diff --git a/pyproject.toml b/pyproject.toml
index 28364cb01..b7b4acaf0 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -239,6 +239,7 @@ select = [
     "RSE",  # flake8-raise
     "RET",  # flake8-return
     "SIM",  # flake8-simplify
+    "TCH",  # flake8-type-checking
 ]
 src = ["samples", "singer_sdk", "tests"]
 target-version = "py37"
diff --git a/samples/sample_mapper/mapper.py b/samples/sample_mapper/mapper.py
index 4aa3587ad..5f478c50a 100644
--- a/samples/sample_mapper/mapper.py
+++ b/samples/sample_mapper/mapper.py
@@ -2,8 +2,7 @@
 
 from __future__ import annotations
 
-from pathlib import PurePath
-from typing import Generator
+from typing import TYPE_CHECKING, Generator
 
 import singer_sdk._singerlib as singer
 import singer_sdk.typing as th
@@ -11,6 +10,9 @@
 from singer_sdk.mapper import PluginMapper
 from singer_sdk.mapper_base import InlineMapper
 
+if TYPE_CHECKING:
+    from pathlib import PurePath
+
 
 class StreamTransform(InlineMapper):
     """A map transformer which implements the Stream Maps capability."""
diff --git a/singer_sdk/_singerlib/messages.py b/singer_sdk/_singerlib/messages.py
index 279037859..af195d031 100644
--- a/singer_sdk/_singerlib/messages.py
+++ b/singer_sdk/_singerlib/messages.py
@@ -6,11 +6,13 @@
 import sys
 import typing as t
 from dataclasses import asdict, dataclass, field
-from datetime import datetime
 
 import pytz
 import simplejson as json
 
+if t.TYPE_CHECKING:
+    from datetime import datetime
+
 
 class SingerMessageType(str, enum.Enum):
     """Singer specification message types."""
diff --git a/singer_sdk/authenticators.py b/singer_sdk/authenticators.py
index 9fb8d656d..58ca0d7a7 100644
--- a/singer_sdk/authenticators.py
+++ b/singer_sdk/authenticators.py
@@ -3,11 +3,10 @@
 from __future__ import annotations
 
 import base64
-import logging
 import math
 from datetime import datetime, timedelta
 from types import MappingProxyType
-from typing import Any, Mapping
+from typing import TYPE_CHECKING, Any, Mapping
 from urllib.parse import parse_qs, urlencode, urlsplit, urlunsplit
 
 import jwt
@@ -16,7 +15,11 @@
 from cryptography.hazmat.primitives import serialization
 
 from singer_sdk.helpers._util import utc_now
-from singer_sdk.streams import Stream as RESTStreamBase
+
+if TYPE_CHECKING:
+    import logging
+
+    from singer_sdk.streams import Stream as RESTStreamBase
 
 
 def _add_parameters(initial_url: str, extra_parameters: dict) -> str:
diff --git a/singer_sdk/connectors/sql.py b/singer_sdk/connectors/sql.py
index 8cf9bcb03..e1dd8a82e 100644
--- a/singer_sdk/connectors/sql.py
+++ b/singer_sdk/connectors/sql.py
@@ -7,16 +7,18 @@
 from contextlib import contextmanager
 from datetime import datetime
 from functools import lru_cache
-from typing import Any, Iterable, Iterator, cast
+from typing import TYPE_CHECKING, Any, Iterable, Iterator, cast
 
 import sqlalchemy
 from sqlalchemy.engine import Engine
-from sqlalchemy.engine.reflection import Inspector
 
 from singer_sdk import typing as th
 from singer_sdk._singerlib import CatalogEntry, MetadataMapping, Schema
 from singer_sdk.exceptions import ConfigValidationError
 
