diff --git a/tests/bin/test_vyper.py b/tests/bin/test_vyper.py
new file mode 100644
index 00000000000..c4b6db8958c
--- /dev/null
+++ b/tests/bin/test_vyper.py
@@ -0,0 +1,62 @@
+import pytest
+
+from vyper import (
+    __version__,
+)
+
+
+@pytest.fixture
+def make_tmp_vy_file(tmp_path):
+    name_counter = 0
+
+    def _make(src):
+        nonlocal name_counter
+
+        name = f'tmp{name_counter}.vy'
+        name_counter += 1
+
+        src_path = tmp_path / name
+        src_path.write_text(src)
+
+        return src_path
+
+    return _make
+
+
+@pytest.fixture
+def tmp_vy_file_1(make_tmp_vy_file):
+    return make_tmp_vy_file("""
+@public
+def a() -> bool:
+    return True
+    """)
+
+
+@pytest.fixture
+def tmp_vy_file_2(make_tmp_vy_file):
+    return make_tmp_vy_file("""
+@public
+def meaning_of_life() -> uint256:
+    return 42
+    """)
+
+
+@pytest.mark.script_launch_mode('subprocess')
+def test_version(script_runner):
+    ret = script_runner.run('vyper', '--version')
+
+    assert ret.stdout == __version__ + '\n'
+
+
+@pytest.mark.script_launch_mode('subprocess')
+def test_compile_one_file(script_runner, tmp_vy_file_1):
+    ret = script_runner.run('vyper', '-f', 'bytecode', tmp_vy_file_1)
+
+    assert ret.stdout == '0x6100c256600035601c52740100000000000000000000000000000000000000006020526f7fffffffffffffffffffffffffffffff6040527fffffffffffffffffffffffffffffffff8000000000000000000000000000000060605274012a05f1fffffffffffffffffffffffffdabf41c006080527ffffffffffffffffffffffffed5fa0e000000000000000000000000000000000060a052630dbe671f60005114156100b85734156100ac57600080fd5b600160005260206000f3005b60006000fd5b6100046100c2036100046000396100046100c2036000f3\n'  # noqa: E501
+
+
+@pytest.mark.script_launch_mode('subprocess')
+def test_compile_two_files(script_runner, tmp_vy_file_1, tmp_vy_file_2):
+    ret = script_runner.run('vyper', '-f', 'bytecode', '--show-gas-estimates', tmp_vy_file_1, tmp_vy_file_2)
+
+    assert ret.stdout == '0x6100c256600035601c52740100000000000000000000000000000000000000006020526f7fffffffffffffffffffffffffffffff6040527fffffffffffffffffffffffffffffffff8000000000000000000000000000000060605274012a05f1fffffffffffffffffffffffffdabf41c006080527ffffffffffffffffffffffffed5fa0e000000000000000000000000000000000060a052630dbe671f60005114156100b85734156100ac57600080fd5b600160005260206000f3005b60006000fd5b6100046100c2036100046000396100046100c2036000f3\n0x6100c256600035601c52740100000000000000000000000000000000000000006020526f7fffffffffffffffffffffffffffffff6040527fffffffffffffffffffffffffffffffff8000000000000000000000000000000060605274012a05f1fffffffffffffffffffffffffdabf41c006080527ffffffffffffffffffffffffed5fa0e000000000000000000000000000000000060a052634f452d6060005114156100b85734156100ac57600080fd5b602a60005260206000f3005b60006000fd5b6100046100c2036100046000396100046100c2036000f3\n'  # noqa: E501