diff --git a/.github/workflows/tests.yaml b/.github/workflows/tests.yaml
index 3406ac0..b6dc7d8 100644
--- a/.github/workflows/tests.yaml
+++ b/.github/workflows/tests.yaml
@@ -16,7 +16,7 @@ on:
 
 jobs:
   test:
-    timeout-minutes: 40
+    timeout-minutes: 45
     defaults:
       run:
         shell: bash
@@ -31,7 +31,7 @@ jobs:
     env:
       OS: ${{ matrix.os }}
       PYTHON: ${{ matrix.python-version }}
-      BELAY_SLEEP_MULTIPLIER: 3.0
+      BELAY_SLEEP_MULTIPLIER: 2.5
 
     steps:
       - name: Set OS Environment Variables (Windows)
diff --git a/belay/device.py b/belay/device.py
index fce5f63..9f80895 100644
--- a/belay/device.py
+++ b/belay/device.py
@@ -650,12 +650,19 @@ def __exit__(self, exc_type, exc_value, exc_tb):
     def close(self) -> None:
         """Close the connection to device."""
         # Invoke all teardown executers prior to closing out connection.
+        if self._board is None:
+            # Has already been closed
+            return
+
         atexit.unregister(self.close)
 
+        self._board.cancel_running_program()
+
         for executer in _sort_executers(self._belay_teardown._belay_executers):
             executer()
 
-        return self._board.close()
+        self._board.close()
+        self._board = None
 
     def reconnect(self, attempts: Optional[int] = None) -> None:
         """Reconnect to the device and replay the command history.
diff --git a/belay/packagemanager/models.py b/belay/packagemanager/models.py
index 2af3e92..bbd764c 100644
--- a/belay/packagemanager/models.py
+++ b/belay/packagemanager/models.py
@@ -34,7 +34,7 @@ def _dependencies_name_validator(dependencies) -> dict:
     return dependencies
 
 
-def _dependencies_preprocessor(dependencies) -> dict[str, List[dict]]:
+def _dependencies_preprocessor(dependencies) -> Dict[str, List[dict]]:
     """Preprocess various dependencies based on dtype.
 
     * ``str`` -> single dependency that may get renamed to __init__.py, if appropriate.
diff --git a/belay/pyboard.py b/belay/pyboard.py
index 478045f..2659b19 100644
--- a/belay/pyboard.py
+++ b/belay/pyboard.py
@@ -402,13 +402,17 @@ def read_until(self, min_num_bytes, ending, timeout=10, data_consumer=None):
                 time.sleep(0.01)
         return data
 
+    def cancel_running_program(self):
+        """Interrupts any running program."""
+        self.serial.write(b"\r\x03\x03")  # ctrl-C twice: interrupt any running program
+
     def enter_raw_repl(self, soft_reset=True):
         # flush input (without relying on serial.flushInput())
         n = self.serial.inWaiting()
         while n > 0:
             self.serial.read(n)
             n = self.serial.inWaiting()
-        self.serial.write(b"\r\x03\x03")  # ctrl-C twice: interrupt any running program
+        self.cancel_running_program()
         self.exit_raw_repl()  # if device is already in raw_repl, b'>>>' won't be printed.
         self.read_until(1, b">>>")
         self.serial.write(b"\r\x01")  # ctrl-A: enter raw REPL
diff --git a/poetry.lock b/poetry.lock
index 976ca7b..94d8378 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -2,106 +2,106 @@
 
 [[package]]
 name = "aiohttp"
-version = "3.8.3"
+version = "3.8.4"
 description = "Async http client/server framework (asyncio)"
 category = "main"
 optional = false
 python-versions = ">=3.6"
 files = [
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 async-timeout = ">=4.0.0a3,<5.0"
 attrs = ">=17.3.0"
-charset-normalizer = ">=2.0,<3.0"
+charset-normalizer = ">=2.0,<4.0"
 frozenlist = ">=1.1.1"
 multidict = ">=4.5,<7.0"
 yarl = ">=1.0,<2.0"
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 ]
 
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+version = "22.3.0"
+description = "The uncompromising code formatter."
+category = "dev"
+optional = false
+python-versions = ">=3.6.2"
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+mypy-extensions = ">=0.4.3"
+pathspec = ">=0.9.0"
+platformdirs = ">=2"
+tomli = {version = ">=1.1.0", markers = "python_version < \"3.11\""}
+typing-extensions = {version = ">=3.10.0.0", markers = "python_version < \"3.10\""}
+
+[package.extras]
+colorama = ["colorama (>=0.4.3)"]
+d = ["aiohttp (>=3.7.4)"]
+jupyter = ["ipython (>=7.8.0)", "tokenize-rt (>=3.2.0)"]
+uvloop = ["uvloop (>=0.15.2)"]
+
 [[package]]
 name = "certifi"
 version = "2022.12.7"
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-version = "2.1.1"
+version = "3.0.1"
 description = "The Real First Universal Charset Detector. Open, modern and actively maintained alternative to Chardet."
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 optional = false
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 ]
 
