diff --git a/.github/ISSUE_TEMPLATE/bug.yml b/.github/ISSUE_TEMPLATE/bug.yml
index 61a0e143a..a6f131479 100644
--- a/.github/ISSUE_TEMPLATE/bug.yml
+++ b/.github/ISSUE_TEMPLATE/bug.yml
@@ -32,6 +32,7 @@ body:
       description: Version of Python you are using
       options:
         - "NA"
+        - "3.13"
         - "3.12"
         - "3.11"
         - "3.10"
diff --git a/.github/workflows/api-changes.yml b/.github/workflows/api-changes.yml
index 9cbae5843..108d5b6f0 100644
--- a/.github/workflows/api-changes.yml
+++ b/.github/workflows/api-changes.yml
@@ -30,7 +30,7 @@ jobs:
     - name: Setup Python
       uses: actions/setup-python@v5
       with:
-        python-version: 3.12
+        python-version: 3.x
 
     - name: Install tools
       env:
diff --git a/.github/workflows/codspeed.yml b/.github/workflows/codspeed.yml
index 122e9d090..41497ffb6 100644
--- a/.github/workflows/codspeed.yml
+++ b/.github/workflows/codspeed.yml
@@ -30,7 +30,7 @@ jobs:
     - uses: actions/checkout@v4
     - uses: actions/setup-python@v5
       with:
-        python-version: 3.12
+        python-version: 3.x
         architecture: x64
 
     - name: Install poetry
diff --git a/.github/workflows/cookiecutter-e2e.yml b/.github/workflows/cookiecutter-e2e.yml
index ef2d5e4d5..64c289d4c 100644
--- a/.github/workflows/cookiecutter-e2e.yml
+++ b/.github/workflows/cookiecutter-e2e.yml
@@ -24,14 +24,8 @@ env:
 
 jobs:
   lint:
-    name: Cookiecutter E2E Python ${{ matrix.python-version }} / ${{ matrix.os }}
-    runs-on: ${{ matrix.os }}
-    strategy:
-      fail-fast: true
-      matrix:
-        include:
-          - { python-version: "3.12",  os: "ubuntu-latest" }
-
+    name: Cookiecutter E2E Python
+    runs-on: ubuntu-latest
     steps:
     - uses: actions/checkout@v4
     - name: Upgrade pip
@@ -50,8 +44,7 @@ jobs:
 
     - uses: actions/setup-python@v5
       with:
-        python-version: ${{ matrix.python-version }}
-        architecture: x64
+        python-version: 3.x
         cache: 'pip'
         cache-dependency-path: 'poetry.lock'
 
@@ -69,12 +62,12 @@ jobs:
 
     - name: Run Nox
       run: |
-        nox --python=${{ matrix.python-version }} --session=test_cookiecutter
+        nox --session=test_cookiecutter
 
     - uses: actions/upload-artifact@v4
       if: always()
       with:
-        name: cookiecutter-${{ matrix.os }}-py${{ matrix.python-version }}
+        name: cookiecutter-ubuntu-latest-py3x
         path: |
           /tmp/tap-*
           /tmp/target-*
diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 89ab95710..29432a002 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -48,11 +48,17 @@ jobs:
       matrix:
         session: [tests]
         os: ["ubuntu-latest", "macos-latest", "windows-latest"]
-        python-version: ["3.8", "3.9", "3.10", "3.11", "3.12"]
+        python-version:
+        - "3.8"
+        - "3.9"
+        - "3.10"
+        - "3.11"
+        - "3.12"
+        - "3.13"
         sqlalchemy: ["2"]
         include:
-        - { session: tests,   python-version: "3.12", os: "ubuntu-latest", sqlalchemy: "1" }
-        - { session: doctest, python-version: "3.12", os: "ubuntu-latest", sqlalchemy: "2" }
+        - { session: tests,   python-version: "3.13", os: "ubuntu-latest", sqlalchemy: "1" }
+        - { session: doctest, python-version: "3.13", os: "ubuntu-latest", sqlalchemy: "2" }
         - { session: mypy,    python-version: "3.12",  os: "ubuntu-latest", sqlalchemy: "2" }
         - { session: deps,    python-version: "3.12",  os: "ubuntu-latest", sqlalchemy: "2" }
 
@@ -64,6 +70,7 @@ jobs:
     - uses: actions/setup-python@v5
       with:
         python-version: ${{ matrix.python-version }}
+        allow-prereleases: true
 
     - name: Upgrade pip
       env:
@@ -88,6 +95,8 @@ jobs:
     - name: Run Nox
       env:
         SQLALCHEMY_VERSION: ${{ matrix.sqlalchemy }}
+        PIP_PRE: "1"
+        UV_PRERELEASE: allow
       run: |
         nox --verbose
 
@@ -134,6 +143,9 @@ jobs:
         nox --version
 
     - name: Run Nox
+      env:
+        PIP_PRE: "1"
+        UV_PRERELEASE: allow
       run: |
         nox -- -m "external"
 
@@ -147,7 +159,7 @@ jobs:
     - uses: actions/checkout@v4
     - uses: actions/setup-python@v5
       with:
-        python-version: '3.12'
+        python-version: '3.x'
 
     - name: Upgrade pip
       env:
diff --git a/.github/workflows/version_bump.yml b/.github/workflows/version_bump.yml
index 7f56cfba6..5d94ddf8d 100644
--- a/.github/workflows/version_bump.yml
+++ b/.github/workflows/version_bump.yml
@@ -47,8 +47,7 @@ jobs:
 
     - uses: actions/setup-python@v5
       with:
-        python-version: "3.12"
-        architecture: x64
+        python-version: "3.x"
 
     - name: Bump version
       id: cz-bump
diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index 18f9fecda..5796aba15 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -37,7 +37,7 @@ repos:
   - id: trailing-whitespace
 
