diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index 9711b9330..163e5e895 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -123,6 +123,19 @@ jobs:
         run: task build
         if: matrix.os == 'macos-10.15'
 
+      - name: Install Python
+        uses: actions/setup-python@v2
+        with:
+          python-version: '3.9'
+          architecture: 'x64'
+        if: matrix.os == 'macos-10.15'
+
+      - name: Run e2e tests
+        run: |
+          pip install poetry
+          task test-e2e
+        if: matrix.os == 'macos-10.15'
+
         # this will create `public/` dir with compressed full bin (<version>/<os>-<arch>.gz) and a json file
       - name: Create autoupdate files
         run: go-selfupdate arduino-create-agent${{ matrix.ext }} ${TAG_VERSION}
diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 5fa3091ff..708f82254 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -91,6 +91,19 @@ jobs:
         run: task build
         if: matrix.os == 'macos-10.15'
 
+      - name: Install Python
+        uses: actions/setup-python@v2
+        with:
+          python-version: '3.9'
+          architecture: 'x64'
+        if: matrix.os == 'macos-10.15'
+
+      - name: Run e2e tests
+        run: |
+          pip install poetry
+          task test-e2e
+        if: matrix.os == 'macos-10.15'
+
         # config.ini is required by the executable when it's run
       - name: Upload artifacts
         uses: actions/upload-artifact@v2
diff --git a/.gitignore b/.gitignore
index cd1c063ca..ea46fe4ee 100644
--- a/.gitignore
+++ b/.gitignore
@@ -7,9 +7,14 @@ rsrc.syso
 snapshot/*
 public/
 artifacts*
+logs/
 
 # IDEs config 
 .idea
+.vscode
 
 # macOS
 .DS_Store
+
+# Python
+__pycache__
diff --git a/Taskfile.yml b/Taskfile.yml
index a744299e0..48c6fb534 100644
--- a/Taskfile.yml
+++ b/Taskfile.yml
@@ -33,6 +33,12 @@ tasks:
     cmds:
       - go test -short -run '{{ default ".*" .TEST_REGEX }}' {{ default "-v" .GOFLAGS }} -coverprofile=coverage_unit.txt {{ default .DEFAULT_TARGETS .TARGETS }} {{.TEST_LDFLAGS}}
 
+  test-e2e:
+    desc: Run end 2 end tests
+    cmds:
+      - poetry install --no-root
+      - poetry run pytest test
+
   check:
     desc: Check fmt and lint
     cmds:
diff --git a/poetry.lock b/poetry.lock
new file mode 100644
index 000000000..0d51c0ae4
--- /dev/null
+++ b/poetry.lock
@@ -0,0 +1,280 @@
+[[package]]
+name = "atomicwrites"
+version = "1.4.0"
+description = "Atomic file writes."
+category = "dev"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
+
+[[package]]
+name = "attrs"
+version = "20.3.0"
+description = "Classes Without Boilerplate"
+category = "dev"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
+
+[package.extras]
+dev = ["coverage[toml] (>=5.0.2)", "hypothesis", "pympler", "pytest (>=4.3.0)", "six", "zope.interface", "furo", "sphinx", "pre-commit"]
+docs = ["furo", "sphinx", "zope.interface"]
+tests = ["coverage[toml] (>=5.0.2)", "hypothesis", "pympler", "pytest (>=4.3.0)", "six", "zope.interface"]
+tests_no_zope = ["coverage[toml] (>=5.0.2)", "hypothesis", "pympler", "pytest (>=4.3.0)", "six"]
+
+[[package]]
+name = "certifi"
+version = "2020.12.5"
+description = "Python package for providing Mozilla's CA Bundle."
+category = "dev"
+optional = false
+python-versions = "*"
+
+[[package]]
+name = "chardet"
+version = "4.0.0"
+description = "Universal encoding detector for Python 2 and 3"
+category = "dev"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
+
+[[package]]
+name = "colorama"
+version = "0.4.4"
+description = "Cross-platform colored terminal text."