+if TYPE_CHECKING:
+    from sqlalchemy.engine.reflection import Inspector
+
 
 class SQLConnector:
     """Base class for SQLAlchemy-based connectors.
diff --git a/singer_sdk/exceptions.py b/singer_sdk/exceptions.py
index 5d7e91d94..c3b9bda42 100644
--- a/singer_sdk/exceptions.py
+++ b/singer_sdk/exceptions.py
@@ -2,7 +2,10 @@
 
 from __future__ import annotations
 
-import requests
+import typing as t
+
+if t.TYPE_CHECKING:
+    import requests
 
 
 class ConfigValidationError(Exception):
diff --git a/singer_sdk/helpers/_catalog.py b/singer_sdk/helpers/_catalog.py
index c025868e0..cc91ff42b 100644
--- a/singer_sdk/helpers/_catalog.py
+++ b/singer_sdk/helpers/_catalog.py
@@ -3,14 +3,17 @@
 from __future__ import annotations
 
 from copy import deepcopy
-from logging import Logger
-from typing import Any
+from typing import TYPE_CHECKING, Any
 
 from memoization import cached
 
-from singer_sdk._singerlib import Catalog, SelectionMask
 from singer_sdk.helpers._typing import is_object_type
 
+if TYPE_CHECKING:
+    from logging import Logger
+
+    from singer_sdk._singerlib import Catalog, SelectionMask
+
 _MAX_LRU_CACHE = 500
 
 
diff --git a/singer_sdk/helpers/_resources.py b/singer_sdk/helpers/_resources.py
index 5dc9655f7..9d40964ba 100644
--- a/singer_sdk/helpers/_resources.py
+++ b/singer_sdk/helpers/_resources.py
@@ -1,8 +1,10 @@
 from __future__ import annotations
 
 import sys
-from types import ModuleType
-from typing import cast
+from typing import TYPE_CHECKING, cast
+
+if TYPE_CHECKING:
+    from types import ModuleType
 
 if sys.version_info < (3, 9):
     import importlib_resources
diff --git a/singer_sdk/helpers/_state.py b/singer_sdk/helpers/_state.py
index 693e438b5..69909290c 100644
--- a/singer_sdk/helpers/_state.py
+++ b/singer_sdk/helpers/_state.py
@@ -2,12 +2,14 @@
 
 from __future__ import annotations
 
-import datetime
-from typing import Any, Callable, cast
+from typing import TYPE_CHECKING, Any, Callable, cast
 
 from singer_sdk.exceptions import InvalidStreamSortException
 from singer_sdk.helpers._typing import to_json_compatible
 
+if TYPE_CHECKING:
+    import datetime
+
 PROGRESS_MARKERS = "progress_markers"
 PROGRESS_MARKER_NOTE = "Note"
 SIGNPOST_MARKER = "replication_key_signpost"
diff --git a/singer_sdk/helpers/_typing.py b/singer_sdk/helpers/_typing.py
index 726b1aeac..a608ec7a4 100644
--- a/singer_sdk/helpers/_typing.py
+++ b/singer_sdk/helpers/_typing.py
@@ -4,13 +4,15 @@
 
 import copy
 import datetime
-import logging
 from enum import Enum
 from functools import lru_cache
-from typing import Any, cast
+from typing import TYPE_CHECKING, Any, cast
 
 import pendulum
 
+if TYPE_CHECKING:
+    import logging
+
 _MAX_TIMESTAMP = "9999-12-31 23:59:59.999999"
 _MAX_TIME = "23:59:59.999999"
 JSONSCHEMA_ANNOTATION_SECRET = "secret"
diff --git a/singer_sdk/helpers/jsonpath.py b/singer_sdk/helpers/jsonpath.py
index 6e96cd0b3..477e8c2de 100644
--- a/singer_sdk/helpers/jsonpath.py
+++ b/singer_sdk/helpers/jsonpath.py
@@ -2,12 +2,14 @@
 
 from __future__ import annotations
 
-from typing import Any, Generator
+from typing import TYPE_CHECKING, Any, Generator
 
-import jsonpath_ng
 import memoization
 from jsonpath_ng.ext import parse
 
+if TYPE_CHECKING:
+    import jsonpath_ng
+
 
 def extract_jsonpath(expression: str, input: dict | list) -> Generator[Any, None, None]:
     """Extract records from an input based on a JSONPath expression.
diff --git a/singer_sdk/mapper.py b/singer_sdk/mapper.py
index 34253a7e9..6efd6505d 100644
--- a/singer_sdk/mapper.py
+++ b/singer_sdk/mapper.py
@@ -10,10 +10,8 @@
 import datetime
 import hashlib
 import logging
-import sys
-from typing import Any, Callable, Dict, Union
+from typing import TYPE_CHECKING, Any, Callable, Dict, Union
 
