diff --git a/.github/workflows/ci.yaml b/.github/workflows/ci.yaml
index ca9b4d3ab..8a0c73672 100644
--- a/.github/workflows/ci.yaml
+++ b/.github/workflows/ci.yaml
@@ -14,10 +14,10 @@ jobs:
       fail-fast: false
       matrix:
         platform: [ubuntu-latest, windows-latest]
-        python-version: ["3.8", "3.9"]
+        python-version: ["3.9"]
     runs-on: ${{ matrix.platform }}
     env:
-      IS_MAIN_PYTHON: ${{ matrix.python-version == '3.8' && matrix.platform == 'ubuntu-latest' }}
+      IS_MAIN_PYTHON: ${{ matrix.python-version == '3.9' && matrix.platform == 'ubuntu-latest' }}
     steps:
       - uses: actions/checkout@v4
       - name: Install Python tools
diff --git a/.github/workflows/lint.yml b/.github/workflows/lint.yml
index c803e66cd..9e2552ab1 100644
--- a/.github/workflows/lint.yml
+++ b/.github/workflows/lint.yml
@@ -7,7 +7,7 @@ on:
       - master
 
 env:
-  PYTHON_VERSION: 3.8
+  PYTHON_VERSION: 3.9
 
 jobs:
   changed-files:
@@ -131,7 +131,7 @@ jobs:
         run: echo "::add-matcher::.github/sphinx-problem-matcher.json"
 
       - name: Build docs
-        run: |
+        run: |-
           poe docs |& tee /tmp/output
           # fail the job if there are issues
           grep -q " WARNING:" /tmp/output && exit 1 || exit 0
diff --git a/CONTRIBUTING.rst b/CONTRIBUTING.rst
index ee4edbdcb..f44e89b6e 100644
--- a/CONTRIBUTING.rst
+++ b/CONTRIBUTING.rst
@@ -118,10 +118,10 @@ command. Instead, you can activate the virtual environment in your shell with::
 
     $ poetry shell
 
-You should see ``(beets-py38)`` prefix in your shell prompt. Now you can run
+You should see ``(beets-py3.9)`` prefix in your shell prompt. Now you can run
 commands directly, for example::
 
-    $ (beets-py38) pytest
+    $ (beets-py3.9) pytest
 
 Additionally, `poethepoet`_ task runner assists us with the most common
 operations. Formatting, linting, testing are defined as ``poe`` tasks in
diff --git a/docs/changelog.rst b/docs/changelog.rst
index bec25ece4..34c1e6413 100644
--- a/docs/changelog.rst
+++ b/docs/changelog.rst
@@ -6,6 +6,9 @@ Changelog goes here! Please add your entry to the bottom of one of the lists bel
 Unreleased
 ----------
 
+Beets now requires Python 3.9 or later since support for EOL Python 3.8 has
+been dropped.
+
 New features:
 
 Bug fixes:
@@ -19,6 +22,8 @@ Bug fixes:
 
 For packagers:
 
+* The minimum supported Python version is now 3.9.
+
 Other changes:
 
 * Release workflow: fix the issue where the new release tag is created for the
@@ -46,8 +51,6 @@ Bug fixes:
 * Bring back test files and the manual to the source distribution tarball.
   :bug:`5513`
 
-For packagers:
-
 Other changes:
 
 * Changed `bitesize` label to `good first issue`. Our `contribute`_ page is now
diff --git a/pyproject.toml b/pyproject.toml
index e929f7275..a65184837 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -240,7 +240,7 @@ done
 interpreter = "zsh"
 
 [tool.ruff]
-target-version = "py38"
+target-version = "py39"
 line-length = 80
 
 [tool.ruff.lint]
diff --git a/test/plugins/test_advancedrewrite.py b/test/plugins/test_advancedrewrite.py
index 756d6d5fa..d2be1fa6c 100644
--- a/test/plugins/test_advancedrewrite.py
+++ b/test/plugins/test_advancedrewrite.py
@@ -87,23 +87,29 @@ class AdvancedRewritePluginTest(PluginTestCase):
             assert item.artists == ["유빈", "미미"]
 
