diff --git a/.github/workflows/build-images.yml b/.github/workflows/build-images.yml
index f29e199e4fb84..ec8f4354d0908 100644
--- a/.github/workflows/build-images.yml
+++ b/.github/workflows/build-images.yml
@@ -148,7 +148,6 @@ jobs:
       BACKEND: postgres
       PYTHON_MAJOR_MINOR_VERSION: ${{ matrix.python-version }}
       UPGRADE_TO_NEWER_DEPENDENCIES: ${{ needs.build-info.outputs.upgradeToNewerDependencies }}
-      CONTINUE_ON_PIP_CHECK_FAILURE: "true"
       DOCKER_CACHE: ${{ needs.build-info.outputs.cacheDirective }}
       CHECK_IF_BASE_PYTHON_IMAGE_UPDATED: >
         ${{ github.event_name == 'pull_request_target' && 'false' || 'true' }}
diff --git a/BREEZE.rst b/BREEZE.rst
index 90663657a85ad..683d2fb320f98 100644
--- a/BREEZE.rst
+++ b/BREEZE.rst
@@ -1280,9 +1280,6 @@ This is the current syntax for  `./breeze <./breeze>`_:
   --upgrade-to-newer-dependencies
           Upgrades PIP packages to latest versions available without looking at the constraints.
 
-  --continue-on-pip-check-failure
-          Continue even if 'pip check' fails.
-
   -I, --production-image
           Use production image for entering the environment and builds (not for tests).
 
@@ -2393,9 +2390,9 @@ This is the current syntax for  `./breeze <./breeze>`_:
           Helm version - only used in case one of kind-cluster commands is used.
           One of:
 
-                 v3.2.4
+                 v3.6.3
 
-          Default: v3.2.4
+          Default: v3.6.3
 
   --executor EXECUTOR
           Executor to use in a kubernetes cluster.
@@ -2446,9 +2443,6 @@ This is the current syntax for  `./breeze <./breeze>`_:
   --upgrade-to-newer-dependencies
           Upgrades PIP packages to latest versions available without looking at the constraints.
 
-  --continue-on-pip-check-failure
-          Continue even if 'pip check' fails.
-
   ****************************************************************************************************
    Use different Airflow version at runtime in CI image
 
diff --git a/Dockerfile b/Dockerfile
index 9a7f8ecdc1fec..782e5b4bbd9a3 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -44,7 +44,8 @@ ARG AIRFLOW_GID="50000"
 
 ARG PYTHON_BASE_IMAGE="python:3.6-slim-buster"
 
-ARG AIRFLOW_PIP_VERSION=21.1.2
+ARG AIRFLOW_PIP_VERSION=21.2.2
+ARG AIRFLOW_IMAGE_REPOSITORY="https://github.com/apache/airflow"
 
 # By default PIP has progress bar but you can disable it.
 ARG PIP_PROGRESS_BAR="on"
@@ -108,12 +109,13 @@ ARG DEV_APT_COMMAND="\
     && curl https://dl.yarnpkg.com/debian/pubkey.gpg | apt-key add - > /dev/null \
     && echo 'deb https://dl.yarnpkg.com/debian/ stable main' > /etc/apt/sources.list.d/yarn.list"
 ARG ADDITIONAL_DEV_APT_COMMAND="echo"
+ARG ADDITIONAL_DEV_APT_ENV=""
 
 ENV DEV_APT_DEPS=${DEV_APT_DEPS} \
     ADDITIONAL_DEV_APT_DEPS=${ADDITIONAL_DEV_APT_DEPS} \
     DEV_APT_COMMAND=${DEV_APT_COMMAND} \
     ADDITIONAL_DEV_APT_COMMAND=${ADDITIONAL_DEV_APT_COMMAND} \
-    ADDITIONAL_DEV_APT_ENV=""
+    ADDITIONAL_DEV_APT_ENV=${ADDITIONAL_DEV_APT_ENV}
 
 # Note missing man directories on debian-buster
 # https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=863199
@@ -216,7 +218,7 @@ ENV AIRFLOW_PRE_CACHED_PIP_PACKAGES=${AIRFLOW_PRE_CACHED_PIP_PACKAGES} \
 RUN bash /scripts/docker/install_pip_version.sh; \
     if [[ ${AIRFLOW_PRE_CACHED_PIP_PACKAGES} == "true" && \
           ${UPGRADE_TO_NEWER_DEPENDENCIES} == "false" ]]; then \
-        bash /scripts/docker/install_airflow_from_branch_tip.sh; \
+        bash /scripts/docker/install_airflow_dependencies_from_branch_tip.sh; \
     fi
 