-from singer_sdk._singerlib.catalog import Catalog
 from singer_sdk.exceptions import MapExpressionError, StreamMapConfigError
 from singer_sdk.helpers import _simpleeval as simpleeval
 from singer_sdk.helpers._catalog import get_selected_schema
@@ -33,10 +31,15 @@
     StringType,
 )
 
-if sys.version_info >= (3, 10):
-    from typing import TypeAlias
-else:
-    from typing_extensions import TypeAlias
+if TYPE_CHECKING:
+    import sys
+
+    if sys.version_info >= (3, 10):
+        from typing import TypeAlias
+    else:
+        from typing_extensions import TypeAlias
+
+    from singer_sdk._singerlib.catalog import Catalog
 
 
 MAPPER_ELSE_OPTION = "__else__"
diff --git a/singer_sdk/mapper_base.py b/singer_sdk/mapper_base.py
index e17b23df5..0b3152625 100644
--- a/singer_sdk/mapper_base.py
+++ b/singer_sdk/mapper_base.py
@@ -3,8 +3,7 @@
 from __future__ import annotations
 
 import abc
-from io import FileIO
-from typing import Callable, Iterable
+from typing import TYPE_CHECKING, Callable, Iterable
 
 import click
 
@@ -16,6 +15,9 @@
 from singer_sdk.io_base import SingerReader
 from singer_sdk.plugin_base import PluginBase
 
+if TYPE_CHECKING:
+    from io import FileIO
+
 
 class InlineMapper(PluginBase, SingerReader, metaclass=abc.ABCMeta):
     """Abstract base class for inline mappers."""
diff --git a/singer_sdk/metrics.py b/singer_sdk/metrics.py
index d6edb287a..1c69a3681 100644
--- a/singer_sdk/metrics.py
+++ b/singer_sdk/metrics.py
@@ -11,13 +11,15 @@
 from dataclasses import asdict, dataclass, field
 from pathlib import Path
 from time import time
-from types import TracebackType
-from typing import Any, Generic, Mapping, TypeVar
+from typing import TYPE_CHECKING, Any, Generic, Mapping, TypeVar
 
 import yaml
 
 from singer_sdk.helpers._resources import Traversable, get_package_files
 
+if TYPE_CHECKING:
+    from types import TracebackType
+
 DEFAULT_LOG_INTERVAL = 60.0
 METRICS_LOGGER_NAME = __name__
 METRICS_LOG_LEVEL_SETTING = "metrics_log_level"
diff --git a/singer_sdk/pagination.py b/singer_sdk/pagination.py
index a6df551ba..52abaf2f2 100644
--- a/singer_sdk/pagination.py
+++ b/singer_sdk/pagination.py
@@ -4,11 +4,9 @@
 
 import sys
 from abc import ABCMeta, abstractmethod
-from typing import Any, Generic, Iterable, Optional, TypeVar
+from typing import TYPE_CHECKING, Any, Generic, Iterable, Optional, TypeVar
 from urllib.parse import ParseResult, urlparse
 
-from requests import Response
-
 from singer_sdk.helpers.jsonpath import extract_jsonpath
 
 if sys.version_info >= (3, 8):
@@ -16,6 +14,9 @@
 else:
     from typing_extensions import Protocol
 
+if TYPE_CHECKING:
+    from requests import Response
+
 T = TypeVar("T")
 TPageToken = TypeVar("TPageToken")
 
diff --git a/singer_sdk/plugin_base.py b/singer_sdk/plugin_base.py
index 49cb00074..60c8d7ed7 100644
--- a/singer_sdk/plugin_base.py
+++ b/singer_sdk/plugin_base.py
@@ -9,7 +9,7 @@
 from collections import OrderedDict
 from pathlib import PurePath
 from types import MappingProxyType
-from typing import Any, Callable, Mapping, cast
+from typing import TYPE_CHECKING, Any, Callable, Mapping, cast
 
 import click
 from jsonschema import Draft7Validator
@@ -27,9 +27,11 @@
     CapabilitiesEnum,
     PluginCapabilities,
 )
-from singer_sdk.mapper import PluginMapper
 from singer_sdk.typing import extend_validator_with_defaults
 