+category = "dev"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
+
+[[package]]
+name = "idna"
+version = "2.10"
+description = "Internationalized Domain Names in Applications (IDNA)"
+category = "dev"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
+
+[[package]]
+name = "iniconfig"
+version = "1.1.1"
+description = "iniconfig: brain-dead simple config-ini parsing"
+category = "dev"
+optional = false
+python-versions = "*"
+
+[[package]]
+name = "invoke"
+version = "1.5.0"
+description = "Pythonic task execution"
+category = "dev"
+optional = false
+python-versions = "*"
+
+[[package]]
+name = "packaging"
+version = "20.8"
+description = "Core utilities for Python packages"
+category = "dev"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
+
+[package.dependencies]
+pyparsing = ">=2.0.2"
+
+[[package]]
+name = "pluggy"
+version = "0.13.1"
+description = "plugin and hook calling mechanisms for python"
+category = "dev"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
+
+[package.extras]
+dev = ["pre-commit", "tox"]
+
+[[package]]
+name = "psutil"
+version = "5.8.0"
+description = "Cross-platform lib for process and system monitoring in Python."
+category = "main"
+optional = false
+python-versions = ">=2.6, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
+
+[package.extras]
+test = ["ipaddress", "mock", "unittest2", "enum34", "pywin32", "wmi"]
+
+[[package]]
+name = "py"
+version = "1.10.0"
+description = "library with cross-python path, ini-parsing, io, code, log facilities"
+category = "dev"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
+
+[[package]]
+name = "pyparsing"
+version = "2.4.7"
+description = "Python parsing module"
+category = "dev"
+optional = false
+python-versions = ">=2.6, !=3.0.*, !=3.1.*, !=3.2.*"
+
+[[package]]
+name = "pytest"
+version = "6.2.1"
+description = "pytest: simple powerful testing with Python"
+category = "dev"
+optional = false
+python-versions = ">=3.6"
+
+[package.dependencies]
+atomicwrites = {version = ">=1.0", markers = "sys_platform == \"win32\""}
+attrs = ">=19.2.0"
+colorama = {version = "*", markers = "sys_platform == \"win32\""}
+iniconfig = "*"
+packaging = "*"
+pluggy = ">=0.12,<1.0.0a1"
+py = ">=1.8.2"
+toml = "*"
+
+[package.extras]
+testing = ["argcomplete", "hypothesis (>=3.56)", "mock", "nose", "requests", "xmlschema"]
+
+[[package]]
+name = "requests"
+version = "2.25.1"
+description = "Python HTTP for Humans."
+category = "dev"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
+
+[package.dependencies]
+certifi = ">=2017.4.17"
+chardet = ">=3.0.2,<5"
+idna = ">=2.5,<3"
+urllib3 = ">=1.21.1,<1.27"
+
+[package.extras]
+security = ["pyOpenSSL (>=0.14)", "cryptography (>=1.3.4)"]
+socks = ["PySocks (>=1.5.6,!=1.5.7)", "win-inet-pton"]
+
+[[package]]
+name = "toml"
+version = "0.10.2"
+description = "Python Library for Tom's Obvious, Minimal Language"
+category = "dev"
+optional = false
+python-versions = ">=2.6, !=3.0.*, !=3.1.*, !=3.2.*"
+
+[[package]]
+name = "urllib3"
+version = "1.26.2"
+description = "HTTP library with thread-safe connection pooling, file post, and more."
+category = "dev"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*, <4"
+
+[package.extras]
+brotli = ["brotlipy (>=0.6.0)"]
+secure = ["pyOpenSSL (>=0.14)", "cryptography (>=1.3.4)", "idna (>=2.0.0)", "certifi", "ipaddress"]
+socks = ["PySocks (>=1.5.6,!=1.5.7,<2.0)"]
+
+[metadata]
+lock-version = "1.1"
+python-versions = "^3.9"
+content-hash = "d4024a50235f771811ce457845b6cfef87950b8eb07a8a6e3ad10005482c8a05"
+
+[metadata.files]
+atomicwrites = [
+    {file = "atomicwrites-1.4.0-py2.py3-none-any.whl", hash = "sha256:6d1784dea7c0c8d4a5172b6c620f40b6e4cbfdf96d783691f2e1302a7b88e197"},
+    {file = "atomicwrites-1.4.0.tar.gz", hash = "sha256:ae70396ad1a434f9c7046fd2dd196fc04b12f9e91ffb859164193be8b6168a7a"},
+]
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+    {file = "attrs-20.3.0.tar.gz", hash = "sha256:832aa3cde19744e49938b91fea06d69ecb9e649c93ba974535d08ad92164f700"},
+]
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+    {file = "certifi-2020.12.5.tar.gz", hash = "sha256:1a4995114262bffbc2413b159f2a1a480c969de6e6eb13ee966d470af86af59c"},
+]
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+    {file = "chardet-4.0.0.tar.gz", hash = "sha256:0d6f53a15db4120f2b08c94f11e7d93d2c911ee118b6b30a04ec3ee8310179fa"},
+]
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+    {file = "colorama-0.4.4.tar.gz", hash = "sha256:5941b2b48a20143d2267e95b1c2a7603ce057ee39fd88e7329b0c292aa16869b"},
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+    {file = "idna-2.10.tar.gz", hash = "sha256:b307872f855b18632ce0c21c5e45be78c0ea7ae4c15c828c20788b26921eb3f6"},
+]
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+]
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+    {file = "invoke-1.5.0.tar.gz", hash = "sha256:f0c560075b5fb29ba14dad44a7185514e94970d1b9d57dcd3723bec5fed92650"},
+]
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+    {file = "packaging-20.8.tar.gz", hash = "sha256:78598185a7008a470d64526a8059de9aaa449238f280fc9eb6b13ba6c4109093"},
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+    {file = "pluggy-0.13.1.tar.gz", hash = "sha256:15b2acde666561e1298d71b523007ed7364de07029219b604cf808bfa1c765b0"},
+]
+psutil = [
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+    {file = "psutil-5.8.0-cp27-none-win32.whl", hash = "sha256:ea313bb02e5e25224e518e4352af4bf5e062755160f77e4b1767dd5ccb65f876"},
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+    {file = "psutil-5.8.0-cp39-cp39-win_amd64.whl", hash = "sha256:f4634b033faf0d968bb9220dd1c793b897ab7f1189956e1aa9eae752527127d3"},
+    {file = "psutil-5.8.0.tar.gz", hash = "sha256:0c9ccb99ab76025f2f0bbecf341d4656e9c1351db8cc8a03ccd62e318ab4b5c6"},
+]
+py = [
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+    {file = "py-1.10.0.tar.gz", hash = "sha256:21b81bda15b66ef5e1a777a21c4dcd9c20ad3efd0b3f817e7a809035269e1bd3"},
+]
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+]
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+]
+requests = [
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+    {file = "requests-2.25.1.tar.gz", hash = "sha256:27973dd4a904a4f13b263a19c866c13b92a39ed1c964655f025f3f8d3d75b804"},
+]
+toml = [
+    {file = "toml-0.10.2-py2.py3-none-any.whl", hash = "sha256:806143ae5bfb6a3c6e736a764057db0e6a0e05e338b5630894a5f779cabb4f9b"},
+    {file = "toml-0.10.2.tar.gz", hash = "sha256:b3bda1d108d5dd99f4a20d24d9c348e91c4db7ab1b749200bded2f839ccbe68f"},
+]
+urllib3 = [
+    {file = "urllib3-1.26.2-py2.py3-none-any.whl", hash = "sha256:d8ff90d979214d7b4f8ce956e80f4028fc6860e4431f731ea4a8c08f23f99473"},
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+]
diff --git a/pyproject.toml b/pyproject.toml
new file mode 100644
index 000000000..c3d576b7c
--- /dev/null
+++ b/pyproject.toml
@@ -0,0 +1,24 @@
+[tool.poetry]
+name = "arduino-create-agent"
+version = "0.1.0"
+description = "Project used to run end-to-end test for the Arduino Create Agent"
+authors = ["Umberto Baldi <u.baldi@arduino.cc>", "Maurizio Branca <m.branca@arduino.cc>"]
+license = "GPLv2"
+
+[tool.poetry.dependencies]
+python = "^3.9"
+psutil = "^5.8.0"
+
+[tool.poetry.dev-dependencies]
+pytest = "^6.2.1"
+requests = "^2.25.1"
+invoke = "^1.5.0"
+
+[build-system]
+requires = ["poetry-core>=1.0.0"]
+build-backend = "poetry.core.masonry.api"
+
+[tool.pytest.ini_options]
+filterwarnings = [
+    "ignore::DeprecationWarning:invoke.loader" # https://github.com/pyinvoke/invoke/issues/675
+]
\ No newline at end of file
diff --git a/test/conftest.py b/test/conftest.py
new file mode 100644
index 000000000..fd50856ec
--- /dev/null
+++ b/test/conftest.py
@@ -0,0 +1,45 @@
+import os
+import platform
+import signal
+import time
+from pathlib import Path
+
+import pytest
+from invoke import Local
+from invoke.context import Context
+
+
+@pytest.fixture(scope="function")
+def agent(pytestconfig):
+    
+    agent_cli = str(Path(pytestconfig.rootdir) / "arduino-create-agent")
+    env = {
+        # "ARDUINO_DATA_DIR": data_dir,
+        # "ARDUINO_DOWNLOADS_DIR": downloads_dir,
+        # "ARDUINO_SKETCHBOOK_DIR": data_dir,
+    }
+    run_context = Context()
+
+    runner = Local(run_context) # execute a command on the local filesystem
+    
+    cd_command = "cd"
+    with run_context.prefix(f'{cd_command} ..'):
+        runner.run(agent_cli, echo=True, hide=True, warn=True, env=env, asynchronous=True)
+        
+        # we give some time to the agent to start and listen to
+        # incoming requests
+        time.sleep(.5)
+
+        # we block here until the test function using this fixture has returned
+        yield runner
+
+    # Kill the runner's process as we finished our test (platform dependent)
+    os_signal = signal.SIGTERM
+    if platform.system() != "Windows":
+        os_signal = signal.SIGKILL
+    os.kill(runner.process.pid, os_signal)
+
+
+@pytest.fixture(scope="session")
+def base_url():
+    return "http://127.0.0.1:8991/"
diff --git a/test/test_certs.py b/test/test_certs.py
new file mode 100644
index 000000000..513208da3
--- /dev/null
+++ b/test/test_certs.py
@@ -0,0 +1,18 @@
+import requests
+
+
+def test_get_cert(base_url, agent):
+    
+    resp = requests.get(f"{base_url}/certificate.crt")
+    assert resp.status_code == 200
+
+    cert = resp.text
+    assert "<!DOCTYPE html>" in cert
+
+
+def test_del_cert(base_url, agent):
+    
+    resp = requests.delete(f"{base_url}/certificate.crt")
+    assert resp.status_code == 200
+
+    # Should rm "ca.cert.pem", "ca.cert.cer", "ca.key.pem"
diff --git a/test/test_info.py b/test/test_info.py
new file mode 100644
index 000000000..7e79b7a07
--- /dev/null
+++ b/test/test_info.py
@@ -0,0 +1,11 @@
+import re
+import requests
+
+
+def test_version(base_url, agent):
+    
+    resp = requests.get(f"{base_url}/info")
+    assert resp.status_code == 200
+
+    info = resp.json()
+    assert re.match("[0-9]+.[0-9]+.[0-9]+", info["version"]) is not None
diff --git a/test/test_update.py b/test/test_update.py
new file mode 100644
index 000000000..481cb655e
--- /dev/null
+++ b/test/test_update.py
@@ -0,0 +1,33 @@
+# import json
+import psutil
+import requests
+import pytest
+
+# test if the update process succeeds in terminating the binary
+@pytest.mark.skip(reason="no way of currently testing this")
+def test_update_shutdown(base_url, agent):
+
+    procs=[]
+    for p in psutil.process_iter():
+        if p.name() == "arduino-create-agent":
+            procs.append(p)
+
+    resp = requests.post(f"{base_url}/update")
+    # assert resp.status_code == 200
+    # assert "Please wait a moment while the agent reboots itself" in info['success'] # failing on macos see https://github.com/arduino/arduino-create-agent/issues/608
+    gone, alive = psutil.wait_procs(procs, timeout=3, callback=on_terminate) # wait for "arduino-create-agent" to terminate
+
+def on_terminate(proc):
+    print("process {} terminated with exit code {}".format(proc, proc.returncode))
+    assert True
+
+# the version currently running is the latest available
+@pytest.mark.skip(reason="no way of currently testing this")
+def test_latest_version(base_url, agent):
+    resp = requests.get(f"{base_url}/info")
+    assert resp.status_code == 200
+    latest_version = requests.get("https://s3.amazonaws.com/arduino-create-static/agent-metadata/agent-version.json") # get the latest version available
+
+    version = latest_version.json()
+    info = resp.json()
+    assert info["version"] == version["Version"]
diff --git a/test/test_v2.py b/test/test_v2.py
new file mode 100644
index 000000000..9815571cb
--- /dev/null
+++ b/test/test_v2.py
@@ -0,0 +1,9 @@
+import requests
+
+
+def test_get_tools(base_url, agent):
+    
+    resp = requests.get(f"{base_url}/v2/pkgs/tools/installed")
+    assert resp.status_code == 200
+
+    tools = resp.json()
\ No newline at end of file