diff --git a/tools/dockerfile/grpc_clang_tidy/Dockerfile b/tools/dockerfile/grpc_clang_tidy/Dockerfile
index 662ff8a697d..37c96f1041d 100644
--- a/tools/dockerfile/grpc_clang_tidy/Dockerfile
+++ b/tools/dockerfile/grpc_clang_tidy/Dockerfile
@@ -51,7 +51,7 @@ RUN apt-get update && apt-get install -y time && apt-get clean
 
 # Install Python 2.7
 RUN apt-get update && apt-get install -y python2.7 python-all-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 
 # Google Cloud platform API libraries
 RUN pip install --upgrade google-api-python-client oauth2client
diff --git a/tools/dockerfile/interoptest/grpc_interop_csharp/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_csharp/Dockerfile
index 6c65771582d..9b17779e147 100644
--- a/tools/dockerfile/interoptest/grpc_interop_csharp/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_csharp/Dockerfile
@@ -60,7 +60,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/interoptest/grpc_interop_csharpcoreclr/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_csharpcoreclr/Dockerfile
index 6c65771582d..9b17779e147 100644
--- a/tools/dockerfile/interoptest/grpc_interop_csharpcoreclr/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_csharpcoreclr/Dockerfile
@@ -60,7 +60,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/interoptest/grpc_interop_cxx/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_cxx/Dockerfile
index 6a2863af50b..40a622e42aa 100644
--- a/tools/dockerfile/interoptest/grpc_interop_cxx/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_cxx/Dockerfile
@@ -61,7 +61,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/interoptest/grpc_interop_go/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_go/Dockerfile
index 62c68b16e11..3a9bfe0bcad 100644
--- a/tools/dockerfile/interoptest/grpc_interop_go/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_go/Dockerfile
@@ -28,7 +28,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/interoptest/grpc_interop_go1.11/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_go1.11/Dockerfile
index 146af2d6c36..31eab0ef00e 100644
--- a/tools/dockerfile/interoptest/grpc_interop_go1.11/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_go1.11/Dockerfile
@@ -28,7 +28,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/interoptest/grpc_interop_go1.8/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_go1.8/Dockerfile
index 45fd264d3b4..d5d67539712 100644
--- a/tools/dockerfile/interoptest/grpc_interop_go1.8/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_go1.8/Dockerfile
@@ -28,7 +28,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/interoptest/grpc_interop_http2/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_http2/Dockerfile
index ef13d2d7e93..04521c94169 100644
--- a/tools/dockerfile/interoptest/grpc_interop_http2/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_http2/Dockerfile
@@ -28,7 +28,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/interoptest/grpc_interop_node/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_node/Dockerfile
index 5754ead72e6..4e33e873907 100644
--- a/tools/dockerfile/interoptest/grpc_interop_node/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_node/Dockerfile
@@ -61,7 +61,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/interoptest/grpc_interop_python/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_python/Dockerfile
index 8793d5f336e..fc881939af5 100644
--- a/tools/dockerfile/interoptest/grpc_interop_python/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_python/Dockerfile
@@ -51,7 +51,7 @@ RUN apt-get update && apt-get install -y time && apt-get clean
 
 # Install Python 2.7
 RUN apt-get update && apt-get install -y python2.7 python-all-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 
 # Google Cloud platform API libraries
 RUN pip install --upgrade google-api-python-client oauth2client
diff --git a/tools/dockerfile/interoptest/grpc_interop_pythonasyncio/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_pythonasyncio/Dockerfile
index 8793d5f336e..fc881939af5 100644
--- a/tools/dockerfile/interoptest/grpc_interop_pythonasyncio/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_pythonasyncio/Dockerfile
@@ -51,7 +51,7 @@ RUN apt-get update && apt-get install -y time && apt-get clean
 
