diff --git a/pex/pex.py b/pex/pex.py
index 02f2d642c..651bfd55c 100644
--- a/pex/pex.py
+++ b/pex/pex.py
@@ -73,7 +73,7 @@ def _activate(self):
       pex_info = self._pex_info.copy()
       pex_info.update(self._pex_info_overrides)
       pex_info.merge_pex_path(self._vars.PEX_PATH)
-      self._envs.append(PEXEnvironment(self._pex, pex_info))
+      self._envs.append(PEXEnvironment(self._pex, pex_info, interpreter=self._interpreter))
       # N.B. by this point, `pex_info.pex_path` will contain a single pex path
       # merged from pex_path in `PEX-INFO` and `PEX_PATH` set in the environment.
       # `PEX_PATH` entries written into `PEX-INFO` take precedence over those set
@@ -83,7 +83,7 @@ def _activate(self):
         for pex_path in filter(None, pex_info.pex_path.split(os.pathsep)):
           pex_info = PexInfo.from_pex(pex_path)
           pex_info.update(self._pex_info_overrides)
-          self._envs.append(PEXEnvironment(pex_path, pex_info))
+          self._envs.append(PEXEnvironment(pex_path, pex_info, interpreter=self._interpreter))
 
       # activate all of them
       for env in self._envs:
diff --git a/pex/testing.py b/pex/testing.py
index 35198414b..718048cff 100644
--- a/pex/testing.py
+++ b/pex/testing.py
@@ -126,13 +126,13 @@ def write_zipfile(directory, dest, reverse=False):
 
 @contextlib.contextmanager
 def make_installer(name='my_project', version='0.0.0', installer_impl=EggInstaller, zip_safe=True,
-                   install_reqs=None):
+                   install_reqs=None, **kwargs):
   interp = {'project_name': name,
             'version': version,
             'zip_safe': zip_safe,
             'install_requires': install_reqs or []}
   with temporary_content(PROJECT_CONTENT, interp=interp) as td:
-    yield installer_impl(td)
+    yield installer_impl(td, **kwargs)
 
 
 @contextlib.contextmanager
@@ -145,19 +145,20 @@ def make_source_dir(name='my_project', version='0.0.0', install_reqs=None):
     yield td
 
 
-def make_sdist(name='my_project', version='0.0.0', zip_safe=True, install_reqs=None):
+def make_sdist(name='my_project', version='0.0.0', zip_safe=True, install_reqs=None, **kwargs):
   with make_installer(name=name, version=version, installer_impl=Packager, zip_safe=zip_safe,
-                      install_reqs=install_reqs) as packager:
+                      install_reqs=install_reqs, **kwargs) as packager:
     return packager.sdist()
 
 
 @contextlib.contextmanager
 def make_bdist(name='my_project', version='0.0.0', installer_impl=EggInstaller, zipped=False,
-               zip_safe=True):
+               zip_safe=True, **kwargs):
   with make_installer(name=name,
                       version=version,
                       installer_impl=installer_impl,
-                      zip_safe=zip_safe) as installer:
+                      zip_safe=zip_safe,
+                      **kwargs) as installer:
     dist_location = installer.bdist()
     if zipped:
       yield DistributionHelper.distribution_from_path(dist_location)
diff --git a/tests/test_pex.py b/tests/test_pex.py
index ac3d2017b..8f5efa34e 100644
--- a/tests/test_pex.py
+++ b/tests/test_pex.py
@@ -10,17 +10,21 @@
 import pytest
 from twitter.common.contextutil import temporary_file
 
-from pex.compatibility import WINDOWS, nested, to_bytes
+from pex.bin.pex import get_interpreter
+from pex.compatibility import PY2, WINDOWS, nested, to_bytes
 from pex.installer import EggInstaller, WheelInstaller
 from pex.pex import PEX
 from pex.pex_builder import PEXBuilder
+from pex.pex_info import PexInfo
 from pex.testing import (
-    make_installer,
-    named_temporary_file,
-    run_simple_pex_test,
-    temporary_dir,
-    write_simple_pex
-)
+  IS_PYPY,
+  ensure_python_interpreter,
+  make_installer,
+  named_temporary_file,
+  run_simple_pex_test,
+  temporary_dir,
+  write_simple_pex,
+  make_bdist)
 from pex.util import DistributionHelper
 
 try:
@@ -309,3 +313,31 @@ def test_pex_verify_entry_point_module_should_fail():
       PEX(pex_builder.path(),
           interpreter=pex_builder.interpreter,
           verify_entry_point=True)
+
+
+@pytest.mark.skipif(IS_PYPY)
+def test_activate_interpreter_different_from_current():
+  with temporary_dir() as pex_root:
+    interp_version = '3.6.3' if PY2 else '2.7.10'
+    custom_interpreter = get_interpreter(
+      python_interpreter=ensure_python_interpreter(interp_version),
+      interpreter_cache_dir=os.path.join(pex_root, 'interpreters'),
+      repos=None,  # Default to PyPI.
+      use_wheel=True
+    )
+    pex_info = PexInfo.default(custom_interpreter)
+    pex_info.pex_root = pex_root
+    with temporary_dir() as pex_chroot:
+      pex_builder = PEXBuilder(path=pex_chroot,
+                               interpreter=custom_interpreter,
+                               pex_info=pex_info)
+      with make_bdist(installer_impl=WheelInstaller, interpreter=custom_interpreter) as bdist:
+        pex_builder.add_distribution(bdist)
+        pex_builder.set_entry_point('sys:exit')
+        pex_builder.freeze()
+
+        pex = PEX(pex_builder.path(), interpreter=custom_interpreter)
+        try:
+          pex._activate()
+        except SystemExit as e:
+          pytest.fail('PEX activation of %s failed with %s' % (pex, e))