diff --git a/requirements.txt b/requirements.txt
index 3392d79445..ef37868f7c 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -8,7 +8,8 @@ setuptools>=21
 # importlib_metadata: is part of python3.8 and newer as importlib.metadata
 importlib_metadata; python_version < "3.8"
 packaging
-click>=7.0
+click==7.0; python_version == "3.4"
+click>=7.0; python_version != "3.4"
 pyserial>=3.0
 future>=0.15.2
 cryptography>=2.1.4,<35
@@ -17,6 +18,8 @@ cffi<1.15;python_version<'3.6'
 pyparsing>=2.0.3,<2.4.0
 pyelftools>=0.22
 idf-component-manager~=1.0
+packaging<21.0; python_version<"3.6"
+urllib3<1.25,>=1.21.1; python_version == "3.4"
 
 gdbgui==0.13.2.0; python_version < "3.11"
 # 0.13.2.1 supports Python 3.6+ only
diff --git a/tools/docker/Dockerfile b/tools/docker/Dockerfile
index e46f14cb59..ca9c87f067 100644
--- a/tools/docker/Dockerfile
+++ b/tools/docker/Dockerfile
@@ -69,6 +69,62 @@ RUN echo IDF_CHECKOUT_REF=$IDF_CHECKOUT_REF IDF_CLONE_BRANCH_OR_TAG=$IDF_CLONE_B
 
 # Install all the required tools
 ARG CRYPTOGRAPHY_DONT_BUILD_RUST=1
+
+# Bypass to help pip resolver to install the right tool versions
+RUN : \
+ && python -m virtualenv /opt/esp/python_env/idf4.3_py3.6_env \
+ && /opt/esp/python_env/idf4.3_py3.6_env/bin/python -m pip install \
+ Flask==0.12.5 \
+ Flask-Compress==1.13 \
+ Flask-SocketIO==2.9.6 \
+ MarkupSafe==2.0.1 \
+ Pygments==2.14.0 \
+ Werkzeug==0.16.1 \
+ bitstring==3.1.9 \
+ brotli==1.0.9 \
+ cachecontrol==0.12.14 \
+ certifi==2023.5.7 \
+ cffi==1.15.1 \
+ charset-normalizer==2.0.12 \
+ click==8.0.4 \
+ colorama==0.4.5 \
+ construct==2.10.54 \
+ contextlib2==21.6.0 \
+ cryptography==3.4.8 \
+ ecdsa==0.18.0 \
+ future==0.18.3 \
+ gdbgui==0.13.2.0 \
+ gevent==1.5.0 \
+ greenlet==2.0.2 \
+ idf-component-manager==1.2.3 \
+ idna==3.4 \
+ importlib-metadata==4.8.3 \
+ importlib-resources==5.4.0 \
+ itsdangerous==2.0.1 \
+ jinja2==3.0.3 \
+ kconfiglib==13.7.1 \
+ lockfile==0.12.2 \
+ msgpack==1.0.5 \
+ packaging==21.3 \
+ pycparser==2.21 \
+ pyelftools==0.29 \
+ pygdbmi==0.9.0.2 \
+ pyparsing==2.3.1 \
+ pyserial==3.5 \
+ python-engineio==3.14.2 \
+ python-socketio==4.6.1 \
+ pyyaml==6.0 \
+ reedsolo==1.5.4 \
+ requests==2.27.1 \
+ requests-file==1.5.1 \
+ requests-toolbelt==1.0.0 \
+ schema==0.7.5 \
+ six==1.16.0 \
+ tqdm==4.64.1 \
+ typing-extensions==4.1.1 \
+ urllib3==1.26.16 \
+ zipp==3.6.0
+
 RUN : \
   && update-ca-certificates --fresh \
   && $IDF_PATH/tools/idf_tools.py --non-interactive install required --targets=${IDF_INSTALL_TARGETS} \