 - repo: https://github.com/python-jsonschema/check-jsonschema
-  rev: 0.29.3
+  rev: 0.29.4
   hooks:
   - id: check-dependabot
   - id: check-github-workflows
diff --git a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
index 919a92dc6..fee771429 100644
--- a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
+++ b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
@@ -20,6 +20,7 @@ classifiers = [
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
+    "Programming Language :: Python :: 3.13",
 ]
 license = "Apache-2.0"
 {%- if cookiecutter.variant != "None (Skip)" %}
diff --git a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini
index fb5b1cf87..90c122a54 100644
--- a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini
+++ b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini
@@ -1,7 +1,7 @@
 # This file can be used to customize tox tests as well as other test frameworks like flake8 and mypy
 
 [tox]
-envlist = py3{9,10,11,12}
+envlist = py3{9,10,11,12,13}
 requires =
     tox>=4.19
 
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
index 38ef2b94f..19f1ee931 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
@@ -19,6 +19,7 @@ classifiers = [
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
+    "Programming Language :: Python :: 3.13",
 ]
 license = "Apache-2.0"
 {%- if cookiecutter.variant != "None (Skip)" %}
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini
index fb5b1cf87..90c122a54 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini
@@ -1,7 +1,7 @@
 # This file can be used to customize tox tests as well as other test frameworks like flake8 and mypy
 
 [tox]
-envlist = py3{9,10,11,12}
+envlist = py3{9,10,11,12,13}
 requires =
     tox>=4.19
 
diff --git a/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml b/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
index 27cb43531..4deff5c78 100644
--- a/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
+++ b/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
@@ -19,6 +19,7 @@ classifiers = [
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
+    "Programming Language :: Python :: 3.13",
 ]
 license = "Apache-2.0"
 {%- if cookiecutter.variant != "None (Skip)" %}
diff --git a/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini b/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini
index fb5b1cf87..90c122a54 100644
--- a/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini
+++ b/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini
@@ -1,7 +1,7 @@
 # This file can be used to customize tox tests as well as other test frameworks like flake8 and mypy
 
 [tox]
-envlist = py3{9,10,11,12}
+envlist = py3{9,10,11,12,13}
 requires =
     tox>=4.19
 
diff --git a/docs/implementation/cli.md b/docs/implementation/cli.md
index 94077fc5d..92d77fa37 100644
--- a/docs/implementation/cli.md
+++ b/docs/implementation/cli.md
@@ -68,9 +68,19 @@ values from environment variables, and from a `.env` file if present within the
 working directory, which match the exact name of a setting, along with a prefix determined
 by the plugin name.
 
-> For example: For a sample plugin named `tap-my-example` and settings named "username" and "access_key", the SDK will automatically scrape
-> the settings from environment variables `TAP_MY_EXAMPLE_USERNAME` and
-> `TAP_MY_EXAMPLE_ACCESS_KEY`, if they exist.
+```{note}
+For example, for a sample plugin named `tap-my-example` and settings named `username` and `access_key`, the SDK will automatically scrape
+the settings from environment variables `TAP_MY_EXAMPLE_USERNAME` and
+`TAP_MY_EXAMPLE_ACCESS_KEY` respectively, if they exist.
+```
+
+The following value types are automatically cast to the appropriate Python type:
+
+- integer (e.g. `TAP_MY_EXAMPLE_PORT=5432`)
+- boolean (e.g. `TAP_MY_EXAMPLE_DEBUG=true`)
+- JSON arrays (e.g. `TAP_MY_EXAMPLE_ARRAY='["a", "b", "c"]'`)
+- JSON objects (e.g. `TAP_MY_EXAMPLE_OBJECT='{"key": "value"}'`)
+
 
 ## Tap-Specific CLI Options
 
diff --git a/noxfile.py b/noxfile.py
index 1641901e9..3a94fe9fa 100644
--- a/noxfile.py
+++ b/noxfile.py
@@ -6,6 +6,7 @@
 import shutil
 import sys
 import tempfile
+import typing as t
 from pathlib import Path
 
 import nox
@@ -23,7 +24,14 @@
 COOKIECUTTER_REPLAY_FILES = list(Path("./e2e-tests/cookiecutters").glob("*.json"))
 
 package = "singer_sdk"
-python_versions = ["3.12", "3.11", "3.10", "3.9", "3.8"]
+python_versions = [
+    "3.13",
+    "3.12",
+    "3.11",
+    "3.10",
+    "3.9",
+    "3.8",
+]
 main_python_version = "3.12"
 locations = "singer_sdk", "tests", "noxfile.py", "docs/conf.py"
 nox.options.sessions = (
@@ -35,7 +43,7 @@
 )
 
 poetry_config = nox.project.load_toml("pyproject.toml")["tool"]["poetry"]
-test_dependencies = poetry_config["group"]["dev"]["dependencies"].keys()
+test_dependencies: dict[str, t.Any] = poetry_config["group"]["dev"]["dependencies"]
 typing_dependencies = poetry_config["group"]["typing"]["dependencies"].keys()
 
 
@@ -53,7 +61,18 @@ def mypy(session: nox.Session) -> None:
 @nox.session(python=python_versions)
 def tests(session: nox.Session) -> None:
     """Execute pytest tests and compute coverage."""
-    session.install(".[faker,jwt,parquet,s3]")
+    extras = [
+        "faker",
+        "jwt",
+        "parquet",
+        "s3",
+    ]
+
+    if session.python == "3.13":
+        # https://github.com/apache/arrow/issues/43519
+        extras.remove("parquet")
+
+    session.install(f".[{','.join(extras)}]")
     session.install(*test_dependencies)
 
     sqlalchemy_version = os.environ.get("SQLALCHEMY_VERSION")
@@ -95,7 +114,7 @@ def benches(session: nox.Session) -> None:
     )
 
 
-@nox.session(name="deps", python=python_versions)
+@nox.session(name="deps", python=main_python_version)
 def dependencies(session: nox.Session) -> None:
     """Check issues with dependencies."""
     session.install(".[s3,testing]")
diff --git a/poetry.lock b/poetry.lock
index 159f296c1..30ae812f5 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry 1.8.3 and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.8.4 and should not be changed by hand.
 
 [[package]]
 name = "aiobotocore"
@@ -932,13 +932,13 @@ test = ["pytest (>=6)"]
 
 [[package]]
 name = "faker"
-version = "30.3.0"
+version = "30.6.0"
 description = "Faker is a Python package that generates fake data for you."
 optional = true
 python-versions = ">=3.8"
 files = [
-    {file = "Faker-30.3.0-py3-none-any.whl", hash = "sha256:e8a15fd1b0f72992b008f5ea94c70d3baa0cb51b0d5a0e899c17b1d1b23d2771"},
-    {file = "faker-30.3.0.tar.gz", hash = "sha256:8760fbb34564fbb2f394345eef24aec5b8f6506b6cfcefe8195ed66dd1032bdb"},
+    {file = "Faker-30.6.0-py3-none-any.whl", hash = "sha256:37b5ab951f7367ea93edb865120e9717a7a649d6a4b223f1e4a47a8a20d9e85f"},
+    {file = "faker-30.6.0.tar.gz", hash = "sha256:be0e548352c1be6f6d9c982003848a0d305868f160bb1fb7f945acffc347e676"},
 ]
 
 [package.dependencies]
@@ -3122,60 +3122,68 @@ test = ["pytest"]
 
 [[package]]
 name = "sqlalchemy"
-version = "2.0.35"
+version = "2.0.36"
 description = "Database Abstraction Library"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "SQLAlchemy-2.0.35-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:67219632be22f14750f0d1c70e62f204ba69d28f62fd6432ba05ab295853de9b"},
-    {file = "SQLAlchemy-2.0.35-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:4668bd8faf7e5b71c0319407b608f278f279668f358857dbfd10ef1954ac9f90"},
-    {file = "SQLAlchemy-2.0.35-cp310-cp310-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:cb8bea573863762bbf45d1e13f87c2d2fd32cee2dbd50d050f83f87429c9e1ea"},
-    {file = "SQLAlchemy-2.0.35-cp310-cp310-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:f552023710d4b93d8fb29a91fadf97de89c5926c6bd758897875435f2a939f33"},
-    {file = "SQLAlchemy-2.0.35-cp310-cp310-musllinux_1_2_aarch64.whl", hash = "sha256:016b2e665f778f13d3c438651dd4de244214b527a275e0acf1d44c05bc6026a9"},
-    {file = "SQLAlchemy-2.0.35-cp310-cp310-musllinux_1_2_x86_64.whl", hash = "sha256:7befc148de64b6060937231cbff8d01ccf0bfd75aa26383ffdf8d82b12ec04ff"},
-    {file = "SQLAlchemy-2.0.35-cp310-cp310-win32.whl", hash = "sha256:22b83aed390e3099584b839b93f80a0f4a95ee7f48270c97c90acd40ee646f0b"},
-    {file = "SQLAlchemy-2.0.35-cp310-cp310-win_amd64.whl", hash = "sha256:a29762cd3d116585278ffb2e5b8cc311fb095ea278b96feef28d0b423154858e"},
-    {file = "SQLAlchemy-2.0.35-cp311-cp311-macosx_10_9_x86_64.whl", hash = "sha256:e21f66748ab725ade40fa7af8ec8b5019c68ab00b929f6643e1b1af461eddb60"},
-    {file = "SQLAlchemy-2.0.35-cp311-cp311-macosx_11_0_arm64.whl", hash = "sha256:8a6219108a15fc6d24de499d0d515c7235c617b2540d97116b663dade1a54d62"},
-    {file = "SQLAlchemy-2.0.35-cp311-cp311-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:042622a5306c23b972192283f4e22372da3b8ddf5f7aac1cc5d9c9b222ab3ff6"},
-    {file = "SQLAlchemy-2.0.35-cp311-cp311-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:627dee0c280eea91aed87b20a1f849e9ae2fe719d52cbf847c0e0ea34464b3f7"},
-    {file = "SQLAlchemy-2.0.35-cp311-cp311-musllinux_1_2_aarch64.whl", hash = "sha256:4fdcd72a789c1c31ed242fd8c1bcd9ea186a98ee8e5408a50e610edfef980d71"},
-    {file = "SQLAlchemy-2.0.35-cp311-cp311-musllinux_1_2_x86_64.whl", hash = "sha256:89b64cd8898a3a6f642db4eb7b26d1b28a497d4022eccd7717ca066823e9fb01"},
-    {file = "SQLAlchemy-2.0.35-cp311-cp311-win32.whl", hash = "sha256:6a93c5a0dfe8d34951e8a6f499a9479ffb9258123551fa007fc708ae2ac2bc5e"},
-    {file = "SQLAlchemy-2.0.35-cp311-cp311-win_amd64.whl", hash = "sha256:c68fe3fcde03920c46697585620135b4ecfdfc1ed23e75cc2c2ae9f8502c10b8"},
-    {file = "SQLAlchemy-2.0.35-cp312-cp312-macosx_10_9_x86_64.whl", hash = "sha256:eb60b026d8ad0c97917cb81d3662d0b39b8ff1335e3fabb24984c6acd0c900a2"},
-    {file = "SQLAlchemy-2.0.35-cp312-cp312-macosx_11_0_arm64.whl", hash = "sha256:6921ee01caf375363be5e9ae70d08ce7ca9d7e0e8983183080211a062d299468"},
-    {file = "SQLAlchemy-2.0.35-cp312-cp312-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:8cdf1a0dbe5ced887a9b127da4ffd7354e9c1a3b9bb330dce84df6b70ccb3a8d"},
-    {file = "SQLAlchemy-2.0.35-cp312-cp312-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:93a71c8601e823236ac0e5d087e4f397874a421017b3318fd92c0b14acf2b6db"},
-    {file = "SQLAlchemy-2.0.35-cp312-cp312-musllinux_1_2_aarch64.whl", hash = "sha256:e04b622bb8a88f10e439084486f2f6349bf4d50605ac3e445869c7ea5cf0fa8c"},
-    {file = "SQLAlchemy-2.0.35-cp312-cp312-musllinux_1_2_x86_64.whl", hash = "sha256:1b56961e2d31389aaadf4906d453859f35302b4eb818d34a26fab72596076bb8"},
-    {file = "SQLAlchemy-2.0.35-cp312-cp312-win32.whl", hash = "sha256:0f9f3f9a3763b9c4deb8c5d09c4cc52ffe49f9876af41cc1b2ad0138878453cf"},
-    {file = "SQLAlchemy-2.0.35-cp312-cp312-win_amd64.whl", hash = "sha256:25b0f63e7fcc2a6290cb5f7f5b4fc4047843504983a28856ce9b35d8f7de03cc"},
-    {file = "SQLAlchemy-2.0.35-cp37-cp37m-macosx_10_9_x86_64.whl", hash = "sha256:f021d334f2ca692523aaf7bbf7592ceff70c8594fad853416a81d66b35e3abf9"},
-    {file = "SQLAlchemy-2.0.35-cp37-cp37m-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:05c3f58cf91683102f2f0265c0db3bd3892e9eedabe059720492dbaa4f922da1"},
-    {file = "SQLAlchemy-2.0.35-cp37-cp37m-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:032d979ce77a6c2432653322ba4cbeabf5a6837f704d16fa38b5a05d8e21fa00"},
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-    {file = "SQLAlchemy-2.0.35-cp37-cp37m-musllinux_1_2_x86_64.whl", hash = "sha256:cc32b2990fc34380ec2f6195f33a76b6cdaa9eecf09f0c9404b74fc120aef36f"},
-    {file = "SQLAlchemy-2.0.35-cp37-cp37m-win32.whl", hash = "sha256:9509c4123491d0e63fb5e16199e09f8e262066e58903e84615c301dde8fa2e87"},
-    {file = "SQLAlchemy-2.0.35-cp37-cp37m-win_amd64.whl", hash = "sha256:3655af10ebcc0f1e4e06c5900bb33e080d6a1fa4228f502121f28a3b1753cde5"},
-    {file = "SQLAlchemy-2.0.35-cp38-cp38-macosx_10_9_x86_64.whl", hash = "sha256:4c31943b61ed8fdd63dfd12ccc919f2bf95eefca133767db6fbbd15da62078ec"},
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+    {file = "SQLAlchemy-2.0.36-py3-none-any.whl", hash = "sha256:fddbe92b4760c6f5d48162aef14824add991aeda8ddadb3c31d56eb15ca69f8e"},
+    {file = "sqlalchemy-2.0.36.tar.gz", hash = "sha256:7f2767680b6d2398aea7082e45a774b2b0767b5c8d8ffb9c8b683088ea9b29c5"},
 ]
 