-[package.extras]
-unicode-backport = ["unicodedata2"]
-
 [[package]]
 name = "click"
 version = "8.1.3"
@@ -662,14 +792,14 @@ gitdb = ">=4.0.1,<5"
 
 [[package]]
 name = "identify"
-version = "2.5.16"
+version = "2.5.18"
 description = "File identification library for Python"
 category = "dev"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "identify-2.5.16-py2.py3-none-any.whl", hash = "sha256:832832a58ecc1b8f33d5e8cb4f7d3db2f5c7fbe922dfee5f958b48fed691501a"},
-    {file = "identify-2.5.16.tar.gz", hash = "sha256:c47acedfe6495b1c603ed7e93469b26e839cab38db4155113f36f718f8b3dc47"},
+    {file = "identify-2.5.18-py2.py3-none-any.whl", hash = "sha256:93aac7ecf2f6abf879b8f29a8002d3c6de7086b8c28d88e1ad15045a15ab63f9"},
+    {file = "identify-2.5.18.tar.gz", hash = "sha256:89e144fa560cc4cffb6ef2ab5e9fb18ed9f9b3cb054384bab4b95c12f6c309fe"},
 ]
 
 [package.extras]
@@ -750,14 +880,14 @@ tomli = {version = "*", markers = "python_version > \"3.6\" and python_version <
 
 [[package]]
 name = "ipython"
-version = "8.9.0"
+version = "8.10.0"
 description = "IPython: Productive Interactive Computing"
 category = "dev"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "ipython-8.9.0-py3-none-any.whl", hash = "sha256:9c207b0ef2d276d1bfcfeb9a62804336abbe4b170574ea061500952319b1d78c"},
-    {file = "ipython-8.9.0.tar.gz", hash = "sha256:71618e82e6d59487bea059626e7c79fb4a5b760d1510d02fab1160db6fdfa1f7"},
+    {file = "ipython-8.10.0-py3-none-any.whl", hash = "sha256:b38c31e8fc7eff642fc7c597061fff462537cf2314e3225a19c906b7b0d8a345"},
+    {file = "ipython-8.10.0.tar.gz", hash = "sha256:b13a1d6c1f5818bd388db53b7107d17454129a70de2b87481d555daede5eb49e"},
 ]
 
 [package.dependencies]
@@ -775,7 +905,7 @@ stack-data = "*"
 traitlets = ">=5"
 
 [package.extras]
-all = ["black", "curio", "docrepr", "ipykernel", "ipyparallel", "ipywidgets", "matplotlib", "matplotlib (!=3.2.0)", "nbconvert", "nbformat", "notebook", "numpy (>=1.20)", "pandas", "pytest (<7)", "pytest (<7.1)", "pytest-asyncio", "qtconsole", "setuptools (>=18.5)", "sphinx (>=1.3)", "sphinx-rtd-theme", "stack-data", "testpath", "trio", "typing-extensions"]
+all = ["black", "curio", "docrepr", "ipykernel", "ipyparallel", "ipywidgets", "matplotlib", "matplotlib (!=3.2.0)", "nbconvert", "nbformat", "notebook", "numpy (>=1.21)", "pandas", "pytest (<7)", "pytest (<7.1)", "pytest-asyncio", "qtconsole", "setuptools (>=18.5)", "sphinx (>=1.3)", "sphinx-rtd-theme", "stack-data", "testpath", "trio", "typing-extensions"]
 black = ["black"]
 doc = ["docrepr", "ipykernel", "matplotlib", "pytest (<7)", "pytest (<7.1)", "pytest-asyncio", "setuptools (>=18.5)", "sphinx (>=1.3)", "sphinx-rtd-theme", "stack-data", "testpath", "typing-extensions"]
 kernel = ["ipykernel"]
@@ -785,7 +915,7 @@ notebook = ["ipywidgets", "notebook"]
 parallel = ["ipyparallel"]
 qtconsole = ["qtconsole"]
 test = ["pytest (<7.1)", "pytest-asyncio", "testpath"]
-test-extra = ["curio", "matplotlib (!=3.2.0)", "nbformat", "numpy (>=1.20)", "pandas", "pytest (<7.1)", "pytest-asyncio", "testpath", "trio"]
+test-extra = ["curio", "matplotlib (!=3.2.0)", "nbformat", "numpy (>=1.21)", "pandas", "pytest (<7.1)", "pytest-asyncio", "testpath", "trio"]
 
