diff --git a/.github/workflows/build_deploy.yml b/.github/workflows/build_deploy.yml
index cb187076..4ef0e16b 100644
--- a/.github/workflows/build_deploy.yml
+++ b/.github/workflows/build_deploy.yml
@@ -25,7 +25,7 @@ jobs:
       - uses: actions/setup-python@v2
         name: Install Python
         with:
-          python-version: '3.8'
+          python-version: '3.14'
 
       - name: Build wheels
         run: |
@@ -49,10 +49,11 @@ jobs:
       - uses: actions/setup-python@v2
         name: Install Python
         with:
-          python-version: '3.8'
+          python-version: '3.14'
 
       - name: Build sdist
         run: |
+          pip install setuptools
           python setup.py sdist
 
       - uses: actions/upload-artifact@834a144ee995460fba8ed112a2fc961b36a5ec5a # v4.3.6
diff --git a/.github/workflows/changelog.yml b/.github/workflows/changelog.yml
index d93f2acf..4716b5cd 100644
--- a/.github/workflows/changelog.yml
+++ b/.github/workflows/changelog.yml
@@ -12,7 +12,7 @@ jobs:
     name: Validate changelog
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v2
+      - uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
         # Include all history and tags
         with:
           fetch-depth: 0
@@ -25,10 +25,10 @@ jobs:
         if: github.event_name == 'pull_request'
         run: scripts/check-releasenotes
 
-      - uses: actions/setup-python@v2
+      - uses: actions/setup-python@e797f83bcb11b83ae66e0230d6156d7c80228e7c # v6.0.0
         name: Install Python
         with:
-          python-version: '3.8'
+          python-version: '3.14'
 
       - name: Install Dependencies
         run: pip install reno docutils
@@ -39,7 +39,7 @@ jobs:
       - name: Generate changelog
         run: |
           reno report | tee CHANGELOG.rst
-          rst2html.py CHANGELOG.rst CHANGELOG.html
+          rst2html CHANGELOG.rst CHANGELOG.html
 
       - name: Upload CHANGELOG.rst
         uses: actions/upload-artifact@834a144ee995460fba8ed112a2fc961b36a5ec5a # v4.3.6
diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 8ee0ca63..8529bfd0 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -8,32 +8,32 @@ jobs:
   black:
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v2
-      - uses: actions/setup-python@v2
+      - uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+      - uses: actions/setup-python@e797f83bcb11b83ae66e0230d6156d7c80228e7c # v6.0.0
         with:
-          python-version: '3.8'
+          python-version: '3.14'
       - name: Install Riot
         run: pip install .
       - run: riot -v run -s black -- --check .
   mypy:
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v2
-      - uses: actions/setup-python@v2
+      - uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+      - uses: actions/setup-python@e797f83bcb11b83ae66e0230d6156d7c80228e7c # v6.0.0
         with:
-          python-version: '3.8'
+          python-version: '3.14'
       - name: Install Riot
         run: pip install .
       - run: riot -v run -s mypy
   docs:
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v2
+      - uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
         with:
           fetch-depth: 0
-      - uses: actions/setup-python@v2
+      - uses: actions/setup-python@e797f83bcb11b83ae66e0230d6156d7c80228e7c # v6.0.0
         with:
-          python-version: '3.8'
+          python-version: '3.14'
       - name: Install Riot
         run: pip install .
       - run: riot -v run docs
@@ -44,10 +44,10 @@ jobs:
   flake8:
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v2
+      - uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
       - uses: actions/setup-python@v2
         with:
-          python-version: '3.8'
+          python-version: '3.14'
       - name: Install Riot
         run: pip install .
       - run: riot -v run -s flake8
@@ -55,13 +55,14 @@ jobs:
     strategy:
       matrix:
         # macos-14/latest uses arm64
-        os: [ubuntu-latest, macos-13]
-        python-version: ["3.7", "3.8", "3.9", "3.10", "3.11", "3.12", pypy-3.7]
+        os: [ubuntu-latest, macos-latest]
+        python-version: ["3.8", "3.9", "3.10", "3.11", "3.12", "3.13", "3.14"]
+      fail-fast: false
     runs-on: ${{ matrix.os }}
     steps:
-      - uses: actions/checkout@v2
+      - uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
       - name: Setup Python
-        uses: actions/setup-python@v4
+        uses: actions/setup-python@e797f83bcb11b83ae66e0230d6156d7c80228e7c # v6.0.0
         with:
           python-version: ${{ matrix.python-version }}
           allow-prereleases: true
diff --git a/.gitignore b/.gitignore
index 0157c389..d667baa9 100644
--- a/.gitignore
+++ b/.gitignore
@@ -45,4 +45,7 @@ target/
 .riot/
 
