diff --git a/news/2718.behavior b/news/2718.behavior
new file mode 100644
index 00000000..c00b1d46
--- /dev/null
+++ b/news/2718.behavior
@@ -0,0 +1 @@
+Fallback to shell mode if `run` fails with Windows error 193 to handle non-executable commands. This should improve usability on Windows, where some users run non-executable files without specifying a command, relying on Windows file association to choose the current command.
diff --git a/pipenv/core.py b/pipenv/core.py
index baea6373..bab12f93 100644
--- a/pipenv/core.py
+++ b/pipenv/core.py
@@ -2102,15 +2102,31 @@ def inline_activate_virtual_environment():
         os.environ["VIRTUAL_ENV"] = root
 
 
-def do_run_nt(script):
+def _launch_windows_subprocess(script):
     import subprocess
 
     command = system_which(script.command)
     options = {"universal_newlines": True}
-    if command:  # Try to use CreateProcess directly if possible.
-        p = subprocess.Popen([command] + script.args, **options)
-    else:  # Command not found, maybe this is a shell built-in?
-        p = subprocess.Popen(script.cmdify(), shell=True, **options)
+
+    # Command not found, maybe this is a shell built-in?
+    if not command:
+        return subprocess.Popen(script.cmdify(), shell=True, **options)
+
+    # Try to use CreateProcess directly if possible. Specifically catch
+    # Windows error 193 "Command is not a valid Win32 application" to handle
+    # a "command" that is non-executable. See pypa/pipenv#2727.
+    try:
+        return subprocess.Popen([command] + script.args, **options)
+    except WindowsError as e:
+        if e.winerror != 193:
+            raise
+
+    # Try shell mode to use Windows's file association for file launch.
+    return subprocess.Popen(script.cmdify(), shell=True, **options)
+
+
+def do_run_nt(script):
+    p = _launch_windows_subprocess(script)
     p.communicate()
     sys.exit(p.returncode)
 
diff --git a/pipenv/project.py b/pipenv/project.py
index e32296e5..c6e9e4fa 100644
--- a/pipenv/project.py
+++ b/pipenv/project.py
@@ -34,6 +34,7 @@ from .utils import (
     is_star,
     get_workon_home,
     is_virtual_environment,
+    looks_like_dir
 )
 from .environments import (
     PIPENV_MAX_DEPTH,
@@ -267,7 +268,17 @@ class Project(object):
     def get_location_for_virtualenv(self):
         if self.is_venv_in_project():
             return os.path.join(self.project_directory, ".venv")
-        return str(get_workon_home().joinpath(self.virtualenv_name))
+
+        name = self.virtualenv_name
+        if self.project_directory:
+            venv_path = os.path.join(self.project_directory, ".venv")
+            if os.path.exists(venv_path) and not os.path.isdir(".venv"):
+                with io.open(venv_path, "r") as f:
+                    name = f.read().strip()
+                # Assume file's contents is a path if it contains slashes.
+                if looks_like_dir(name):
+                    return Path(name).absolute().as_posix()
+        return str(get_workon_home().joinpath(name))
 
     def get_installed_packages(self):
         from . import PIPENV_ROOT, PIPENV_VENDOR, PIPENV_PATCHED
diff --git a/pipenv/utils.py b/pipenv/utils.py
index 21a1ec20..fa7a809b 100644
--- a/pipenv/utils.py
+++ b/pipenv/utils.py
@@ -1376,3 +1376,8 @@ def chdir(path):
         yield
     finally:
         os.chdir(prev_cwd)
+
+
+def looks_like_dir(path):
+    seps = (sep for sep in (os.path.sep, os.path.altsep) if sep is not None)
+    return any(sep in path for sep in seps)
diff --git a/run-tests.sh b/run-tests.sh
index 1243e033..64d79648 100755
--- a/run-tests.sh
+++ b/run-tests.sh
@@ -6,6 +6,7 @@ set -eo pipefail
 
 export PYTHONIOENCODING="utf-8"
 export LANG=C.UTF-8
+export PIP_PROCESS_DEPENDENCY_LINKS="1"
 
 prefix() {
 	sed "s/^/   $1:    /"
diff --git a/tests/integration/conftest.py b/tests/integration/conftest.py
index 9cb4b7b1..76a429e0 100644
--- a/tests/integration/conftest.py
+++ b/tests/integration/conftest.py
@@ -16,6 +16,9 @@ if six.PY2:
         pass
 
