diff --git a/airflow-core/newsfragments/66633.bugfix.rst b/airflow-core/newsfragments/66633.bugfix.rst
new file mode 100644
index 0000000000000..5ea85be3152d7
--- /dev/null
+++ b/airflow-core/newsfragments/66633.bugfix.rst
@@ -0,0 +1 @@
+Fix remote task logs being silently dropped when ``dictConfig`` closes a remote logging handler during configuration.
diff --git a/task-sdk/src/airflow/sdk/log.py b/task-sdk/src/airflow/sdk/log.py
index e105fd70d762e..849a7eca20932 100644
--- a/task-sdk/src/airflow/sdk/log.py
+++ b/task-sdk/src/airflow/sdk/log.py
@@ -74,7 +74,7 @@ def logging_processors(
     if mask_secrets:
         extra_processors += (mask_logs,)
 
-    if (remote := load_remote_log_handler()) and (remote_processors := getattr(remote, "processors")):
+    if (remote := load_remote_log_handler()) and (remote_processors := getattr(remote, "processors", None)):
         extra_processors += remote_processors
 
     procs, _, final_writer = structlog_processors(
@@ -119,9 +119,6 @@ def configure_logging(
     if mask_secrets:
         extra_processors += (mask_logs,)
 
-    if (remote := load_remote_log_handler()) and (remote_processors := getattr(remote, "processors")):
-        extra_processors += remote_processors
-
     configure_logging(
         json_output=json_output,
         log_level=log_level,
@@ -134,6 +131,16 @@ def configure_logging(
         callsite_parameters=callsite_params,
     )
 
+    # Build the remote handler after dictConfig(), which closes every previously registered handler.
+    if (
+        not sending_to_supervisor
+        and (remote := load_remote_log_handler())
+        and (remote_processors := getattr(remote, "processors", None))
+    ):
+        current_processors = list(structlog.get_config()["processors"])
+        updated_processors = current_processors[:-1] + list(remote_processors) + [current_processors[-1]]
+        structlog.configure(processors=updated_processors)
+
 
 def logger_at_level(name: str, level: int) -> Logger:
     """Create a new logger at the given level."""
diff --git a/task-sdk/tests/task_sdk/test_log.py b/task-sdk/tests/task_sdk/test_log.py
new file mode 100644
index 0000000000000..aa955a87a60a4
--- /dev/null
+++ b/task-sdk/tests/task_sdk/test_log.py
@@ -0,0 +1,89 @@
+#
+# Licensed to the Apache Software Foundation (ASF) under one
+# or more contributor license agreements.  See the NOTICE file
+# distributed with this work for additional information
+# regarding copyright ownership.  The ASF licenses this file
+# to you under the Apache License, Version 2.0 (the
+# "License"); you may not use this file except in compliance
+# with the License.  You may obtain a copy of the License at
+#
+#   http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing,
+# software distributed under the License is distributed on an
+# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+# KIND, either express or implied.  See the License for the
+# specific language governing permissions and limitations
+# under the License.
+from __future__ import annotations
+
+from unittest import mock
+
+import pytest
+import structlog
+
+from airflow.sdk import log as sdk_log
+
+
+class TestConfigureLogging:
+    @pytest.mark.parametrize("sending_to_supervisor", [True, False])
+    @mock.patch("airflow.sdk.log.load_remote_log_handler")
+    @mock.patch("airflow.sdk._shared.logging.configure_logging")
+    def test_injects_remote_processors_after_dictconfig(
+        self, mock_configure_logging, mock_load_remote_log_handler, sending_to_supervisor
+    ):
+        initial_processor = mock.Mock()
+        final_renderer = mock.Mock()
+        remote_processor = mock.Mock()
+        remote_handler = mock.Mock(spec=["processors"])
+        remote_handler.processors = (remote_processor,)
+        calls = []
+
+        def configure_structlog(**_):
+            calls.append("dictConfig")
+            structlog.configure(processors=[initial_processor, final_renderer])
+
+        def load_remote_handler():
+            calls.append("load_remote_log_handler")
+            return remote_handler
+
+        mock_configure_logging.side_effect = configure_structlog
+        mock_load_remote_log_handler.side_effect = load_remote_handler
+        original_processors = structlog.get_config()["processors"]
+        sdk_log.configure_logging.cache_clear()
+
+        try:
+            sdk_log.configure_logging(sending_to_supervisor=sending_to_supervisor)
+
+            assert mock_configure_logging.called
+            if sending_to_supervisor:
+                assert calls == ["dictConfig"]
+                assert structlog.get_config()["processors"] == [initial_processor, final_renderer]
+            else:
+                assert calls == ["dictConfig", "load_remote_log_handler"]
+                assert structlog.get_config()["processors"] == [
+                    initial_processor,
+                    remote_processor,
+                    final_renderer,
+                ]
+        finally:
+            structlog.configure(processors=original_processors)
+            sdk_log.configure_logging.cache_clear()
+
+    @mock.patch("airflow.sdk._shared.logging.structlog.structlog_processors")
+    @mock.patch("airflow.sdk.log.load_remote_log_handler", return_value=object())
+    def test_allows_remote_handler_without_processors(
+        self, mock_load_remote_log_handler, mock_structlog_processors
+    ):
+        initial_processor = mock.Mock()
+        final_renderer = mock.Mock()
+        mock_structlog_processors.return_value = ([initial_processor], None, final_renderer)
+        sdk_log.logging_processors.cache_clear()
+
+        try:
+            processors = sdk_log.logging_processors(json_output=False)
+        finally:
+            sdk_log.logging_processors.cache_clear()
+
+        mock_load_remote_log_handler.assert_called_once_with()
+        assert processors == (initial_processor, sdk_log.mask_logs, final_renderer)