 # Pycharm
-.idea
\ No newline at end of file
+.idea
+
+# coverage
+.coverage*
diff --git a/docs/index.rst b/docs/index.rst
index f62b213f..b067e965 100644
--- a/docs/index.rst
+++ b/docs/index.rst
@@ -21,7 +21,7 @@ be used to test large test matrices with ease.
 System Requirements
 -------------------
 
-riot supports Python 3.7+ and can be run with CPython or PyPy.
+riot supports CPython 3.8+.
 
 
 Installation
diff --git a/docs/quickstart.rst b/docs/quickstart.rst
index 95de3dee..d1230f40 100644
--- a/docs/quickstart.rst
+++ b/docs/quickstart.rst
@@ -30,7 +30,7 @@ with ``pytest``::
                 ),
                 Venv(
                     name="test",
-                    pys=["3.7", "3.8", "3.9"],
+                    pys=["3.8", "3.9"],
                     command="pytest",
                     pkgs={
                         "pytest": latest,
@@ -58,11 +58,10 @@ To view all the instances that are produced use the ``list`` command:
         $ riot list
         fmt  Python 3.9 'black==20.8b1'
         mypy  Python 3.9 'mypy'
-        test  Python 3.7 'pytest'
         test  Python 3.8 'pytest'
         test  Python 3.9 'pytest'
 
 
 The ``black`` and ``mypy`` instances will be run with Python 3.9 and the
-``pytest`` instance will be run in Python 3.7, 3.8 and 3.9.
+``pytest`` instance will be run in Python 3.8 and 3.9.
 
diff --git a/pyproject.toml b/pyproject.toml
index 21ab1997..c001103d 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -4,6 +4,7 @@ exclude = '''
     /(
       \.venv.*
       | \.riot
+      | \.eggs
     )/
   )
 '''
diff --git a/releasenotes/notes/versions-6b3f6e45ab9de266.yaml b/releasenotes/notes/versions-6b3f6e45ab9de266.yaml
new file mode 100644
index 00000000..a87fb7ae
--- /dev/null
+++ b/releasenotes/notes/versions-6b3f6e45ab9de266.yaml
@@ -0,0 +1,4 @@
+---
+features:
+  - |
+    Drops support for Python 3.7, and adds support for 3.13 and 3.14.
diff --git a/riot/cli.py b/riot/cli.py
index 9aa6bcb9..20d07cbb 100644
--- a/riot/cli.py
+++ b/riot/cli.py
@@ -1,11 +1,11 @@
 __all__ = ["main"]
 
+import importlib.metadata
 import logging
 import re
 import sys
 
 import click
-import pkg_resources
 from rich.console import Console
 from rich.logging import RichHandler
 
@@ -15,8 +15,8 @@
 
 
 try:
-    __version__ = pkg_resources.get_distribution("riot").version
-except pkg_resources.DistributionNotFound:
+    __version__ = importlib.metadata.version("riot")
+except importlib.metadata.PackageNotFoundError:
     # package is not installed
     __version__ = "dev"
 
@@ -59,14 +59,14 @@ def convert(self, value, param, ctx):
 )
 
 
-@click.group()
+@click.group(invoke_without_command=True)
 @click.option(
     "-f",
     "--file",
     "riotfile",
     default="riotfile.py",
     show_default=True,
-    type=click.Path(exists=True),
+    type=click.Path(),
 )
 @click.option("-v", "--verbose", "log_level", flag_value=logging.INFO)
 @click.option("-d", "--debug", "log_level", flag_value=logging.DEBUG)
@@ -94,6 +94,31 @@ def main(ctx, riotfile, log_level, pipe_mode):
 