+if TYPE_CHECKING:
+    from singer_sdk.mapper import PluginMapper
+
 SDK_PACKAGE_NAME = "singer_sdk"
 
 
diff --git a/singer_sdk/sinks/core.py b/singer_sdk/sinks/core.py
index 9e58e165c..219581014 100644
--- a/singer_sdk/sinks/core.py
+++ b/singer_sdk/sinks/core.py
@@ -8,9 +8,8 @@
 import time
 from gzip import GzipFile
 from gzip import open as gzip_open
-from logging import Logger
 from types import MappingProxyType
-from typing import IO, Any, Mapping, Sequence
+from typing import IO, TYPE_CHECKING, Any, Mapping, Sequence
 
 from dateutil import parser
 from jsonschema import Draft7Validator, FormatChecker
@@ -27,7 +26,11 @@
     get_datelike_property_type,
     handle_invalid_timestamp_in_record,
 )
-from singer_sdk.plugin_base import PluginBase
+
+if TYPE_CHECKING:
+    from logging import Logger
+
+    from singer_sdk.plugin_base import PluginBase
 
 JSONSchemaValidator = Draft7Validator
 
diff --git a/singer_sdk/sinks/sql.py b/singer_sdk/sinks/sql.py
index f975dacab..4f5f8889a 100644
--- a/singer_sdk/sinks/sql.py
+++ b/singer_sdk/sinks/sql.py
@@ -6,19 +6,22 @@
 from collections import defaultdict
 from copy import copy
 from textwrap import dedent
-from typing import Any, Iterable
+from typing import TYPE_CHECKING, Any, Iterable
 
 import sqlalchemy
 from pendulum import now
-from sqlalchemy.sql import Executable
 from sqlalchemy.sql.expression import bindparam
 
 from singer_sdk.connectors import SQLConnector
 from singer_sdk.exceptions import ConformedNameClashException
 from singer_sdk.helpers._conformers import replace_leading_digit
-from singer_sdk.plugin_base import PluginBase
 from singer_sdk.sinks.batch import BatchSink
 
+if TYPE_CHECKING:
+    from sqlalchemy.sql import Executable
+
+    from singer_sdk.plugin_base import PluginBase
+
 
 class SQLSink(BatchSink):
     """SQL-type sink type."""
diff --git a/singer_sdk/streams/core.py b/singer_sdk/streams/core.py
index c929c103e..bd789c849 100644
--- a/singer_sdk/streams/core.py
+++ b/singer_sdk/streams/core.py
@@ -8,11 +8,19 @@
 import gzip
 import itertools
 import json
-import logging
 from os import PathLike
 from pathlib import Path
 from types import MappingProxyType
-from typing import Any, Generator, Iterable, Iterator, Mapping, TypeVar, cast
+from typing import (
+    TYPE_CHECKING,
+    Any,
+    Generator,
+    Iterable,
+    Iterator,
+    Mapping,
+    TypeVar,
+    cast,
+)
 from uuid import uuid4
 
 import pendulum
@@ -46,7 +54,11 @@
 )
 from singer_sdk.helpers._util import utc_now
 from singer_sdk.mapper import RemoveRecordTransform, SameRecordTransform, StreamMap
-from singer_sdk.plugin_base import PluginBase as TapBaseClass
+
+if TYPE_CHECKING:
+    import logging
+
+    from singer_sdk.plugin_base import PluginBase as TapBaseClass
 
 # Replication methods
 REPLICATION_FULL_TABLE = "FULL_TABLE"
diff --git a/singer_sdk/streams/rest.py b/singer_sdk/streams/rest.py
index cdf20c224..fc66dd5bf 100644
--- a/singer_sdk/streams/rest.py
+++ b/singer_sdk/streams/rest.py
@@ -5,8 +5,6 @@
 import abc
 import copy
 import logging
-import sys
-from datetime import datetime
 from typing import TYPE_CHECKING, Any, Callable, Generator, Generic, Iterable, TypeVar
 from urllib.parse import urlparse
 from warnings import warn
@@ -15,7 +13,6 @@
 import requests
 
 from singer_sdk import metrics
-from singer_sdk._singerlib import Schema
 from singer_sdk.authenticators import SimpleAuthenticator
 from singer_sdk.exceptions import FatalAPIError, RetriableAPIError
 from singer_sdk.helpers.jsonpath import extract_jsonpath
@@ -25,17 +22,22 @@
     LegacyStreamPaginator,
     SimpleHeaderPaginator,
 )
-from singer_sdk.plugin_base import PluginBase as TapBaseClass
 from singer_sdk.streams.core import Stream
 