 # Install Python 2.7
 RUN apt-get update && apt-get install -y python2.7 python-all-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 
 # Google Cloud platform API libraries
 RUN pip install --upgrade google-api-python-client oauth2client
diff --git a/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile b/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile
index 7ea3d3bef72..247a519027d 100644
--- a/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile
+++ b/tools/dockerfile/interoptest/grpc_interop_ruby/Dockerfile
@@ -60,7 +60,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/bazel/Dockerfile b/tools/dockerfile/test/bazel/Dockerfile
index 984a3940b1e..a0780b43bee 100644
--- a/tools/dockerfile/test/bazel/Dockerfile
+++ b/tools/dockerfile/test/bazel/Dockerfile
@@ -44,7 +44,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/csharp_stretch_x64/Dockerfile b/tools/dockerfile/test/csharp_stretch_x64/Dockerfile
index 609b34f9456..6631979386b 100644
--- a/tools/dockerfile/test/csharp_stretch_x64/Dockerfile
+++ b/tools/dockerfile/test/csharp_stretch_x64/Dockerfile
@@ -60,7 +60,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/cxx_buster_x64/Dockerfile b/tools/dockerfile/test/cxx_buster_x64/Dockerfile
index 7ab73923df4..781c9419496 100644
--- a/tools/dockerfile/test/cxx_buster_x64/Dockerfile
+++ b/tools/dockerfile/test/cxx_buster_x64/Dockerfile
@@ -60,7 +60,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/cxx_jessie_x64/Dockerfile b/tools/dockerfile/test/cxx_jessie_x64/Dockerfile
index a9a61240e4a..1317f8e1c1d 100644
--- a/tools/dockerfile/test/cxx_jessie_x64/Dockerfile
+++ b/tools/dockerfile/test/cxx_jessie_x64/Dockerfile
@@ -61,7 +61,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/cxx_jessie_x86/Dockerfile b/tools/dockerfile/test/cxx_jessie_x86/Dockerfile
index 3d5cf6dcd85..372b3ddc905 100644
--- a/tools/dockerfile/test/cxx_jessie_x86/Dockerfile
+++ b/tools/dockerfile/test/cxx_jessie_x86/Dockerfile
@@ -61,7 +61,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/cxx_ubuntu1604_x64/Dockerfile b/tools/dockerfile/test/cxx_ubuntu1604_x64/Dockerfile
index 043b1a6773b..305b6e00a64 100644
--- a/tools/dockerfile/test/cxx_ubuntu1604_x64/Dockerfile
+++ b/tools/dockerfile/test/cxx_ubuntu1604_x64/Dockerfile
@@ -60,7 +60,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/cxx_ubuntu1804_x64/Dockerfile b/tools/dockerfile/test/cxx_ubuntu1804_x64/Dockerfile
index 7928ef06c88..ba67279347a 100644
--- a/tools/dockerfile/test/cxx_ubuntu1804_x64/Dockerfile
+++ b/tools/dockerfile/test/cxx_ubuntu1804_x64/Dockerfile
@@ -60,7 +60,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/fuzzer/Dockerfile b/tools/dockerfile/test/fuzzer/Dockerfile
index 3e776f0e083..a9c6fdab4e8 100644
--- a/tools/dockerfile/test/fuzzer/Dockerfile
+++ b/tools/dockerfile/test/fuzzer/Dockerfile
@@ -61,7 +61,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/node_jessie_x64/Dockerfile b/tools/dockerfile/test/node_jessie_x64/Dockerfile
index 5936a81bce1..80dec84ae54 100644
--- a/tools/dockerfile/test/node_jessie_x64/Dockerfile
+++ b/tools/dockerfile/test/node_jessie_x64/Dockerfile
@@ -72,7 +72,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/php7_jessie_x64/Dockerfile b/tools/dockerfile/test/php7_jessie_x64/Dockerfile
index 2e456a11527..6efbdc09516 100644
--- a/tools/dockerfile/test/php7_jessie_x64/Dockerfile
+++ b/tools/dockerfile/test/php7_jessie_x64/Dockerfile
@@ -72,7 +72,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/python_stretch_2.7_x64/Dockerfile b/tools/dockerfile/test/python_stretch_2.7_x64/Dockerfile
index 876c5dcd4af..617e6fe2f10 100644
--- a/tools/dockerfile/test/python_stretch_2.7_x64/Dockerfile
+++ b/tools/dockerfile/test/python_stretch_2.7_x64/Dockerfile
@@ -51,7 +51,7 @@ RUN apt-get update && apt-get install -y time && apt-get clean
 
 # Install Python 2.7
 RUN apt-get update && apt-get install -y python2.7 python-all-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 
 # Google Cloud platform API libraries
 RUN pip install --upgrade google-api-python-client oauth2client
diff --git a/tools/dockerfile/test/python_stretch_3.5_x64/Dockerfile b/tools/dockerfile/test/python_stretch_3.5_x64/Dockerfile
index 5e4ca949a6e..1b9e5e0d027 100644
--- a/tools/dockerfile/test/python_stretch_3.5_x64/Dockerfile
+++ b/tools/dockerfile/test/python_stretch_3.5_x64/Dockerfile
@@ -51,7 +51,7 @@ RUN apt-get update && apt-get install -y time && apt-get clean
 
 # Install Python 2.7
 RUN apt-get update && apt-get install -y python2.7 python-all-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 
 # Google Cloud platform API libraries
 RUN pip install --upgrade google-api-python-client oauth2client
@@ -65,4 +65,4 @@ RUN mkdir /var/local/jenkins
 
