diff --git a/pex/pip.py b/pex/pip.py
index 4f7392843..62623cdf7 100644
--- a/pex/pip.py
+++ b/pex/pip.py
@@ -8,6 +8,7 @@
 from collections import deque
 
 from pex import third_party
+from pex.compatibility import urlparse
 from pex.interpreter import PythonInterpreter
 from pex.platforms import Platform
 from pex.variables import ENV
@@ -46,6 +47,16 @@ def execute_pip_isolated(args, cache=None, interpreter=None):
 
 
 def _calculate_package_index_options(indexes=None, find_links=None):
+  trusted_hosts = []
+
+  def maybe_trust_insecure_host(url):
+    url_info = urlparse.urlparse(url)
+    if 'http' == url_info.scheme:
+      # Implicitly trust explicitly asked for http indexes and find_links repos instead of requiring
+      # seperate trust configuration.
+      trusted_hosts.append(url_info.netloc)
+    return url
+
   # N.B.: We interpret None to mean accept pip index defaults, [] to mean turn off all index use.
   if indexes is not None:
     if len(indexes) == 0:
@@ -53,16 +64,20 @@ def _calculate_package_index_options(indexes=None, find_links=None):
     else:
       all_indexes = deque(indexes)
       yield '--index-url'
-      yield all_indexes.popleft()
+      yield maybe_trust_insecure_host(all_indexes.popleft())
       if all_indexes:
         for extra_index in all_indexes:
           yield '--extra-index-url'
-          yield extra_index
+          yield maybe_trust_insecure_host(extra_index)
 
   if find_links:
     for find_link_url in find_links:
       yield '--find-links'
-      yield find_link_url
+      yield maybe_trust_insecure_host(find_link_url)
+
+  for trusted_host in trusted_hosts:
+    yield '--trusted-host'
+    yield trusted_host
 
 
 def download_distributions(target,
diff --git a/tests/test_integration.py b/tests/test_integration.py
index ada77eb70..a27a2590d 100644
--- a/tests/test_integration.py
+++ b/tests/test_integration.py
@@ -19,7 +19,6 @@
 from pex.pex_info import PexInfo
 from pex.pip import build_wheels, download_distributions
 from pex.testing import (
-    IS_PYPY,
     NOT_CPYTHON27,
     NOT_CPYTHON27_OR_OSX,
     NOT_CPYTHON36_OR_LINUX,
@@ -1096,9 +1095,7 @@ def test_pex_interpreter_interact_custom_setuptools_useable():
     assert rc == 0, stdout
 
 
-@pytest.mark.skipif(IS_PYPY,
-                    reason='Our pyenv interpreter setup fails under pypy: '
-                           'https://github.com/pantsbuild/pex/issues/477')
+@skip_for_pyenv_use_under_pypy
 def test_setup_python():
   interpreter = ensure_python_interpreter(PY27)
   with temporary_dir() as out:
@@ -1111,9 +1108,7 @@ def test_setup_python():
     subprocess.check_call([pex, '-c', 'import jsonschema'])
 
 
-@pytest.mark.skipif(IS_PYPY,
-                    reason='Our pyenv interpreter setup fails under pypy: '
-                           'https://github.com/pantsbuild/pex/issues/477')
+@skip_for_pyenv_use_under_pypy
 def test_setup_interpreter_constraint():
   interpreter = ensure_python_interpreter(PY27)
   with temporary_dir() as out:
@@ -1133,9 +1128,7 @@ def test_setup_interpreter_constraint():
     assert rc == 0
 
 
-@pytest.mark.skipif(IS_PYPY,
-                    reason='Our pyenv interpreter setup fails under pypy: '
-                           'https://github.com/pantsbuild/pex/issues/477')
+@skip_for_pyenv_use_under_pypy
 def test_setup_python_multiple_transitive_markers():
   py27_interpreter = ensure_python_interpreter(PY27)
   py36_interpreter = ensure_python_interpreter(PY36)
@@ -1169,9 +1162,7 @@ def test_setup_python_multiple_transitive_markers():
     assert to_bytes(os.path.realpath(py36_interpreter)) == stdout.strip()
 
 
-@pytest.mark.skipif(IS_PYPY,
-                    reason='Our pyenv interpreter setup fails under pypy: '
-                           'https://github.com/pantsbuild/pex/issues/477')
+@skip_for_pyenv_use_under_pypy
 def test_setup_python_direct_markers():
   py36_interpreter = ensure_python_interpreter(PY36)
   with temporary_dir() as out:
@@ -1189,9 +1180,7 @@ def test_setup_python_direct_markers():
       subprocess.check_call(py2_only_program, env=make_env(PATH=os.path.dirname(py36_interpreter)))
 
 
-@pytest.mark.skipif(IS_PYPY,
-                    reason='Our pyenv interpreter setup fails under pypy: '
-                           'https://github.com/pantsbuild/pex/issues/477')
+@skip_for_pyenv_use_under_pypy
 def test_setup_python_multiple_direct_markers():
   py36_interpreter = ensure_python_interpreter(PY36)
   py27_interpreter = ensure_python_interpreter(PY27)
@@ -1562,9 +1551,7 @@ def test_pex_reexec_constraints_dont_match_current_pex_python():
                      interpreter_constraints=['=={}'.format(version)])
 
 
-@pytest.mark.skipif(IS_PYPY,
-                    reason='Our pyenv interpreter setup fails under pypy: '
-                           'https://github.com/pantsbuild/pex/issues/477')
+@skip_for_pyenv_use_under_pypy
 def test_issues_745_extras_isolation():
   # Here we ensure one of our extras, `subprocess32`, is properly isolated in the transition from
   # pex bootstrapping where it is imported by `pex.executor` to execution of user code.
@@ -1604,3 +1591,20 @@ def test_issues_745_extras_isolation():
 
     subprocess32_location = os.path.realpath(output.decode('utf-8').strip())
     assert subprocess32_location.startswith(pex_root)
+
+
+@skip_for_pyenv_use_under_pypy
+def test_trusted_host_handling():
+  python = ensure_python_interpreter(PY27)
+  # Since we explicitly ask Pex to find links at http://www.antlr3.org/download/Python, it should
+  # implicitly trust the www.antlr3.org host.
+  results = run_pex_command(
+    args=[
+      '--find-links=http://www.antlr3.org/download/Python',
+      'antlr_python_runtime==3.1.3',
+      '--',
+      '-c', 'import antlr3'
+    ],
+    python=python
+  )
+  results.assert_success()