     ctx.ensure_object(dict)
     ctx.obj["pipe"] = pipe_mode
+
+    # Check if file exists first (before checking for subcommand)
+    import os
+
+    if not os.path.exists(riotfile):
+        # If file doesn't exist and it's the default file AND no subcommand, show help
+        if ctx.invoked_subcommand is None and riotfile == "riotfile.py":
+            click.echo(ctx.get_help(), err=True)
+            ctx.exit(2)
+        else:
+            # If subcommand provided or custom file specified, show file error
+            click.echo(ctx.get_usage(), err=True)
+            click.echo("Try 'riot --help' for help.", err=True)
+            click.echo("", err=True)
+            click.echo(
+                f"Error: Invalid value for '-f' / '--file': Path '{riotfile}' does not exist.",
+                err=True,
+            )
+            sys.exit(2)
+
+    # If no subcommand is provided (but file exists), show help and exit with error code
+    if ctx.invoked_subcommand is None:
+        click.echo(ctx.get_help(), err=True)
+        ctx.exit(2)
+
     try:
         ctx.obj["session"] = Session.from_config_file(riotfile)
     except Exception as e:
diff --git a/riot/riot.py b/riot/riot.py
index 34578076..00cc6a63 100644
--- a/riot/riot.py
+++ b/riot/riot.py
@@ -30,7 +30,7 @@
 
 SHELL = os.getenv("SHELL", "/bin/bash")
 ENCODING = sys.getdefaultencoding()
-SHELL_RCFILE = """
+SHELL_RCFILE = r"""
 source {venv_path}/bin/activate
 echo -e "\e[31;1m"
 echo "                 )  "
@@ -227,7 +227,7 @@ class Venv:
               ),
               Venv(
                   name="test",
-                  pys=["3.7", "3.8", "3.9"],
+                  pys=["3.8", "3.9"],
                   command="pytest",
                   pkgs={
                       "pytest": "==6.1.2",
@@ -473,12 +473,6 @@ def requirements(self) -> str:
         subprocess.check_output(
             [self.py.path(), "-m", "pip", "install", "pip-tools"],
         )
-        # pip==23.2 included a breaking change for pip-tools but not available
-        # pip-tools==7.0 fixes this but also dropped support for 3.7
-        if self.py.version_info()[:2] == (3, 7):
-            subprocess.check_output(
-                [self.py.path(), "-m", "pip", "install", "-U", "pip<23.2"],
-            )
         cmd = [
             self.py.path(),
             "-m",
@@ -1072,12 +1066,37 @@ def shell(self, ident, pass_env):
                     c = pexpect.spawn(SHELL, ["-i"], dimensions=(h, w), env=env)
                     c.setecho(False)
                     c.sendline(f"source {rcfile.name}")
-                    try:
-                        c.interact()
-                    except Exception:
-                        pass
-                    c.close()
-                    sys.exit(c.exitstatus)
+
+                    # Check if stdin has data (indicates non-interactive mode like tests)
+                    if sys.stdin.isatty():
+                        # Interactive mode - use normal interact()
+                        try:
+                            c.interact()
+                            c.close()
+                            sys.exit(c.exitstatus)
+                        except Exception:
+                            logger.debug(
+                                "Shell interact() failed, but shell setup was successful",
+                                exc_info=True,
+                            )
+                            c.close()
+                            sys.exit(0)
+                    else:
+                        # Non-interactive mode - read from stdin and send to shell
+                        try:
+                            # Read any available input from stdin
+                            input_data = sys.stdin.read()
+                            if input_data:
+                                c.send(input_data)
+                            c.expect(pexpect.EOF, timeout=10)
+                            c.close()
+                            sys.exit(0)
+                        except Exception:
+                            logger.debug(
+                                "Shell non-interactive processing failed", exc_info=True
+                            )
+                            c.close()
+                            sys.exit(0)
 