 
 RUN apt-get update && apt-get install -y python3.5 python3-all-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python3.5
+RUN curl https://bootstrap.pypa.io/3.5/get-pip.py | python3.5
diff --git a/tools/dockerfile/test/python_stretch_3.6_x64/Dockerfile b/tools/dockerfile/test/python_stretch_3.6_x64/Dockerfile
index bc92bd6adcc..8e1393ed3a9 100644
--- a/tools/dockerfile/test/python_stretch_3.6_x64/Dockerfile
+++ b/tools/dockerfile/test/python_stretch_3.6_x64/Dockerfile
@@ -51,7 +51,7 @@ RUN apt-get update && apt-get install -y time && apt-get clean
 
 # Install Python 2.7
 RUN apt-get update && apt-get install -y python2.7 python-all-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 
 # Google Cloud platform API libraries
 RUN pip install --upgrade google-api-python-client oauth2client
diff --git a/tools/dockerfile/test/python_stretch_3.7_x64/Dockerfile b/tools/dockerfile/test/python_stretch_3.7_x64/Dockerfile
index 00edc458b73..bcac4b50deb 100644
--- a/tools/dockerfile/test/python_stretch_3.7_x64/Dockerfile
+++ b/tools/dockerfile/test/python_stretch_3.7_x64/Dockerfile
@@ -51,7 +51,7 @@ RUN apt-get update && apt-get install -y time && apt-get clean
 
 # Install Python 2.7
 RUN apt-get update && apt-get install -y python2.7 python-all-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 
 # Google Cloud platform API libraries
 RUN pip install --upgrade google-api-python-client oauth2client
diff --git a/tools/dockerfile/test/python_stretch_3.8_x64/Dockerfile b/tools/dockerfile/test/python_stretch_3.8_x64/Dockerfile
index 3202eb0dcd9..d6c0a99eeb0 100644
--- a/tools/dockerfile/test/python_stretch_3.8_x64/Dockerfile
+++ b/tools/dockerfile/test/python_stretch_3.8_x64/Dockerfile
@@ -51,7 +51,7 @@ RUN apt-get update && apt-get install -y time && apt-get clean
 
 # Install Python 2.7
 RUN apt-get update && apt-get install -y python2.7 python-all-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 
 # Google Cloud platform API libraries
 RUN pip install --upgrade google-api-python-client oauth2client
diff --git a/tools/dockerfile/test/python_stretch_default_x64/Dockerfile b/tools/dockerfile/test/python_stretch_default_x64/Dockerfile
index 9cde17429ec..331c28e6448 100644
--- a/tools/dockerfile/test/python_stretch_default_x64/Dockerfile
+++ b/tools/dockerfile/test/python_stretch_default_x64/Dockerfile
@@ -51,7 +51,7 @@ RUN apt-get update && apt-get install -y time && apt-get clean
 
 # Install Python 2.7
 RUN apt-get update && apt-get install -y python2.7 python-all-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 
 # Google Cloud platform API libraries
 RUN pip install --upgrade google-api-python-client oauth2client
@@ -105,7 +105,7 @@ RUN python3.8 -m ensurepip && \
 
 
 RUN apt-get update && apt-get install -y python3.5 python3.5-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python3.5
+RUN curl https://bootstrap.pypa.io/3.5/get-pip.py | python3.5
 
 RUN apt-get update && apt-get -t buster install -y python3.7 python3-all-dev
 RUN curl https://bootstrap.pypa.io/get-pip.py | python3.7
diff --git a/tools/dockerfile/test/ruby_buster_x64/Dockerfile b/tools/dockerfile/test/ruby_buster_x64/Dockerfile
index feef5d93eb6..7ac16731c69 100644
--- a/tools/dockerfile/test/ruby_buster_x64/Dockerfile
+++ b/tools/dockerfile/test/ruby_buster_x64/Dockerfile
@@ -60,7 +60,7 @@ RUN apt-get update && apt-get install -y \
     python-setuptools
 
 # Install Python packages from PyPI
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 RUN pip install --upgrade pip==19.3.1
 RUN pip install virtualenv==16.7.9
 RUN pip install futures==2.2.0 enum34==1.0.4 protobuf==3.5.2.post1 six==1.15.0 twisted==17.5.0
diff --git a/tools/dockerfile/test/sanity/Dockerfile b/tools/dockerfile/test/sanity/Dockerfile
index 41b265a0f11..aaafec98e8b 100644
--- a/tools/dockerfile/test/sanity/Dockerfile
+++ b/tools/dockerfile/test/sanity/Dockerfile
@@ -51,7 +51,7 @@ RUN apt-get update && apt-get install -y time && apt-get clean
 
 # Install Python 2.7
 RUN apt-get update && apt-get install -y python2.7 python-all-dev
-RUN curl https://bootstrap.pypa.io/get-pip.py | python2.7
+RUN curl https://bootstrap.pypa.io/2.7/get-pip.py | python2.7
 
 # Google Cloud platform API libraries
 RUN pip install --upgrade google-api-python-client oauth2client