diff --git a/.github/boring-cyborg.yml b/.github/boring-cyborg.yml
index 7d97c2f6eafce..8afc30e0e5a90 100644
--- a/.github/boring-cyborg.yml
+++ b/.github/boring-cyborg.yml
@@ -41,7 +41,7 @@ labelPRBasedOnFilePath:
 
   provider:Snowflake:
     - airflow/providers/snowflake/**/*
-    - docs/howto/operator/snowflake/*
+    - docs/apache-airflow-providers-snowflake/**/*
     - tests/providers/snowflake/**/*
 
   area:providers:
@@ -68,7 +68,7 @@ labelPRBasedOnFilePath:
     - airflow/api_connexion/**/*
     - airflow/www/api/**/*
     - clients/**/*
-    - docs/apache-airflow/rest-api-ref.rst
+    - docs/apache-airflow/deprecated-rest-api-ref.rst
     - docs/apache-airflow/stable-rest-api-ref.rst
     - tests/api_connexion/**/*
     - tests/www/api/**/*
@@ -106,6 +106,7 @@ labelPRBasedOnFilePath:
 
   area:helm-chart:
     - chart/**/*
+    - docs/helm-chart/**
 
   area:Webserver:
     - airflow/cli/commands/webserver_command.py
@@ -142,7 +143,7 @@ labelPRBasedOnFilePath:
   area:Logging:
     - airflow/providers/**/log/*
     - airflow/utils/log/**/*
-    - docs/apache-airflow/howto/write-logs.rst
+    - docs/apache-airflow/logging-monitoring/logging-*.rst
     - tests/providers/**/log/*
     - tests/utils/log/**/*
 
@@ -168,7 +169,7 @@ labelPRBasedOnFilePath:
     - airflow/providers/**/secrets/*
     - tests/secrets/**/*
     - tests/providers/**/secrets/*
-    - docs/apache-airflow/howto/secrets-backend/*
+    - docs/apache-airflow/security/secrets/**/*
 
   area:Serialization:
     - airflow/serialization/**/*
@@ -187,6 +188,13 @@ labelPRBasedOnFilePath:
     - docs/apache-airflow/operators-and-hooks-ref.rst
     - docs/apache-airflow/howto/operator/*
 
+  area:production-image:
+    - Dockerfile
+    - docs/docker-stack/**/*
+    - scripts/in_container/prod/*
+    - scripts/ci/tools/verify_docker_image.sh
+    - scripts/ci/libraries/_verify_image.sh
+
 # Various Flags to control behaviour of the "Labeler"
 labelerFlags:
   # If this flag is changed to 'false', labels would only be added when the PR is first created