 
+HAS_WARNED_GITHUB = False
+
+
 def check_internet():
     try:
         # Kenneth represents the Internet LGTM.
@@ -40,13 +43,15 @@ def check_github_ssh():
         res = True if c.return_code == 1 else False
     except Exception:
         pass
-    if not res:
+    global HAS_WARNED_GITHUB
+    if not res and not HAS_WARNED_GITHUB:
         warnings.warn(
             'Cannot connect to GitHub via SSH', ResourceWarning
         )
         warnings.warn(
             'Will skip tests requiring SSH access to GitHub', ResourceWarning
         )
+        HAS_WARNED_GITHUB = True
     return res
 
 
diff --git a/tests/integration/test_dot_venv.py b/tests/integration/test_dot_venv.py
index 2063701b..53f5fb1d 100644
--- a/tests/integration/test_dot_venv.py
+++ b/tests/integration/test_dot_venv.py
@@ -41,15 +41,17 @@ def test_reuse_previous_venv(PipenvInstance, pypi):
         assert c.return_code == 0
         assert normalize_drive(p.path) in p.pipenv('--venv').out
 
+
 @pytest.mark.dotvenv
-def test_venv_file_exists(PipenvInstance, pypi):
-    """Tests virtualenv creation & package installation when a .venv file exists
-    at the project root.
+@pytest.mark.parametrize('venv_name', ('test-venv', os.path.join('foo', 'test-venv')))
+def test_venv_file(venv_name, PipenvInstance, pypi):
+    """Tests virtualenv creation when a .venv file exists at the project root
+    and contains a venv name.
     """
     with PipenvInstance(pypi=pypi, chdir=True) as p:
         file_path = os.path.join(p.path, '.venv')
         with open(file_path, 'w') as f:
-            f.write('')
+            f.write(venv_name)
 
         with temp_environ(), TemporaryDirectory(
             prefix='pipenv-', suffix='temp_workon_home'
@@ -58,12 +60,43 @@ def test_venv_file_exists(PipenvInstance, pypi):
             if 'PIPENV_VENV_IN_PROJECT' in os.environ:
                 del os.environ['PIPENV_VENV_IN_PROJECT']
 
-            c = p.pipenv('install requests')
+            c = p.pipenv('install')
             assert c.return_code == 0
 
-            venv_loc = None
-            for line in c.err.splitlines():
-                if line.startswith('Virtualenv location:'):
-                    venv_loc = Path(line.split(':', 1)[-1].strip())
-            assert venv_loc is not None
+            c = p.pipenv('--venv')
+            assert c.return_code == 0
+            venv_loc = Path(c.out.strip()).absolute()
+            assert venv_loc.exists()
             assert venv_loc.joinpath('.project').exists()
+            venv_path = venv_loc.as_posix()
+            if os.path.sep in venv_name:
+                venv_expected_path = Path(p.path).joinpath(venv_name).absolute().as_posix()
+            else:
+                venv_expected_path = Path(workon_home.name).joinpath(venv_name).absolute().as_posix()
+            assert venv_path == venv_expected_path
+
+
+@pytest.mark.dotvenv
+def test_venv_file_with_path(PipenvInstance, pypi):
+    """Tests virtualenv creation when a .venv file exists at the project root
+    and contains an absolute path.
+    """
+    with temp_environ(), PipenvInstance(chdir=True, pypi=pypi) as p:
+        with TemporaryDirectory(
+            prefix='pipenv-', suffix='-test_venv'
+        ) as venv_path:
+            if 'PIPENV_VENV_IN_PROJECT' in os.environ:
+                del os.environ['PIPENV_VENV_IN_PROJECT']
+
+            file_path = os.path.join(p.path, '.venv')
+            with open(file_path, 'w') as f:
+                f.write(venv_path.name)
+
+            c = p.pipenv('install')
+            assert c.return_code == 0
+            c = p.pipenv('--venv')
+            assert c.return_code == 0
+            venv_loc = Path(c.out.strip())
+
+            assert venv_loc.joinpath('.project').exists()
+            assert venv_loc == Path(venv_path.name)
diff --git a/tests/integration/test_install_basic.py b/tests/integration/test_install_basic.py
index ab6648f4..c04dc3f6 100644
--- a/tests/integration/test_install_basic.py
+++ b/tests/integration/test_install_basic.py
@@ -44,7 +44,7 @@ def test_basic_install(PipenvInstance, pypi):
 @pytest.mark.install
 @flaky
 def test_mirror_install(PipenvInstance, pypi):
-    with temp_environ(), PipenvInstance(chdir=True) as p:
+    with temp_environ(), PipenvInstance(chdir=True, pypi=pypi) as p:
         mirror_url = os.environ.pop(
             "PIPENV_TEST_INDEX", "https://pypi.python.org/simple"
         )
diff --git a/tests/pytest-pypi/pytest_pypi/certs.py b/tests/pytest-pypi/pytest_pypi/certs.py
index c099cfa2..f9e33870 100644
--- a/tests/pytest-pypi/pytest_pypi/certs.py
+++ b/tests/pytest-pypi/pytest_pypi/certs.py
@@ -15,7 +15,7 @@ import os.path
 def where():
     """Return the preferred certificate bundle."""
     # vendored bundle inside Requests
-    return os.path.join(os.path.dirname(__file__), 'certs', 'cacert.pem')
+    return os.path.join(os.path.abspath(os.path.dirname(__file__)), 'certs', 'cacert.pem')
 
 if __name__ == '__main__':
     print(where())