 [package.dependencies]
@@ -3188,7 +3196,7 @@ aioodbc = ["aioodbc", "greenlet (!=0.4.17)"]
 aiosqlite = ["aiosqlite", "greenlet (!=0.4.17)", "typing_extensions (!=3.10.0.1)"]
 asyncio = ["greenlet (!=0.4.17)"]
 asyncmy = ["asyncmy (>=0.2.3,!=0.2.4,!=0.2.6)", "greenlet (!=0.4.17)"]
-mariadb-connector = ["mariadb (>=1.0.1,!=1.1.2,!=1.1.5)"]
+mariadb-connector = ["mariadb (>=1.0.1,!=1.1.2,!=1.1.5,!=1.1.10)"]
 mssql = ["pyodbc"]
 mssql-pymssql = ["pymssql"]
 mssql-pyodbc = ["pyodbc"]
@@ -3349,13 +3357,13 @@ types-urllib3 = "*"
 
 [[package]]
 name = "types-requests"
-version = "2.32.0.20240914"
+version = "2.32.0.20241016"
 description = "Typing stubs for requests"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "types-requests-2.32.0.20240914.tar.gz", hash = "sha256:2850e178db3919d9bf809e434eef65ba49d0e7e33ac92d588f4a5e295fffd405"},
-    {file = "types_requests-2.32.0.20240914-py3-none-any.whl", hash = "sha256:59c2f673eb55f32a99b2894faf6020e1a9f4a402ad0f192bfee0b64469054310"},
+    {file = "types-requests-2.32.0.20241016.tar.gz", hash = "sha256:0d9cad2f27515d0e3e3da7134a1b6f28fb97129d86b867f24d9c726452634d95"},
+    {file = "types_requests-2.32.0.20241016-py3-none-any.whl", hash = "sha256:4195d62d6d3e043a4eaaf08ff8a62184584d2e8684e9d2aa178c7915a7da3747"},
 ]
 
 [package.dependencies]
@@ -3566,13 +3574,13 @@ tests-strict = ["pytest (==4.6.0)", "pytest (==6.2.5)", "pytest-cov (==3.0.0)"]
 
 [[package]]
 name = "xmltodict"
-version = "0.14.1"
+version = "0.14.2"
 description = "Makes working with XML feel like you are working with JSON"
 optional = false
 python-versions = ">=3.6"
 files = [
-    {file = "xmltodict-0.14.1-py2.py3-none-any.whl", hash = "sha256:3ef4a7b71c08f19047fcbea572e1d7f4207ab269da1565b5d40e9823d3894e63"},
-    {file = "xmltodict-0.14.1.tar.gz", hash = "sha256:338c8431e4fc554517651972d62f06958718f6262b04316917008e8fd677a6b0"},
+    {file = "xmltodict-0.14.2-py2.py3-none-any.whl", hash = "sha256:20cc7d723ed729276e808f26fb6b3599f786cbc37e06c65e192ba77c40f20aac"},
+    {file = "xmltodict-0.14.2.tar.gz", hash = "sha256:201e7c28bb210e374999d1dde6382923ab0ed1a8a5faeece48ab525b7810a553"},
 ]
 
 [[package]]
diff --git a/pyproject.toml b/pyproject.toml
index 329705b8a..e137cdd8b 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -173,6 +173,8 @@ filterwarnings = [
     "ignore:No records were available to test:UserWarning",
     # https://github.com/meltano/sdk/issues/1354
     "ignore:The function singer_sdk.testing.get_standard_tap_tests is deprecated:DeprecationWarning",
+    # TODO: Address this SQLite warning in Python 3.13+
+    "ignore::ResourceWarning",
 ]
 log_cli_level = "INFO"
 markers = [
diff --git a/samples/sample_tap_dummy_json/pyproject.toml b/samples/sample_tap_dummy_json/pyproject.toml
index c72347748..4542c6448 100644
--- a/samples/sample_tap_dummy_json/pyproject.toml
+++ b/samples/sample_tap_dummy_json/pyproject.toml
@@ -15,6 +15,7 @@ classifiers = [
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
+    "Programming Language :: Python :: 3.13",
 ]
 license = "Apache-2.0"
 
diff --git a/samples/sample_tap_dummy_json/ruff.toml b/samples/sample_tap_dummy_json/ruff.toml
index dd2f13459..c6af4cfef 100644
--- a/samples/sample_tap_dummy_json/ruff.toml
+++ b/samples/sample_tap_dummy_json/ruff.toml
@@ -1,5 +1,5 @@
 src = ["tap_dummyjson"]
-target-version = "py38"
+target-version = "py39"
 
 [lint]
 ignore = [
diff --git a/samples/sample_tap_dummy_json/tox.ini b/samples/sample_tap_dummy_json/tox.ini
index 6be1c116a..8b89a4ef1 100644
--- a/samples/sample_tap_dummy_json/tox.ini
+++ b/samples/sample_tap_dummy_json/tox.ini
@@ -1,7 +1,7 @@
 # This file can be used to customize tox tests as well as other test frameworks like flake8 and mypy
 
 [tox]
-envlist = py{38,39,310,311,312}
+envlist = py3{9,10,11,12,13}
 isolated_build = true
 
 [testenv]
@@ -13,7 +13,7 @@ commands =
 [testenv:pytest]
 # Run the python tests.
 # To execute, run `tox -e pytest`
-envlist = py{38,39,310,311,312}
+envlist = py3{8,9,10,11,12,313}
 commands =
     poetry install -v
     poetry run pytest
diff --git a/samples/sample_target_parquet/parquet_target_sink.py b/samples/sample_target_parquet/parquet_target_sink.py
index e98dca2b1..fbdd13cd1 100644
--- a/samples/sample_target_parquet/parquet_target_sink.py
+++ b/samples/sample_target_parquet/parquet_target_sink.py
@@ -4,11 +4,14 @@
 
 import typing as t
 
-import pyarrow as pa
-import pyarrow.parquet as pq
-
 from singer_sdk.sinks import BatchSink
 
+try:
+    import pyarrow as pa
+    import pyarrow.parquet as pq
+except ImportError:
+    pass
+
 
 def json_schema_to_arrow(schema: dict[str, t.Any]) -> pa.Schema:
     """Convert a JSON Schema to an Arrow schema.
diff --git a/singer_sdk/about.py b/singer_sdk/about.py
index ab3062295..4b0cc1b8d 100644
--- a/singer_sdk/about.py
+++ b/singer_sdk/about.py
@@ -24,7 +24,7 @@
 
 # Keep these in sync with the supported Python versions in pyproject.toml
 _PY_MIN_VERSION = 8
-_PY_MAX_VERSION = 12
+_PY_MAX_VERSION = 13
 
 
 def _get_min_version(specifiers: SpecifierSet) -> int:
diff --git a/singer_sdk/configuration/_dict_config.py b/singer_sdk/configuration/_dict_config.py
index fd8217f01..af1d19f29 100644
--- a/singer_sdk/configuration/_dict_config.py
+++ b/singer_sdk/configuration/_dict_config.py
@@ -10,11 +10,21 @@
 from dotenv import find_dotenv
 from dotenv.main import DotEnv
 
-from singer_sdk.helpers._typing import is_string_array_type
-from singer_sdk.helpers._util import read_json_file
+from singer_sdk.helpers import _typing
+from singer_sdk.helpers._util import load_json, read_json_file
 
 logger = logging.getLogger(__name__)
 
+TRUTHY = ("true", "1", "yes", "on")
+
+
+def _parse_array(value: str) -> list[str]:
+    return load_json(value)  # type: ignore[return-value]
+
+
+def _legacy_parse_array_of_strings(value: str) -> list[str]:
+    return value.split(",")
+
 
 def parse_environment_config(
     config_schema: dict[str, t.Any],
@@ -29,9 +39,6 @@ def parse_environment_config(
         dotenv_path: Path to a .env file. If None, will try to find one in increasingly
             higher folders.
 
-    Raises:
-        ValueError: If an un-parsable setting is found.
-
     Returns:
         A configuration dictionary.
     """
@@ -43,7 +50,7 @@ def parse_environment_config(
     logger.debug("Loading configuration from %s", dotenv_path)
     DotEnv(dotenv_path).set_as_environment_variables()
 
-    for config_key in config_schema["properties"]:
+    for config_key, schema in config_schema.get("properties", {}).items():
         env_var_name = prefix + config_key.upper().replace("-", "_")
         if env_var_name in os.environ:
             env_var_value = os.environ[env_var_name]
@@ -52,15 +59,25 @@ def parse_environment_config(
                 config_key,
                 env_var_name,
             )
-            if is_string_array_type(config_schema["properties"][config_key]):
-                if env_var_value[0] == "[" and env_var_value[-1] == "]":
-                    msg = (
-                        "A bracketed list was detected in the environment variable "
-                        f"'{env_var_name}'. This syntax is no longer supported. Please "
-                        "remove the brackets and try again."
+            if _typing.is_integer_type(schema):
+                result[config_key] = int(env_var_value)
+            elif _typing.is_boolean_type(schema):
+                result[config_key] = env_var_value.lower() in TRUTHY
+            elif _typing.is_string_array_type(schema):
+                try:
+                    result[config_key] = _parse_array(env_var_value)
+                except Exception:  # noqa: BLE001
+                    # TODO(edgarrmondragon): Make this a deprecation warning.
+                    # https://github.com/meltano/sdk/issues/2724
+                    logger.warning(
+                        "Parsing array of the form 'x,y,z' is deprecated and will be "
+                        "removed in future versions.",
                     )
-                    raise ValueError(msg)
-                result[config_key] = env_var_value.split(",")
+                    result[config_key] = _legacy_parse_array_of_strings(env_var_value)
+            elif _typing.is_array_type(schema):
+                result[config_key] = _parse_array(env_var_value)
+            elif _typing.is_object_type(schema):
+                result[config_key] = load_json(env_var_value)
             else:
                 result[config_key] = env_var_value
     return result
diff --git a/singer_sdk/helpers/_typing.py b/singer_sdk/helpers/_typing.py
index 1e7370fd9..b02ecb512 100644
--- a/singer_sdk/helpers/_typing.py
+++ b/singer_sdk/helpers/_typing.py
@@ -279,6 +279,17 @@ def is_boolean_type(property_schema: dict) -> bool | None:
     return False
 
 
+def _is_exclusive_boolean_type(property_schema: dict) -> bool:
+    if "type" not in property_schema:
+        return False
+
+    return (
+        property_schema["type"] == "boolean"
+        or property_schema["type"] == ["boolean"]
+        or set(property_schema["type"]) == {"boolean", "null"}
+    )
+
+
 def is_integer_type(property_schema: dict) -> bool | None:
     """Return true if the JSON Schema type is an integer or None if detection fails."""
     if "anyOf" not in property_schema and "type" not in property_schema:
@@ -523,6 +534,6 @@ def _conform_primitive_property(  # noqa: PLR0911
     if isinstance(elem, bytes):
         # for BIT value, treat 0 as False and anything else as True
         return elem != b"\x00" if is_boolean_type(property_schema) else elem.hex()
-    if is_boolean_type(property_schema):
+    if _is_exclusive_boolean_type(property_schema):
         return None if elem is None else elem != 0
     return elem
diff --git a/singer_sdk/typing.py b/singer_sdk/typing.py
index 53c379265..8b48b7074 100644
--- a/singer_sdk/typing.py
+++ b/singer_sdk/typing.py
@@ -206,15 +206,18 @@ def __init__(
         *,
         allowed_values: list[T] | None = None,
         examples: list[T] | None = None,
+        nullable: bool | None = None,
     ) -> None:
         """Initialize the type helper.
 
         Args:
             allowed_values: A list of allowed values.
             examples: A list of example values.
+            nullable: If True, the property may be null.
         """
         self.allowed_values = allowed_values
         self.examples = examples
+        self.nullable = nullable
 
     @DefaultInstanceProperty
     def type_dict(self) -> dict:
@@ -273,6 +276,8 @@ class StringType(JSONTypeHelper[str]):
         {'type': ['string'], 'enum': ['a', 'b']}
         >>> StringType(max_length=10).type_dict
         {'type': ['string'], 'maxLength': 10}
+        >>> StringType(max_length=10, nullable=True).type_dict
+        {'type': ['string', 'null'], 'maxLength': 10}
     """
 
     string_format: str | None = None
@@ -321,7 +326,7 @@ def type_dict(self) -> dict:
             A dictionary describing the type.
         """
         result = {
-            "type": ["string"],
+            "type": ["string", "null"] if self.nullable else ["string"],
             **self._format,
             **self.extras,
         }
@@ -460,7 +465,10 @@ def type_dict(self) -> dict:
         Returns:
             A dictionary describing the type.
         """
-        return {"type": ["boolean"], **self.extras}
+        return {
+            "type": ["boolean", "null"] if self.nullable else ["boolean"],
+            **self.extras,
+        }
 
 
 class _NumericType(JSONTypeHelper[T]):
@@ -507,7 +515,12 @@ def type_dict(self) -> dict:
         Returns:
             A dictionary describing the type.
         """
-        result = {"type": [self.__type_name__], **self.extras}
+        result = {
+            "type": [self.__type_name__, "null"]
+            if self.nullable
+            else [self.__type_name__],
+            **self.extras,
+        }
 
         if self.minimum is not None:
             result["minimum"] = self.minimum
@@ -592,7 +605,11 @@ def type_dict(self) -> dict:  # type: ignore[override]
         Returns:
             A dictionary describing the type.
         """
-        return {"type": "array", "items": self.wrapped_type.type_dict, **self.extras}
+        return {
+            "type": ["array", "null"] if self.nullable else "array",
+            "items": self.wrapped_type.type_dict,
+            **self.extras,
+        }
 
 
 class AnyType(JSONTypeHelper):
@@ -835,7 +852,10 @@ def type_dict(self) -> dict:  # type: ignore[override]
             merged_props.update(w.to_dict())
             if not w.optional:
                 required.append(w.name)
-        result: dict[str, t.Any] = {"type": "object", "properties": merged_props}
+        result: dict[str, t.Any] = {
+            "type": ["object", "null"] if self.nullable else "object",
+            "properties": merged_props,
+        }
 
         if required:
             result["required"] = required
diff --git a/tests/contrib/test_batch_encoder_parquet.py b/tests/contrib/test_batch_encoder_parquet.py
index 0318e41d3..90af43619 100644
--- a/tests/contrib/test_batch_encoder_parquet.py
+++ b/tests/contrib/test_batch_encoder_parquet.py
@@ -2,8 +2,11 @@
 
 from __future__ import annotations
 
+import sys
 import typing as t
 
+import pytest
+
 from singer_sdk.contrib.batch_encoder_parquet import ParquetBatcher
 from singer_sdk.helpers._batch import BatchConfig, ParquetEncoding, StorageTarget
 
@@ -11,6 +14,11 @@
     from pathlib import Path
 
 
+@pytest.mark.xfail(
+    sys.version_info >= (3, 13),
+    reason="Parquet not supported on Python 3.13 due to PyArrow incompatibility",
+    strict=True,
+)
 def test_batcher(tmp_path: Path) -> None:
     root = tmp_path.joinpath("batches")
     root.mkdir()
@@ -30,6 +38,11 @@ def test_batcher(tmp_path: Path) -> None:
     assert batches[0][0].endswith(".parquet")
 
 
+@pytest.mark.xfail(
+    sys.version_info >= (3, 13),
+    reason="Parquet not supported on Python 3.13 due to PyArrow incompatibility",
+    strict=True,
+)
 def test_batcher_gzip(tmp_path: Path) -> None:
     root = tmp_path.joinpath("batches")
     root.mkdir()
diff --git a/tests/core/configuration/test_dict_config.py b/tests/core/configuration/test_dict_config.py
index 136b72e72..851f9970a 100644
--- a/tests/core/configuration/test_dict_config.py
+++ b/tests/core/configuration/test_dict_config.py
@@ -1,6 +1,8 @@
 from __future__ import annotations
 
 import json
+import logging
+import typing as t
 from pathlib import Path
 
 import pytest
@@ -11,10 +13,23 @@
     parse_environment_config,
 )
 
+if t.TYPE_CHECKING:
+    from pytest_subtests import SubTests
+
 CONFIG_JSONSCHEMA = th.PropertiesList(
     th.Property("prop1", th.StringType, required=True),
     th.Property("prop2", th.StringType),
     th.Property("prop3", th.ArrayType(th.StringType)),
+    th.Property("prop4", th.IntegerType),
+    th.Property("prop5", th.BooleanType),
+    th.Property("prop6", th.ArrayType(th.IntegerType)),
+    th.Property(
+        "prop7",
+        th.ObjectType(
+            th.Property("sub_prop1", th.StringType),
+            th.Property("sub_prop2", th.IntegerType),
+        ),
+    ),
 ).to_dict()
 
 
@@ -36,30 +51,75 @@ def config_file2(tmpdir) -> str:
     return filepath
 
 
-def test_get_env_var_config(monkeypatch: pytest.MonkeyPatch):
+def test_get_env_var_config(
+    monkeypatch: pytest.MonkeyPatch,
+    subtests: SubTests,
+    caplog: pytest.LogCaptureFixture,
+):
     """Test settings parsing from environment variables."""
     with monkeypatch.context() as m:
         m.setenv("PLUGIN_TEST_PROP1", "hello")
-        m.setenv("PLUGIN_TEST_PROP3", "val1,val2")
-        m.setenv("PLUGIN_TEST_PROP4", "not-a-tap-setting")
+        m.setenv("PLUGIN_TEST_PROP3", '["val1","val2"]')
+        m.setenv("PLUGIN_TEST_PROP4", "123")
+        m.setenv("PLUGIN_TEST_PROP5", "TRUE")
+        m.setenv("PLUGIN_TEST_PROP6", "[1,2,3]")
+        m.setenv("PLUGIN_TEST_PROP7", '{"sub_prop1": "hello", "sub_prop2": 123}')
+        m.setenv("PLUGIN_TEST_PROP999", "not-a-tap-setting")
         env_config = parse_environment_config(CONFIG_JSONSCHEMA, "PLUGIN_TEST_")
-        assert env_config["prop1"] == "hello"
-        assert env_config["prop3"] == ["val1", "val2"]
-        assert "PROP1" not in env_config
-        assert "prop2" not in env_config
-        assert "PROP2" not in env_config
-        assert "prop4" not in env_config
-        assert "PROP4" not in env_config
+
+        with subtests.test(msg="Parse string from environment"):
+            assert env_config["prop1"] == "hello"
+
+        with subtests.test(msg="Parse array from environment"):
+            assert env_config["prop3"] == ["val1", "val2"]
+
+        with subtests.test(msg="Parse integer from environment"):
+            assert env_config["prop4"] == 123
+
+        with subtests.test(msg="Parse boolean from environment"):
+            assert env_config["prop5"] is True
+
+        with subtests.test(msg="Parse array of integers from environment"):
+            assert env_config["prop6"] == [1, 2, 3]
+
+        with subtests.test(msg="Parse object from environment"):
+            assert env_config["prop7"] == {"sub_prop1": "hello", "sub_prop2": 123}
+
+        with subtests.test(msg="Ignore non-tap setting"):
+            missing_props = {"PROP1", "prop2", "PROP2", "prop999", "PROP999"}
+            assert not set.intersection(missing_props, env_config)
+
+        m.setenv("PLUGIN_TEST_PROP3", "val1,val2")
+        with subtests.test(msg="Legacy array parsing"), caplog.at_level(
+            logging.WARNING,
+        ):
+            parsed = parse_environment_config(CONFIG_JSONSCHEMA, "PLUGIN_TEST_")
+            assert parsed["prop3"] == ["val1", "val2"]
+
+            assert any(
+                "Parsing array of the form 'x,y,z'" in log.message
+                for log in caplog.records
+            )
 
