diff --git a/doc/code/scoring/8_scorer_metrics.ipynb b/doc/code/scoring/8_scorer_metrics.ipynb
index a82bf84ec1..5dd26b483a 100644
--- a/doc/code/scoring/8_scorer_metrics.ipynb
+++ b/doc/code/scoring/8_scorer_metrics.ipynb
@@ -552,7 +552,7 @@
     ")\n",
     "\n",
     "if metrics:\n",
-    "    objective_metrics = cast(ObjectiveScorerMetrics, metrics)\n",
+    "    objective_metrics = cast(\"ObjectiveScorerMetrics\", metrics)\n",
     "    print(f\" Accuracy: {objective_metrics.accuracy}\")\n",
     "else:\n",
     "    raise RuntimeError(\"Evaluation failed, no metrics returned\")"
@@ -604,7 +604,7 @@
     ")\n",
     "\n",
     "if metrics:\n",
-    "    harm_metrics = cast(HarmScorerMetrics, metrics)\n",
+    "    harm_metrics = cast(\"HarmScorerMetrics\", metrics)\n",
     "    print(f'Metrics for harm category \"{harm_metrics.harm_category}\" created')\n",
     "else:\n",
     "    raise RuntimeError(\"Evaluation failed, no metrics returned\")"
diff --git a/doc/code/scoring/8_scorer_metrics.py b/doc/code/scoring/8_scorer_metrics.py
index 2a1443da32..3430556b13 100644
--- a/doc/code/scoring/8_scorer_metrics.py
+++ b/doc/code/scoring/8_scorer_metrics.py
@@ -286,7 +286,7 @@
 )
 
 if metrics:
-    objective_metrics = cast(ObjectiveScorerMetrics, metrics)
+    objective_metrics = cast("ObjectiveScorerMetrics", metrics)
     print(f" Accuracy: {objective_metrics.accuracy}")
 else:
     raise RuntimeError("Evaluation failed, no metrics returned")
@@ -318,7 +318,7 @@
 )
 
 if metrics:
-    harm_metrics = cast(HarmScorerMetrics, metrics)
+    harm_metrics = cast("HarmScorerMetrics", metrics)
     print(f'Metrics for harm category "{harm_metrics.harm_category}" created')
 else:
     raise RuntimeError("Evaluation failed, no metrics returned")
diff --git a/pyproject.toml b/pyproject.toml
index 9e9d492040..dfe62409a8 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -261,6 +261,7 @@ select = [
     "PIE",  # https://docs.astral.sh/ruff/rules/#flake8-pie-pie
     "RET",  # https://docs.astral.sh/ruff/rules/#flake8-return-ret
     "SIM",  # https://docs.astral.sh/ruff/rules/#flake8-simplify-sim
+    "TCH",  # https://docs.astral.sh/ruff/rules/#flake8-type-checking-tch
     "UP",  # https://docs.astral.sh/ruff/rules/#pyupgrade-up
     "W",  # https://docs.astral.sh/ruff/rules/#pycodestyle-w
 ]
@@ -293,7 +294,7 @@ notice-rgx = "Copyright \\(c\\) Microsoft Corporation\\.\\s*\\n.*Licensed under
 # Ignore D and DOC rules everywhere except for the pyrit/ directory
 "!pyrit/**.py" = ["D", "DOC"]
 # Ignore copyright check only in doc/ directory
-"doc/**" = ["CPY001"]
+"doc/**" = ["CPY001", "TCH"]
 # Temporary ignores for pyrit/ subdirectories until issue #1176
 # https://github.com/Azure/PyRIT/issues/1176 is fully resolved
 # TODO: Remove these ignores once the issues are fixed
diff --git a/pyrit/auth/azure_auth.py b/pyrit/auth/azure_auth.py
index a1f526545d..5192379382 100644
--- a/pyrit/auth/azure_auth.py
+++ b/pyrit/auth/azure_auth.py
@@ -5,7 +5,6 @@
 
 import logging
 import time
-from collections.abc import Callable
 from typing import TYPE_CHECKING, Any, Union, cast
 from urllib.parse import urlparse
 
@@ -24,6 +23,8 @@
 )
 
 if TYPE_CHECKING:
+    from collections.abc import Callable
+
     import azure.cognitiveservices.speech as speechsdk
 
 from pyrit.auth.auth_config import REFRESH_TOKEN_BEFORE_MSEC
@@ -136,7 +137,7 @@ def get_access_token_from_azure_cli(*, scope: str, tenant_id: str = "") -> str:
     try:
         credential = AzureCliCredential(tenant_id=tenant_id)
         token = credential.get_token(scope)
-        return cast(str, token.token)
+        return cast("str", token.token)
     except Exception as e:
         logger.error(f"Failed to obtain token for '{scope}' with tenant ID '{tenant_id}': {e}")
         raise
@@ -158,7 +159,7 @@ def get_access_token_from_azure_msi(*, client_id: str, scope: str) -> str:
     try:
         credential = ManagedIdentityCredential(client_id=client_id)
         token = credential.get_token(scope)
-        return cast(str, token.token)
+        return cast("str", token.token)
     except Exception as e:
         logger.error(f"Failed to obtain token for '{scope}' with client ID '{client_id}': {e}")
         raise
@@ -179,7 +180,7 @@ def get_access_token_from_msa_public_client(*, client_id: str, scope: str) -> st
     try:
         app = msal.PublicClientApplication(client_id)
         result = app.acquire_token_interactive(scopes=[scope])
-        return cast(str, result["access_token"])
+        return cast("str", result["access_token"])
     except Exception as e:
         logger.error(f"Failed to obtain token for '{scope}' with client ID '{client_id}': {e}")
         raise
diff --git a/pyrit/backend/mappers/attack_mappers.py b/pyrit/backend/mappers/attack_mappers.py
index e910c2b69c..c9c8dc7af2 100644
--- a/pyrit/backend/mappers/attack_mappers.py
+++ b/pyrit/backend/mappers/attack_mappers.py
@@ -12,9 +12,8 @@
 
 import mimetypes
 import uuid
-from collections.abc import Sequence
 from datetime import datetime, timezone
-from typing import Optional, cast
+from typing import TYPE_CHECKING, Optional, cast
 
 from pyrit.backend.models.attacks import (
     AddMessageRequest,
@@ -29,6 +28,9 @@
 from pyrit.models import MessagePiece as PyritMessagePiece
 from pyrit.models import Score as PyritScore
 
+if TYPE_CHECKING:
+    from collections.abc import Sequence
+
 # ============================================================================
 # Domain → DTO  (for API responses)
 # ============================================================================
@@ -194,9 +196,9 @@ def request_piece_to_pyrit_message_piece(
     return PyritMessagePiece(
         role=role,
         original_value=piece.original_value,
-        original_value_data_type=cast(PromptDataType, piece.data_type),
+        original_value_data_type=cast("PromptDataType", piece.data_type),
         converted_value=piece.converted_value or piece.original_value,
-        converted_value_data_type=cast(PromptDataType, piece.data_type),
+        converted_value_data_type=cast("PromptDataType", piece.data_type),
         conversation_id=conversation_id,
         sequence=sequence,
         prompt_metadata=metadata,
diff --git a/pyrit/cli/frontend_core.py b/pyrit/cli/frontend_core.py
index 809c3450ca..5c49525ec5 100644
--- a/pyrit/cli/frontend_core.py
+++ b/pyrit/cli/frontend_core.py
@@ -18,7 +18,6 @@
 import json
 import logging
 import sys
-from collections.abc import Callable, Sequence
 from pathlib import Path
 from typing import TYPE_CHECKING, Any, Optional
 
@@ -43,6 +42,8 @@ def cprint(text: str, color: str = None, attrs: list = None) -> None:  # type: i
 
 
 if TYPE_CHECKING:
+    from collections.abc import Callable, Sequence
+
     from pyrit.models.scenario_result import ScenarioResult
     from pyrit.registry import (
         InitializerMetadata,
diff --git a/pyrit/common/deprecation.py b/pyrit/common/deprecation.py
index b730f934fa..89da08bdb9 100644
--- a/pyrit/common/deprecation.py
+++ b/pyrit/common/deprecation.py
@@ -4,8 +4,10 @@
 from __future__ import annotations
 
 import warnings
-from collections.abc import Callable
-from typing import Any
+from typing import TYPE_CHECKING, Any
+
+if TYPE_CHECKING:
+    from collections.abc import Callable
 
 
 def print_deprecation_message(
diff --git a/pyrit/common/json_helper.py b/pyrit/common/json_helper.py
index 668b4335fb..17b49335de 100644
--- a/pyrit/common/json_helper.py
+++ b/pyrit/common/json_helper.py
@@ -12,7 +12,7 @@ def read_json(file: IO[Any]) -> list[dict[str, str]]:
     Returns:
         List[Dict[str, str]]: Parsed JSON content.
     """
-    return cast(list[dict[str, str]], json.load(file))
+    return cast("list[dict[str, str]]", json.load(file))
 
 
 def write_json(file: IO[Any], examples: list[dict[str, str]]) -> None:
diff --git a/pyrit/datasets/seed_datasets/remote/remote_dataset_loader.py b/pyrit/datasets/seed_datasets/remote/remote_dataset_loader.py
index ff7babb9bd..5cd9212846 100644
--- a/pyrit/datasets/seed_datasets/remote/remote_dataset_loader.py
+++ b/pyrit/datasets/seed_datasets/remote/remote_dataset_loader.py
@@ -92,7 +92,7 @@ def _read_cache(self, *, cache_file: Path, file_type: str) -> list[dict[str, str
         """
         self._validate_file_type(file_type)
         with cache_file.open("r", encoding="utf-8") as file:
-            return cast(list[dict[str, str]], FILE_TYPE_HANDLERS[file_type]["read"](file))
+            return cast("list[dict[str, str]]", FILE_TYPE_HANDLERS[file_type]["read"](file))
 