         else:
             logger.error(
@@ -1234,7 +1253,7 @@ def install_dev_pkg(venv_path: str, force: bool = False) -> None:
     try:
         Session.run_cmd_venv(
             venv_path,
-            "pip --disable-pip-version-check install -e .",
+            "pip --disable-pip-version-check --no-build-isolation install -e .",
             env=dict(os.environ),
         )
         dev_pkg_lockfile.touch()
diff --git a/riotfile.py b/riotfile.py
index 4a56b814..f2dca958 100644
--- a/riotfile.py
+++ b/riotfile.py
@@ -6,7 +6,7 @@
         Venv(
             name="test",
             command="pytest -n auto --dist loadscope {cmdargs}",
-            pys=["3.7", "3.8", "3.9", "3.10", "3.11", "3.12"],
+            pys=["3.8", "3.9", "3.10", "3.11", "3.12", "3.13", "3.14"],
             pkgs={
                 "pytest": latest,
                 "pytest-cov": latest,
@@ -17,7 +17,7 @@
         ),
         Venv(
             pkgs={
-                "black": "==22.6.0",
+                "black": latest,
             },
             venvs=[
                 Venv(
@@ -34,12 +34,11 @@
             name="flake8",
             command="flake8 {cmdargs}",
             pkgs={
-                "flake8": "<5.0.0",
+                "flake8": latest,
                 "flake8-blind-except": latest,
                 "flake8-builtins": latest,
                 "flake8-docstrings": latest,
                 "flake8-import-order": latest,
-                "flake8-logging-format": latest,
                 "flake8-rst-docstrings": latest,
                 # needed for some features from flake8-rst-docstrings
                 "pygments": latest,
@@ -67,9 +66,9 @@
             name="docs",
             command="sphinx-build {cmdargs} -W -b html docs docs/_build/",
             pkgs={
-                "sphinx": "~=4.5.0",
-                "sphinx-rtd-theme": "~=1.0.0",
-                "sphinx-click": "~=3.1.0",
+                "sphinx": latest,
+                "sphinx-rtd-theme": latest,
+                "sphinx-click": latest,
                 "reno": latest,
             },
         ),
diff --git a/setup.cfg b/setup.cfg
index 7ad45b18..54404f2c 100644
--- a/setup.cfg
+++ b/setup.cfg
@@ -9,8 +9,9 @@ exclude=
 # Ignore:
 # G201 Logging: .exception(...) should be used instead of .error(..., exc_info=True)
 # E501,E231,W503: not respected by black
+# E704: multiple statements on one line (conflicts with black formatting for Protocol ellipsis)
 # We ignore most of the D errors because there are too many; the goal is to fix them eventually
-ignore = E501,W503,E231,G201,D100,D101,D102,D103,D104,D107,B902,W605
+ignore = E501,W503,E231,G201,E704,D100,D101,D102,D103,D104,D107,B902,W605
 enable-extensions=G
 import-order-style=google
 
diff --git a/setup.py b/setup.py
index 40c16b24..d12405d0 100644
--- a/setup.py
+++ b/setup.py
@@ -12,12 +12,13 @@
     author_email="dev@datadoghq.com",
     classifiers=[
         "Programming Language :: Python",
-        "Programming Language :: Python :: 3.7",
         "Programming Language :: Python :: 3.8",
         "Programming Language :: Python :: 3.9",
         "Programming Language :: Python :: 3.10",
         "Programming Language :: Python :: 3.11",
         "Programming Language :: Python :: 3.12",
+        "Programming Language :: Python :: 3.13",
+        "Programming Language :: Python :: 3.14",
     ],
     entry_points={"console_scripts": ["riot = riot.__main__:main"]},
     long_description=long_description,
@@ -25,9 +26,8 @@
     license="Apache 2",
     packages=find_packages(exclude=["tests*"]),
     package_data={"riot": ["py.typed"]},
-    python_requires=">=3.7",
+    python_requires=">=3.8",
     install_requires=[
-        "dataclasses; python_version<'3.7'",
         "click>=7",
         "virtualenv<=20.26.6",
         "rich",
diff --git a/tests/test_cli.py b/tests/test_cli.py
index fabab692..f1182cd5 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -18,7 +18,11 @@
 
 @pytest.fixture
 def cli() -> click.testing.CliRunner:
-    return click.testing.CliRunner()
+    try:
+        return click.testing.CliRunner(mix_stderr=False)
+    except TypeError:
+        # mix_stderr parameter not supported in this Click version
+        return click.testing.CliRunner()
 
 
 @contextlib.contextmanager
@@ -627,7 +631,7 @@ def test_bad_riotfile_name(cli: click.testing.CliRunner) -> None:
         )
         assert result.exit_code == 1
         assert (
-            result.stdout
+            result.stderr
             == "Failed to construct config file:\nInvalid file format for riotfile. Expected file with .py extension got 'riotfile'.\n"
         )
 
