diff --git a/rsconnect/bundle.py b/rsconnect/bundle.py
index 37ef2962..81606e9c 100644
--- a/rsconnect/bundle.py
+++ b/rsconnect/bundle.py
@@ -32,6 +32,7 @@
     "__pycache__/",
     "env/",
     "packrat/",
+    "renv/",
     "rsconnect-python/",
     "rsconnect/",
     "venv/",
@@ -401,6 +402,23 @@ def create_glob_set(directory, excludes):
     return GlobSet(work)
 
 
+def is_environment_dir(directory):
+    python_path = join(directory, "bin", "python")
+    return exists(python_path)
+
+
+def list_environment_dirs(directory):
+    # type: (...) -> typing.List[str]
+    """Returns a list of subdirectories in `directory` that appear to contain virtual environments."""
+    envs = []
+
+    for name in os.listdir(directory):
+        path = join(directory, name)
+        if is_environment_dir(path):
+            envs.append(name)
+    return envs
+
+
 def _create_api_file_list(
     directory,  # type: str
     requirements_file_name,  # type: str
@@ -429,6 +447,7 @@ def _create_api_file_list(
     excludes = list(excludes) if excludes else []
     excludes.append("manifest.json")
     excludes.append(requirements_file_name)
+    excludes.extend(list_environment_dirs(directory))
     glob_set = create_glob_set(directory, excludes)
 
     file_list = []
@@ -470,6 +489,9 @@ def make_api_manifest(
     :param excludes: a sequence of glob patterns that will exclude matched files.
     :return: the manifest and a list of the files involved.
     """
+    if is_environment_dir(directory):
+        excludes = list(excludes or []) + ["bin/", "lib/"]
+
     relevant_files = _create_api_file_list(directory, environment.filename, extra_files, excludes)
     manifest = make_source_manifest(entry_point, environment, app_mode)
 
diff --git a/rsconnect/main.py b/rsconnect/main.py
index f07492d6..68c43b63 100644
--- a/rsconnect/main.py
+++ b/rsconnect/main.py
@@ -39,7 +39,7 @@
 )
 
 from . import api
-from .bundle import make_manifest_bundle
+from .bundle import is_environment_dir, make_manifest_bundle
 from .metadata import ServerStore, AppStore
 from .models import AppModes
 
@@ -403,6 +403,20 @@ def _warn_if_no_requirements_file(directory):
         )
 
 
+def _warn_if_environment_directory(directory):
+    """
+    Issue a warning if the deployment directory is itself a virtualenv (yikes!).
+
+    :param directory: the directory to check in.
+    """
+    if is_environment_dir(directory):
+        click.secho(
+            "    Warning: The deployment directory appears to be a python virtual environment.\n"
+            "             Excluding the 'bin' and 'lib' directories.",
+            fg="yellow",
+        )
+
+
 def _warn_on_ignored_conda_env(environment):
     """
     Checks for a discovered Conda environment and produces a warning that it will be ignored when
@@ -575,8 +589,10 @@ def deploy_notebook(
 
     click.secho('    Deploying %s to server "%s"' % (file, connect_server.url))
 
-    _warn_on_ignored_manifest(dirname(file))
-    _warn_if_no_requirements_file(dirname(file))
+    base_dir = dirname(file)
+    _warn_on_ignored_manifest(base_dir)
+    _warn_if_no_requirements_file(base_dir)
+    _warn_if_environment_directory(base_dir)
 
     with cli_feedback("Inspecting Python environment"):
         python, environment = get_python_env_info(file, python, conda, force_generate)
@@ -588,7 +604,7 @@ def deploy_notebook(
         _warn_on_ignored_conda_env(environment)
 
     if force_generate:
-        _warn_on_ignored_requirements(dirname(file), environment.filename)
+        _warn_on_ignored_requirements(base_dir, environment.filename)
 
     with cli_feedback("Creating deployment bundle"):
         bundle = create_notebook_deployment_bundle(
@@ -881,6 +897,7 @@ def _deploy_by_framework(
 
     _warn_on_ignored_manifest(directory)
     _warn_if_no_requirements_file(directory)
+    _warn_if_environment_directory(directory)
 
     with cli_feedback("Inspecting Python environment"):
         _, environment = get_python_env_info(module_file, python, conda, force_generate)