     def _write_cache(self, *, cache_file: Path, examples: list[dict[str, str]], file_type: str) -> None:
         """
@@ -130,9 +130,11 @@ def _fetch_from_public_url(self, *, source: str, file_type: str) -> list[dict[st
         if response.status_code == 200:
             if file_type in FILE_TYPE_HANDLERS:
                 if file_type == "json":
-                    return cast(list[dict[str, str]], FILE_TYPE_HANDLERS[file_type]["read"](io.StringIO(response.text)))
+                    return cast(
+                        "list[dict[str, str]]", FILE_TYPE_HANDLERS[file_type]["read"](io.StringIO(response.text))
+                    )
                 return cast(
-                    list[dict[str, str]],
+                    "list[dict[str, str]]",
                     FILE_TYPE_HANDLERS[file_type]["read"](io.StringIO("\n".join(response.text.splitlines()))),
                 )
             valid_types = ", ".join(FILE_TYPE_HANDLERS.keys())
@@ -155,7 +157,7 @@ def _fetch_from_file(self, *, source: str, file_type: str) -> list[dict[str, str
         """
         with open(source, encoding="utf-8") as file:
             if file_type in FILE_TYPE_HANDLERS:
-                return cast(list[dict[str, str]], FILE_TYPE_HANDLERS[file_type]["read"](file))
+                return cast("list[dict[str, str]]", FILE_TYPE_HANDLERS[file_type]["read"](file))
             valid_types = ", ".join(FILE_TYPE_HANDLERS.keys())
             raise ValueError(f"Invalid file_type. Expected one of: {valid_types}.")
 
diff --git a/pyrit/executor/attack/core/attack_strategy.py b/pyrit/executor/attack/core/attack_strategy.py
index a8a6ecec67..dac86d10aa 100644
--- a/pyrit/executor/attack/core/attack_strategy.py
+++ b/pyrit/executor/attack/core/attack_strategy.py
@@ -4,14 +4,13 @@
 from __future__ import annotations
 
 import dataclasses
-import logging
+import logging  # noqa: TC003
 import time
 from abc import ABC
 from dataclasses import dataclass, field
-from typing import Any, Generic, Optional, TypeVar, Union, overload
+from typing import TYPE_CHECKING, Any, Generic, Optional, TypeVar, Union, overload
 
 from pyrit.common.logger import logger
-from pyrit.executor.attack.core.attack_config import AttackScoringConfig
 from pyrit.executor.attack.core.attack_parameters import AttackParameters, AttackParamsT
 from pyrit.executor.core import (
     Strategy,
@@ -28,7 +27,10 @@
     ConversationReference,
     Message,
 )
-from pyrit.prompt_target import PromptTarget
+
+if TYPE_CHECKING:
+    from pyrit.executor.attack.core.attack_config import AttackScoringConfig
+    from pyrit.prompt_target import PromptTarget
 
 AttackStrategyContextT = TypeVar("AttackStrategyContextT", bound="AttackContext[Any]")
 AttackStrategyResultT = TypeVar("AttackStrategyResultT", bound="AttackResult")
diff --git a/pyrit/executor/attack/multi_turn/chunked_request.py b/pyrit/executor/attack/multi_turn/chunked_request.py
index 3b8592018a..392aa0333e 100644
--- a/pyrit/executor/attack/multi_turn/chunked_request.py
+++ b/pyrit/executor/attack/multi_turn/chunked_request.py
@@ -5,7 +5,7 @@
 import textwrap
 from dataclasses import dataclass, field
 from string import Formatter
-from typing import Any, Optional
+from typing import TYPE_CHECKING, Any, Optional
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.exceptions import ComponentRole, execution_context
@@ -28,7 +28,9 @@
 )
 from pyrit.prompt_normalizer import PromptNormalizer
 from pyrit.prompt_target import PromptTarget
-from pyrit.score import TrueFalseScorer
+
+if TYPE_CHECKING:
+    from pyrit.score import TrueFalseScorer
 
 logger = logging.getLogger(__name__)
 
diff --git a/pyrit/executor/attack/multi_turn/crescendo.py b/pyrit/executor/attack/multi_turn/crescendo.py
index d9af83e540..cacf51c6e4 100644
--- a/pyrit/executor/attack/multi_turn/crescendo.py
+++ b/pyrit/executor/attack/multi_turn/crescendo.py
@@ -3,10 +3,9 @@
 
 import json
 import logging
-from collections.abc import Callable
 from dataclasses import dataclass
 from pathlib import Path
-from typing import Any, Optional, Union, cast
+from typing import TYPE_CHECKING, Any, Optional, Union, cast
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import EXECUTOR_SEED_PROMPT_PATH
@@ -52,6 +51,9 @@
 )
 from pyrit.score.score_utils import normalize_score_to_float
 
+if TYPE_CHECKING:
+    from collections.abc import Callable
+
 logger = logging.getLogger(__name__)
 
 
@@ -78,7 +80,7 @@ def backtrack_count(self) -> int:
         Returns:
             int: The number of backtracks.
         """
-        return cast(int, self.metadata.get("backtrack_count", 0))
+        return cast("int", self.metadata.get("backtrack_count", 0))
 
     @backtrack_count.setter
     def backtrack_count(self, value: int) -> None:
diff --git a/pyrit/executor/attack/multi_turn/multi_turn_attack_strategy.py b/pyrit/executor/attack/multi_turn/multi_turn_attack_strategy.py
index 2bcdeb391e..5620c90032 100644
--- a/pyrit/executor/attack/multi_turn/multi_turn_attack_strategy.py
+++ b/pyrit/executor/attack/multi_turn/multi_turn_attack_strategy.py
@@ -3,11 +3,11 @@
 
 from __future__ import annotations
 
-import logging
+import logging  # noqa: TC003
 import uuid
 from abc import ABC
 from dataclasses import dataclass, field
-from typing import Any, Optional, TypeVar
+from typing import TYPE_CHECKING, Any, Optional, TypeVar
 
 from pyrit.common.logger import logger
 from pyrit.executor.attack.core.attack_parameters import AttackParameters, AttackParamsT
@@ -16,11 +16,13 @@
     AttackStrategy,
     AttackStrategyResultT,
 )
-from pyrit.models import (
-    Message,
-    Score,
-)
-from pyrit.prompt_target import PromptTarget
+
+if TYPE_CHECKING:
+    from pyrit.models import (
+        Message,
+        Score,
+    )
+    from pyrit.prompt_target import PromptTarget
 
 MultiTurnAttackStrategyContextT = TypeVar("MultiTurnAttackStrategyContextT", bound="MultiTurnAttackContext[Any]")
 
diff --git a/pyrit/executor/attack/multi_turn/red_teaming.py b/pyrit/executor/attack/multi_turn/red_teaming.py
index 26473e52ff..3c27842366 100644
--- a/pyrit/executor/attack/multi_turn/red_teaming.py
+++ b/pyrit/executor/attack/multi_turn/red_teaming.py
@@ -5,9 +5,8 @@
 
 import enum
 import logging
-from collections.abc import Callable
 from pathlib import Path
-from typing import Any, Optional, Union
+from typing import TYPE_CHECKING, Any, Optional, Union
 
 from pyrit.common.apply_defaults import REQUIRED_VALUE, apply_defaults
 from pyrit.common.path import EXECUTOR_RED_TEAM_PATH
@@ -38,7 +37,11 @@
     SeedPrompt,
 )
 from pyrit.prompt_normalizer import PromptNormalizer
-from pyrit.prompt_target.common.prompt_target import PromptTarget
+
+if TYPE_CHECKING:
+    from collections.abc import Callable
+
+    from pyrit.prompt_target.common.prompt_target import PromptTarget
 
 logger = logging.getLogger(__name__)
 
diff --git a/pyrit/executor/attack/multi_turn/simulated_conversation.py b/pyrit/executor/attack/multi_turn/simulated_conversation.py
index cb77e55984..40c3bb515a 100644
--- a/pyrit/executor/attack/multi_turn/simulated_conversation.py
+++ b/pyrit/executor/attack/multi_turn/simulated_conversation.py
@@ -11,8 +11,7 @@
 from __future__ import annotations
 
 import logging
-from pathlib import Path
-from typing import Optional, Union
+from typing import TYPE_CHECKING, Optional, Union
 
 from pyrit.executor.attack.core.attack_config import (
     AttackAdversarialConfig,
@@ -23,8 +22,12 @@
 from pyrit.memory import CentralMemory
 from pyrit.message_normalizer import ConversationContextNormalizer
 from pyrit.models import Message, SeedPrompt, SeedSimulatedConversation
-from pyrit.prompt_target import PromptChatTarget
-from pyrit.score import TrueFalseScorer
+
+if TYPE_CHECKING:
+    from pathlib import Path
+
+    from pyrit.prompt_target import PromptChatTarget
+    from pyrit.score import TrueFalseScorer
 
 logger = logging.getLogger(__name__)
 
diff --git a/pyrit/executor/attack/multi_turn/tree_of_attacks.py b/pyrit/executor/attack/multi_turn/tree_of_attacks.py
index 7414bcbdc6..1c9c0bc6ee 100644
--- a/pyrit/executor/attack/multi_turn/tree_of_attacks.py
+++ b/pyrit/executor/attack/multi_turn/tree_of_attacks.py
@@ -166,7 +166,7 @@ class TAPAttackResult(AttackResult):
     @property
     def tree_visualization(self) -> Optional[Tree]:
         """Get the tree visualization from metadata."""
-        return cast(Optional[Tree], self.metadata.get("tree_visualization", None))
+        return cast("Optional[Tree]", self.metadata.get("tree_visualization", None))
 
     @tree_visualization.setter
     def tree_visualization(self, value: Tree) -> None:
@@ -176,7 +176,7 @@ def tree_visualization(self, value: Tree) -> None:
     @property
     def nodes_explored(self) -> int:
         """Get the total number of nodes explored during the attack."""
-        return cast(int, self.metadata.get("nodes_explored", 0))
+        return cast("int", self.metadata.get("nodes_explored", 0))
 