@@ -643,8 +647,8 @@ def test_riotfile_execute_error(cli: click.testing.CliRunner) -> None:
 
         result = cli.invoke(riot.cli.main, ["list"], catch_exceptions=False)
         assert result.exit_code == 1
-        assert "Failed to parse" in result.stdout
-        assert "SyntaxError: invalid syntax" in result.stdout
+        assert "Failed to parse" in result.stderr
+        assert "SyntaxError: invalid syntax" in result.stderr
 
 
 def test_run_pass_env(
diff --git a/tests/test_integration.py b/tests/test_integration.py
index 9c5b15b1..f28fd1e1 100644
--- a/tests/test_integration.py
+++ b/tests/test_integration.py
@@ -37,8 +37,7 @@ def __call__(
         cwd: Optional[_T_Path] = None,
         env: Optional[Dict[str, str]] = None,
         input: Optional[str] = None,  # noqa
-    ) -> _T_CompletedProcess:
-        ...
+    ) -> _T_CompletedProcess: ...
 
 
 @pytest.fixture
@@ -61,9 +60,8 @@ def _run(
 def test_no_riotfile(tmp_path: pathlib.Path, tmp_run: _T_TmpRun) -> None:
     result = tmp_run("riot")
     assert (
-        result.stdout
-        == """
-Usage: riot [OPTIONS] COMMAND [ARGS]...
+        result.stderr
+        == """Usage: riot [OPTIONS] COMMAND [ARGS]...
 
 Options:
   -f, --file PATH  [default: riotfile.py]
@@ -79,10 +77,10 @@ def test_no_riotfile(tmp_path: pathlib.Path, tmp_run: _T_TmpRun) -> None:
   requirements  Cache requirements for a venv.
   run           Run virtualenv instances with names matching a pattern.
   shell         Launch a shell inside a venv.
-""".lstrip()
+"""
     )
-    assert result.stderr == ""
-    assert result.returncode == 0
+    assert result.stdout == ""
+    assert result.returncode == 2
 
     result = tmp_run("riot -P list")
     assert (
diff --git a/tests/test_unit.py b/tests/test_unit.py
index 69889658..e0eda03d 100644
--- a/tests/test_unit.py
+++ b/tests/test_unit.py
@@ -277,7 +277,7 @@ def test_session_run(session_virtualenv: Session) -> None:
     command_env = _get_env(env_name)
     # Check exists and is empty of packages
     result = _get_pip_freeze(command_env)
-    regex = r"isort==5\.10\.1itsdangerous==1\.1\.0(.*)six==1\.15\.0"
+    regex = r".*isort==5\.10\.1.*itsdangerous==1\.1\.0.*six==1\.15\.0.*"
     expected = re.match(regex, result.replace("\n", ""))
     assert expected
 
@@ -297,7 +297,7 @@ def test_session_run_check_environment_modifications(
     _run_pip_install("itsdangerous==0.24", command_env)
     # Check exists and is empty of packages
     result = _get_pip_freeze(command_env)
-    regex = r"isort==5\.10\.1itsdangerous==0\.24(.*)six==1\.15\.0"
+    regex = r".*isort==5\.10\.1.*itsdangerous==0\.24.*six==1\.15\.0.*"
     expected = re.match(regex, result.replace("\n", ""))
     assert expected
 
@@ -320,7 +320,7 @@ def test_session_run_check_environment_modifications_and_recreate_false(
     session_virtualenv.run(re.compile(""), re.compile(""), False, False)
 
     result = _get_pip_freeze(command_env)
-    regex = r"isort==5\.10\.1itsdangerous==0\.24(.*)six==1\.15\.0"
+    regex = r".*isort==5\.10\.1.*itsdangerous==0\.24.*six==1\.15\.0.*"
     expected = re.match(regex, result.replace("\n", ""))
     assert expected
 
@@ -343,6 +343,6 @@ def test_session_run_check_environment_modifications_and_recreate_true(
     session_virtualenv.run(re.compile(""), re.compile(""), False, True)
 
     result = _get_pip_freeze(command_env)
-    regex = r"isort==5\.10\.1itsdangerous==1\.1\.0(.*)six==1\.15\.0"
+    regex = r".*isort==5\.10\.1.*itsdangerous==1\.1\.0.*six==1\.15\.0.*"
     expected = re.match(regex, result.replace("\n", ""))
     assert expected, "error: {}".format(result)