 [[package]]
 name = "jedi"
@@ -1058,6 +1188,18 @@ files = [
     {file = "multidict-6.0.4.tar.gz", hash = "sha256:3666906492efb76453c0e7b97f2cf459b0682e7402c0489a95484965dbc1da49"},
 ]
 
+[[package]]
+name = "mypy-extensions"
+version = "1.0.0"
+description = "Type system extensions for programs checked with the mypy type checker."
+category = "dev"
+optional = false
+python-versions = ">=3.5"
+files = [
+    {file = "mypy_extensions-1.0.0-py3-none-any.whl", hash = "sha256:4392f6c0eb8a5668a69e23d168ffa70f0be9ccfd32b5cc2d26a34ae5b844552d"},
+    {file = "mypy_extensions-1.0.0.tar.gz", hash = "sha256:75dbf8955dc00442a438fc4d0666508a9a97b6bd41aa2f0ffe9d2f2725af0782"},
+]
+
 [[package]]
 name = "nodeenv"
 version = "1.7.0"
@@ -1142,19 +1284,19 @@ files = [
 
 [[package]]
 name = "platformdirs"
-version = "2.6.2"
+version = "3.0.0"
 description = "A small Python package for determining appropriate platform-specific dirs, e.g. a \"user data dir\"."
 category = "dev"
 optional = false
 python-versions = ">=3.7"
 files = [
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-    {file = "platformdirs-2.6.2.tar.gz", hash = "sha256:e1fea1fe471b9ff8332e229df3cb7de4f53eeea4998d3b6bfff542115e998bd2"},
+    {file = "platformdirs-3.0.0-py3-none-any.whl", hash = "sha256:b1d5eb14f221506f50d6604a561f4c5786d9e80355219694a1b244bcd96f4567"},
+    {file = "platformdirs-3.0.0.tar.gz", hash = "sha256:8a1228abb1ef82d788f74139988b137e78692984ec7b08eaa6c65f1723af28f9"},
 ]
 
 [package.extras]
-docs = ["furo (>=2022.12.7)", "proselint (>=0.13)", "sphinx (>=5.3)", "sphinx-autodoc-typehints (>=1.19.5)"]
-test = ["appdirs (==1.4.4)", "covdefaults (>=2.2.2)", "pytest (>=7.2)", "pytest-cov (>=4)", "pytest-mock (>=3.10)"]
+docs = ["furo (>=2022.12.7)", "proselint (>=0.13)", "sphinx (>=6.1.3)", "sphinx-autodoc-typehints (>=1.22,!=1.23.4)"]
+test = ["appdirs (==1.4.4)", "covdefaults (>=2.2.2)", "pytest (>=7.2.1)", "pytest-cov (>=4)", "pytest-mock (>=3.10)"]
 
 [[package]]
 name = "pluggy"
@@ -1532,14 +1674,14 @@ jupyter = ["ipywidgets (>=7.5.1,<8.0.0)"]
 
 [[package]]
 name = "setuptools"
-version = "67.0.0"
+version = "67.3.1"
 description = "Easily download, build, install, upgrade, and uninstall Python packages"
 category = "dev"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "setuptools-67.0.0-py3-none-any.whl", hash = "sha256:9d790961ba6219e9ff7d9557622d2fe136816a264dd01d5997cfc057d804853d"},
-    {file = "setuptools-67.0.0.tar.gz", hash = "sha256:883131c5b6efa70b9101c7ef30b2b7b780a4283d5fc1616383cdf22c83cbefe6"},
+    {file = "setuptools-67.3.1-py3-none-any.whl", hash = "sha256:23c86b4e44432bfd8899384afc08872ec166a24f48a3f99f293b0a557e6a6b5d"},
+    {file = "setuptools-67.3.1.tar.gz", hash = "sha256:daec07fd848d80676694d6bf69c009d28910aeece68a38dbe88b7e1bb6dba12e"},
 ]
 
 [package.extras]
@@ -1549,14 +1691,14 @@ testing-integration = ["build[virtualenv]", "filelock (>=3.4.0)", "jaraco.envs (
 