 COPY ${AIRFLOW_SOURCES_FROM} ${AIRFLOW_SOURCES_TO}
@@ -236,14 +238,11 @@ ARG INSTALL_FROM_PYPI="true"
 # * pyjwt<2.0.0: flask-jwt-extended requires it
 # * dill<0.3.3 required by apache-beam
 ARG EAGER_UPGRADE_ADDITIONAL_REQUIREMENTS="pyjwt<2.0.0 dill<0.3.3 certifi<2021.0.0"
-ARG CONTINUE_ON_PIP_CHECK_FAILURE="false"
-
 
 ENV ADDITIONAL_PYTHON_DEPS=${ADDITIONAL_PYTHON_DEPS} \
     INSTALL_FROM_DOCKER_CONTEXT_FILES=${INSTALL_FROM_DOCKER_CONTEXT_FILES} \
     INSTALL_FROM_PYPI=${INSTALL_FROM_PYPI} \
-    EAGER_UPGRADE_ADDITIONAL_REQUIREMENTS=${EAGER_UPGRADE_ADDITIONAL_REQUIREMENTS} \
-    CONTINUE_ON_PIP_CHECK_FAILURE=${CONTINUE_ON_PIP_CHECK_FAILURE}
+    EAGER_UPGRADE_ADDITIONAL_REQUIREMENTS=${EAGER_UPGRADE_ADDITIONAL_REQUIREMENTS}
 
 WORKDIR /opt/airflow
 
@@ -276,7 +275,7 @@ RUN if [[ -f /docker-context-files/requirements.txt ]]; then \
 
 ARG BUILD_ID
 ARG COMMIT_SHA
-ARG AIRFLOW_IMAGE_REPOSITORY="https://github.com/apache/airflow"
+ARG AIRFLOW_IMAGE_REPOSITORY
 ARG AIRFLOW_IMAGE_DATE_CREATED
 
 ENV BUILD_ID=${BUILD_ID} COMMIT_SHA=${COMMIT_SHA}
@@ -293,15 +292,14 @@ LABEL org.apache.airflow.distro="debian" \
   org.opencontainers.image.created=${AIRFLOW_IMAGE_DATE_CREATED} \
   org.opencontainers.image.authors="dev@airflow.apache.org" \
   org.opencontainers.image.url="https://airflow.apache.org" \
-  org.opencontainers.image.documentation="https://airflow.apache.org/docs/apache-airflow/stable/production-deployment.html" \
-  org.opencontainers.image.source="https://github.com/apache/airflow" \
+  org.opencontainers.image.documentation="https://airflow.apache.org/docs/docker-stack/index.html" \
   org.opencontainers.image.version="${AIRFLOW_VERSION}" \
   org.opencontainers.image.revision="${COMMIT_SHA}" \
   org.opencontainers.image.vendor="Apache Software Foundation" \
   org.opencontainers.image.licenses="Apache-2.0" \
   org.opencontainers.image.ref.name="airflow-build-image" \
   org.opencontainers.image.title="Build Image Segment for Production Airflow Image" \
-  org.opencontainers.image.description="Installed Apache Airflow with build-time dependencies"
+  org.opencontainers.image.description="Reference build-time dependencies image for production-ready Apache Airflow image"
 