-if sys.version_info >= (3, 10):
-    from typing import TypeAlias
-else:
-    from typing_extensions import TypeAlias
-
 if TYPE_CHECKING:
+    import sys
+    from datetime import datetime
+
     from backoff.types import Details
 
+    from singer_sdk._singerlib import Schema
+    from singer_sdk.plugin_base import PluginBase as TapBaseClass
+
+    if sys.version_info >= (3, 10):
+        from typing import TypeAlias
+    else:
+        from typing_extensions import TypeAlias
+
 DEFAULT_PAGE_SIZE = 1000
 DEFAULT_REQUEST_TIMEOUT = 300  # 5 minutes
 
diff --git a/singer_sdk/streams/sql.py b/singer_sdk/streams/sql.py
index 04c6db313..8fb1a2dc0 100644
--- a/singer_sdk/streams/sql.py
+++ b/singer_sdk/streams/sql.py
@@ -3,16 +3,18 @@
 from __future__ import annotations
 
 import abc
-from typing import Any, Iterable, cast
+from typing import TYPE_CHECKING, Any, Iterable, cast
 
 import sqlalchemy
 
 import singer_sdk.helpers._catalog as catalog
 from singer_sdk._singerlib import CatalogEntry, MetadataMapping
 from singer_sdk.connectors import SQLConnector
-from singer_sdk.plugin_base import PluginBase as TapBaseClass
 from singer_sdk.streams.core import Stream
 
+if TYPE_CHECKING:
+    from singer_sdk.plugin_base import PluginBase as TapBaseClass
+
 
 class SQLStream(Stream, metaclass=abc.ABCMeta):
     """Base class for SQLAlchemy-based streams."""
diff --git a/singer_sdk/tap_base.py b/singer_sdk/tap_base.py
index 2e9e8ca86..5ad9e0e9d 100644
--- a/singer_sdk/tap_base.py
+++ b/singer_sdk/tap_base.py
@@ -7,7 +7,7 @@
 import json
 from enum import Enum
 from pathlib import Path, PurePath
-from typing import Any, Callable, Sequence, cast
+from typing import TYPE_CHECKING, Any, Callable, Sequence, cast
 
 import click
 
@@ -26,7 +26,9 @@
 )
 from singer_sdk.mapper import PluginMapper
 from singer_sdk.plugin_base import PluginBase
-from singer_sdk.streams import SQLStream, Stream
+
+if TYPE_CHECKING:
+    from singer_sdk.streams import SQLStream, Stream
 
 STREAM_MAPS_CONFIG = "stream_maps"
 
diff --git a/singer_sdk/target_base.py b/singer_sdk/target_base.py
index f2a34009e..a5022c80d 100644
--- a/singer_sdk/target_base.py
+++ b/singer_sdk/target_base.py
@@ -7,9 +7,8 @@
 import json
 import sys
 import time
-from io import FileIO
 from pathlib import Path, PurePath
-from typing import IO, Callable, Counter
+from typing import IO, TYPE_CHECKING, Callable, Counter
 
 import click
 from joblib import Parallel, delayed, parallel_backend
@@ -28,7 +27,11 @@
 from singer_sdk.io_base import SingerMessageType, SingerReader
 from singer_sdk.mapper import PluginMapper
 from singer_sdk.plugin_base import PluginBase
-from singer_sdk.sinks import Sink
+
+if TYPE_CHECKING:
+    from io import FileIO
+
+    from singer_sdk.sinks import Sink
 