 [[package]]
 name = "shellingham"
-version = "1.5.0.post1"
+version = "1.5.1"
 description = "Tool to Detect Surrounding Shell"
 category = "main"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "shellingham-1.5.0.post1-py2.py3-none-any.whl", hash = "sha256:368bf8c00754fd4f55afb7bbb86e272df77e4dc76ac29dbcbb81a59e9fc15744"},
-    {file = "shellingham-1.5.0.post1.tar.gz", hash = "sha256:823bc5fb5c34d60f285b624e7264f4dda254bc803a3774a147bf99c0e3004a28"},
+    {file = "shellingham-1.5.1-py2.py3-none-any.whl", hash = "sha256:ce5f6d0062c719deabf696bccfab5273e09a6ea1b0ed32867aff03392adbdc51"},
+    {file = "shellingham-1.5.1.tar.gz", hash = "sha256:41bc81fa8d74afb04338e0398f9732ee2217407ade778ae1e2709bde89d85c45"},
 ]
 
 [[package]]
@@ -1684,14 +1826,14 @@ test = ["pytest"]
 
 [[package]]
 name = "sphinxcontrib-htmlhelp"
-version = "2.0.0"
+version = "2.0.1"
 description = "sphinxcontrib-htmlhelp is a sphinx extension which renders HTML help files"
 category = "dev"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.8"
 files = [
-    {file = "sphinxcontrib-htmlhelp-2.0.0.tar.gz", hash = "sha256:f5f8bb2d0d629f398bf47d0d69c07bc13b65f75a81ad9e2f71a63d4b7a2f6db2"},
-    {file = "sphinxcontrib_htmlhelp-2.0.0-py2.py3-none-any.whl", hash = "sha256:d412243dfb797ae3ec2b59eca0e52dac12e75a241bf0e4eb861e450d06c6ed07"},
+    {file = "sphinxcontrib-htmlhelp-2.0.1.tar.gz", hash = "sha256:0cbdd302815330058422b98a113195c9249825d681e18f11e8b1f78a2f11efff"},
+    {file = "sphinxcontrib_htmlhelp-2.0.1-py3-none-any.whl", hash = "sha256:c38cb46dccf316c79de6e5515e1770414b797162b23cd3d06e67020e1d2a6903"},
 ]
 
 [package.extras]
@@ -1803,14 +1945,14 @@ files = [
 
 [[package]]
 name = "traitlets"
-version = "5.8.1"
+version = "5.9.0"
 description = "Traitlets Python configuration system"
 category = "dev"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "traitlets-5.8.1-py3-none-any.whl", hash = "sha256:a1ca5df6414f8b5760f7c5f256e326ee21b581742114545b462b35ffe3f04861"},
-    {file = "traitlets-5.8.1.tar.gz", hash = "sha256:32500888f5ff7bbf3b9267ea31748fa657aaf34d56d85e60f91dda7dc7f5785b"},
+    {file = "traitlets-5.9.0-py3-none-any.whl", hash = "sha256:9e6ec080259b9a5940c797d58b613b5e31441c2257b87c2e795c5228ae80d2d8"},
+    {file = "traitlets-5.9.0.tar.gz", hash = "sha256:f6cde21a9c68cf756af02035f72d5a723bf607e862e7be33ece505abf4a3bad9"},
 ]
 
 [package.extras]
@@ -1843,14 +1985,14 @@ test = ["black (>=22.3.0,<23.0.0)", "coverage (>=5.2,<6.0)", "isort (>=5.0.6,<6.
 
 [[package]]
 name = "typing-extensions"
-version = "4.4.0"
+version = "4.5.0"
 description = "Backported and Experimental Type Hints for Python 3.7+"
 category = "main"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "typing_extensions-4.4.0-py3-none-any.whl", hash = "sha256:16fa4864408f655d35ec496218b85f79b3437c829e93320c7c9215ccfd92489e"},
-    {file = "typing_extensions-4.4.0.tar.gz", hash = "sha256:1511434bb92bf8dd198c12b1cc812e800d4181cfcb867674e0f8279cc93087aa"},
+    {file = "typing_extensions-4.5.0-py3-none-any.whl", hash = "sha256:fb33085c39dd998ac16d1431ebc293a8b3eedd00fd4a32de0ff79002c19511b4"},
+    {file = "typing_extensions-4.5.0.tar.gz", hash = "sha256:5cb5f4a79139d699607b3ef622a1dedafa84e115ab0024e0d9c044a9479ca7cb"},
 ]
 
 [[package]]
@@ -1872,24 +2014,24 @@ socks = ["PySocks (>=1.5.6,!=1.5.7,<2.0)"]
 
 [[package]]
 name = "virtualenv"
-version = "20.17.1"
+version = "20.19.0"
 description = "Virtual Python Environment builder"
 category = "dev"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.7"
 files = [
-    {file = "virtualenv-20.17.1-py3-none-any.whl", hash = "sha256:ce3b1684d6e1a20a3e5ed36795a97dfc6af29bc3970ca8dab93e11ac6094b3c4"},
-    {file = "virtualenv-20.17.1.tar.gz", hash = "sha256:f8b927684efc6f1cc206c9db297a570ab9ad0e51c16fa9e45487d36d1905c058"},
+    {file = "virtualenv-20.19.0-py3-none-any.whl", hash = "sha256:54eb59e7352b573aa04d53f80fc9736ed0ad5143af445a1e539aada6eb947dd1"},
+    {file = "virtualenv-20.19.0.tar.gz", hash = "sha256:37a640ba82ed40b226599c522d411e4be5edb339a0c0de030c0dc7b646d61590"},
 ]
 
 [package.dependencies]
 distlib = ">=0.3.6,<1"
 filelock = ">=3.4.1,<4"
-platformdirs = ">=2.4,<3"
+platformdirs = ">=2.4,<4"
 
 [package.extras]
-docs = ["proselint (>=0.13)", "sphinx (>=5.3)", "sphinx-argparse (>=0.3.2)", "sphinx-rtd-theme (>=1)", "towncrier (>=22.8)"]
-testing = ["coverage (>=6.2)", "coverage-enable-subprocess (>=1)", "flaky (>=3.7)", "packaging (>=21.3)", "pytest (>=7.0.1)", "pytest-env (>=0.6.2)", "pytest-freezegun (>=0.4.2)", "pytest-mock (>=3.6.1)", "pytest-randomly (>=3.10.3)", "pytest-timeout (>=2.1)"]
+docs = ["furo (>=2022.12.7)", "proselint (>=0.13)", "sphinx (>=6.1.3)", "sphinx-argparse (>=0.4)", "sphinxcontrib-towncrier (>=0.2.1a0)", "towncrier (>=22.12)"]
+test = ["covdefaults (>=2.2.2)", "coverage (>=7.1)", "coverage-enable-subprocess (>=1)", "flaky (>=3.7)", "packaging (>=23)", "pytest (>=7.2.1)", "pytest-env (>=0.8.1)", "pytest-freezegun (>=0.4.2)", "pytest-mock (>=3.10)", "pytest-randomly (>=3.12)", "pytest-timeout (>=2.1)"]
 
 [[package]]
 name = "wcwidth"
@@ -1993,14 +2135,14 @@ multidict = ">=4.0"
 
 [[package]]
 name = "zipp"
-version = "3.12.0"
+version = "3.13.0"
 description = "Backport of pathlib-compatible object wrapper for zip files"
 category = "dev"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "zipp-3.12.0-py3-none-any.whl", hash = "sha256:9eb0a4c5feab9b08871db0d672745b53450d7f26992fd1e4653aa43345e97b86"},
-    {file = "zipp-3.12.0.tar.gz", hash = "sha256:73efd63936398aac78fd92b6f4865190119d6c91b531532e798977ea8dd402eb"},
+    {file = "zipp-3.13.0-py3-none-any.whl", hash = "sha256:e8b2a36ea17df80ffe9e2c4fda3f693c3dad6df1697d3cd3af232db680950b0b"},
+    {file = "zipp-3.13.0.tar.gz", hash = "sha256:23f70e964bc11a34cef175bc90ba2914e1e4545ea1e3e2f67c079671883f9cb6"},
 ]
 
 [package.extras]
@@ -2010,4 +2152,4 @@ testing = ["flake8 (<5)", "func-timeout", "jaraco.functools", "jaraco.itertools"
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.8"
-content-hash = "201b909eeae97c3b6ea806258ad66992b0989c031095e10be74659920d8a6bdf"
+content-hash = "ab7549446fca715356950409a17013b4635c9dc874a2439880a9a2f579059477"
diff --git a/pyproject.toml b/pyproject.toml
index 3eda365..8a6112e 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -40,6 +40,7 @@ sphinx = "~4.5.0"
 sphinx_rtd_theme = "~1.0.0"
 
 [tool.poetry.group.dev.dependencies]
+black = "22.3.0"
 coverage = {extras = ["toml"], version = "^5.1"}
 flake8 = "^4.0.1"
 poetry-dynamic-versioning = "^0.16.0"