 ##############################################################################################
 # This is the actual Airflow image - much smaller than the build one. We copy
@@ -379,7 +377,7 @@ ARG AIRFLOW_HOME
 ARG AIRFLOW_INSTALLATION_METHOD="apache-airflow"
 ARG BUILD_ID
 ARG COMMIT_SHA
-ARG AIRFLOW_IMAGE_REPOSITORY="https://github.com/apache/airflow"
+ARG AIRFLOW_IMAGE_REPOSITORY
 ARG AIRFLOW_IMAGE_DATE_CREATED
 # By default PIP will install everything in ~/.local
 ARG PIP_USER="true"
@@ -468,15 +466,14 @@ LABEL org.apache.airflow.distro="debian" \
   org.opencontainers.image.created=${AIRFLOW_IMAGE_DATE_CREATED} \
   org.opencontainers.image.authors="dev@airflow.apache.org" \
   org.opencontainers.image.url="https://airflow.apache.org" \
-  org.opencontainers.image.documentation="https://airflow.apache.org/docs/apache-airflow/stable/production-deployment.html" \
-  org.opencontainers.image.source="https://github.com/apache/airflow" \
+  org.opencontainers.image.documentation="https://airflow.apache.org/docs/docker-stack/index.html" \
   org.opencontainers.image.version="${AIRFLOW_VERSION}" \
   org.opencontainers.image.revision="${COMMIT_SHA}" \
   org.opencontainers.image.vendor="Apache Software Foundation" \
   org.opencontainers.image.licenses="Apache-2.0" \
   org.opencontainers.image.ref.name="airflow" \
   org.opencontainers.image.title="Production Airflow Image" \
-  org.opencontainers.image.description="Installed Apache Airflow"
+  org.opencontainers.image.description="Reference, production-ready Apache Airflow image"
 
 
 ENTRYPOINT ["/usr/bin/dumb-init", "--", "/entrypoint"]
diff --git a/Dockerfile.ci b/Dockerfile.ci
index 552afd8f4d418..13e9107137576 100644
--- a/Dockerfile.ci
+++ b/Dockerfile.ci
@@ -22,6 +22,8 @@ SHELL ["/bin/bash", "-o", "pipefail", "-e", "-u", "-x", "-c"]
 
 ARG PYTHON_BASE_IMAGE="python:3.6-slim-buster"
 ARG AIRFLOW_VERSION="2.2.0.dev0"
+ARG AIRFLOW_IMAGE_REPOSITORY="https://github.com/apache/airflow"
+
 # By increasing this number we can do force build of all dependencies
 ARG DEPENDENCIES_EPOCH_NUMBER="6"
 
@@ -126,6 +128,15 @@ ARG RUNTIME_APT_DEPS="\
       unzip \
       vim \
       xxd"
+
+# Install Helm
+ARG HELM_VERSION="v3.6.3"
+
+RUN SYSTEM=$(uname -s | tr '[:upper:]' '[:lower:]') \
+    && HELM_URL="https://get.helm.sh/helm-${HELM_VERSION}-${SYSTEM}-amd64.tar.gz" \
+    && curl --location "${HELM_URL}" | tar -xvz -O "${SYSTEM}"-amd64/helm > /usr/local/bin/helm \
+    && chmod +x /usr/local/bin/helm
+
 ARG ADDITIONAL_RUNTIME_APT_DEPS=""
 ARG RUNTIME_APT_COMMAND=""
 ARG ADDITIONAL_RUNTIME_APT_COMMAND=""
@@ -219,7 +230,7 @@ ARG AIRFLOW_PRE_CACHED_PIP_PACKAGES="true"
 # By default in the image, we are installing all providers when installing from sources
 ARG INSTALL_PROVIDERS_FROM_SOURCES="true"
 ARG INSTALL_FROM_PYPI="true"
-ARG AIRFLOW_PIP_VERSION=21.1.2
+ARG AIRFLOW_PIP_VERSION=21.2.2
 # Setup PIP
 # By default PIP install run without cache to make image smaller
 ARG PIP_NO_CACHE_DIR="true"
@@ -282,7 +293,7 @@ ENV EAGER_UPGRADE_ADDITIONAL_REQUIREMENTS=${EAGER_UPGRADE_ADDITIONAL_REQUIREMENT
 RUN bash /scripts/docker/install_pip_version.sh; \
     if [[ ${AIRFLOW_PRE_CACHED_PIP_PACKAGES} == "true" && \
           ${UPGRADE_TO_NEWER_DEPENDENCIES} == "false" ]]; then \
-        bash /scripts/docker/install_airflow_from_branch_tip.sh; \
+        bash /scripts/docker/install_airflow_dependencies_from_branch_tip.sh; \
     fi
 
 # Generate random hex dump file so that we can determine whether it's faster to rebuild the image
@@ -311,8 +322,6 @@ COPY setup.cfg ${AIRFLOW_SOURCES}/setup.cfg
 
 COPY airflow/__init__.py ${AIRFLOW_SOURCES}/airflow/__init__.py
 
-ARG CONTINUE_ON_PIP_CHECK_FAILURE="false"
-
 # The goal of this line is to install the dependencies from the most current setup.py from sources
 # This will be usually incremental small set of packages in CI optimized build, so it will be very fast
 # In non-CI optimized build this will install all dependencies before installing sources.
@@ -337,11 +346,13 @@ RUN chmod a+x /entrypoint
 
 COPY scripts/docker/load.bash /opt/bats/lib/
 
-# We can copy everything here. The Context is filtered by dockerignore. This makes sure we are not
-# copying over stuff that is accidentally generated or that we do not need (such as egg-info)
-# if you want to add something that is missing and you expect to see it in the image you can
-# add it with ! in .dockerignore next to the airflow, test etc. directories there
-COPY . ${AIRFLOW_SOURCES}/
+# Additional python deps to install
+ARG ADDITIONAL_PYTHON_DEPS=""
+
+RUN bash /scripts/docker/install_pip_version.sh; \
+    if [[ -n "${ADDITIONAL_PYTHON_DEPS}" ]]; then \
+            bash /scripts/docker/install_additional_dependencies.sh; \
+    fi
 
 # Install autocomplete for airflow
 RUN if command -v airflow; then \
@@ -351,27 +362,16 @@ RUN if command -v airflow; then \
 # Install autocomplete for Kubectl
 RUN echo "source /etc/bash_completion" >> ~/.bashrc
 
-WORKDIR ${AIRFLOW_SOURCES}
-
-# Install Helm
-ARG HELM_VERSION="v3.2.4"
-
-RUN SYSTEM=$(uname -s | tr '[:upper:]' '[:lower:]') \
-    && HELM_URL="https://get.helm.sh/helm-${HELM_VERSION}-${SYSTEM}-amd64.tar.gz" \
-    && curl --location "${HELM_URL}" | tar -xvz -O "${SYSTEM}"-amd64/helm > /usr/local/bin/helm \
-    && chmod +x /usr/local/bin/helm
-
-# Additional python deps to install
-ARG ADDITIONAL_PYTHON_DEPS=""
+# We can copy everything here. The Context is filtered by dockerignore. This makes sure we are not
+# copying over stuff that is accidentally generated or that we do not need (such as egg-info)
+# if you want to add something that is missing and you expect to see it in the image you can
+# add it with ! in .dockerignore next to the airflow, test etc. directories there
+COPY . ${AIRFLOW_SOURCES}/
 
-RUN bash /scripts/docker/install_pip_version.sh; \
-    if [[ -n "${ADDITIONAL_PYTHON_DEPS}" ]]; then \
-            bash /scripts/docker/install_additional_dependencies.sh; \
-    fi
+WORKDIR ${AIRFLOW_SOURCES}
 
 ARG BUILD_ID
 ARG COMMIT_SHA
-ARG AIRFLOW_IMAGE_REPOSITORY="https://github.com/apache/airflow"
 ARG AIRFLOW_IMAGE_DATE_CREATED
 
 ENV PATH="/files/bin/:/opt/airflow/scripts/in_container/bin/:${HOME}:${PATH}" \
diff --git a/IMAGES.rst b/IMAGES.rst
index 82e69895f3842..bc34e6c6abe37 100644
--- a/IMAGES.rst
+++ b/IMAGES.rst
@@ -445,12 +445,6 @@ The following build arguments (``--build-arg`` in docker build command) can be u
 |                                          |                                          | upgraded to newer versions matching      |
 |                                          |                                          | setup.py before installation.            |
 +------------------------------------------+------------------------------------------+------------------------------------------+
-| ``CONTINUE_ON_PIP_CHECK_FAILURE``        | ``false``                                | By default the image will fail if pip    |
-|                                          |                                          | check fails for it. This is good for     |
-|                                          |                                          | interactive building but on CI the       |
-|                                          |                                          | image should be built regardless - we    |
-|                                          |                                          | have a separate step to verify image.    |
-+------------------------------------------+------------------------------------------+------------------------------------------+
 | ``AIRFLOW_PRE_CACHED_PIP_PACKAGES``      | ``true``                                 | Allows to pre-cache airflow PIP packages |
 |                                          |                                          | from the GitHub of Apache Airflow        |
 |                                          |                                          | This allows to optimize iterations for   |
diff --git a/breeze b/breeze
index 7aa42952fb7cb..420861eefb53d 100755
--- a/breeze
+++ b/breeze
@@ -1199,12 +1199,6 @@ function breeze::parse_arguments() {
             echo
             shift
             ;;
-        --continue-on-pip-check-failure)
-            export CONTINUE_ON_PIP_CHECK_FAILURE="true"
-            echo "Skip PIP check failure."
-            echo
-            shift
-            ;;
         --package-format)
             export PACKAGE_FORMAT="${2}"
             echo "Selected package type: ${PACKAGE_FORMAT}"
@@ -2439,9 +2433,6 @@ ${FORMATTED_INSTALLATION_METHOD}
 --upgrade-to-newer-dependencies
         Upgrades PIP packages to latest versions available without looking at the constraints.
 
---continue-on-pip-check-failure
-        Continue even if 'pip check' fails.
-
 "
 }
 
diff --git a/breeze-complete b/breeze-complete
index e5b5d3f254d7f..01efc7c79cc6c 100644
--- a/breeze-complete
+++ b/breeze-complete
@@ -29,7 +29,7 @@ _breeze_allowed_integrations="cassandra kerberos mongo openldap pinot rabbitmq r
 _breeze_allowed_generate_constraints_modes="source-providers pypi-providers no-providers"
 _breeze_allowed_kubernetes_modes="image"
 _breeze_allowed_kubernetes_versions="v1.20.2 v1.19.7 v1.18.15"
-_breeze_allowed_helm_versions="v3.2.4"
+_breeze_allowed_helm_versions="v3.6.3"
 _breeze_allowed_kind_versions="v0.11.1"
 _breeze_allowed_mysql_versions="5.7 8"
 _breeze_allowed_mssql_versions="2017-latest 2019-latest"
diff --git a/docs/docker-stack/build-arg-ref.rst b/docs/docker-stack/build-arg-ref.rst
index 8780970f613c5..f2507e05db423 100644
--- a/docs/docker-stack/build-arg-ref.rst
+++ b/docs/docker-stack/build-arg-ref.rst
@@ -79,12 +79,6 @@ for examples of using those arguments.
 +------------------------------------------+------------------------------------------+------------------------------------------+
 | Build argument                           | Default value                            | Description                              |
 +==========================================+==========================================+==========================================+
-| ``CONTINUE_ON_PIP_CHECK_FAILURE``        | ``false``                                | By default the image build fails if pip  |
-|                                          |                                          | check fails for it. This is good for     |
-|                                          |                                          | interactive building but on CI the       |
-|                                          |                                          | image should be built regardless - we    |
-|                                          |                                          | have a separate step to verify image.    |
-+------------------------------------------+------------------------------------------+------------------------------------------+
 | ``UPGRADE_TO_NEWER_DEPENDENCIES``        | ``false``                                | If set to true, the dependencies are     |
 |                                          |                                          | upgraded to newer versions matching      |
 |                                          |                                          | setup.py before installation.            |
diff --git a/scripts/ci/libraries/_build_images.sh b/scripts/ci/libraries/_build_images.sh
index ca94e4cf316b6..4ead442d9d9de 100644
--- a/scripts/ci/libraries/_build_images.sh
+++ b/scripts/ci/libraries/_build_images.sh
@@ -669,7 +669,6 @@ Docker building ${AIRFLOW_CI_IMAGE}.
         --build-arg ADDITIONAL_RUNTIME_APT_DEPS="${ADDITIONAL_RUNTIME_APT_DEPS}" \
         --build-arg ADDITIONAL_RUNTIME_APT_ENV="${ADDITIONAL_RUNTIME_APT_ENV}" \
         --build-arg UPGRADE_TO_NEWER_DEPENDENCIES="${UPGRADE_TO_NEWER_DEPENDENCIES}" \
-        --build-arg CONTINUE_ON_PIP_CHECK_FAILURE="${CONTINUE_ON_PIP_CHECK_FAILURE}" \
         --build-arg CONSTRAINTS_GITHUB_REPOSITORY="${CONSTRAINTS_GITHUB_REPOSITORY}" \
         --build-arg AIRFLOW_CONSTRAINTS_REFERENCE="${DEFAULT_CONSTRAINTS_BRANCH}" \
         --build-arg AIRFLOW_CONSTRAINTS="${AIRFLOW_CONSTRAINTS}" \
@@ -810,7 +809,6 @@ function build_images::build_prod_images() {
         --build-arg INSTALL_FROM_PYPI="${INSTALL_FROM_PYPI}" \
         --build-arg INSTALL_FROM_DOCKER_CONTEXT_FILES="${INSTALL_FROM_DOCKER_CONTEXT_FILES}" \
         --build-arg UPGRADE_TO_NEWER_DEPENDENCIES="${UPGRADE_TO_NEWER_DEPENDENCIES}" \
-        --build-arg CONTINUE_ON_PIP_CHECK_FAILURE="${CONTINUE_ON_PIP_CHECK_FAILURE}" \
         --build-arg BUILD_ID="${CI_BUILD_ID}" \
         --build-arg COMMIT_SHA="${COMMIT_SHA}" \
         --build-arg CONSTRAINTS_GITHUB_REPOSITORY="${CONSTRAINTS_GITHUB_REPOSITORY}" \
@@ -845,7 +843,6 @@ function build_images::build_prod_images() {
         --build-arg INSTALL_FROM_PYPI="${INSTALL_FROM_PYPI}" \
         --build-arg INSTALL_FROM_DOCKER_CONTEXT_FILES="${INSTALL_FROM_DOCKER_CONTEXT_FILES}" \
         --build-arg UPGRADE_TO_NEWER_DEPENDENCIES="${UPGRADE_TO_NEWER_DEPENDENCIES}" \
-        --build-arg CONTINUE_ON_PIP_CHECK_FAILURE="${CONTINUE_ON_PIP_CHECK_FAILURE}" \
         --build-arg AIRFLOW_VERSION="${AIRFLOW_VERSION}" \
         --build-arg AIRFLOW_BRANCH="${AIRFLOW_BRANCH_FOR_PYPI_PRELOADING}" \
         --build-arg AIRFLOW_EXTRAS="${AIRFLOW_EXTRAS}" \
@@ -1014,23 +1011,6 @@ ${COLOR_BLUE}
      ./breeze build-image --production-image --upgrade-to-newer-dependencies --python 3.6
 ${COLOR_RESET}
 
-* If you want to build the image regardless if 'pip check' fails for it, you can add
-  --continue-on-pip-check-failure flag and enter the image and inspect dependencies.
-
-CI image:
-
-${COLOR_BLUE}
-     ./breeze build-image --upgrade-to-newer-dependencies --python 3.6 --continue-on-pip-check-failure
-     docker run -it apache/airflow:main-3.6-ci bash
-${COLOR_RESET}
-
-Production image:
-
-${COLOR_BLUE}
-     ./breeze build-image --production-image --upgrade-to-newer-dependencies --python 3.6 --continue-on-pip-check-failure
-     docker run -it apache/airflow:main-3.6 bash
-${COLOR_RESET}
-
 * You will see error messages there telling which requirements are conflicting and which packages caused the
   conflict. Add the limitation that caused the conflict to EAGER_UPGRADE_ADDITIONAL_REQUIREMENTS
   variable in Dockerfile.ci. Note that the limitations might be different for Dockerfile.ci and Dockerfile
diff --git a/scripts/ci/libraries/_initialization.sh b/scripts/ci/libraries/_initialization.sh
index fefcb1a5b4040..223d9ea999343 100644
--- a/scripts/ci/libraries/_initialization.sh
+++ b/scripts/ci/libraries/_initialization.sh
@@ -221,7 +221,7 @@ function initialization::initialize_files_for_rebuild_check() {
         "scripts/docker/common.sh"
         "scripts/docker/install_additional_dependencies.sh"
         "scripts/docker/install_airflow.sh"
-        "scripts/docker/install_airflow_from_branch_tip.sh"
+        "scripts/docker/install_airflow_dependencies_from_branch_tip.sh"
         "scripts/docker/install_from_docker_context_files.sh"
         "scripts/docker/install_mysql.sh"
         "airflow/www/package.json"
@@ -422,7 +422,7 @@ function initialization::initialize_image_build_variables() {
     export INSTALLED_PROVIDERS
     export INSTALLED_EXTRAS="async,amazon,celery,cncf.kubernetes,docker,dask,elasticsearch,ftp,grpc,hashicorp,http,imap,ldap,google,microsoft.azure,mysql,postgres,redis,sendgrid,sftp,slack,ssh,statsd,virtualenv"
 
-    AIRFLOW_PIP_VERSION=${AIRFLOW_PIP_VERSION:="21.1"}
+    AIRFLOW_PIP_VERSION=${AIRFLOW_PIP_VERSION:="21.2.2"}
     export AIRFLOW_PIP_VERSION
 
     # We also pin version of wheel used to get consistent builds
@@ -446,9 +446,6 @@ function initialization::initialize_image_build_variables() {
     # Installs different airflow version than current from the sources
     export INSTALL_AIRFLOW_VERSION=${INSTALL_AIRFLOW_VERSION:=""}
 
-    # Continue on PIP CHECK failure
-    export CONTINUE_ON_PIP_CHECK_FAILURE=${CONTINUE_ON_PIP_CHECK_FAILURE:="false"}
-
     # Determines if airflow should be installed from a specified reference in GitHub
     export INSTALL_AIRFLOW_REFERENCE=${INSTALL_AIRFLOW_REFERENCE:=""}
 
@@ -503,7 +500,7 @@ function initialization::initialize_kubernetes_variables() {
     CURRENT_KIND_VERSIONS+=("v0.11.1")
     export CURRENT_KIND_VERSIONS
     # Currently supported versions of Helm
-    CURRENT_HELM_VERSIONS+=("v3.2.4")
+    CURRENT_HELM_VERSIONS+=("v3.6.3")
     export CURRENT_HELM_VERSIONS
     # Current executor in chart
     CURRENT_EXECUTOR+=("KubernetesExecutor")
@@ -684,7 +681,6 @@ Common image build variables:
     INSTALL_FROM_PYPI: '${INSTALL_FROM_PYPI}'
     AIRFLOW_PRE_CACHED_PIP_PACKAGES: '${AIRFLOW_PRE_CACHED_PIP_PACKAGES}'
     UPGRADE_TO_NEWER_DEPENDENCIES: '${UPGRADE_TO_NEWER_DEPENDENCIES}'
-    CONTINUE_ON_PIP_CHECK_FAILURE: '${CONTINUE_ON_PIP_CHECK_FAILURE}'
     CHECK_IMAGE_FOR_REBUILD: '${CHECK_IMAGE_FOR_REBUILD}'
     AIRFLOW_CONSTRAINTS_LOCATION: '${AIRFLOW_CONSTRAINTS_LOCATION}'
     AIRFLOW_CONSTRAINTS_REFERENCE: '${AIRFLOW_CONSTRAINTS_REFERENCE}'
diff --git a/scripts/docker/install_additional_dependencies.sh b/scripts/docker/install_additional_dependencies.sh
index 6c035ae5def09..4f9c05f6b7680 100755
--- a/scripts/docker/install_additional_dependencies.sh
+++ b/scripts/docker/install_additional_dependencies.sh
@@ -23,7 +23,6 @@ test -v ADDITIONAL_PYTHON_DEPS
 test -v EAGER_UPGRADE_ADDITIONAL_REQUIREMENTS
 test -v AIRFLOW_INSTALL_USER_FLAG
 test -v AIRFLOW_PIP_VERSION
-test -v CONTINUE_ON_PIP_CHECK_FAILURE
 
 # shellcheck source=scripts/docker/common.sh
 . "$( dirname "${BASH_SOURCE[0]}" )/common.sh"
@@ -41,7 +40,7 @@ function install_additional_dependencies() {
             ${ADDITIONAL_PYTHON_DEPS} ${EAGER_UPGRADE_ADDITIONAL_REQUIREMENTS}
         # make sure correct PIP version is used
         pip install ${AIRFLOW_INSTALL_USER_FLAG} --upgrade "pip==${AIRFLOW_PIP_VERSION}"
-        pip check || ${CONTINUE_ON_PIP_CHECK_FAILURE}
+        pip check
     else
         echo
         echo Installing additional dependencies upgrading only if needed
@@ -51,7 +50,7 @@ function install_additional_dependencies() {
             ${ADDITIONAL_PYTHON_DEPS}
         # make sure correct PIP version is used
         pip install ${AIRFLOW_INSTALL_USER_FLAG} --upgrade "pip==${AIRFLOW_PIP_VERSION}"
-        pip check || ${CONTINUE_ON_PIP_CHECK_FAILURE}
+        pip check
     fi
 }
 
diff --git a/scripts/docker/install_airflow.sh b/scripts/docker/install_airflow.sh
index 49040275a04ac..e2bca4fc839a0 100755
--- a/scripts/docker/install_airflow.sh
+++ b/scripts/docker/install_airflow.sh
@@ -60,7 +60,7 @@ function install_airflow() {
 
         # make sure correct PIP version is used
         pip install ${AIRFLOW_INSTALL_USER_FLAG} --upgrade "pip==${AIRFLOW_PIP_VERSION}"
-        pip check || ${CONTINUE_ON_PIP_CHECK_FAILURE}
+        pip check
     else \
         echo
         echo Installing all packages with constraints and upgrade if needed
@@ -76,7 +76,7 @@ function install_airflow() {
             "${AIRFLOW_INSTALLATION_METHOD}[${AIRFLOW_EXTRAS}]${AIRFLOW_VERSION_SPECIFICATION}" \
         # make sure correct PIP version is used
         pip install ${AIRFLOW_INSTALL_USER_FLAG} --upgrade "pip==${AIRFLOW_PIP_VERSION}"
-        pip check || ${CONTINUE_ON_PIP_CHECK_FAILURE}
+        pip check
     fi
 
 }
diff --git a/scripts/docker/install_airflow_from_branch_tip.sh b/scripts/docker/install_airflow_dependencies_from_branch_tip.sh
similarity index 85%
rename from scripts/docker/install_airflow_from_branch_tip.sh
rename to scripts/docker/install_airflow_dependencies_from_branch_tip.sh
index 925a872fa50ea..61aaa13ef467f 100755
--- a/scripts/docker/install_airflow_from_branch_tip.sh
+++ b/scripts/docker/install_airflow_dependencies_from_branch_tip.sh
@@ -30,28 +30,29 @@
 . "$( dirname "${BASH_SOURCE[0]}" )/common.sh"
 
 
-function install_airflow_from_branch_tip() {
+function install_airflow_dependencies_from_branch_tip() {
     echo
     echo "Installing airflow from ${AIRFLOW_BRANCH}. It is used to cache dependencies"
     echo
     if [[ ${INSTALL_MYSQL_CLIENT} != "true" ]]; then
        AIRFLOW_EXTRAS=${AIRFLOW_EXTRAS/mysql,}
     fi
-    # Install latest set of dependencies using constraints
+    # Install latest set of dependencies using constraints. In case constraints were upgraded and there
+    # are conflicts, this might fail, but it should be fixed in the following installation steps
     pip install ${AIRFLOW_INSTALL_USER_FLAG} \
       "https://github.com/${AIRFLOW_REPO}/archive/${AIRFLOW_BRANCH}.tar.gz#egg=apache-airflow[${AIRFLOW_EXTRAS}]" \
-      --constraint "${AIRFLOW_CONSTRAINTS_LOCATION}"
+      --constraint "${AIRFLOW_CONSTRAINTS_LOCATION}" || true
     # make sure correct PIP version is used
     pip install ${AIRFLOW_INSTALL_USER_FLAG} --upgrade "pip==${AIRFLOW_PIP_VERSION}"
     pip freeze | grep apache-airflow-providers | xargs pip uninstall --yes || true
     echo
     echo Uninstalling just airflow. Dependencies remain.
     echo
-    pip uninstall --yes apache-airflow
+    pip uninstall --yes apache-airflow || true
 }
 
 common::get_airflow_version_specification
 common::override_pip_version_if_needed
 common::get_constraints_location
 
-install_airflow_from_branch_tip
+install_airflow_dependencies_from_branch_tip
diff --git a/scripts/docker/install_from_docker_context_files.sh b/scripts/docker/install_from_docker_context_files.sh
index 813d1b02df7e0..d8ed6bc72bd9a 100755
--- a/scripts/docker/install_from_docker_context_files.sh
+++ b/scripts/docker/install_from_docker_context_files.sh
@@ -96,7 +96,7 @@ function install_airflow_and_providers_from_docker_context_files(){
 
     # make sure correct PIP version is left installed
     pip install ${AIRFLOW_INSTALL_USER_FLAG} --upgrade "pip==${AIRFLOW_PIP_VERSION}"
-    pip check || ${CONTINUE_ON_PIP_CHECK_FAILURE}
+    pip check
 
 }