diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index 22afab4937a464..1c08645e6b118f 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -172,7 +172,7 @@ repos:
         entry: ./scripts/ci/pre_commit/pre_commit_update_common_sql_api_stubs.py
         language: python
         files: ^scripts/ci/pre_commit/pre_commit_update_common_sql_api\.py|^airflow/providers/common/sql/.*\.pyi?$
-        additional_dependencies: ['rich>=12.4.4', 'mypy==1.2.0', 'black==23.10.0', 'jinja2']
+        additional_dependencies: ['rich>=12.4.4', 'mypy==1.8.0', 'black==23.10.0', 'jinja2']
         pass_filenames: false
         require_serial: true
       - id: update-black-version
diff --git a/airflow/models/dagrun.py b/airflow/models/dagrun.py
index 59cd7e58b70333..3cf5d3b04b7e01 100644
--- a/airflow/models/dagrun.py
+++ b/airflow/models/dagrun.py
@@ -83,7 +83,6 @@
     from airflow.utils.types import ArgNotSet
 
     CreatedTasks = TypeVar("CreatedTasks", Iterator["dict[str, Any]"], Iterator[TI])
-    TaskCreator = Callable[[Operator, Iterable[int]], CreatedTasks]
 
 RUN_ID_REGEX = r"^(?:manual|scheduled|dataset_triggered)__(?:\d{4}-\d{2}-\d{2}T\d{2}:\d{2}:\d{2}\+00:00)$"
 
@@ -1284,7 +1283,7 @@ def create_ti(task: Operator, indexes: Iterable[int]) -> Iterator[TI]:
     def _create_tasks(
         self,
         tasks: Iterable[Operator],
-        task_creator: TaskCreator,
+        task_creator: Callable[[Operator, Iterable[int]], CreatedTasks],
         *,
         session: Session,
     ) -> CreatedTasks:
diff --git a/airflow/providers/amazon/aws/hooks/base_aws.py b/airflow/providers/amazon/aws/hooks/base_aws.py
index d608a87b8cd2a9..8ab3bab55016bf 100644
--- a/airflow/providers/amazon/aws/hooks/base_aws.py
+++ b/airflow/providers/amazon/aws/hooks/base_aws.py
@@ -314,7 +314,7 @@ def _get_idp_response(
             idp_request_retry_kwargs = saml_config["idp_request_retry_kwargs"]
             self.log.info("idp_request_retry_kwargs= %s", idp_request_retry_kwargs)
             from requests.adapters import HTTPAdapter
-            from requests.packages.urllib3.util.retry import Retry
+            from urllib3.util.retry import Retry
 
             retry_strategy = Retry(**idp_request_retry_kwargs)
             adapter = HTTPAdapter(max_retries=retry_strategy)
diff --git a/airflow/providers/amazon/aws/utils/connection_wrapper.py b/airflow/providers/amazon/aws/utils/connection_wrapper.py
index f0b8d7c1c26b4f..166214a8f441c6 100644
--- a/airflow/providers/amazon/aws/utils/connection_wrapper.py
+++ b/airflow/providers/amazon/aws/utils/connection_wrapper.py
@@ -165,7 +165,7 @@ def get_service_endpoint_url(
 
         return service_config.get("endpoint_url", global_endpoint_url)
 
-    def __post_init__(self, conn: Connection):
+    def __post_init__(self, conn: Connection | AwsConnectionWrapper | _ConnectionMetadata | None) -> None:
         if isinstance(conn, type(self)):
             # For every field with init=False we copy reference value from original wrapper
             # For every field with init=True we use init values if it not equal default
@@ -192,6 +192,9 @@ def __post_init__(self, conn: Connection):
         elif not conn:
             return
 
+        if TYPE_CHECKING:
+            assert isinstance(conn, (Connection, _ConnectionMetadata))
+
         # Assign attributes from AWS Connection
         self.conn_id = conn.conn_id
         self.conn_type = conn.conn_type or "aws"
diff --git a/airflow/providers/google/cloud/triggers/cloud_storage_transfer_service.py b/airflow/providers/google/cloud/triggers/cloud_storage_transfer_service.py
index aff5c71041f1ff..32cb855f1785fe 100644
--- a/airflow/providers/google/cloud/triggers/cloud_storage_transfer_service.py
+++ b/airflow/providers/google/cloud/triggers/cloud_storage_transfer_service.py
@@ -18,7 +18,7 @@
 from __future__ import annotations
 
 import asyncio
-from typing import Any, AsyncIterator
+from typing import Any, AsyncIterator, Iterable
 
 from google.api_core.exceptions import GoogleAPIError
 from google.cloud.storage_transfer_v1.types import TransferOperation
@@ -67,11 +67,11 @@ async def run(self) -> AsyncIterator[TriggerEvent]:  # type: ignore[override]
                 jobs_pager = await async_hook.get_jobs(job_names=self.job_names)
                 jobs, awaitable_operations = [], []
                 async for job in jobs_pager:
-                    operation = async_hook.get_latest_operation(job)
+                    awaitable_operation = async_hook.get_latest_operation(job)
                     jobs.append(job)
-                    awaitable_operations.append(operation)
+                    awaitable_operations.append(awaitable_operation)
 
-                operations: list[TransferOperation] = await asyncio.gather(*awaitable_operations)
+                operations: Iterable[TransferOperation | None] = await asyncio.gather(*awaitable_operations)
 
                 for job, operation in zip(jobs, operations):
                     if operation is None:
diff --git a/airflow/providers/http/hooks/http.py b/airflow/providers/http/hooks/http.py
index 5b6063a3f7d7c7..56cbe4b569af42 100644
--- a/airflow/providers/http/hooks/http.py
+++ b/airflow/providers/http/hooks/http.py
@@ -244,7 +244,8 @@ def run_with_advanced_retry(self, _retry_args: dict[Any, Any], *args: Any, **kwa
         """
         self._retry_obj = tenacity.Retrying(**_retry_args)
 
-        return self._retry_obj(self.run, *args, **kwargs)
+        # TODO: remove ignore type when https://github.com/jd/tenacity/issues/428 is resolved
+        return self._retry_obj(self.run, *args, **kwargs)  # type: ignore
 
     def url_from_endpoint(self, endpoint: str | None) -> str:
         """Combine base url with endpoint."""
diff --git a/pyproject.toml b/pyproject.toml
index 4e4a088cf49786..7c82856292be50 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -299,7 +299,7 @@ devel-mypy = [
     # TODO: upgrade to newer versions of MyPy continuously as they are released
     # Make sure to upgrade the mypy version in update-common-sql-api-stubs in .pre-commit-config.yaml
     # when you upgrade it here !!!!
-    "mypy==1.2.0",
+    "mypy==1.8.0",
     "types-Deprecated",
     "types-Markdown",
     "types-PyMySQL",