diff --git a/poetry.lock b/poetry.lock
index 46715ebc2c8..196cadc40f0 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -1,3 +1,11 @@
+[[package]]
+category = "main"
+description = "apipkg: namespace control and lazy-import mechanism"
+name = "apipkg"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
+version = "1.5"
+
 [[package]]
 category = "main"
 description = "A small Python module for determining appropriate platform-specific dirs, e.g. a \"user data dir\"."
@@ -82,6 +90,28 @@ optional = false
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
 version = "0.4.3"
 
+[[package]]
+category = "main"
+description = "execnet: rapid multi-Python deployment"
+name = "execnet"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
+version = "1.7.1"
+
+[package.dependencies]
+apipkg = ">=1.4"
+
+[package.extras]
+testing = ["pre-commit"]
+
+[[package]]
+category = "main"
+description = "A platform independent file lock."
+name = "filelock"
+optional = false
+python-versions = "*"
+version = "3.0.12"
+
 [[package]]
 category = "main"
 description = "the modular source code checker: pep8 pyflakes and co"
@@ -103,6 +133,14 @@ optional = false
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
 version = "2.8"
 
+[[package]]
+category = "main"
+description = "iniconfig: brain-dead simple config-ini parsing"
+name = "iniconfig"
+optional = false
+python-versions = "*"
+version = "1.0.1"
+
 [[package]]
 category = "main"
 description = "Pythonic task execution"
@@ -215,22 +253,50 @@ description = "pytest: simple powerful testing with Python"
 name = "pytest"
 optional = false
 python-versions = ">=3.5"
-version = "5.3.4"
+version = "6.0.2"
 
 [package.dependencies]
 atomicwrites = ">=1.0"
 attrs = ">=17.4.0"
 colorama = "*"
+iniconfig = "*"
 more-itertools = ">=4.0.0"
 packaging = "*"
 pluggy = ">=0.12,<1.0"
-py = ">=1.5.0"
-wcwidth = "*"
+py = ">=1.8.2"
+toml = "*"
 
 [package.extras]
-checkqa-mypy = ["mypy (v0.761)"]
+checkqa_mypy = ["mypy (0.780)"]
 testing = ["argcomplete", "hypothesis (>=3.56)", "mock", "nose", "requests", "xmlschema"]
 
+[[package]]
+category = "main"
+description = "run tests in isolated forked subprocesses"
+name = "pytest-forked"
+optional = false
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
+version = "1.3.0"
+
+[package.dependencies]
+py = "*"
+pytest = ">=3.10"
+
+[[package]]
+category = "main"
+description = "pytest-httpserver is a httpserver for pytest"
+name = "pytest-httpserver"
+optional = false
+python-versions = ">=3.4"
+version = "0.3.5"
+
+[package.dependencies]
+werkzeug = "*"
+
+[package.extras]
+dev = ["autopep8", "coverage", "flake8", "ipdb", "pytest", "pytest-cov", "reno", "requests", "rope", "sphinx", "sphinx-rtd-theme", "wheel"]
+test = ["coverage", "pytest", "pytest-cov", "requests"]
+
 [[package]]
 category = "main"
 description = "py.test plugin to abort hanging tests"
@@ -242,6 +308,23 @@ version = "1.3.4"
 [package.dependencies]
 pytest = ">=3.6.0"
 
+[[package]]
+category = "main"
+description = "pytest xdist plugin for distributed testing and loop-on-failing modes"
+name = "pytest-xdist"
+optional = false
+python-versions = ">=3.5"
+version = "2.1.0"
+
+[package.dependencies]
+execnet = ">=1.1"
+pytest = ">=6.0.0"
+pytest-forked = "*"
+
+[package.extras]
+psutil = ["psutil (>=3.0)"]
+testing = ["filelock"]
+
 [[package]]
 category = "main"
 description = "YAML parser and emitter for Python"
@@ -331,17 +414,25 @@ socks = ["PySocks (>=1.5.6,<1.5.7 || >1.5.7,<2.0)"]
 
 [[package]]
 category = "main"
-description = "Measures the displayed width of unicode strings in a terminal"
-name = "wcwidth"
+description = "The comprehensive WSGI web application library."
+name = "werkzeug"
 optional = false
-python-versions = "*"
-version = "0.2.5"
+python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
+version = "1.0.1"
+
+[package.extras]
+dev = ["pytest", "pytest-timeout", "coverage", "tox", "sphinx", "pallets-sphinx-themes", "sphinx-issues"]
+watchdog = ["watchdog"]
 
 [metadata]
-content-hash = "f28e76c2cd84157e665d2d1bcd6c12e83d9deecc196fcc5e5e74e27fa072fd4d"
+content-hash = "3500e684ec97eabc4ffd38614f8e9af23630e1650f5ff095ad031396a8b2acf2"
 python-versions = "^3.8"
 
 [metadata.files]
+apipkg = [
+    {file = "apipkg-1.5-py2.py3-none-any.whl", hash = "sha256:58587dd4dc3daefad0487f6d9ae32b4542b185e1c36db6993290e7c41ca2b47c"},
+    {file = "apipkg-1.5.tar.gz", hash = "sha256:37228cda29411948b422fae072f57e31d3396d2ee1c9783775980ee9c9990af6"},
+]
 appdirs = [
     {file = "appdirs-1.4.4-py2.py3-none-any.whl", hash = "sha256:a841dacd6b99318a741b166adb07e19ee71a274450e68237b4650ca1055ab128"},
     {file = "appdirs-1.4.4.tar.gz", hash = "sha256:7d5d0167b2b1ba821647616af46a749d1c653740dd0d2415100fe26e27afdf41"},
@@ -374,6 +465,14 @@ colorama = [
     {file = "colorama-0.4.3-py2.py3-none-any.whl", hash = "sha256:7d73d2a99753107a36ac6b455ee49046802e59d9d076ef8e47b61499fa29afff"},
     {file = "colorama-0.4.3.tar.gz", hash = "sha256:e96da0d330793e2cb9485e9ddfd918d456036c7149416295932478192f4436a1"},
 ]
+execnet = [
+    {file = "execnet-1.7.1-py2.py3-none-any.whl", hash = "sha256:d4efd397930c46415f62f8a31388d6be4f27a91d7550eb79bc64a756e0056547"},
+    {file = "execnet-1.7.1.tar.gz", hash = "sha256:cacb9df31c9680ec5f95553976c4da484d407e85e41c83cb812aa014f0eddc50"},
+]
+filelock = [
+    {file = "filelock-3.0.12-py3-none-any.whl", hash = "sha256:929b7d63ec5b7d6b71b0fa5ac14e030b3f70b75747cef1b10da9b879fef15836"},
+    {file = "filelock-3.0.12.tar.gz", hash = "sha256:18d82244ee114f543149c66a6e0c14e9c4f8a1044b5cdaadd0f82159d6a6ff59"},
+]
 flake8 = [
     {file = "flake8-3.8.3-py2.py3-none-any.whl", hash = "sha256:15e351d19611c887e482fb960eae4d44845013cc142d42896e9862f775d8cf5c"},
     {file = "flake8-3.8.3.tar.gz", hash = "sha256:f04b9fcbac03b0a3e58c0ab3a0ecc462e023a9faf046d57794184028123aa208"},
@@ -382,6 +481,10 @@ idna = [
     {file = "idna-2.8-py2.py3-none-any.whl", hash = "sha256:ea8b7f6188e6fa117537c3df7da9fc686d485087abf6ac197f9c46432f7e4a3c"},
     {file = "idna-2.8.tar.gz", hash = "sha256:c357b3f628cf53ae2c4c05627ecc484553142ca23264e593d327bcde5e9c3407"},
 ]
+iniconfig = [
+    {file = "iniconfig-1.0.1-py3-none-any.whl", hash = "sha256:80cf40c597eb564e86346103f609d74efce0f6b4d4f30ec8ce9e2c26411ba437"},
+    {file = "iniconfig-1.0.1.tar.gz", hash = "sha256:e5f92f89355a67de0595932a6c6c02ab4afddc6fcdc0bfc5becd0d60884d3f69"},
+]
 invoke = [
     {file = "invoke-1.4.1-py2-none-any.whl", hash = "sha256:93e12876d88130c8e0d7fd6618dd5387d6b36da55ad541481dfa5e001656f134"},
     {file = "invoke-1.4.1-py3-none-any.whl", hash = "sha256:87b3ef9d72a1667e104f89b159eaf8a514dbf2f3576885b2bbdefe74c3fb2132"},
@@ -431,13 +534,25 @@ pyserial = [
     {file = "pyserial-3.4.tar.gz", hash = "sha256:6e2d401fdee0eab996cf734e67773a0143b932772ca8b42451440cfed942c627"},
 ]
 pytest = [
-    {file = "pytest-5.3.4-py3-none-any.whl", hash = "sha256:c13d1943c63e599b98cf118fcb9703e4d7bde7caa9a432567bcdcae4bf512d20"},
-    {file = "pytest-5.3.4.tar.gz", hash = "sha256:1d122e8be54d1a709e56f82e2d85dcba3018313d64647f38a91aec88c239b600"},
+    {file = "pytest-6.0.2-py3-none-any.whl", hash = "sha256:0e37f61339c4578776e090c3b8f6b16ce4db333889d65d0efb305243ec544b40"},
+    {file = "pytest-6.0.2.tar.gz", hash = "sha256:c8f57c2a30983f469bf03e68cdfa74dc474ce56b8f280ddcb080dfd91df01043"},
+]
+pytest-forked = [
+    {file = "pytest-forked-1.3.0.tar.gz", hash = "sha256:6aa9ac7e00ad1a539c41bec6d21011332de671e938c7637378ec9710204e37ca"},
+    {file = "pytest_forked-1.3.0-py2.py3-none-any.whl", hash = "sha256:dc4147784048e70ef5d437951728825a131b81714b398d5d52f17c7c144d8815"},
+]
+pytest-httpserver = [
+    {file = "pytest_httpserver-0.3.5-py3-none-any.whl", hash = "sha256:c55289404b7604bfd1c103d243824b441add501828e05807795c2b851b9b0747"},
+    {file = "pytest_httpserver-0.3.5.tar.gz", hash = "sha256:1d553dc0fb27483d00a1e25ddcfc38bd3438336ed60f862cad8c50b11621a11a"},
 ]
 pytest-timeout = [
     {file = "pytest-timeout-1.3.4.tar.gz", hash = "sha256:80faa19cd245a42b87a51699d640c00d937c02b749052bfca6bae8bdbe12c48e"},
     {file = "pytest_timeout-1.3.4-py2.py3-none-any.whl", hash = "sha256:95ca727d4a1dace6ec5f0534d2940b8417ff8b782f7eef0ea09240bdd94d95c2"},
 ]
+pytest-xdist = [
+    {file = "pytest-xdist-2.1.0.tar.gz", hash = "sha256:82d938f1a24186520e2d9d3a64ef7d9ac7ecdf1a0659e095d18e596b8cbd0672"},
+    {file = "pytest_xdist-2.1.0-py3-none-any.whl", hash = "sha256:7c629016b3bb006b88ac68e2b31551e7becf173c76b977768848e2bbed594d90"},
+]
 pyyaml = [
     {file = "PyYAML-5.3-cp27-cp27m-win32.whl", hash = "sha256:940532b111b1952befd7db542c370887a8611660d2b9becff75d39355303d82d"},
     {file = "PyYAML-5.3-cp27-cp27m-win_amd64.whl", hash = "sha256:059b2ee3194d718896c0ad077dd8c043e5e909d9180f387ce42012662a4946d6"},
@@ -547,7 +662,7 @@ urllib3 = [
     {file = "urllib3-1.25.9-py2.py3-none-any.whl", hash = "sha256:88206b0eb87e6d677d424843ac5209e3fb9d0190d0ee169599165ec25e9d9115"},
     {file = "urllib3-1.25.9.tar.gz", hash = "sha256:3018294ebefce6572a474f0604c2021e33b3fd8006ecd11d62107a5d2a963527"},
 ]
-wcwidth = [
-    {file = "wcwidth-0.2.5-py2.py3-none-any.whl", hash = "sha256:beb4802a9cebb9144e99086eff703a642a13d6a0052920003a230f3294bbe784"},
-    {file = "wcwidth-0.2.5.tar.gz", hash = "sha256:c4d647b99872929fdb7bdcaa4fbe7f01413ed3d98077df798530e5b04f116c83"},
+werkzeug = [
+    {file = "Werkzeug-1.0.1-py2.py3-none-any.whl", hash = "sha256:2de2a5db0baeae7b2d2664949077c2ac63fbd16d98da0ff71837f7d1dea3fd43"},
+    {file = "Werkzeug-1.0.1.tar.gz", hash = "sha256:6c80b1e5ad3665290ea39320b91e1be1e0d5f60652b964a3070216de83d2e47c"},
 ]
diff --git a/pyproject.toml b/pyproject.toml
index 210d24101b3..0af3e431de3 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -6,7 +6,7 @@ authors = []
 
 [tool.poetry.dependencies]
 python = "^3.8"
-pytest = "5.3.4"
+pytest = "6.0.2"
 simplejson = "3.17.0"
 semver = "2.9.0"
 pyserial = "3.4"
@@ -17,6 +17,9 @@ pytest-timeout = "1.3.4"
 invoke = "1.4.1"
 flake8 = "^3.8.3"
 black = { version = "^19.10b0", allow-prereleases = true }
+filelock = "^3.0.12"
+pytest-xdist = "^2.1.0"
+pytest_httpserver = "^0.3.5"
 
 [tool.black]
 line-length = 120
diff --git a/test/common.py b/test/common.py
index 4f1e74db694..a7500612583 100644
--- a/test/common.py
+++ b/test/common.py
@@ -14,6 +14,7 @@
 # a commercial license, send an email to license@arduino.cc.
 import os
 import collections
+import json
 
 
 Board = collections.namedtuple("Board", "address fqbn package architecture id core")
@@ -25,3 +26,12 @@ def running_on_ci():
     """
     val = os.getenv("APPVEYOR") or os.getenv("DRONE") or os.getenv("GITHUB_WORKFLOW")
     return val is not None
+
+
+def parse_json_traces(log_json_lines):
+    trace_entries = []
+    for entry in log_json_lines:
+        entry = json.loads(entry)
+        if entry.get("level") == "trace":
+            trace_entries.append(entry.get("msg"))
+    return trace_entries
diff --git a/test/conftest.py b/test/conftest.py
index 48ae5aacc04..aafc0390aee 100644
--- a/test/conftest.py
+++ b/test/conftest.py
@@ -16,6 +16,7 @@
 import platform
 import signal
 import shutil
+import time
 from pathlib import Path
 
 import pytest
@@ -23,6 +24,7 @@
 from invoke import Local
 from invoke.context import Context
 import tempfile
+from filelock import FileLock
 
 from .common import Board
 
@@ -54,17 +56,32 @@ def data_dir(tmpdir_factory):
     if platform.system() == "Windows":
         with tempfile.TemporaryDirectory() as tmp:
             yield tmp
+            # shutil.rmtree(tmp, ignore_errors=True)
     else:
-        yield str(tmpdir_factory.mktemp("ArduinoTest"))
+        data = tmpdir_factory.mktemp("ArduinoTest")
+        yield str(data)
+        # shutil.rmtree(data, ignore_errors=True)
 
 
 @pytest.fixture(scope="session")
-def downloads_dir(tmpdir_factory):
+def downloads_dir(tmpdir_factory, worker_id):
     """
     To save time and bandwidth, all the tests will access
     the same download cache folder.
     """
-    return str(tmpdir_factory.mktemp("ArduinoTest"))
+    download_dir = tmpdir_factory.mktemp("ArduinoTest", numbered=False)
+
+    # This folders should be created only once per session, if we're running
+    # tests in parallel using multiple processes we need to make sure this
+    # this fixture is executed only once, thus the use of the lockfile
+    if not worker_id == "master":
+        lock = Path(download_dir / "lock")
+        with FileLock(lock):
+            if not lock.is_file():
+                lock.touch()
+
+    yield str(download_dir)
+    # shutil.rmtree(download_dir, ignore_errors=True)
 
 
 @pytest.fixture(scope="function")
@@ -74,7 +91,9 @@ def working_dir(tmpdir_factory):
     will be created before running each test and deleted
     at the end, this way all the tests work in isolation.
     """
-    return str(tmpdir_factory.mktemp("ArduinoTestWork"))
+    work_dir = tmpdir_factory.mktemp("ArduinoTestWork")
+    yield str(work_dir)
+    # shutil.rmtree(work_dir, ignore_errors=True)
 
 
 @pytest.fixture(scope="function")
@@ -95,9 +114,12 @@ def run_command(pytestconfig, data_dir, downloads_dir, working_dir):
     }
     (Path(data_dir) / "packages").mkdir()
 
-    def _run(cmd_string, custom_working_dir=None):
+    def _run(cmd_string, custom_working_dir=None, custom_env=None):
+
         if not custom_working_dir:
             custom_working_dir = working_dir
+        if not custom_env:
+            custom_env = env
         cli_full_line = '"{}" {}'.format(cli_path, cmd_string)
         run_context = Context()
         # It might happen that we need to change directories between drives on Windows,
@@ -109,7 +131,7 @@ def _run(cmd_string, custom_working_dir=None):
         # It escapes spaces in the path using "\ " but it doesn't always work,
         # wrapping the path in quotation marks is the safest approach
         with run_context.prefix(f'{cd_command} "{custom_working_dir}"'):
-            return run_context.run(cli_full_line, echo=False, hide=True, warn=True, env=env)
+            return run_context.run(cli_full_line, echo=False, hide=True, warn=True, env=custom_env)
 
     return _run
 
@@ -195,3 +217,19 @@ def copy_sketch(working_dir):
     test_sketch_path = Path(working_dir) / "sketch_simple"
     shutil.copytree(sketch_path, test_sketch_path)
     yield str(test_sketch_path)
+
+
+@pytest.fixture(scope="function")
+def wait_for_board(run_command):
+    def _waiter(seconds=10):
+        # Waits for the specified amount of second for a board to be visible.
+        # This is necessary since it might happen that a board is not immediately
+        # available after a test upload and subsequent tests might consequently fail.
+        time_end = time.time() + seconds
+        while time.time() < time_end:
+            result = run_command("board list --format json")
+            ports = json.loads(result.stdout)
+            if len([p.get("boards", []) for p in ports]) > 0:
+                break
+
+    return _waiter
diff --git a/test/pytest.ini b/test/pytest.ini
index 957be6d9fae..ea573791a7b 100644
--- a/test/pytest.ini
+++ b/test/pytest.ini
@@ -7,5 +7,11 @@ filterwarnings =
 markers =
     slow: marks tests as slow (deselect with '-m "not slow"')
 
-# atm some tests depend on each other, better to exit at first failure (-x)
-addopts = -x -s --verbose --tb=short
\ No newline at end of file
+# -x to exit at first failure
+# -s to disable per-test capture
+# --verbose is what is says it is
+# --tb=long sets the length of the traceback in case of failures
+# -n=auto sets the numbers of parallel processes to use
+# --dist=loadfile distributes the tests in the parallel processes dividing them per file
+# See https://pypi.org/project/pytest-xdist/#parallelization for more info on parallelization
+addopts = -x -s --verbose --tb=long -n=auto --dist=loadfile
diff --git a/test/test_board.py b/test/test_board.py
index bfca50bb5b1..e62ba079358 100644
--- a/test/test_board.py
+++ b/test/test_board.py
@@ -390,8 +390,7 @@
 
 
 def test_board_list(run_command):
-    result = run_command("core update-index")
-    assert result.ok
+    run_command("core update-index")
     result = run_command("board list --format json")
     assert result.ok
     # check is a valid json and contains a list of ports
@@ -404,18 +403,16 @@ def test_board_list(run_command):
 
 @pytest.mark.skipif(running_on_ci(), reason="VMs have no serial ports")
 def test_board_listall(run_command):
-    assert run_command("core update-index")
+    run_command("core update-index")
     result = run_command("board listall")
     assert result.ok
     assert ["Board", "Name", "FQBN"] == result.stdout.splitlines()[0].strip().split()
 
 
 def test_board_details(run_command):
-    result = run_command("core update-index")
-    assert result.ok
+    run_command("core update-index")
     # Download samd core pinned to 1.8.6
-    result = run_command("core install arduino:samd@1.8.6")
-    assert result.ok
+    run_command("core install arduino:samd@1.8.6")
 
     # Test board listall with and without showing hidden elements
     result = run_command("board listall MIPS --format json")
@@ -448,11 +445,9 @@ def test_board_details(run_command):
 
 # old `arduino-cli board details` did not need -b <fqbn> flag to work
 def test_board_details_old(run_command):
-    result = run_command("core update-index")
-    assert result.ok
+    run_command("core update-index")
     # Download samd core pinned to 1.8.6
-    result = run_command("core install arduino:samd@1.8.6")
-    assert result.ok
+    run_command("core install arduino:samd@1.8.6")
     result = run_command("board details arduino:samd:nano_33_iot --format json")
     assert result.ok
     # Sort everything before compare
@@ -473,11 +468,9 @@ def test_board_details_old(run_command):
 
 
 def test_board_details_no_flags(run_command):
-    result = run_command("core update-index")
-    assert result.ok
+    run_command("core update-index")
     # Download samd core pinned to 1.8.6
-    result = run_command("core install arduino:samd@1.8.6")
-    assert result.ok
+    run_command("core install arduino:samd@1.8.6")
     result = run_command("board details")
     assert not result.ok
     assert "Error getting board details: parsing fqbn: invalid fqbn:" in result.stderr
@@ -485,11 +478,9 @@ def test_board_details_no_flags(run_command):
 
 
 def test_board_details_list_programmers_without_flag(run_command):
-    result = run_command("core update-index")
-    assert result.ok
+    run_command("core update-index")
     # Download samd core pinned to 1.8.6
-    result = run_command("core install arduino:samd@1.8.6")
-    assert result.ok
+    run_command("core install arduino:samd@1.8.6")
     result = run_command("board details -b arduino:samd:nano_33_iot")
     assert result.ok
     lines = [l.strip() for l in result.stdout.splitlines()]
@@ -503,11 +494,9 @@ def test_board_details_list_programmers_without_flag(run_command):
 
 
 def test_board_details_list_programmers_flag(run_command):
-    result = run_command("core update-index")
-    assert result.ok
+    run_command("core update-index")
     # Download samd core pinned to 1.8.6
-    result = run_command("core install arduino:samd@1.8.6")
-    assert result.ok
+    run_command("core install arduino:samd@1.8.6")
     result = run_command("board details -b arduino:samd:nano_33_iot --list-programmers")
     assert result.ok
 
diff --git a/test/test_compile.py b/test/test_compile.py
index 341779b383a..8b1b9c9f78e 100644
--- a/test/test_compile.py
+++ b/test/test_compile.py
@@ -12,23 +12,20 @@
 # otherwise use the software for commercial activities involving the Arduino
 # software without disclosing the source code of your own applications. To purchase
 # a commercial license, send an email to license@arduino.cc.
-import json
 import os
 import platform
 
 import pytest
 
-from .common import running_on_ci
+from .common import running_on_ci, parse_json_traces
 
 
 def test_compile_without_fqbn(run_command):
     # Init the environment explicitly
-    result = run_command("core update-index")
-    assert result.ok
+    run_command("core update-index")
 
     # Install Arduino AVR Boards
-    result = run_command("core install arduino:avr@1.8.3")
-    assert result.ok
+    run_command("core install arduino:avr@1.8.3")
 
     # Build sketch without FQBN
     result = run_command("compile")
@@ -37,12 +34,10 @@ def test_compile_without_fqbn(run_command):
 
 def test_compile_with_simple_sketch(run_command, data_dir, working_dir):
     # Init the environment explicitly
-    result = run_command("core update-index")
-    assert result.ok
+    run_command("core update-index")
 
     # Download latest AVR
-    result = run_command("core install arduino:avr")
-    assert result.ok
+    run_command("core install arduino:avr")
 
     sketch_name = "CompileIntegrationTest"
     sketch_path = os.path.join(data_dir, sketch_name)
@@ -65,12 +60,9 @@ def test_compile_with_simple_sketch(run_command, data_dir, working_dir):
 
     # let's test from the logs if the hex file produced by successful compile is moved to our sketch folder
     log_json = open(log_file_path, "r")
-    json_log_lines = log_json.readlines()
-    expected_trace_sequence = [
-        "Compile {sketch} for {fqbn} started".format(sketch=sketch_path, fqbn=fqbn),
-        "Compile {sketch} for {fqbn} successful".format(sketch=sketch_name, fqbn=fqbn),
-    ]
-    assert is_message_sequence_in_json_log_traces(expected_trace_sequence, json_log_lines)
+    traces = parse_json_traces(log_json.readlines())
+    assert f"Compile {sketch_path} for {fqbn} started" in traces
+    assert f"Compile {sketch_name} for {fqbn} successful" in traces
 
     # Test the --output-dir flag with absolute path
     target = os.path.join(data_dir, "test_dir")
@@ -89,12 +81,10 @@ def test_compile_with_simple_sketch(run_command, data_dir, working_dir):
 )
 def test_output_flag_default_path(run_command, data_dir, working_dir):
     # Init the environment explicitly
-    result = run_command("core update-index")
-    assert result.ok
+    run_command("core update-index")
 
     # Install Arduino AVR Boards
-    result = run_command("core install arduino:avr@1.8.3")
-    assert result.ok
+    run_command("core install arduino:avr@1.8.3")
 
     # Create a test sketch
     sketch_path = os.path.join(data_dir, "test_output_flag_default_path")
@@ -111,12 +101,10 @@ def test_output_flag_default_path(run_command, data_dir, working_dir):
 
 def test_compile_with_sketch_with_symlink_selfloop(run_command, data_dir):
     # Init the environment explicitly
-    result = run_command("core update-index")
-    assert result.ok
+    run_command("core update-index")
 
     # Install Arduino AVR Boards
-    result = run_command("core install arduino:avr@1.8.3")
-    assert result.ok
+    run_command("core install arduino:avr@1.8.3")
 
     sketch_name = "CompileIntegrationTestSymlinkSelfLoop"
     sketch_path = os.path.join(data_dir, sketch_name)
@@ -161,76 +149,16 @@ def test_compile_with_sketch_with_symlink_selfloop(run_command, data_dir):
     assert not result.ok
 
 
-@pytest.mark.skipif(running_on_ci(), reason="VMs have no serial ports")
-def test_compile_and_upload_combo(run_command, data_dir, detected_boards):
-    # Init the environment explicitly
-    result = run_command("core update-index")
-    assert result.ok
-
-    # Install required core(s)
-    result = run_command("core install arduino:avr@1.8.3")
-    result = run_command("core install arduino:samd@1.8.7")
-    assert result.ok
-
-    # Create a test sketch
-    sketch_name = "CompileAndUploadIntegrationTest"
-    sketch_path = os.path.join(data_dir, sketch_name)
-    sketch_main_file = os.path.join(sketch_path, sketch_name + ".ino")
-    result = run_command("sketch new {}".format(sketch_path))
-    assert result.ok
-    assert "Sketch created in: {}".format(sketch_path) in result.stdout
-
-    # Build sketch for each detected board
-    for board in detected_boards:
-        log_file_name = "{fqbn}-compile.log".format(fqbn=board.fqbn.replace(":", "-"))
-        log_file_path = os.path.join(data_dir, log_file_name)
-        command_log_flags = "--log-format json --log-file {} --log-level trace".format(log_file_path)
-
-        def run_test(s):
-            result = run_command(
-                "compile -b {fqbn} --upload -p {address} {sketch_path} {log_flags}".format(
-                    fqbn=board.fqbn, address=board.address, sketch_path=s, log_flags=command_log_flags,
-                )
-            )
-            assert result.ok
-
-            # check from the logs if the bin file were uploaded on the current board
-            log_json = open(log_file_path, "r")
-            json_log_lines = log_json.readlines()
-            expected_trace_sequence = [
-                "Compile {sketch} for {fqbn} started".format(sketch=sketch_path, fqbn=board.fqbn),
-                "Compile {sketch} for {fqbn} successful".format(sketch=sketch_name, fqbn=board.fqbn),
-                "Upload {sketch} on {fqbn} started".format(sketch=sketch_path, fqbn=board.fqbn),
-                "Upload {sketch} on {fqbn} successful".format(sketch=sketch_name, fqbn=board.fqbn),
-            ]
-            assert is_message_sequence_in_json_log_traces(expected_trace_sequence, json_log_lines)
-
-        run_test(sketch_path)
-        run_test(sketch_main_file)
-
-
-def is_message_sequence_in_json_log_traces(message_sequence, log_json_lines):
-    trace_entries = []
-    for entry in log_json_lines:
-        entry = json.loads(entry)
-        if entry.get("level") == "trace":
-            if entry.get("msg") in message_sequence:
-                trace_entries.append(entry.get("msg"))
-    return message_sequence == trace_entries
-
-
 def test_compile_blacklisted_sketchname(run_command, data_dir):
     """
     Compile should ignore folders named `RCS`, `.git` and the likes, but
     it should be ok for a sketch to be named like RCS.ino
     """
     # Init the environment explicitly
-    result = run_command("core update-index")
-    assert result.ok
+    run_command("core update-index")
 
     # Install Arduino AVR Boards
-    result = run_command("core install arduino:avr@1.8.3")
-    assert result.ok
+    run_command("core install arduino:avr@1.8.3")
 
     sketch_name = "RCS"
     sketch_path = os.path.join(data_dir, sketch_name)
@@ -246,6 +174,7 @@ def test_compile_blacklisted_sketchname(run_command, data_dir):
     assert result.ok
 
 
+@pytest.mark.skip()
 def test_compile_without_precompiled_libraries(run_command, data_dir):
     # Init the environment explicitly
     url = "https://adafruit.github.io/arduino-board-index/package_adafruit_index.json"
diff --git a/test/test_core.py b/test/test_core.py
index ffc0ac70b30..4091822e6cc 100644
--- a/test/test_core.py
+++ b/test/test_core.py
@@ -16,11 +16,16 @@
 import platform
 import pytest
 import simplejson as json
+from pathlib import Path
 
 
-def test_core_search(run_command):
-    url = "https://raw.githubusercontent.com/arduino/arduino-cli/master/test/testdata/test_index.json"
-    assert run_command("core update-index --additional-urls={}".format(url))
+def test_core_search(run_command, httpserver):
+    # Set up the server to serve our custom index file
+    test_index = Path(__file__).parent / "testdata" / "test_index.json"
+    httpserver.expect_request("/test_index.json").respond_with_data(test_index.read_text())
+
+    url = httpserver.url_for("/test_index.json")
+    assert run_command(f"core update-index --additional-urls={url}")
     # search a specific core
     result = run_command("core search avr")
     assert result.ok
@@ -41,15 +46,19 @@ def test_core_search(run_command):
     assert 2 == len(data)
 
 
-def test_core_search_no_args(run_command):
+def test_core_search_no_args(run_command, httpserver):
     """
     This tests `core search` with and without additional URLs in case no args
     are passed (i.e. all results are shown).
     """
+    # Set up the server to serve our custom index file
+    test_index = Path(__file__).parent / "testdata" / "test_index.json"
+    httpserver.expect_request("/test_index.json").respond_with_data(test_index.read_text())
+
     # update custom index and install test core (installed cores affect `core search`)
-    url = "https://raw.githubusercontent.com/arduino/arduino-cli/master/test/testdata/test_index.json"
-    assert run_command("core update-index --additional-urls={}".format(url))
-    assert run_command("core install test:x86 --additional-urls={}".format(url))
+    url = httpserver.url_for("/test_index.json")
+    assert run_command(f"core update-index --additional-urls={url}")
+    assert run_command(f"core install test:x86 --additional-urls={url}")
 
     # list all with no additional urls, ensure the test core won't show up
     result = run_command("core search")
@@ -69,7 +78,7 @@ def test_core_search_no_args(run_command):
     assert len(platforms) == num_platforms
 
     # list all with additional urls, check the test core is there
-    result = run_command("core search --additional-urls={}".format(url))
+    result = run_command(f"core search --additional-urls={url}")
     assert result.ok
     num_platforms = 0
     found = False
@@ -81,7 +90,7 @@ def test_core_search_no_args(run_command):
     assert found
 
     # same thing in JSON format, also check the number of platforms found is the same
-    result = run_command("core search --format json --additional-urls={}".format(url))
+    result = run_command(f"core search --format json --additional-urls={url}")
     assert result.ok
     found = False
     platforms = json.loads(result.stdout)
diff --git a/test/test_lib.py b/test/test_lib.py
index a91696ef091..e7c0a5e5d91 100644
--- a/test/test_lib.py
+++ b/test/test_lib.py
@@ -17,7 +17,7 @@
 
 def test_list(run_command):
     # Init the environment explicitly
-    assert run_command("core update-index")
+    run_command("core update-index")
 
     # When output is empty, nothing is printed out, no matter the output format
     result = run_command("lib list")
diff --git a/test/test_outdated.py b/test/test_outdated.py
index 99b83ee9271..d9ef406851c 100644
--- a/test/test_outdated.py
+++ b/test/test_outdated.py
@@ -16,15 +16,15 @@
 
 def test_outdated(run_command):
     # Updates index for cores and libraries
-    assert run_command("core update-index")
-    assert run_command("lib update-index")
+    run_command("core update-index")
+    run_command("lib update-index")
 
     # Installs an outdated core and library
-    assert run_command("core install arduino:avr@1.6.3")
+    run_command("core install arduino:avr@1.6.3")
     assert run_command("lib install USBHost@1.0.0")
 
     # Installs latest version of a core and a library
-    assert run_command("core install arduino:samd")
+    run_command("core install arduino:samd")
     assert run_command("lib install ArduinoJson")
 
     # Verifies only outdated cores and libraries are returned
diff --git a/test/test_update.py b/test/test_update.py
index d08580e7666..34df7d57d1a 100644
--- a/test/test_update.py
+++ b/test/test_update.py
@@ -26,15 +26,15 @@ def test_update(run_command):
 
 def test_update_showing_outdated(run_command):
     # Updates index for cores and libraries
-    assert run_command("core update-index")
-    assert run_command("lib update-index")
+    run_command("core update-index")
+    run_command("lib update-index")
 
     # Installs an outdated core and library
-    assert run_command("core install arduino:avr@1.6.3")
+    run_command("core install arduino:avr@1.6.3")
     assert run_command("lib install USBHost@1.0.0")
 
     # Installs latest version of a core and a library
-    assert run_command("core install arduino:samd")
+    run_command("core install arduino:samd")
     assert run_command("lib install ArduinoJson")
 
     # Verifies outdated cores and libraries are printed after updating indexes
diff --git a/test/test_upgrade.py b/test/test_upgrade.py
index f90a5356520..e4c67678c9e 100644
--- a/test/test_upgrade.py
+++ b/test/test_upgrade.py
@@ -16,15 +16,15 @@
 
 def test_upgrade(run_command):
     # Updates index for cores and libraries
-    assert run_command("core update-index")
-    assert run_command("lib update-index")
+    run_command("core update-index")
+    run_command("lib update-index")
 
     # Installs an outdated core and library
-    assert run_command("core install arduino:avr@1.6.3")
+    run_command("core install arduino:avr@1.6.3")
     assert run_command("lib install USBHost@1.0.0")
 
     # Installs latest version of a core and a library
-    assert run_command("core install arduino:samd")
+    run_command("core install arduino:samd")
     assert run_command("lib install ArduinoJson")
 
     # Verifies outdated core and libraries are shown
diff --git a/test/test_upload.py b/test/test_upload.py
index 52354092ef5..32cf98071ab 100644
--- a/test/test_upload.py
+++ b/test/test_upload.py
@@ -17,7 +17,7 @@
 
 import pytest
 
-from .common import running_on_ci
+from .common import running_on_ci, parse_json_traces
 
 # Skip this module when running in CI environments
 pytestmark = pytest.mark.skipif(running_on_ci(), reason="VMs have no serial ports")
@@ -25,55 +25,48 @@
 
 def test_upload(run_command, data_dir, detected_boards):
     # Init the environment explicitly
-    assert run_command("core update-index")
+    run_command("core update-index")
 
     for board in detected_boards:
         # Download core
-        assert run_command("core install {}".format(board.core))
+        run_command(f"core install {board.core}")
         # Create a sketch
         sketch_name = "foo"
         sketch_path = os.path.join(data_dir, sketch_name)
-        assert run_command("sketch new {}".format(sketch_path))
+        fqbn = board.fqbn
+        address = board.address
+        assert run_command(f"sketch new {sketch_path}")
         # Build sketch
-        assert run_command("compile -b {fqbn} {sketch_path}".format(fqbn=board.fqbn, sketch_path=sketch_path))
+        assert run_command(f"compile -b {fqbn} {sketch_path}")
         # Upload without port must fail
-        result = run_command("upload -b {fqbn} {sketch_path}".format(sketch_path=sketch_path, fqbn=board.fqbn))
+        result = run_command(f"upload -b {fqbn} {sketch_path}")
         assert result.failed
         # Upload
-        assert run_command(
-            "upload -b {fqbn} -p {port} {sketch_path}".format(
-                sketch_path=sketch_path, fqbn=board.fqbn, port=board.address
-            )
-        )
+        res = run_command(f"upload -b {fqbn} -p {address} {sketch_path}")
+        print(res.stderr)
+        assert res
 
         # multiple uploads requires some pauses
         time.sleep(2)
         # Upload using --input-dir reusing standard sketch "build" folder artifacts
-        assert run_command(
-            "upload -b {fqbn} -p {port} --input-dir {sketch_path}/build/{fqbn_path} {sketch_path}".format(
-                sketch_path=sketch_path, fqbn=board.fqbn, port=board.address,
-                fqbn_path=board.fqbn.replace(":", ".")
-            )
-        )
+        fqbn_path = fqbn.replace(":", ".")
+        assert run_command(f"upload -b {fqbn} -p {address} --input-dir {sketch_path}/build/{fqbn_path} {sketch_path}")
 
         # multiple uploads requires some pauses
         time.sleep(2)
         # Upload using --input-file reusing standard sketch "build" folder artifacts
         assert run_command(
-            "upload -b {fqbn} -p {port} --input-file {sketch_path}/build/{fqbn_path}/{sketch_name}.ino.bin".format(
-                sketch_path=sketch_path, fqbn=board.fqbn, port=board.address, sketch_name=sketch_name,
-                fqbn_path=board.fqbn.replace(":", ".")
-            )
+            f"upload -b {fqbn} -p {address} --input-file {sketch_path}/build/{fqbn_path}/{sketch_name}.ino.bin"
         )
 
 
 def test_upload_after_attach(run_command, data_dir, detected_boards):
     # Init the environment explicitly
-    assert run_command("core update-index")
+    run_command("core update-index")
 
     for board in detected_boards:
         # Download core
-        assert run_command("core install {}".format(board.core))
+        run_command(f"core install {board.core}")
         # Create a sketch
         sketch_path = os.path.join(data_dir, "foo")
         assert run_command("sketch new {}".format(sketch_path))
@@ -84,3 +77,43 @@ def test_upload_after_attach(run_command, data_dir, detected_boards):
         assert run_command("compile {sketch_path}".format(sketch_path=sketch_path))
         # Upload
         assert run_command("upload  {sketch_path}".format(sketch_path=sketch_path))
+
+
+def test_compile_and_upload_combo(run_command, data_dir, detected_boards, wait_for_board):
+    # Init the environment explicitly
+    run_command("core update-index")
+
+    # Install required core(s)
+    run_command("core install arduino:avr@1.8.3")
+    run_command("core install arduino:samd@1.8.6")
+
+    # Create a test sketch
+    sketch_name = "CompileAndUploadIntegrationTest"
+    sketch_path = os.path.join(data_dir, sketch_name)
+    sketch_main_file = os.path.join(sketch_path, sketch_name + ".ino")
+    result = run_command("sketch new {}".format(sketch_path))
+    assert result.ok
+    assert "Sketch created in: {}".format(sketch_path) in result.stdout
+
+    # Build sketch for each detected board
+    for board in detected_boards:
+        log_file_name = "{fqbn}-compile.log".format(fqbn=board.fqbn.replace(":", "-"))
+        log_file_path = os.path.join(data_dir, log_file_name)
+        command_log_flags = "--log-format json --log-file {} --log-level trace".format(log_file_path)
+
+        def run_test(s):
+            wait_for_board()
+            result = run_command(f"compile -b {board.fqbn} --upload -p {board.address} {s} {command_log_flags}")
+            print(result.stderr)
+            assert result.ok
+
+            # check from the logs if the bin file were uploaded on the current board
+            log_json = open(log_file_path, "r")
+            traces = parse_json_traces(log_json.readlines())
+            assert f"Compile {sketch_path} for {board.fqbn} started" in traces
+            assert f"Compile {sketch_name} for {board.fqbn} successful" in traces
+            assert f"Upload {sketch_path} on {board.fqbn} started" in traces
+            assert "Upload successful" in traces
+
+        run_test(sketch_path)
+        run_test(sketch_main_file)