     @nodes_explored.setter
     def nodes_explored(self, value: int) -> None:
@@ -186,7 +186,7 @@ def nodes_explored(self, value: int) -> None:
     @property
     def nodes_pruned(self) -> int:
         """Get the number of nodes pruned during the attack."""
-        return cast(int, self.metadata.get("nodes_pruned", 0))
+        return cast("int", self.metadata.get("nodes_pruned", 0))
 
     @nodes_pruned.setter
     def nodes_pruned(self, value: int) -> None:
@@ -196,7 +196,7 @@ def nodes_pruned(self, value: int) -> None:
     @property
     def max_depth_reached(self) -> int:
         """Get the maximum depth reached in the attack tree."""
-        return cast(int, self.metadata.get("max_depth_reached", 0))
+        return cast("int", self.metadata.get("max_depth_reached", 0))
 
     @max_depth_reached.setter
     def max_depth_reached(self, value: int) -> None:
@@ -206,7 +206,7 @@ def max_depth_reached(self, value: int) -> None:
     @property
     def auxiliary_scores_summary(self) -> dict[str, float]:
         """Get a summary of auxiliary scores from the best node."""
-        return cast(dict[str, float], self.metadata.get("auxiliary_scores_summary", {}))
+        return cast("dict[str, float]", self.metadata.get("auxiliary_scores_summary", {}))
 
     @auxiliary_scores_summary.setter
     def auxiliary_scores_summary(self, value: dict[str, float]) -> None:
@@ -216,7 +216,7 @@ def auxiliary_scores_summary(self, value: dict[str, float]) -> None:
     @property
     def best_adversarial_conversation_id(self) -> Optional[str]:
         """Get the adversarial conversation ID for the best-scoring branch."""
-        return cast(Optional[str], self.metadata.get("best_adversarial_conversation_id", None))
+        return cast("Optional[str]", self.metadata.get("best_adversarial_conversation_id", None))
 
     @best_adversarial_conversation_id.setter
     def best_adversarial_conversation_id(self, value: Optional[str]) -> None:
@@ -493,7 +493,7 @@ async def _generate_adversarial_prompt_async(self, objective: str) -> str:
         prompt = await self._generate_red_teaming_prompt_async(objective=objective)
         self.last_prompt_sent = prompt
         logger.debug(f"Node {self.node_id}: Generated adversarial prompt")
-        return cast(str, prompt)
+        return cast("str", prompt)
 
     async def _send_prompt_to_target_async(self, prompt: str) -> Message:
         """
@@ -1136,7 +1136,7 @@ def _parse_red_teaming_response(self, red_teaming_response: str) -> str:
             raise InvalidJsonException(message="The response from the red teaming chat is not in JSON format.")
 
         try:
-            return cast(str, red_teaming_response_dict["prompt"])
+            return cast("str", red_teaming_response_dict["prompt"])
         except KeyError:
             logger.error(f"The response from the red teaming chat does not contain a prompt: {red_teaming_response}")
             raise InvalidJsonException(message="The response from the red teaming chat does not contain a prompt.")
@@ -1838,7 +1838,7 @@ def _create_attack_node(
                 generate adversarial prompts and evaluate responses.
         """
         node = _TreeOfAttacksNode(
-            objective_target=cast(PromptChatTarget, self._objective_target),
+            objective_target=cast("PromptChatTarget", self._objective_target),
             adversarial_chat=self._adversarial_chat,
             adversarial_chat_seed_prompt=self._adversarial_chat_seed_prompt,
             adversarial_chat_system_seed_prompt=self._adversarial_chat_system_seed_prompt,
diff --git a/pyrit/executor/attack/single_turn/many_shot_jailbreak.py b/pyrit/executor/attack/single_turn/many_shot_jailbreak.py
index 4aae80cf90..500dacb898 100644
--- a/pyrit/executor/attack/single_turn/many_shot_jailbreak.py
+++ b/pyrit/executor/attack/single_turn/many_shot_jailbreak.py
@@ -33,7 +33,7 @@ def fetch_many_shot_jailbreaking_dataset() -> list[dict[str, str]]:
     source = "https://raw.githubusercontent.com/KutalVolkan/many-shot-jailbreaking-dataset/5eac855/examples.json"
     response = requests.get(source)
     response.raise_for_status()
-    return cast(list[dict[str, str]], response.json())
+    return cast("list[dict[str, str]]", response.json())
 
 
 class ManyShotJailbreakAttack(PromptSendingAttack):
diff --git a/pyrit/executor/attack/single_turn/single_turn_attack_strategy.py b/pyrit/executor/attack/single_turn/single_turn_attack_strategy.py
index e3c0560bf5..508f83db1c 100644
--- a/pyrit/executor/attack/single_turn/single_turn_attack_strategy.py
+++ b/pyrit/executor/attack/single_turn/single_turn_attack_strategy.py
@@ -3,17 +3,19 @@
 
 from __future__ import annotations
 
-import logging
+import logging  # noqa: TC003
 import uuid
 from abc import ABC
 from dataclasses import dataclass, field
-from typing import Any, Optional, Union
+from typing import TYPE_CHECKING, Any, Optional, Union
 
 from pyrit.common.logger import logger
 from pyrit.executor.attack.core.attack_parameters import AttackParameters, AttackParamsT
 from pyrit.executor.attack.core.attack_strategy import AttackContext, AttackStrategy
 from pyrit.models import AttackResult
-from pyrit.prompt_target import PromptTarget
+
+if TYPE_CHECKING:
+    from pyrit.prompt_target import PromptTarget
 
 
 @dataclass
diff --git a/pyrit/executor/benchmark/fairness_bias.py b/pyrit/executor/benchmark/fairness_bias.py
index f728d27dba..39f8ce68f6 100644
--- a/pyrit/executor/benchmark/fairness_bias.py
+++ b/pyrit/executor/benchmark/fairness_bias.py
@@ -369,7 +369,7 @@ def get_last_context(self) -> Optional[FairnessBiasBenchmarkContext]:
             Optional[FairnessBiasBenchmarkContext]: The context from the most recent execution,
                 or None if no execution has occurred
         """
-        return cast(Optional[FairnessBiasBenchmarkContext], getattr(self, "_last_context", None))
+        return cast("Optional[FairnessBiasBenchmarkContext]", getattr(self, "_last_context", None))
 
     async def _teardown_async(self, *, context: FairnessBiasBenchmarkContext) -> None:
         """
diff --git a/pyrit/executor/core/strategy.py b/pyrit/executor/core/strategy.py
index 383465aacf..29fd4a8322 100644
--- a/pyrit/executor/core/strategy.py
+++ b/pyrit/executor/core/strategy.py
@@ -8,18 +8,20 @@
 import logging
 import uuid
 from abc import ABC, abstractmethod
-from collections.abc import AsyncIterator, MutableMapping
 from contextlib import asynccontextmanager
 from copy import deepcopy
 from dataclasses import dataclass
 from enum import Enum
-from typing import Any, Generic, Optional, TypeVar
+from typing import TYPE_CHECKING, Any, Generic, Optional, TypeVar
 
 from pyrit.common import default_values
 from pyrit.common.logger import logger
 from pyrit.exceptions import clear_execution_context, get_execution_context
 from pyrit.models import StrategyResultT
 
+if TYPE_CHECKING:
+    from collections.abc import AsyncIterator, MutableMapping
+
 StrategyContextT = TypeVar("StrategyContextT", bound="StrategyContext")
 
 
diff --git a/pyrit/executor/promptgen/anecdoctor.py b/pyrit/executor/promptgen/anecdoctor.py
index adf3c97628..208c4040d7 100644
--- a/pyrit/executor/promptgen/anecdoctor.py
+++ b/pyrit/executor/promptgen/anecdoctor.py
@@ -7,7 +7,7 @@
 import uuid
 from dataclasses import dataclass, field
 from pathlib import Path
-from typing import Any, Optional, Union, overload
+from typing import TYPE_CHECKING, Any, Optional, Union, overload
 
 import yaml
 
@@ -24,7 +24,9 @@
     Message,
 )
 from pyrit.prompt_normalizer import PromptNormalizer
-from pyrit.prompt_target import PromptChatTarget
+
+if TYPE_CHECKING:
+    from pyrit.prompt_target import PromptChatTarget
 
 logger = logging.getLogger(__name__)
 
diff --git a/pyrit/executor/promptgen/core/prompt_generator_strategy.py b/pyrit/executor/promptgen/core/prompt_generator_strategy.py
index 39eb0b6b31..29068611ba 100644
--- a/pyrit/executor/promptgen/core/prompt_generator_strategy.py
+++ b/pyrit/executor/promptgen/core/prompt_generator_strategy.py
@@ -3,7 +3,7 @@
 
 from __future__ import annotations
 
-import logging
+import logging  # noqa: TC003
 from abc import ABC
 from dataclasses import dataclass
 from typing import Optional, TypeVar
diff --git a/pyrit/executor/promptgen/fuzzer/fuzzer.py b/pyrit/executor/promptgen/fuzzer/fuzzer.py
index b86473188e..ebd67c2bda 100644
--- a/pyrit/executor/promptgen/fuzzer/fuzzer.py
+++ b/pyrit/executor/promptgen/fuzzer/fuzzer.py
@@ -8,7 +8,7 @@
 import textwrap
 import uuid
 from dataclasses import dataclass, field
-from typing import Any, Optional, Union, overload
+from typing import TYPE_CHECKING, Any, Optional, Union, overload
 
 import numpy as np
 from colorama import Fore, Style
@@ -23,7 +23,6 @@
     PromptGeneratorStrategyContext,
     PromptGeneratorStrategyResult,
 )
-from pyrit.executor.promptgen.fuzzer.fuzzer_converter_base import FuzzerConverter
 from pyrit.identifiers import ComponentIdentifier, Identifiable
 from pyrit.memory import CentralMemory
 from pyrit.models import (
@@ -33,9 +32,12 @@
     SeedPrompt,
 )
 from pyrit.prompt_normalizer import NormalizerRequest, PromptNormalizer
-from pyrit.prompt_target import PromptChatTarget, PromptTarget
 from pyrit.score import FloatScaleThresholdScorer, Scorer, SelfAskScaleScorer
 
+if TYPE_CHECKING:
+    from pyrit.executor.promptgen.fuzzer.fuzzer_converter_base import FuzzerConverter
+    from pyrit.prompt_target import PromptChatTarget, PromptTarget
+
 logger = logging.getLogger(__name__)
 
 
diff --git a/pyrit/executor/workflow/core/workflow_strategy.py b/pyrit/executor/workflow/core/workflow_strategy.py
index 695d3b3aae..80dc3a298d 100644
--- a/pyrit/executor/workflow/core/workflow_strategy.py
+++ b/pyrit/executor/workflow/core/workflow_strategy.py
@@ -3,7 +3,7 @@
 
 from __future__ import annotations
 
-import logging
+import logging  # noqa: TC003
 from abc import ABC
 from dataclasses import dataclass
 from typing import Optional, TypeVar
diff --git a/pyrit/memory/azure_sql_memory.py b/pyrit/memory/azure_sql_memory.py
index 6fe26f445b..6702f22407 100644
--- a/pyrit/memory/azure_sql_memory.py
+++ b/pyrit/memory/azure_sql_memory.py
@@ -6,9 +6,8 @@
 from collections.abc import MutableSequence, Sequence
 from contextlib import closing
 from datetime import datetime, timedelta, timezone
-from typing import Any, Optional, TypeVar, Union
+from typing import TYPE_CHECKING, Any, Optional, TypeVar, Union
 
-from azure.core.credentials import AccessToken
 from sqlalchemy import and_, create_engine, event, exists, text
 from sqlalchemy.engine.base import Engine
 from sqlalchemy.exc import SQLAlchemyError
@@ -31,6 +30,9 @@
     MessagePiece,
 )
 
+if TYPE_CHECKING:
+    from azure.core.credentials import AccessToken
+
 logger = logging.getLogger(__name__)
 
 Model = TypeVar("Model")
diff --git a/pyrit/memory/memory_interface.py b/pyrit/memory/memory_interface.py
index c3cea3b483..67e6dcfb6d 100644
--- a/pyrit/memory/memory_interface.py
+++ b/pyrit/memory/memory_interface.py
@@ -11,12 +11,11 @@
 from contextlib import closing
 from datetime import datetime
 from pathlib import Path
-from typing import Any, Optional, TypeVar, Union
+from typing import TYPE_CHECKING, Any, Optional, TypeVar, Union
 
 from sqlalchemy import MetaData, and_, or_
 from sqlalchemy.engine.base import Engine
 from sqlalchemy.orm.attributes import InstrumentedAttribute
-from sqlalchemy.sql.elements import ColumnElement
 
 from pyrit.common.path import DB_DATA_PATH
 from pyrit.memory.memory_embedding import (
@@ -50,6 +49,9 @@
     sort_message_pieces,
 )
 
+if TYPE_CHECKING:
+    from sqlalchemy.sql.elements import ColumnElement
+
 logger = logging.getLogger(__name__)
 
 
diff --git a/pyrit/message_normalizer/chat_message_normalizer.py b/pyrit/message_normalizer/chat_message_normalizer.py
index 3a11938edf..0ebfa37946 100644
--- a/pyrit/message_normalizer/chat_message_normalizer.py
+++ b/pyrit/message_normalizer/chat_message_normalizer.py
@@ -4,7 +4,7 @@
 import base64
 import json
 import os
-from typing import Any, Union
+from typing import TYPE_CHECKING, Any, Union
 
 from pyrit.common import convert_local_image_to_data_url
 from pyrit.message_normalizer.message_normalizer import (
@@ -14,9 +14,11 @@
     apply_system_message_behavior,
 )
 from pyrit.models import ChatMessage, DataTypeSerializer, Message
-from pyrit.models.literals import ChatMessageRole
 from pyrit.models.message_piece import MessagePiece
 
+if TYPE_CHECKING:
+    from pyrit.models.literals import ChatMessageRole
+
 # Supported audio formats for OpenAI input_audio
 # https://platform.openai.com/docs/guides/audio
 SUPPORTED_AUDIO_FORMATS = {".wav": "wav", ".mp3": "mp3"}
diff --git a/pyrit/message_normalizer/tokenizer_template_normalizer.py b/pyrit/message_normalizer/tokenizer_template_normalizer.py
index db31126efd..bd7e81b02f 100644
--- a/pyrit/message_normalizer/tokenizer_template_normalizer.py
+++ b/pyrit/message_normalizer/tokenizer_template_normalizer.py
@@ -122,10 +122,10 @@ def _load_tokenizer(model_name: str, token: Optional[str]) -> "PreTrainedTokeniz
         Returns:
             The loaded tokenizer.
         """
-        from transformers import AutoTokenizer, PreTrainedTokenizerBase
+        from transformers import AutoTokenizer
 
         return cast(
-            PreTrainedTokenizerBase,
+            "PreTrainedTokenizerBase",
             AutoTokenizer.from_pretrained(model_name, token=token or None),  # type: ignore[no-untyped-call, unused-ignore]
         )
 
diff --git a/pyrit/models/attack_result.py b/pyrit/models/attack_result.py
index e40d0d228b..cd9efff5ce 100644
--- a/pyrit/models/attack_result.py
+++ b/pyrit/models/attack_result.py
@@ -5,14 +5,16 @@
 
 from dataclasses import dataclass, field
 from enum import Enum
-from typing import Any, Optional, TypeVar
+from typing import TYPE_CHECKING, Any, Optional, TypeVar
 
-from pyrit.identifiers.component_identifier import ComponentIdentifier
-from pyrit.models.conversation_reference import ConversationReference, ConversationType
-from pyrit.models.message_piece import MessagePiece
-from pyrit.models.score import Score
 from pyrit.models.strategy_result import StrategyResult
 
+if TYPE_CHECKING:
+    from pyrit.identifiers.component_identifier import ComponentIdentifier
+    from pyrit.models.conversation_reference import ConversationReference, ConversationType
+    from pyrit.models.message_piece import MessagePiece
+    from pyrit.models.score import Score
+
 AttackResultT = TypeVar("AttackResultT", bound="AttackResult")
 
 
diff --git a/pyrit/models/data_type_serializer.py b/pyrit/models/data_type_serializer.py
index ca2473c278..c2004160fb 100644
--- a/pyrit/models/data_type_serializer.py
+++ b/pyrit/models/data_type_serializer.py
@@ -17,11 +17,11 @@
 import aiofiles
 
 from pyrit.common.path import DB_DATA_PATH
-from pyrit.models.literals import PromptDataType
 from pyrit.models.storage_io import DiskStorageIO, StorageIO
 
 if TYPE_CHECKING:
     from pyrit.memory import MemoryInterface
+    from pyrit.models.literals import PromptDataType
 
 # Define allowed categories for validation
 AllowedCategories = Literal["seed-prompt-entries", "prompt-memory-entries"]
diff --git a/pyrit/models/message.py b/pyrit/models/message.py
index 91f604f2bc..ba6c09c937 100644
--- a/pyrit/models/message.py
+++ b/pyrit/models/message.py
@@ -6,14 +6,17 @@
 import copy
 import uuid
 import warnings
-from collections.abc import MutableSequence, Sequence
 from datetime import datetime
-from typing import Optional, Union
+from typing import TYPE_CHECKING, Optional, Union
 
 from pyrit.common.utils import combine_dict
-from pyrit.models.literals import ChatMessageRole, PromptDataType, PromptResponseError
 from pyrit.models.message_piece import MessagePiece
 
+if TYPE_CHECKING:
+    from collections.abc import MutableSequence, Sequence
+
+    from pyrit.models.literals import ChatMessageRole, PromptDataType, PromptResponseError
+
 
 class Message:
     """
diff --git a/pyrit/models/message_piece.py b/pyrit/models/message_piece.py
index 9f1a0ea30e..62a6e4890d 100644
--- a/pyrit/models/message_piece.py
+++ b/pyrit/models/message_piece.py
@@ -5,12 +5,14 @@
 
 import uuid
 from datetime import datetime
-from typing import Any, Literal, Optional, Union, get_args
+from typing import TYPE_CHECKING, Any, Literal, Optional, Union, get_args
 from uuid import uuid4
 
 from pyrit.identifiers.component_identifier import ComponentIdentifier
 from pyrit.models.literals import ChatMessageRole, PromptDataType, PromptResponseError
-from pyrit.models.score import Score
+
+if TYPE_CHECKING:
+    from pyrit.models.score import Score
 
 Originator = Literal["attack", "converter", "undefined", "scorer"]
 
diff --git a/pyrit/models/seeds/seed.py b/pyrit/models/seeds/seed.py
index 25129a4091..c506a49a12 100644
--- a/pyrit/models/seeds/seed.py
+++ b/pyrit/models/seeds/seed.py
@@ -13,16 +13,19 @@
 import logging
 import re
 import uuid
-from collections.abc import Iterator, Sequence
 from dataclasses import dataclass, field
 from datetime import datetime
-from pathlib import Path
-from typing import Any, Optional, TypeVar, Union
+from typing import TYPE_CHECKING, Any, Optional, TypeVar, Union
 
 from jinja2 import BaseLoader, Environment, StrictUndefined, Template, Undefined
 
 from pyrit.common.yaml_loadable import YamlLoadable
-from pyrit.models.literals import PromptDataType
+
+if TYPE_CHECKING:
+    from collections.abc import Iterator, Sequence
+    from pathlib import Path
+
+    from pyrit.models.literals import PromptDataType
 
 logger = logging.getLogger(__name__)
 
diff --git a/pyrit/models/seeds/seed_attack_group.py b/pyrit/models/seeds/seed_attack_group.py
index 3a71c75625..b994f5108e 100644
--- a/pyrit/models/seeds/seed_attack_group.py
+++ b/pyrit/models/seeds/seed_attack_group.py
@@ -9,13 +9,16 @@
 
 from __future__ import annotations
 
-from collections.abc import Sequence
-from typing import Any, Union
+from typing import TYPE_CHECKING, Any, Union
 
-from pyrit.models.seeds.seed import Seed
 from pyrit.models.seeds.seed_group import SeedGroup
 from pyrit.models.seeds.seed_objective import SeedObjective
 
+if TYPE_CHECKING:
+    from collections.abc import Sequence
+
+    from pyrit.models.seeds.seed import Seed
+
 
 class SeedAttackGroup(SeedGroup):
     """
diff --git a/pyrit/models/seeds/seed_attack_technique_group.py b/pyrit/models/seeds/seed_attack_technique_group.py
index 0d7dd91693..7f5e16d28e 100644
--- a/pyrit/models/seeds/seed_attack_technique_group.py
+++ b/pyrit/models/seeds/seed_attack_technique_group.py
@@ -11,12 +11,15 @@
 
 from __future__ import annotations
 
-from collections.abc import Sequence
-from typing import Any, Union
+from typing import TYPE_CHECKING, Any, Union
 
-from pyrit.models.seeds.seed import Seed
 from pyrit.models.seeds.seed_group import SeedGroup
 
+if TYPE_CHECKING:
+    from collections.abc import Sequence
+
+    from pyrit.models.seeds.seed import Seed
+
 
 class SeedAttackTechniqueGroup(SeedGroup):
     """
diff --git a/pyrit/models/seeds/seed_dataset.py b/pyrit/models/seeds/seed_dataset.py
index 6ae4ff91ce..413f216a97 100644
--- a/pyrit/models/seeds/seed_dataset.py
+++ b/pyrit/models/seeds/seed_dataset.py
@@ -12,22 +12,25 @@
 import uuid
 import warnings
 from collections import defaultdict
-from collections.abc import Sequence
 from datetime import datetime
-from typing import Any, Optional, Union
-
-from pydantic.types import PositiveInt
+from typing import TYPE_CHECKING, Any, Optional, Union
 
 from pyrit.common import utils
 from pyrit.common.yaml_loadable import YamlLoadable
-from pyrit.models.literals import PromptDataType, SeedType
-from pyrit.models.seeds.seed import Seed
 from pyrit.models.seeds.seed_attack_group import SeedAttackGroup
 from pyrit.models.seeds.seed_group import SeedGroup
 from pyrit.models.seeds.seed_objective import SeedObjective
 from pyrit.models.seeds.seed_prompt import SeedPrompt
 from pyrit.models.seeds.seed_simulated_conversation import SeedSimulatedConversation
 
+if TYPE_CHECKING:
+    from collections.abc import Sequence
+
+    from pydantic.types import PositiveInt
+
+    from pyrit.models.literals import PromptDataType, SeedType
+    from pyrit.models.seeds.seed import Seed
+
 logger = logging.getLogger(__name__)
 
 
diff --git a/pyrit/models/seeds/seed_group.py b/pyrit/models/seeds/seed_group.py
index cff0ca81ee..0c25e41ae0 100644
--- a/pyrit/models/seeds/seed_group.py
+++ b/pyrit/models/seeds/seed_group.py
@@ -14,8 +14,7 @@
 import uuid
 import warnings
 from collections import defaultdict
-from collections.abc import Sequence
-from typing import Any, Optional, Union
+from typing import TYPE_CHECKING, Any, Optional, Union
 
 from pyrit.common.yaml_loadable import YamlLoadable
 from pyrit.models.message import Message
@@ -25,6 +24,9 @@
 from pyrit.models.seeds.seed_prompt import SeedPrompt
 from pyrit.models.seeds.seed_simulated_conversation import SeedSimulatedConversation
 
+if TYPE_CHECKING:
+    from collections.abc import Sequence
+
 logger = logging.getLogger(__name__)
 
 
diff --git a/pyrit/models/seeds/seed_objective.py b/pyrit/models/seeds/seed_objective.py
index dde787ea05..85010e404e 100644
--- a/pyrit/models/seeds/seed_objective.py
+++ b/pyrit/models/seeds/seed_objective.py
@@ -9,12 +9,14 @@
 
 import logging
 from dataclasses import dataclass
-from pathlib import Path
-from typing import Optional, Union
+from typing import TYPE_CHECKING, Optional, Union
 
 from pyrit.common.path import PATHS_DICT
 from pyrit.models.seeds.seed import Seed
 
+if TYPE_CHECKING:
+    from pathlib import Path
+
 logger = logging.getLogger(__name__)
 
 
diff --git a/pyrit/models/seeds/seed_prompt.py b/pyrit/models/seeds/seed_prompt.py
index 63859531af..b507cf3173 100644
--- a/pyrit/models/seeds/seed_prompt.py
+++ b/pyrit/models/seeds/seed_prompt.py
@@ -9,21 +9,22 @@
 
 import logging
 import os
-import uuid
-from collections.abc import Sequence
 from dataclasses import dataclass, field
-from pathlib import Path
 from typing import TYPE_CHECKING, Optional, Union
 
 from tinytag import TinyTag
 
 from pyrit.common.path import PATHS_DICT
 from pyrit.models import DataTypeSerializer
-from pyrit.models.literals import ChatMessageRole, PromptDataType
 from pyrit.models.seeds.seed import Seed
 
 if TYPE_CHECKING:
+    import uuid
+    from collections.abc import Sequence
+    from pathlib import Path
+
     from pyrit.models import Message
+    from pyrit.models.literals import ChatMessageRole, PromptDataType
 
 logger = logging.getLogger(__name__)
 
diff --git a/pyrit/prompt_converter/add_image_text_converter.py b/pyrit/prompt_converter/add_image_text_converter.py
index 8488e1eaf2..8cbf4d8671 100644
--- a/pyrit/prompt_converter/add_image_text_converter.py
+++ b/pyrit/prompt_converter/add_image_text_converter.py
@@ -98,7 +98,7 @@ def _load_font(self) -> FreeTypeFont:
             font = ImageFont.truetype(self._font_name, self._font_size)
         except OSError:
             logger.warning(f"Cannot open font resource: {self._font_name}. Using default font.")
-            font = cast(FreeTypeFont, ImageFont.load_default())
+            font = cast("FreeTypeFont", ImageFont.load_default())
         return font
 
     def _add_text_to_image(self, text: str) -> Image.Image:
diff --git a/pyrit/prompt_converter/add_text_image_converter.py b/pyrit/prompt_converter/add_text_image_converter.py
index e1cf11f669..91fd265e57 100644
--- a/pyrit/prompt_converter/add_text_image_converter.py
+++ b/pyrit/prompt_converter/add_text_image_converter.py
@@ -100,7 +100,7 @@ def _load_font(self) -> FreeTypeFont:
             font = ImageFont.truetype(self._font_name, self._font_size)
         except OSError:
             logger.warning(f"Cannot open font resource: {self._font_name}. Using default font.")
-            font = cast(FreeTypeFont, ImageFont.load_default())
+            font = cast("FreeTypeFont", ImageFont.load_default())
         return font
 
     def _add_text_to_image(self, image: Image.Image) -> Image.Image:
diff --git a/pyrit/prompt_converter/binary_converter.py b/pyrit/prompt_converter/binary_converter.py
index 700cfd29b5..12b139f22a 100644
--- a/pyrit/prompt_converter/binary_converter.py
+++ b/pyrit/prompt_converter/binary_converter.py
@@ -4,12 +4,14 @@
 from __future__ import annotations
 
 from enum import Enum
-from typing import Optional
+from typing import TYPE_CHECKING, Optional
 
-from pyrit.identifiers import ComponentIdentifier
-from pyrit.prompt_converter.text_selection_strategy import WordSelectionStrategy
 from pyrit.prompt_converter.word_level_converter import WordLevelConverter
 
+if TYPE_CHECKING:
+    from pyrit.identifiers import ComponentIdentifier
+    from pyrit.prompt_converter.text_selection_strategy import WordSelectionStrategy
+
 
 class BinaryConverter(WordLevelConverter):
     """
diff --git a/pyrit/prompt_converter/word_doc_converter.py b/pyrit/prompt_converter/word_doc_converter.py
index 48fea1d2ba..05c67f7ca4 100644
--- a/pyrit/prompt_converter/word_doc_converter.py
+++ b/pyrit/prompt_converter/word_doc_converter.py
@@ -7,17 +7,20 @@
 import hashlib
 from dataclasses import dataclass
 from io import BytesIO
-from pathlib import Path
-from typing import Any, Optional
+from typing import TYPE_CHECKING, Any, Optional
 
 from docx import Document
 
 from pyrit.common.logger import logger
-from pyrit.identifiers import ComponentIdentifier
 from pyrit.models import PromptDataType, SeedPrompt, data_serializer_factory
-from pyrit.models.data_type_serializer import DataTypeSerializer
 from pyrit.prompt_converter.prompt_converter import ConverterResult, PromptConverter
 
+if TYPE_CHECKING:
+    from pathlib import Path
+
+    from pyrit.identifiers import ComponentIdentifier
+    from pyrit.models.data_type_serializer import DataTypeSerializer
+
 
 @dataclass
 class _WordDocInjectionConfig:
diff --git a/pyrit/prompt_target/hugging_face/hugging_face_chat_target.py b/pyrit/prompt_target/hugging_face/hugging_face_chat_target.py
index 6eff804f66..15f1cc80b7 100644
--- a/pyrit/prompt_target/hugging_face/hugging_face_chat_target.py
+++ b/pyrit/prompt_target/hugging_face/hugging_face_chat_target.py
@@ -331,7 +331,7 @@ async def send_prompt_async(self, *, message: Message) -> list[Message]:
 
             # Decode the assistant's response from the generated token IDs
             assistant_response = cast(
-                str,
+                "str",
                 self.tokenizer.decode(generated_tokens, skip_special_tokens=self.skip_special_tokens),
             ).strip()
 
@@ -372,7 +372,7 @@ def _apply_chat_template(self, messages: list[dict[str, str]]) -> Any:
 
             # Apply the chat template to format and tokenize the messages
             return cast(
-                BatchEncoding,
+                "BatchEncoding",
                 self.tokenizer.apply_chat_template(
                     messages,
                     tokenize=True,
diff --git a/pyrit/prompt_target/openai/openai_response_target.py b/pyrit/prompt_target/openai/openai_response_target.py
index d61923bc32..c338a80710 100644
--- a/pyrit/prompt_target/openai/openai_response_target.py
+++ b/pyrit/prompt_target/openai/openai_response_target.py
@@ -720,7 +720,7 @@ def _find_last_pending_tool_call(self, reply: Message) -> Optional[dict[str, Any
                     continue
                 if isinstance(section, dict) and section.get("type") == "function_call":
                     # Do NOT skip function_call even if status == "completed" — we still need to emit the output.
-                    return cast(dict[str, Any], section)
+                    return cast("dict[str, Any]", section)
         return None
 
     async def _execute_call_section(self, tool_call_section: dict[str, Any]) -> dict[str, Any]:
diff --git a/pyrit/prompt_target/openai/openai_video_target.py b/pyrit/prompt_target/openai/openai_video_target.py
index 3e915a37d5..276bbfc2c7 100644
--- a/pyrit/prompt_target/openai/openai_video_target.py
+++ b/pyrit/prompt_target/openai/openai_video_target.py
@@ -93,7 +93,9 @@ def __init__(
         """
         super().__init__(**kwargs)
 
-        self._n_seconds: VideoSeconds = cast(VideoSeconds, str(n_seconds)) if isinstance(n_seconds, int) else n_seconds
+        self._n_seconds: VideoSeconds = (
+            cast("VideoSeconds", str(n_seconds)) if isinstance(n_seconds, int) else n_seconds
+        )
         self._validate_duration()
         self._size: VideoSize = self._validate_resolution(resolution_dimensions=resolution_dimensions)
 
diff --git a/pyrit/registry/instance_registries/base_instance_registry.py b/pyrit/registry/instance_registries/base_instance_registry.py
index 55946abc89..558ef70157 100644
--- a/pyrit/registry/instance_registries/base_instance_registry.py
+++ b/pyrit/registry/instance_registries/base_instance_registry.py
@@ -16,12 +16,14 @@
 from __future__ import annotations
 
 from abc import ABC, abstractmethod
-from collections.abc import Iterator
-from typing import Any, Generic, Optional, TypeVar
+from typing import TYPE_CHECKING, Any, Generic, Optional, TypeVar
 
 from pyrit.identifiers import ComponentIdentifier
 from pyrit.registry.base import RegistryProtocol
 
+if TYPE_CHECKING:
+    from collections.abc import Iterator
+
 T = TypeVar("T")  # The type of instances stored
 MetadataT = TypeVar("MetadataT", bound=ComponentIdentifier)
 
diff --git a/pyrit/scenario/core/dataset_configuration.py b/pyrit/scenario/core/dataset_configuration.py
index 70d9256b73..2b78ced2f9 100644
--- a/pyrit/scenario/core/dataset_configuration.py
+++ b/pyrit/scenario/core/dataset_configuration.py
@@ -11,14 +11,15 @@
 from __future__ import annotations
 
 import random
-from collections.abc import Sequence
 from typing import TYPE_CHECKING, Optional
 
 from pyrit.memory import CentralMemory
 from pyrit.models import SeedAttackGroup, SeedGroup
-from pyrit.models.seeds.seed import Seed
 
 if TYPE_CHECKING:
+    from collections.abc import Sequence
+
+    from pyrit.models.seeds.seed import Seed
     from pyrit.scenario.core.scenario_strategy import ScenarioCompositeStrategy
 
 # Key used when seed_groups are provided directly (not from a named dataset)
diff --git a/pyrit/scenario/core/scenario.py b/pyrit/scenario/core/scenario.py
index d4b39f8b97..a3e260fe3a 100644
--- a/pyrit/scenario/core/scenario.py
+++ b/pyrit/scenario/core/scenario.py
@@ -20,7 +20,6 @@
 
 from pyrit.common import REQUIRED_VALUE, apply_defaults
 from pyrit.executor.attack.single_turn.prompt_sending import PromptSendingAttack
-from pyrit.identifiers import ComponentIdentifier
 from pyrit.memory import CentralMemory
 from pyrit.memory.memory_models import ScenarioResultEntry
 from pyrit.models import AttackResult
@@ -36,6 +35,7 @@
 
 if TYPE_CHECKING:
     from pyrit.executor.attack.core.attack_config import AttackScoringConfig
+    from pyrit.identifiers import ComponentIdentifier
     from pyrit.models import SeedAttackGroup
 
 logger = logging.getLogger(__name__)
@@ -340,7 +340,7 @@ def _get_baseline_data(self) -> tuple[list["SeedAttackGroup"], "AttackScoringCon
         # Import here to avoid circular imports
         from pyrit.executor.attack.core.attack_config import AttackScoringConfig
 
-        attack_scoring_config = AttackScoringConfig(objective_scorer=cast(TrueFalseScorer, self._objective_scorer))
+        attack_scoring_config = AttackScoringConfig(objective_scorer=cast("TrueFalseScorer", self._objective_scorer))
 
         if not attack_scoring_config:
             raise ValueError("Attack scoring config is required to create baseline attack.")
diff --git a/pyrit/scenario/core/scenario_strategy.py b/pyrit/scenario/core/scenario_strategy.py
index 336d35b9f1..c18ed60c14 100644
--- a/pyrit/scenario/core/scenario_strategy.py
+++ b/pyrit/scenario/core/scenario_strategy.py
@@ -1,6 +1,8 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
+from __future__ import annotations
+
 """
 Base class for scenario attack strategies with group-based aggregation.
 
@@ -11,9 +13,11 @@
 It also provides ScenarioCompositeStrategy for representing composed attack strategies.
 """
 
-from collections.abc import Sequence
 from enum import Enum
-from typing import TypeVar
+from typing import TYPE_CHECKING, TypeVar
+
+if TYPE_CHECKING:
+    from collections.abc import Sequence
 
 # TypeVar for the enum subclass itself
 T = TypeVar("T", bound="ScenarioStrategy")
@@ -47,7 +51,7 @@ class ScenarioStrategy(Enum):
 
     _tags: set[str]
 
-    def __new__(cls, value: str, tags: set[str] | None = None) -> "ScenarioStrategy":
+    def __new__(cls, value: str, tags: set[str] | None = None) -> ScenarioStrategy:
         """
         Create a new ScenarioStrategy with value and tags.
 
@@ -195,10 +199,10 @@ def normalize_strategies(cls: type[T], strategies: set[T]) -> set[T]:
     @classmethod
     def prepare_scenario_strategies(
         cls: type[T],
-        strategies: Sequence[T | "ScenarioCompositeStrategy"] | None = None,
+        strategies: Sequence[T | ScenarioCompositeStrategy] | None = None,
         *,
         default_aggregate: T | None = None,
-    ) -> list["ScenarioCompositeStrategy"]:
+    ) -> list[ScenarioCompositeStrategy]:
         """
         Prepare and normalize scenario strategies for use in a scenario.
 
@@ -395,7 +399,7 @@ def is_single_strategy(self) -> bool:
 
     @staticmethod
     def extract_single_strategy_values(
-        composites: Sequence["ScenarioCompositeStrategy"], *, strategy_type: type[T]
+        composites: Sequence[ScenarioCompositeStrategy], *, strategy_type: type[T]
     ) -> set[str]:
         """
         Extract strategy values from single-strategy composites.
@@ -474,8 +478,8 @@ def get_composite_name(strategies: Sequence[ScenarioStrategy]) -> str:
 
     @staticmethod
     def normalize_compositions(
-        compositions: list["ScenarioCompositeStrategy"], *, strategy_type: type[T]
-    ) -> list["ScenarioCompositeStrategy"]:
+        compositions: list[ScenarioCompositeStrategy], *, strategy_type: type[T]
+    ) -> list[ScenarioCompositeStrategy]:
         """
         Normalize strategy compositions by expanding aggregates while preserving concrete compositions.
 
diff --git a/pyrit/scenario/scenarios/airt/cyber.py b/pyrit/scenario/scenarios/airt/cyber.py
index e7ecf40650..a05085de4c 100644
--- a/pyrit/scenario/scenarios/airt/cyber.py
+++ b/pyrit/scenario/scenarios/airt/cyber.py
@@ -3,7 +3,7 @@
 
 import logging
 import os
-from typing import Any, Optional
+from typing import TYPE_CHECKING, Any, Optional
 
 from pyrit.common import apply_defaults
 from pyrit.common.deprecation import print_deprecation_message
@@ -12,7 +12,6 @@
     AttackAdversarialConfig,
     AttackScoringConfig,
 )
-from pyrit.executor.attack.core.attack_strategy import AttackStrategy
 from pyrit.executor.attack.multi_turn.red_teaming import RedTeamingAttack
 from pyrit.executor.attack.single_turn.prompt_sending import PromptSendingAttack
 from pyrit.models import SeedAttackGroup, SeedObjective
@@ -33,6 +32,9 @@
     TrueFalseScorer,
 )
 
+if TYPE_CHECKING:
+    from pyrit.executor.attack.core.attack_strategy import AttackStrategy
+
 logger = logging.getLogger(__name__)
 
 
diff --git a/pyrit/scenario/scenarios/airt/scam.py b/pyrit/scenario/scenarios/airt/scam.py
index 5232f2ce05..2ced987199 100644
--- a/pyrit/scenario/scenarios/airt/scam.py
+++ b/pyrit/scenario/scenarios/airt/scam.py
@@ -4,7 +4,7 @@
 import logging
 import os
 from pathlib import Path
-from typing import Any, Optional
+from typing import TYPE_CHECKING, Any, Optional
 
 from pyrit.common import apply_defaults
 from pyrit.common.path import (
@@ -21,7 +21,6 @@
     AttackAdversarialConfig,
     AttackScoringConfig,
 )
-from pyrit.executor.attack.core.attack_strategy import AttackStrategy
 from pyrit.models import SeedAttackGroup, SeedObjective
 from pyrit.prompt_target import OpenAIChatTarget, PromptChatTarget
 from pyrit.scenario.core.atomic_attack import AtomicAttack
@@ -40,6 +39,9 @@
     TrueFalseScorer,
 )
 
+if TYPE_CHECKING:
+    from pyrit.executor.attack.core.attack_strategy import AttackStrategy
+
 logger = logging.getLogger(__name__)
 PERSUASION_DECEPTION_PATH = Path(EXECUTOR_RED_TEAM_PATH, "persuasion_deception").resolve()
 
diff --git a/pyrit/scenario/scenarios/foundry/red_team_agent.py b/pyrit/scenario/scenarios/foundry/red_team_agent.py
index bba9703e7f..bfd51592ae 100644
--- a/pyrit/scenario/scenarios/foundry/red_team_agent.py
+++ b/pyrit/scenario/scenarios/foundry/red_team_agent.py
@@ -13,7 +13,7 @@
 import os
 from collections.abc import Sequence
 from inspect import signature
-from typing import Any, Optional, TypeVar
+from typing import TYPE_CHECKING, Any, Optional, TypeVar
 
 from pyrit.common import apply_defaults
 from pyrit.common.deprecation import print_deprecation_message
@@ -29,7 +29,6 @@
     AttackConverterConfig,
     AttackScoringConfig,
 )
-from pyrit.executor.attack.core.attack_strategy import AttackStrategy
 from pyrit.models import SeedAttackGroup, SeedObjective
 from pyrit.prompt_converter import (
     AnsiAttackConverter,
@@ -78,6 +77,9 @@
     TrueFalseScoreAggregator,
 )
 
+if TYPE_CHECKING:
+    from pyrit.executor.attack.core.attack_strategy import AttackStrategy
+
 AttackStrategyT = TypeVar("AttackStrategyT", bound="AttackStrategy[Any, Any]")
 logger = logging.getLogger(__name__)
 
diff --git a/pyrit/score/conversation_scorer.py b/pyrit/score/conversation_scorer.py
index 3e55f00c5a..333a2e812a 100644
--- a/pyrit/score/conversation_scorer.py
+++ b/pyrit/score/conversation_scorer.py
@@ -92,7 +92,7 @@ async def _score_async(self, message: Message, *, objective: Optional[str] = Non
                     response_error=original_piece.response_error,
                     originator=original_piece.originator,
                     original_prompt_id=(
-                        cast(UUID, original_piece.original_prompt_id)
+                        cast("UUID", original_piece.original_prompt_id)
                         if isinstance(original_piece.original_prompt_id, str)
                         else original_piece.original_prompt_id
                     ),
diff --git a/pyrit/score/float_scale/self_ask_general_float_scale_scorer.py b/pyrit/score/float_scale/self_ask_general_float_scale_scorer.py
index 5a63853028..ae9e0acc4b 100644
--- a/pyrit/score/float_scale/self_ask_general_float_scale_scorer.py
+++ b/pyrit/score/float_scale/self_ask_general_float_scale_scorer.py
@@ -3,14 +3,16 @@
 
 from __future__ import annotations
 
-from typing import Optional
+from typing import TYPE_CHECKING, Optional
 
-from pyrit.identifiers import ComponentIdentifier
-from pyrit.models import MessagePiece, Score, UnvalidatedScore
-from pyrit.prompt_target import PromptChatTarget
 from pyrit.score.float_scale.float_scale_scorer import FloatScaleScorer
 from pyrit.score.scorer_prompt_validator import ScorerPromptValidator
 
+if TYPE_CHECKING:
+    from pyrit.identifiers import ComponentIdentifier
+    from pyrit.models import MessagePiece, Score, UnvalidatedScore
+    from pyrit.prompt_target import PromptChatTarget
+
 
 class SelfAskGeneralFloatScaleScorer(FloatScaleScorer):
     """
diff --git a/pyrit/score/float_scale/video_float_scale_scorer.py b/pyrit/score/float_scale/video_float_scale_scorer.py
index 14ce664017..4cadb91c1a 100644
--- a/pyrit/score/float_scale/video_float_scale_scorer.py
+++ b/pyrit/score/float_scale/video_float_scale_scorer.py
@@ -1,7 +1,7 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT license.
 
-from typing import Optional
+from typing import TYPE_CHECKING, Optional
 
 from pyrit.identifiers import ComponentIdentifier
 from pyrit.models import MessagePiece, Score
@@ -10,10 +10,12 @@
     FloatScaleScorerByCategory,
 )
 from pyrit.score.float_scale.float_scale_scorer import FloatScaleScorer
-from pyrit.score.score_aggregator_result import ScoreAggregatorResult
 from pyrit.score.scorer_prompt_validator import ScorerPromptValidator
 from pyrit.score.video_scorer import _BaseVideoScorer
 
+if TYPE_CHECKING:
+    from pyrit.score.score_aggregator_result import ScoreAggregatorResult
+
 
 class VideoFloatScaleScorer(
     FloatScaleScorer,
diff --git a/pyrit/score/scorer.py b/pyrit/score/scorer.py
index bd5a1b2294..0680d243d4 100644
--- a/pyrit/score/scorer.py
+++ b/pyrit/score/scorer.py
@@ -9,7 +9,6 @@
 import logging
 import uuid
 from abc import abstractmethod
-from collections.abc import Sequence
 from typing import (
     TYPE_CHECKING,
     Any,
@@ -35,16 +34,18 @@
     ScoreType,
     UnvalidatedScore,
 )
-from pyrit.prompt_target import PromptChatTarget, PromptTarget
 from pyrit.prompt_target.batch_helper import batch_task_async
-from pyrit.score.scorer_prompt_validator import ScorerPromptValidator
 
 if TYPE_CHECKING:
+    from collections.abc import Sequence
+
+    from pyrit.prompt_target import PromptChatTarget, PromptTarget
     from pyrit.score.scorer_evaluation.metrics_type import RegistryUpdateBehavior
     from pyrit.score.scorer_evaluation.scorer_evaluator import (
         ScorerEvalDatasetFiles,
     )
     from pyrit.score.scorer_evaluation.scorer_metrics import ScorerMetrics
+    from pyrit.score.scorer_prompt_validator import ScorerPromptValidator
 
 logger = logging.getLogger(__name__)
 
@@ -410,7 +411,7 @@ async def score_prompts_batch_async(
         results = await batch_task_async(
             task_func=self.score_async,
             task_arguments=["message", "objective"],
-            prompt_target=cast(PromptTarget, prompt_target),
+            prompt_target=cast("PromptTarget", prompt_target),
             batch_size=batch_size,
             items_to_batch=[messages, objectives],
             role_filter=role_filter,
diff --git a/pyrit/score/scorer_evaluation/human_labeled_dataset.py b/pyrit/score/scorer_evaluation/human_labeled_dataset.py
index d0eab8d1a3..34dd7dc001 100644
--- a/pyrit/score/scorer_evaluation/human_labeled_dataset.py
+++ b/pyrit/score/scorer_evaluation/human_labeled_dataset.py
@@ -310,7 +310,7 @@ def from_csv(
                         MessagePiece(
                             role="assistant",
                             original_value=response_to_score,
-                            original_value_data_type=cast(PromptDataType, data_type),
+                            original_value_data_type=cast("PromptDataType", data_type),
                         )
                     ],
                 )
diff --git a/pyrit/score/scorer_evaluation/scorer_evaluator.py b/pyrit/score/scorer_evaluation/scorer_evaluator.py
index 2ff8022d65..d5ecfe1480 100644
--- a/pyrit/score/scorer_evaluation/scorer_evaluator.py
+++ b/pyrit/score/scorer_evaluation/scorer_evaluator.py
@@ -7,15 +7,12 @@
 import logging
 import time
 from dataclasses import dataclass
-from pathlib import Path
-from typing import Optional, cast
+from typing import TYPE_CHECKING, Optional, cast
 
 import numpy as np
 from scipy.stats import ttest_1samp
 
 from pyrit.common.path import SCORER_EVALS_PATH
-from pyrit.models import Message
-from pyrit.score import Scorer
 from pyrit.score.scorer_evaluation.human_labeled_dataset import (
     HarmHumanLabeledEntry,
     HumanLabeledDataset,
@@ -38,6 +35,12 @@
 )
 from pyrit.score.true_false.true_false_scorer import TrueFalseScorer
 
+if TYPE_CHECKING:
+    from pathlib import Path
+
+    from pyrit.models import Message
+    from pyrit.score import Scorer
+
 logger = logging.getLogger(__name__)
 
 # Standard column names for evaluation datasets
@@ -523,7 +526,7 @@ def _validate_and_extract_data(
         human_scores_list: list[list[float]] = []
 
         for entry in labeled_dataset.entries:
-            harm_entry = cast(HarmHumanLabeledEntry, entry)
+            harm_entry = cast("HarmHumanLabeledEntry", entry)
             for message in harm_entry.conversation:
                 self.scorer._memory.add_message_to_memory(request=message)
                 assistant_responses.append(message)
@@ -553,7 +556,7 @@ def _compute_metrics(
         diff[np.abs(diff) < 1e-10] = 0.0
 
         abs_error = np.abs(diff)
-        t_statistic, p_value = cast(tuple[float, float], ttest_1samp(diff, 0))
+        t_statistic, p_value = cast("tuple[float, float]", ttest_1samp(diff, 0))
 
         num_responses = all_human_scores.shape[1]
         num_human_raters = all_human_scores.shape[0]
@@ -624,7 +627,7 @@ def _validate_and_extract_data(
         objectives: list[str] = []
 
         for entry in labeled_dataset.entries:
-            objective_entry = cast(ObjectiveHumanLabeledEntry, entry)
+            objective_entry = cast("ObjectiveHumanLabeledEntry", entry)
             for message in objective_entry.conversation:
                 self.scorer._memory.add_message_to_memory(request=message)
                 assistant_responses.append(message)
diff --git a/pyrit/score/scorer_evaluation/scorer_metrics.py b/pyrit/score/scorer_evaluation/scorer_metrics.py
index 560e53654e..81f254d9b9 100644
--- a/pyrit/score/scorer_evaluation/scorer_metrics.py
+++ b/pyrit/score/scorer_evaluation/scorer_metrics.py
@@ -5,14 +5,15 @@
 
 import json
 from dataclasses import asdict, dataclass, field
-from pathlib import Path
 from typing import TYPE_CHECKING, Generic, Optional, TypeVar, Union
 
-import numpy as np
-
 from pyrit.common.utils import verify_and_resolve_path
 
 if TYPE_CHECKING:
+    from pathlib import Path
+
+    import numpy as np
+
     from pyrit.identifiers import ComponentIdentifier
     from pyrit.models.harm_definition import HarmDefinition
 
diff --git a/pyrit/score/true_false/question_answer_scorer.py b/pyrit/score/true_false/question_answer_scorer.py
index 5d6010376a..ea6b0b4e4c 100644
--- a/pyrit/score/true_false/question_answer_scorer.py
+++ b/pyrit/score/true_false/question_answer_scorer.py
@@ -3,9 +3,8 @@
 
 from __future__ import annotations
 
-from typing import Optional
+from typing import TYPE_CHECKING, Optional
 
-from pyrit.identifiers import ComponentIdentifier
 from pyrit.models import MessagePiece, Score
 from pyrit.score.scorer_prompt_validator import ScorerPromptValidator
 from pyrit.score.true_false.true_false_score_aggregator import (
@@ -14,6 +13,9 @@
 )
 from pyrit.score.true_false.true_false_scorer import TrueFalseScorer
 
+if TYPE_CHECKING:
+    from pyrit.identifiers import ComponentIdentifier
+
 
 class QuestionAnswerScorer(TrueFalseScorer):
     """
diff --git a/pyrit/score/true_false/self_ask_general_true_false_scorer.py b/pyrit/score/true_false/self_ask_general_true_false_scorer.py
index 6e2c9948bf..44bb362748 100644
--- a/pyrit/score/true_false/self_ask_general_true_false_scorer.py
+++ b/pyrit/score/true_false/self_ask_general_true_false_scorer.py
@@ -3,11 +3,8 @@
 
 from __future__ import annotations
 
-from typing import Optional
+from typing import TYPE_CHECKING, Optional
 
-from pyrit.identifiers import ComponentIdentifier
-from pyrit.models import MessagePiece, Score, UnvalidatedScore
-from pyrit.prompt_target import PromptChatTarget
 from pyrit.score.scorer_prompt_validator import ScorerPromptValidator
 from pyrit.score.true_false.true_false_score_aggregator import (
     TrueFalseAggregatorFunc,
@@ -15,6 +12,11 @@
 )
 from pyrit.score.true_false.true_false_scorer import TrueFalseScorer
 
+if TYPE_CHECKING:
+    from pyrit.identifiers import ComponentIdentifier
+    from pyrit.models import MessagePiece, Score, UnvalidatedScore
+    from pyrit.prompt_target import PromptChatTarget
+
 
 class SelfAskGeneralTrueFalseScorer(TrueFalseScorer):
     """
diff --git a/pyrit/score/true_false/self_ask_question_answer_scorer.py b/pyrit/score/true_false/self_ask_question_answer_scorer.py
index 93a1dcfcc6..bf1c017dde 100644
--- a/pyrit/score/true_false/self_ask_question_answer_scorer.py
+++ b/pyrit/score/true_false/self_ask_question_answer_scorer.py
@@ -3,13 +3,10 @@
 
 from __future__ import annotations
 
-import pathlib
-from typing import Optional
+from typing import TYPE_CHECKING, Optional
 
 from pyrit.common.path import SCORER_SEED_PROMPT_PATH
 from pyrit.common.utils import verify_and_resolve_path
-from pyrit.models import MessagePiece, Score, UnvalidatedScore
-from pyrit.prompt_target import PromptChatTarget
 from pyrit.score.scorer_prompt_validator import ScorerPromptValidator
 from pyrit.score.true_false.self_ask_true_false_scorer import SelfAskTrueFalseScorer
 from pyrit.score.true_false.true_false_score_aggregator import (
@@ -17,6 +14,12 @@
     TrueFalseScoreAggregator,
 )
 
+if TYPE_CHECKING:
+    import pathlib
+
+    from pyrit.models import MessagePiece, Score, UnvalidatedScore
+    from pyrit.prompt_target import PromptChatTarget
+
 
 class SelfAskQuestionAnswerScorer(SelfAskTrueFalseScorer):
     """
diff --git a/pyrit/setup/configuration_loader.py b/pyrit/setup/configuration_loader.py
index fdd1f31bdf..f31e4640e6 100644
--- a/pyrit/setup/configuration_loader.py
+++ b/pyrit/setup/configuration_loader.py
@@ -297,7 +297,6 @@ def _resolve_initializers(self) -> Sequence["PyRITInitializer"]:
             ValueError: If an initializer name is not found in the registry.
         """
         from pyrit.registry import InitializerRegistry
-        from pyrit.setup.initializers.pyrit_initializer import PyRITInitializer
 
         if not self._initializer_configs:
             return []
diff --git a/tests/unit/executor/attack/multi_turn/test_tree_of_attacks.py b/tests/unit/executor/attack/multi_turn/test_tree_of_attacks.py
index ef49184977..89c0348979 100644
--- a/tests/unit/executor/attack/multi_turn/test_tree_of_attacks.py
+++ b/tests/unit/executor/attack/multi_turn/test_tree_of_attacks.py
@@ -182,7 +182,7 @@ def with_prompt_normalizer(self) -> "AttackBuilder":
         """Add a mock prompt normalizer."""
         normalizer = MagicMock(spec=PromptNormalizer)
         normalizer.send_prompt_async = AsyncMock(return_value=None)
-        self.prompt_normalizer = cast(PromptNormalizer, normalizer)
+        self.prompt_normalizer = cast("PromptNormalizer", normalizer)
         return self
 
     def build(self) -> TreeOfAttacksWithPruningAttack:
@@ -225,7 +225,7 @@ def _create_mock_target() -> PromptTarget:
             class_name="MockTarget",
             class_module="test_module",
         )
-        return cast(PromptTarget, target)
+        return cast("PromptTarget", target)
 
     @staticmethod
     def _create_mock_chat() -> PromptChatTarget:
@@ -236,7 +236,7 @@ def _create_mock_chat() -> PromptChatTarget:
             class_name="MockChatTarget",
             class_module="test_module",
         )
-        return cast(PromptChatTarget, chat)
+        return cast("PromptChatTarget", chat)
 
     @staticmethod
     def _create_mock_scorer(name: str) -> TrueFalseScorer:
@@ -247,7 +247,7 @@ def _create_mock_scorer(name: str) -> TrueFalseScorer:
             class_name=name,
             class_module="test_module",
         )
-        return cast(TrueFalseScorer, scorer)
+        return cast("TrueFalseScorer", scorer)
 
     @staticmethod
     def _create_mock_aux_scorer(name: str) -> Scorer:
@@ -259,7 +259,7 @@ def _create_mock_aux_scorer(name: str) -> Scorer:
             class_name=name,
             class_module="test_module",
         )
-        return cast(Scorer, scorer)
+        return cast("Scorer", scorer)
 
 
 class TestHelpers:
diff --git a/tests/unit/memory/memory_interface/test_interface_attack_results.py b/tests/unit/memory/memory_interface/test_interface_attack_results.py
index 8fadfb013d..3106409fde 100644
--- a/tests/unit/memory/memory_interface/test_interface_attack_results.py
+++ b/tests/unit/memory/memory_interface/test_interface_attack_results.py
@@ -3,8 +3,7 @@
 
 
 import uuid
-from collections.abc import Sequence
-from typing import Optional
+from typing import TYPE_CHECKING, Optional
 
 from pyrit.common.utils import to_sha256
 from pyrit.identifiers import ComponentIdentifier
@@ -19,6 +18,9 @@
     Score,
 )
 
+if TYPE_CHECKING:
+    from collections.abc import Sequence
+
 
 def create_message_piece(conversation_id: str, prompt_num: int, targeted_harm_categories=None, labels=None):
     """Helper function to create MessagePiece with optional targeted harm categories and labels."""
diff --git a/tests/unit/memory/test_azure_sql_memory.py b/tests/unit/memory/test_azure_sql_memory.py
index 6001c2756a..4316270259 100644
--- a/tests/unit/memory/test_azure_sql_memory.py
+++ b/tests/unit/memory/test_azure_sql_memory.py
@@ -4,16 +4,19 @@
 import os
 import uuid
 from collections.abc import Generator, MutableSequence, Sequence
+from typing import TYPE_CHECKING
 
 import pytest
 
 from pyrit.memory import AzureSQLMemory, EmbeddingDataEntry, PromptMemoryEntry
-from pyrit.memory.memory_models import Base
 from pyrit.models import MessagePiece
 from pyrit.prompt_converter.base64_converter import Base64Converter
 from pyrit.prompt_target.text_target import TextTarget
 from unit.mocks import get_azure_sql_memory, get_sample_conversation_entries
 
+if TYPE_CHECKING:
+    from pyrit.memory.memory_models import Base
+
 
 @pytest.fixture
 def memory_interface() -> Generator[AzureSQLMemory, None, None]: