp.read().decode(encoding, 'replace')
 
+  def resolve(self, link):
+    request = urllib_request.Request(link.url)
+    request.get_method = lambda: 'HEAD'
+    with contextlib.closing(urllib_request.urlopen(request)) as response:
+      return link.wrap(response.url)
+
   def __init__(self, *args, **kw):
     TRACER.log('Warning, using a UrllibContext which is known to be flaky.')
     TRACER.log('Please build pex with the requests module for more reliable downloads.')
@@ -246,6 +259,12 @@ def content(self, link):
     with contextlib.closing(self.open(link)) as request:
       return request.read().decode(request.encoding or self.DEFAULT_ENCODING, 'replace')
 
+  def resolve(self, link):
+    return link.wrap(self._session.head(
+        link.url, verify=self._verify, allow_redirects=True,
+        headers={'User-Agent': self.USER_AGENT}
+    ).url)
+
 
 if requests:
   Context.register(RequestsContext)
diff --git a/tests/test_crawler.py b/tests/test_crawler.py
index 3fc44ebec..7e7fcbebb 100644
--- a/tests/test_crawler.py
+++ b/tests/test_crawler.py
@@ -152,6 +152,7 @@ def test_crawler_remote():
   Crawler.reset_cache()
 
   mock_context = mock.create_autospec(Context, spec_set=True)
+  mock_context.resolve = lambda link: link
   mock_context.content.side_effect = [MOCK_INDEX_A, MOCK_INDEX_B, Exception('shouldnt get here')]
   expected_output = set([Link('http://url1.test.com/3to2-1.0.tar.gz'),
                          Link('http://url2.test.com/APScheduler-2.1.0.tar.gz')])
@@ -164,4 +165,17 @@ def test_crawler_remote():
   assert c.crawl(test_links) == expected_output
 
 
+def test_crawler_remote_redirect():
+  Crawler.reset_cache()
+
+  mock_context = mock.create_autospec(Context, spec_set=True)
+  mock_context.resolve = lambda link: Link('http://url2.test.com')
+  mock_context.content.side_effect = [MOCK_INDEX_A]
+  expected_output = set([Link('http://url2.test.com/3to2-1.0.tar.gz')])
+
+  c = Crawler(mock_context)
+  test_links = [Link('http://url1.test.com')]
+  assert c.crawl(test_links) == expected_output
+
+
 # TODO(wickman): test page decoding via mock