 _MAX_PARALLELISM = 8
 
diff --git a/singer_sdk/testing/factory.py b/singer_sdk/testing/factory.py
index 62638ec4b..1c90f2d68 100644
--- a/singer_sdk/testing/factory.py
+++ b/singer_sdk/testing/factory.py
@@ -2,12 +2,10 @@
 
 from __future__ import annotations
 
-from typing import Any, cast
+from typing import TYPE_CHECKING, Any, cast
 
 import pytest
 
-from singer_sdk import Tap, Target
-
 from .config import SuiteConfig
 from .runners import TapTestRunner, TargetTestRunner
 from .suites import (
@@ -17,6 +15,9 @@
     target_tests,
 )
 
+if TYPE_CHECKING:
+    from singer_sdk import Tap, Target
+
 
 def get_test_class(
     test_runner: TapTestRunner | TargetTestRunner,
diff --git a/singer_sdk/testing/legacy.py b/singer_sdk/testing/legacy.py
index d7ef3c155..5c1204537 100644
--- a/singer_sdk/testing/legacy.py
+++ b/singer_sdk/testing/legacy.py
@@ -4,12 +4,14 @@
 
 import io
 from contextlib import redirect_stderr, redirect_stdout
-from typing import Callable, cast
+from typing import TYPE_CHECKING, Callable, cast
 
 import singer_sdk._singerlib as singer
-from singer_sdk.mapper_base import InlineMapper
-from singer_sdk.tap_base import Tap
-from singer_sdk.target_base import Target
+
+if TYPE_CHECKING:
+    from singer_sdk.mapper_base import InlineMapper
+    from singer_sdk.tap_base import Tap
+    from singer_sdk.target_base import Target
 
 
 def get_standard_tap_tests(
diff --git a/singer_sdk/testing/runners.py b/singer_sdk/testing/runners.py
index c70afa91c..9c60ea9a8 100644
--- a/singer_sdk/testing/runners.py
+++ b/singer_sdk/testing/runners.py
@@ -7,12 +7,14 @@
 import json
 from collections import defaultdict
 from contextlib import redirect_stderr, redirect_stdout
-from pathlib import Path
-from typing import IO, Any, cast
+from typing import IO, TYPE_CHECKING, Any, cast
 
 from singer_sdk import Tap, Target
 from singer_sdk.testing.config import SuiteConfig
 
+if TYPE_CHECKING:
+    from pathlib import Path
+
 
 class SingerTestRunner(metaclass=abc.ABCMeta):
     """Base Singer Test Runner."""
diff --git a/singer_sdk/testing/suites.py b/singer_sdk/testing/suites.py
index 66d093c7f..068d1ea31 100644
--- a/singer_sdk/testing/suites.py
+++ b/singer_sdk/testing/suites.py
@@ -2,6 +2,7 @@
 
 from __future__ import annotations
 
+import typing as t
 from dataclasses import dataclass
 
 from .tap_tests import (
@@ -38,7 +39,9 @@
     TargetSchemaUpdates,
     TargetSpecialCharsInAttributes,
 )
-from .templates import TapTestTemplate, TargetTestTemplate, TestTemplate
+
+if t.TYPE_CHECKING:
+    from .templates import TapTestTemplate, TargetTestTemplate, TestTemplate
 
 
 @dataclass
diff --git a/singer_sdk/testing/tap_tests.py b/singer_sdk/testing/tap_tests.py
index 44ea43438..ecffc4955 100644
--- a/singer_sdk/testing/tap_tests.py
+++ b/singer_sdk/testing/tap_tests.py
@@ -3,16 +3,18 @@
 from __future__ import annotations
 
 import warnings
-from typing import Type, cast
+from typing import TYPE_CHECKING, Type, cast
 
 from dateutil import parser
 
 import singer_sdk.helpers._typing as th
 from singer_sdk import Tap
-from singer_sdk.streams.core import Stream
 
 from .templates import AttributeTestTemplate, StreamTestTemplate, TapTestTemplate
 
+if TYPE_CHECKING:
+    from singer_sdk.streams.core import Stream
+
 
 class TapCLIPrintsTest(TapTestTemplate):
     """Test that the tap is able to print standard metadata."""
diff --git a/singer_sdk/testing/templates.py b/singer_sdk/testing/templates.py
index 18a052993..5359ba08f 100644
--- a/singer_sdk/testing/templates.py
+++ b/singer_sdk/testing/templates.py
@@ -6,12 +6,13 @@
 import os
 import warnings
 from pathlib import Path
-from typing import Any
+from typing import TYPE_CHECKING, Any
 