     def test_fail_when_replacements_empty(self):
-        with pytest.raises(
-            UserError,
-            match="Advanced rewrites must have at least one replacement",
-        ), self.configure_plugin([{"match": "artist:A", "replacements": {}}]):
+        with (
+            pytest.raises(
+                UserError,
+                match="Advanced rewrites must have at least one replacement",
+            ),
+            self.configure_plugin([{"match": "artist:A", "replacements": {}}]),
+        ):
             pass
 
     def test_fail_when_rewriting_single_valued_field_with_list(self):
-        with pytest.raises(
-            UserError,
-            match="Field artist is not a multi-valued field but a list was given: C, D",
-        ), self.configure_plugin(
-            [
-                {
-                    "match": "artist:'A & B'",
-                    "replacements": {"artist": ["C", "D"]},
-                },
-            ]
+        with (
+            pytest.raises(
+                UserError,
+                match="Field artist is not a multi-valued field but a list was given: C, D",  # noqa: E501
+            ),
+            self.configure_plugin(
+                [
+                    {
+                        "match": "artist:'A & B'",
+                        "replacements": {"artist": ["C", "D"]},
+                    },
+                ]
+            ),
         ):
             pass
 
diff --git a/test/plugins/test_zero.py b/test/plugins/test_zero.py
index e21e2cabb..51913c8e0 100644
--- a/test/plugins/test_zero.py
+++ b/test/plugins/test_zero.py
@@ -102,9 +102,12 @@ class ZeroPluginTest(PluginTestCase):
         item.write()
         item_id = item.id
 
-        with self.configure_plugin(
-            {"fields": ["comments"], "update_database": True, "auto": False}
-        ), control_stdin("y"):
+        with (
+            self.configure_plugin(
+                {"fields": ["comments"], "update_database": True, "auto": False}
+            ),
+            control_stdin("y"),
+        ):
             self.run_command("zero")
 
         mf = MediaFile(syspath(item.path))
@@ -122,9 +125,16 @@ class ZeroPluginTest(PluginTestCase):
         item.write()
         item_id = item.id
 
-        with self.configure_plugin(
-            {"fields": ["comments"], "update_database": False, "auto": False}
-        ), control_stdin("y"):
+        with (
+            self.configure_plugin(
+                {
+                    "fields": ["comments"],
+                    "update_database": False,
+                    "auto": False,
+                }
+            ),
+            control_stdin("y"),
+        ):
             self.run_command("zero")
 
         mf = MediaFile(syspath(item.path))
@@ -193,9 +203,12 @@ class ZeroPluginTest(PluginTestCase):
 
         item_id = item.id
 
-        with self.configure_plugin(
-            {"fields": ["year"], "keep_fields": ["comments"]}
-        ), control_stdin("y"):
+        with (
+            self.configure_plugin(
+                {"fields": ["year"], "keep_fields": ["comments"]}
+            ),
+            control_stdin("y"),
+        ):
             self.run_command("zero")
 
         item = self.lib.get_item(item_id)
@@ -242,9 +255,12 @@ class ZeroPluginTest(PluginTestCase):
         )
         item.write()
         item_id = item.id
-        with self.configure_plugin(
-            {"fields": ["comments"], "update_database": True, "auto": False}
-        ), control_stdin("n"):
+        with (
+            self.configure_plugin(
+                {"fields": ["comments"], "update_database": True, "auto": False}
+            ),
+            control_stdin("n"),
+        ):
             self.run_command("zero")
 
         mf = MediaFile(syspath(item.path))
diff --git a/test/test_config_command.py b/test/test_config_command.py
index e30fde382..b68c4f042 100644
--- a/test/test_config_command.py
+++ b/test/test_config_command.py
@@ -112,9 +112,10 @@ class ConfigCommandTest(BeetsTestCase):
 
     def test_config_editor_not_found(self):
         msg_match = "Could not edit configuration.*here is problem"
-        with patch(
-            "os.execlp", side_effect=OSError("here is problem")
-        ), pytest.raises(ui.UserError, match=msg_match):
+        with (
+            patch("os.execlp", side_effect=OSError("here is problem")),
+            pytest.raises(ui.UserError, match=msg_match),
+        ):
             self.run_command("config", "-e")
 
     def test_edit_invalid_config_file(self):