     no_env_config = parse_environment_config(CONFIG_JSONSCHEMA, "PLUGIN_TEST_")
-    assert "prop1" not in no_env_config
-    assert "PROP1" not in env_config
-    assert "prop2" not in no_env_config
-    assert "PROP2" not in env_config
-    assert "prop3" not in no_env_config
-    assert "PROP3" not in env_config
-    assert "prop4" not in no_env_config
-    assert "PROP4" not in env_config
+    missing_props = {
+        "prop1",
+        "PROP1",
+        "prop2",
+        "PROP2",
+        "prop3",
+        "PROP3",
+        "prop4",
+        "PROP4",
+        "prop5",
+        "PROP5",
+        "prop6",
+        "PROP6",
+        "prop999",
+        "PROP999",
+    }
+    with subtests.test(msg="Ignore missing environment variables"):
+        assert not set.intersection(missing_props, no_env_config)
 
 
 def test_get_dotenv_config(tmp_path: Path):
@@ -74,15 +134,6 @@ def test_get_dotenv_config(tmp_path: Path):
     assert dotenv_config["prop1"] == "hello"
 
 
-def test_get_env_var_config_not_parsable(monkeypatch: pytest.MonkeyPatch):
-    """Test settings parsing from environment variables with a non-parsable value."""
-    with monkeypatch.context() as m:
-        m.setenv("PLUGIN_TEST_PROP1", "hello")
-        m.setenv("PLUGIN_TEST_PROP3", '["repeated"]')
-        with pytest.raises(ValueError, match="A bracketed list was detected"):
-            parse_environment_config(CONFIG_JSONSCHEMA, "PLUGIN_TEST_")
-
-
 def test_merge_config_sources(
     config_file1,
     config_file2,
@@ -91,7 +142,7 @@ def test_merge_config_sources(
     """Test merging multiple configuration sources."""
     with monkeypatch.context() as m:
         m.setenv("PLUGIN_TEST_PROP1", "from-env")
-        m.setenv("PLUGIN_TEST_PROP4", "not-a-tap-setting")
+        m.setenv("PLUGIN_TEST_PROP999", "not-a-tap-setting")
         config = merge_config_sources(
             [config_file1, config_file2, "ENV"],
             CONFIG_JSONSCHEMA,
diff --git a/tests/core/test_about.py b/tests/core/test_about.py
index 70a445bb1..5d12fed19 100644
--- a/tests/core/test_about.py
+++ b/tests/core/test_about.py
@@ -106,8 +106,8 @@ def test_get_supported_pythons_sdk():
     "specifiers,expected",
     [
         (">=3.7,<3.12", ["3.7", "3.8", "3.9", "3.10", "3.11"]),
-        (">=3.7", ["3.7", "3.8", "3.9", "3.10", "3.11", "3.12"]),
-        (">3.7", ["3.8", "3.9", "3.10", "3.11", "3.12"]),
+        (">=3.7", ["3.7", "3.8", "3.9", "3.10", "3.11", "3.12", "3.13"]),
+        (">3.7", ["3.8", "3.9", "3.10", "3.11", "3.12", "3.13"]),
         (">3.7,<=3.11", ["3.8", "3.9", "3.10", "3.11"]),
     ],
 )
diff --git a/tests/core/test_typing.py b/tests/core/test_typing.py
index 5043c75e1..25d9c68df 100644
--- a/tests/core/test_typing.py
+++ b/tests/core/test_typing.py
@@ -313,7 +313,16 @@ def test_conform_primitives():
 
     assert _conform_primitive_property(None, {"type": "boolean"}) is None
     assert _conform_primitive_property(0, {"type": "boolean"}) is False
+    assert (
+        _conform_primitive_property(
+            0, {"anyOf": [{"type": "boolean"}, {"type": "integer"}]}
+        )
+        == 0
+    )
+    assert _conform_primitive_property(0, {"type": ["boolean", "integer"]}) == 0
     assert _conform_primitive_property(1, {"type": "boolean"}) is True
+    assert _conform_primitive_property(1, {"type": ["boolean", "null"]}) is True
+    assert _conform_primitive_property(1, {"type": ["boolean"]}) is True
 
 
 @pytest.mark.parametrize(
diff --git a/tests/samples/test_target_parquet.py b/tests/samples/test_target_parquet.py
index 4be4782d5..3ec00352c 100644
--- a/tests/samples/test_target_parquet.py
+++ b/tests/samples/test_target_parquet.py
@@ -3,6 +3,7 @@
 from __future__ import annotations
 
 import shutil
+import sys
 import uuid
 from pathlib import Path
 
@@ -23,6 +24,11 @@
 )
 
 
+@pytest.mark.xfail(
+    sys.version_info >= (3, 13),
+    reason="Parquet not supported on Python 3.13 due to PyArrow incompatibility",
+    raises=NameError,
+)
 class TestSampleTargetParquet(StandardTests):
     """Standard Target Tests."""
 
diff --git a/tests/samples/test_target_sqlite.py b/tests/samples/test_target_sqlite.py
index 4f6d54e60..33566082f 100644
--- a/tests/samples/test_target_sqlite.py
+++ b/tests/samples/test_target_sqlite.py
@@ -4,6 +4,7 @@
 
 import json
 import sqlite3
+import sys
 import typing as t
 from copy import deepcopy
 from io import StringIO
@@ -367,6 +368,11 @@ def test_sqlite_process_batch_message(
     assert cursor.fetchone()[0] == 4
 
 
+@pytest.mark.xfail(
+    sys.version_info >= (3, 13),
+    reason="Parquet not supported on Python 3.13 due to PyArrow incompatibility",
+    strict=True,
+)
 def test_sqlite_process_batch_parquet(
     sqlite_target_test_config: dict,
     sqlite_sample_target_batch: SQLiteTarget,