-from singer_sdk.streams import Stream
+if TYPE_CHECKING:
+    from singer_sdk.streams import Stream
 
-from .config import SuiteConfig
-from .runners import TapTestRunner, TargetTestRunner
+    from .config import SuiteConfig
+    from .runners import TapTestRunner, TargetTestRunner
 
 
 class TestTemplate:
diff --git a/singer_sdk/typing.py b/singer_sdk/typing.py
index 646fa58e2..fe837ef7f 100644
--- a/singer_sdk/typing.py
+++ b/singer_sdk/typing.py
@@ -46,8 +46,8 @@
 from __future__ import annotations
 
 import json
-import sys
 from typing import (
+    TYPE_CHECKING,
     Any,
     Generator,
     Generic,
@@ -70,10 +70,14 @@
     get_datelike_property_type,
 )
 
-if sys.version_info >= (3, 10):
-    from typing import TypeAlias
-else:
-    from typing_extensions import TypeAlias
+if TYPE_CHECKING:
+    import sys
+
+    if sys.version_info >= (3, 10):
+        from typing import TypeAlias
+    else:
+        from typing_extensions import TypeAlias
+
 
 __all__ = [
     "extend_validator_with_defaults",
diff --git a/tests/conftest.py b/tests/conftest.py
index 2ec670257..0f5c2193a 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -6,9 +6,12 @@
 import pathlib
 import platform
 import shutil
+import typing as t
 
 import pytest
-from _pytest.config import Config
+
+if t.TYPE_CHECKING:
+    from _pytest.config import Config
 
 SYSTEMS = {"linux", "darwin", "windows"}
 
diff --git a/tests/core/rest/test_authenticators.py b/tests/core/rest/test_authenticators.py
index 3eb1c6b7c..fa42caef5 100644
--- a/tests/core/rest/test_authenticators.py
+++ b/tests/core/rest/test_authenticators.py
@@ -2,9 +2,10 @@
 
 from __future__ import annotations
 
+import typing as t
+
 import jwt
 import pytest
-import requests_mock
 from cryptography.hazmat.primitives.asymmetric.rsa import (
     RSAPrivateKey,
     RSAPublicKey,
@@ -19,8 +20,12 @@
 from requests.auth import HTTPProxyAuth, _basic_auth_str
 
 from singer_sdk.authenticators import OAuthAuthenticator, OAuthJWTAuthenticator
-from singer_sdk.streams import RESTStream
-from singer_sdk.tap_base import Tap
+
+if t.TYPE_CHECKING:
+    import requests_mock
+
+    from singer_sdk.streams import RESTStream
+    from singer_sdk.tap_base import Tap
 
 
 @pytest.mark.parametrize(
diff --git a/tests/core/test_jsonschema_helpers.py b/tests/core/test_jsonschema_helpers.py
index 28fc40d1b..6a4ef0ba6 100644
--- a/tests/core/test_jsonschema_helpers.py
+++ b/tests/core/test_jsonschema_helpers.py
@@ -3,12 +3,10 @@
 from __future__ import annotations
 
 import re
-from pathlib import Path
 from textwrap import dedent
-from typing import Callable
+from typing import TYPE_CHECKING, Callable
 
 import pytest
-from pytest_snapshot.plugin import Snapshot
 
 from singer_sdk.helpers._typing import (
     JSONSCHEMA_ANNOTATION_SECRET,
@@ -25,7 +23,6 @@
     is_string_array_type,
     is_string_type,
 )
-from singer_sdk.streams.core import Stream
 from singer_sdk.tap_base import Tap
 from singer_sdk.typing import (
     ArrayType,
@@ -55,6 +52,13 @@
     UUIDType,
 )
 
+if TYPE_CHECKING:
+    from pathlib import Path
+
+    from pytest_snapshot.plugin import Snapshot
+
+    from singer_sdk.streams.core import Stream
+
 TYPE_FN_CHECKS: set[Callable] = {
     is_array_type,
     is_boolean_type,
diff --git a/tests/core/test_mapper.py b/tests/core/test_mapper.py
index 00c3fb22f..06b885cf0 100644
--- a/tests/core/test_mapper.py
+++ b/tests/core/test_mapper.py
@@ -6,12 +6,11 @@
 import io
 import json
 import logging
+import typing as t
 from contextlib import redirect_stdout
-from pathlib import Path
 
 import pytest
 from freezegun import freeze_time
-from pytest_snapshot.plugin import Snapshot
 
 from singer_sdk._singerlib import Catalog
 from singer_sdk.exceptions import MapExpressionError
@@ -27,6 +26,11 @@
     StringType,
 )
 
+if t.TYPE_CHECKING:
+    from pathlib import Path
+
+    from pytest_snapshot.plugin import Snapshot
+
 
 @pytest.fixture
 def stream_map_config() -> dict:
diff --git a/tests/core/test_plugin_config.py b/tests/core/test_plugin_config.py
index 5b26d7442..8e23d4b54 100644
--- a/tests/core/test_plugin_config.py
+++ b/tests/core/test_plugin_config.py
@@ -3,12 +3,14 @@
 
 from __future__ import annotations
 
-from typing import Any
+from typing import TYPE_CHECKING, Any
 
-from singer_sdk.streams.core import Stream
 from singer_sdk.tap_base import Tap
 from singer_sdk.typing import BooleanType, PropertiesList, Property
 
+if TYPE_CHECKING:
+    from singer_sdk.streams.core import Stream
+
 SAMPLE_CONFIG: dict[str, Any] = {}
 
 
diff --git a/tests/core/test_typing.py b/tests/core/test_typing.py
index e08e31beb..60a223c1a 100644
--- a/tests/core/test_typing.py
+++ b/tests/core/test_typing.py
@@ -4,8 +4,7 @@
 
 import datetime
 import logging
-
-import pytest
+import typing as t
 
 from singer_sdk.helpers._typing import (
     TypeConformanceLevel,
@@ -20,6 +19,9 @@
     StringType,
 )
 
+if t.TYPE_CHECKING:
+    import pytest
+
 logger = logging.getLogger("log")
 
 
diff --git a/tests/samples/test_tap_sqlite.py b/tests/samples/test_tap_sqlite.py
index 958cc9ed2..b882f4c4c 100644
--- a/tests/samples/test_tap_sqlite.py
+++ b/tests/samples/test_tap_sqlite.py
@@ -1,17 +1,20 @@
 from __future__ import annotations
 
-from pathlib import Path
-from typing import cast
+from typing import TYPE_CHECKING, cast
 
 from samples.sample_target_csv.csv_target import SampleTargetCSV
 from singer_sdk import SQLStream
 from singer_sdk._singerlib import MetadataMapping, StreamMetadata
-from singer_sdk.tap_base import SQLTap
 from singer_sdk.testing import (
     get_standard_tap_tests,
     tap_to_target_sync_test,
 )
 
+if TYPE_CHECKING:
+    from pathlib import Path
+
+    from singer_sdk.tap_base import SQLTap
+
 
 def _discover_and_select_all(tap: SQLTap) -> None:
     """Discover catalog and auto-select all streams."""
diff --git a/tests/samples/test_target_sqlite.py b/tests/samples/test_target_sqlite.py
index 67bad4e75..4b83ce60d 100644
--- a/tests/samples/test_target_sqlite.py
+++ b/tests/samples/test_target_sqlite.py
@@ -4,6 +4,7 @@
 
 import json
 import sqlite3
+import typing as t
 from copy import deepcopy
 from io import StringIO
 from pathlib import Path
@@ -17,8 +18,6 @@
 from samples.sample_tap_sqlite import SQLiteTap
 from samples.sample_target_sqlite import SQLiteSink, SQLiteTarget
 from singer_sdk import typing as th
-from singer_sdk.tap_base import SQLTap
-from singer_sdk.target_base import SQLTarget
 from singer_sdk.testing import (
     _get_tap_catalog,
     tap_sync_test,
@@ -26,6 +25,10 @@
     target_sync_test,
 )
 
+if t.TYPE_CHECKING:
+    from singer_sdk.tap_base import SQLTap
+    from singer_sdk.target_base import SQLTarget
+
 
 @pytest.fixture
 def path_to_target_db(tmp_path: Path) -> Path: