diff --git a/agent-deploy/Dockerfile b/agent-deploy/Dockerfile
index 14c19460..c8ffed4e 100644
--- a/agent-deploy/Dockerfile
+++ b/agent-deploy/Dockerfile
@@ -40,9 +40,6 @@ RUN apt-get update && DEBIAN_FRONTEND=noninteractive apt-get install -y \
     libgmp-dev \
     libssl-dev \
     procps \
-    python-boto \
-    python-deltarpm \
-    python2.7-dev \
     shellcheck \
     make  \
     zlib1g-dev  \
@@ -73,15 +70,6 @@ RUN apt-get update && DEBIAN_FRONTEND=noninteractive apt-get install -y \
 # Use gnupg1 instead of gnupg2, our scripts and rpm-s3 are currently not compatible with gnupg2
 RUN mv /usr/bin/gpg /usr/bin/gpg2 && ln -s /usr/bin/gpg1 /usr/bin/gpg
 
-# Python 2 deps
-RUN curl https://bootstrap.pypa.io/pip/2.7/get-pip.py -o get-pip.py \
-    && python2 get-pip.py
-
-RUN python2 -m pip install \
-    awscli==1.18.140 \
-    boto3==1.14.7 \
-    pexpect==3.2
-
 # Python install
 ENV PYENV_ROOT="/.pyenv"
 ENV PATH="$PYENV_ROOT/shims:$PYENV_ROOT/bin:$PATH"
@@ -128,7 +116,7 @@ RUN git clone https://github.com/chocolatey/choco.git \
     && cp ./docker/choco_wrapper /usr/local/bin/choco \
     && rm -rf /choco
 
-ENV ChocolateyInstall=/opt/chocolatey 
+ENV ChocolateyInstall=/opt/chocolatey
 
 # RVM
 COPY ./rvm/gpg-keys /gpg-keys
diff --git a/build-container.ps1 b/build-container.ps1
index b2f394ac..0908d210 100644
--- a/build-container.ps1
+++ b/build-container.ps1
@@ -39,6 +39,13 @@ foreach ($line in $lines) {
     $arglist += "$line"
 }
 
+# Read arguments from deva.env file
+$lines = Get-Content -Path 'deva.env'
+foreach ($line in $lines) {
+    $arglist += "--build-arg"
+    $arglist += "$line"
+}
+
 foreach ($h in $SoftwareTable.GetEnumerator()){
     if( -not ($($h.Key) -like "*SHA256")){
         $arglist += "--build-arg"
@@ -50,7 +57,7 @@ if( -not $Cache) {
     $arglist += "--no-cache"
 }
 
-$arglist += -split "-m 4096M --build-arg BASE_IMAGE=$($BaseTable[$kernelver]) --build-arg DD_TARGET_ARCH=$Arch --build-arg WINDOWS_VERSION=$kernelver -t $Tag --file .\windows\Dockerfile ." 
+$arglist += -split "-m 4096M --build-arg BASE_IMAGE=$($BaseTable[$kernelver]) --build-arg DD_TARGET_ARCH=$Arch --build-arg WINDOWS_VERSION=$kernelver -t $Tag --file .\windows\Dockerfile ."
 # Write-Host -ForegroundColor Green "Building with the following command:"
 # Write-Host -ForegroundColor Green "$buildcommand `n"
 filter timestamp {"$(Get-Date -Format o): $_"}
diff --git a/deb-arm/Dockerfile b/deb-arm/Dockerfile
index bb716336..20cd8e5e 100644
--- a/deb-arm/Dockerfile
+++ b/deb-arm/Dockerfile
@@ -106,7 +106,7 @@ RUN if [ "$DD_TARGET_ARCH" = "armhf" ] ; then \
 ENV PATH "~/.cargo/bin:${PATH}"
 
 # CONDA
-COPY python-packages-versions.txt setup_python.sh requirements.txt requirements-py2.txt /
+COPY python-packages-versions.txt setup_python.sh requirements.txt /
 COPY requirements /requirements
 ENV DEVA_VERSION=$DEVA_VERSION
 ENV DEVA_NO_DYNAMIC_DEPS=$DEVA_NO_DYNAMIC_DEPS
diff --git a/deb-x64/Dockerfile b/deb-x64/Dockerfile
index 65946a52..d5a7b4b2 100644
--- a/deb-x64/Dockerfile
+++ b/deb-x64/Dockerfile
@@ -142,7 +142,7 @@ RUN curl -fsSL https://github.com/DataDog/datadog-ci/releases/download/v${CI_UPL
     chmod +x /usr/local/bin/datadog-ci
 
 # CONDA
-COPY python-packages-versions.txt setup_python.sh requirements.txt requirements-py2.txt /
+COPY python-packages-versions.txt setup_python.sh requirements.txt /
 COPY requirements /requirements
 ENV DEVA_VERSION=$DEVA_VERSION
 ENV DEVA_NO_DYNAMIC_DEPS=$DEVA_NO_DYNAMIC_DEPS
diff --git a/linux-glibc-2.17-x64/Dockerfile b/linux-glibc-2.17-x64/Dockerfile
index 012c2b00..cd12d6ea 100644
--- a/linux-glibc-2.17-x64/Dockerfile
+++ b/linux-glibc-2.17-x64/Dockerfile
@@ -75,7 +75,7 @@ RUN mkdir -p /opt/mqm \
     && rm -rf /tmp/mq_client.tar.gz
 
 # CONDA
-COPY python-packages-versions.txt setup_python.sh requirements.txt requirements-py2.txt /
+COPY python-packages-versions.txt setup_python.sh requirements.txt /
 COPY requirements /requirements
 ENV DEVA_VERSION=$DEVA_VERSION
 ENV DEVA_NO_DYNAMIC_DEPS=$DEVA_NO_DYNAMIC_DEPS
diff --git a/linux-glibc-2.23-arm64/Dockerfile b/linux-glibc-2.23-arm64/Dockerfile
index 48cc6e44..ebd426da 100644
--- a/linux-glibc-2.23-arm64/Dockerfile
+++ b/linux-glibc-2.23-arm64/Dockerfile
@@ -65,7 +65,7 @@ RUN cd /build && \
 
 
 # CONDA
-COPY python-packages-versions.txt setup_python.sh requirements.txt requirements-py2.txt /
+COPY python-packages-versions.txt setup_python.sh requirements.txt /
 COPY requirements /requirements
 ENV DEVA_VERSION=$DEVA_VERSION
 ENV DEVA_NO_DYNAMIC_DEPS=$DEVA_NO_DYNAMIC_DEPS
diff --git a/python-packages-versions.txt b/python-packages-versions.txt
index e3f0b9e4..5458173a 100644
--- a/python-packages-versions.txt
+++ b/python-packages-versions.txt
@@ -1,9 +1,5 @@
 # NOTE: this is used in both Linux and Windows image builds; only use comments, newlines
 # and variable definitions here. Also don't quote variable values.
 
-# These seem to be the latest version that reliably work with Python 2; don't update
-DD_PIP_VERSION=20.3.3
-DD_SETUPTOOLS_VERSION=44.1.1
-
 DD_PIP_VERSION_PY3=24.2
 DD_SETUPTOOLS_VERSION_PY3=74.1.3
diff --git a/rpm-arm64/Dockerfile b/rpm-arm64/Dockerfile
index be9683ec..21d0bede 100644
--- a/rpm-arm64/Dockerfile
+++ b/rpm-arm64/Dockerfile
@@ -94,7 +94,7 @@ RUN curl -fsSL https://github.com/DataDog/datadog-ci/releases/download/v${CI_UPL
     && chmod +x /usr/local/bin/datadog-ci
 
 # CONDA
-COPY python-packages-versions.txt setup_python.sh requirements.txt requirements-py2.txt /
+COPY python-packages-versions.txt setup_python.sh requirements.txt /
 COPY requirements /requirements
 ENV DEVA_VERSION=$DEVA_VERSION
 ENV DEVA_NO_DYNAMIC_DEPS=$DEVA_NO_DYNAMIC_DEPS
diff --git a/rpm-armhf/Dockerfile b/rpm-armhf/Dockerfile
index 6a184523..fd259baf 100644
--- a/rpm-armhf/Dockerfile
+++ b/rpm-armhf/Dockerfile
@@ -127,7 +127,7 @@ RUN curl -sSL -o rustup-init https://static.rust-lang.org/rustup/archive/${RUSTU
 ENV PATH "~/.cargo/bin:${PATH}"
 
 # CONDA
-COPY python-packages-versions.txt setup_python.sh requirements.txt requirements-py2.txt /
+COPY python-packages-versions.txt setup_python.sh requirements.txt /
 COPY requirements /requirements
 ENV DEVA_VERSION=$DEVA_VERSION
 ENV DEVA_NO_DYNAMIC_DEPS=$DEVA_NO_DYNAMIC_DEPS
diff --git a/rpm-x64/Dockerfile b/rpm-x64/Dockerfile
index 3f943f20..c0f65017 100644
--- a/rpm-x64/Dockerfile
+++ b/rpm-x64/Dockerfile
@@ -127,7 +127,7 @@ RUN git config --global user.email "package@datadoghq.com"
 RUN git config --global user.name "Bits"
 
 # CONDA
-COPY python-packages-versions.txt setup_python.sh requirements.txt requirements-py2.txt /
+COPY python-packages-versions.txt setup_python.sh requirements.txt /
 COPY requirements /requirements
 ENV DEVA_VERSION=$DEVA_VERSION
 ENV DEVA_NO_DYNAMIC_DEPS=$DEVA_NO_DYNAMIC_DEPS
diff --git a/setup_python.sh b/setup_python.sh
index bb2a23dc..8c2cad75 100755
--- a/setup_python.sh
+++ b/setup_python.sh
@@ -9,7 +9,6 @@ function detect_distro(){
     DISTRIBUTION=$(lsb_release -d 2>/dev/null | grep -Eo $KNOWN_DISTRIBUTION  || grep -Eo $KNOWN_DISTRIBUTION /etc/issue 2>/dev/null || grep -Eo $KNOWN_DISTRIBUTION /etc/Eos-release 2>/dev/null || grep -m1 -Eo $KNOWN_DISTRIBUTION /etc/os-release 2>/dev/null || uname -s)
 }
 
-PY2_VERSION=2
 PY3_VERSION=3.12.6
 DD_CONDA_VERSION=4.9.2-7
 
@@ -83,17 +82,8 @@ conda init bash
 source /root/.bashrc
 
 # Setup pythons
-conda create -n ddpy2 python python=$PY2_VERSION
 conda create -n ddpy3 python python=$PY3_VERSION
 
-# Update pip, setuptools and misc deps
-conda activate ddpy2
-pip install -i https://pypi.python.org/simple pip==${DD_PIP_VERSION}
-pip install setuptools==${DD_SETUPTOOLS_VERSION}
-pip install --no-build-isolation "cython<3.0.0" PyYAML==5.4.1
-pip install -r requirements-py2.txt
-pip uninstall -y cython # remove cython to prevent further issue with nghttp2
-
 # Update pip, setuptools and misc deps
 conda activate ddpy3
 pip install -i https://pypi.python.org/simple pip==${DD_PIP_VERSION_PY3}
@@ -103,15 +93,6 @@ pip install "git+https://github.com/DataDog/datadog-agent-dev.git@${DEVA_VERSION
 deva -v self dep sync -f legacy-build
 pip uninstall -y cython # remove cython to prevent further issue with nghttp2
 
-
-if [ "$DD_TARGET_ARCH" = "aarch64" ] ; then
-    # Conda creates "lib" but on Amazon Linux, the embedded Python2 we use in unit tests will look in "lib64" instead
-    ln -s "${CONDA_PATH}/envs/ddpy2/lib" "${CONDA_PATH}/envs/ddpy2/lib64"
-fi
-
-# Add python3's invoke to the PATH even when ddpy3 is not active, since we want to use python3 invoke to run python2 tests
-ln -s ${CONDA_PATH}/envs/ddpy3/bin/inv /usr/local/bin
-
 conda clean -a
 
 echo "conda activate ddpy3" >> /root/.bashrc
diff --git a/system-probe_arm64/Dockerfile b/system-probe_arm64/Dockerfile
index e7074e01..9dd8ec2a 100644
--- a/system-probe_arm64/Dockerfile
+++ b/system-probe_arm64/Dockerfile
@@ -55,7 +55,7 @@ ENV CONDA_PATH /root/miniforge3
 ENV DD_TARGET_ARCH $DD_TARGET_ARCH
 
 # CONDA
-COPY python-packages-versions.txt setup_python.sh requirements.txt requirements-py2.txt /
+COPY python-packages-versions.txt setup_python.sh requirements.txt /
 COPY requirements /requirements
 ENV DEVA_VERSION=$DEVA_VERSION
 ENV DEVA_NO_DYNAMIC_DEPS=$DEVA_NO_DYNAMIC_DEPS
diff --git a/system-probe_x64/Dockerfile b/system-probe_x64/Dockerfile
index 30e07086..49aa8e0e 100644
--- a/system-probe_x64/Dockerfile
+++ b/system-probe_x64/Dockerfile
@@ -60,7 +60,7 @@ ENV CONDA_PATH /root/miniforge3
 ENV DD_TARGET_ARCH $DD_TARGET_ARCH
 
 # CONDA
-COPY python-packages-versions.txt setup_python.sh requirements.txt requirements-py2.txt /
+COPY python-packages-versions.txt setup_python.sh requirements.txt /
 COPY requirements /requirements
 ENV DEVA_VERSION=$DEVA_VERSION
 ENV DEVA_NO_DYNAMIC_DEPS=$DEVA_NO_DYNAMIC_DEPS
diff --git a/windows/Dockerfile b/windows/Dockerfile
index 8a8a6c97..268edb67 100644
--- a/windows/Dockerfile
+++ b/windows/Dockerfile
@@ -35,7 +35,6 @@ ARG WIX_VERSION
 ARG CMAKE_VERSION
 ARG MSYS_VERSION
 ARG PYTHON_VERSION
-ARG EMBEDDED_PYTHON_2_VERSION
 ARG EMBEDDED_PYTHON_3_VERSION
 ARG NUGET_VERSION
 ARG CODEQL_VERSION
@@ -53,7 +52,6 @@ LABEL wix_version=${WIX_VERSION}
 LABEL cmake_version=${CMAKE_VERSION}
 LABEL msys_version=${MSYS_VERSION}
 LABEL system_python_version=${PYTHON_VERSION}
-LABEL embedded_py2_version=${EMBEDDED_PYTHON_2_VERSION}
 LABEL embedded_py3_version=${EMBEDDED_PYTHON_3_VERSION}
 LABEL nuget_version=${NUGET_VERSION}
 LABEL codeql_version=${CODEQL_VERSION}
@@ -67,7 +65,7 @@ COPY ./windows/helpers/*.ps1 c:/scripts/helpers/
 COPY go.env c:/
 COPY deva.env c:/
 
-COPY python-packages-versions.txt requirements.txt requirements-py2.txt /
+COPY python-packages-versions.txt requirements.txt /
 COPY requirements /requirements
 COPY ./windows/set_cpython_compiler.cmd set_cpython_compiler.cmd
 
diff --git a/windows/helpers/phase1/install_vcpython.ps1 b/windows/helpers/phase1/install_vcpython.ps1
deleted file mode 100644
index 71160e2c..00000000
--- a/windows/helpers/phase1/install_vcpython.ps1
+++ /dev/null
@@ -1,21 +0,0 @@
-
-
-$vcpmsi = 'https://s3.amazonaws.com/dd-agent-omnibus/VCForPython27.msi'
-
-Write-host -ForegroundColor Green Downloading VC++ for Python
-$out = "$($PSScriptRoot)\vcp.msi"
-$sha256 = "070474db76a2e625513a5835df4595df9324d820f9cc97eab2a596dcbc2f5cbf"
-
-$isInstalled, $isCurrent = Get-InstallUpgradeStatus -Component "vcpython" -Keyname "DownloadFile" -TargetValue $vcpmsi
-if($isInstalled){
-    Write-Host -ForegroundColor Green "VC++ for Python 2.7 already installed"
-    return
-}
-Get-RemoteFile -RemoteFile $vcpmsi -LocalFile $out -VerifyHash $sha256
-
-Write-host -ForegroundColor Green VC++ for Python downloaded, installing...
-Start-Process msiexec -ArgumentList '/q /i vcp.msi' -Wait
-Remove-Item $out
-
-Set-InstalledVersionKey -Component "vcpython" -Keyname "DownloadFile" -TargetValue $vcpmsi
-Write-Host -ForegroundColor Green Done with Visual C++ for Python
diff --git a/windows/helpers/phase2/install_embedded_pythons.ps1 b/windows/helpers/phase2/install_embedded_pythons.ps1
index f899d71c..f398b7e4 100644
--- a/windows/helpers/phase2/install_embedded_pythons.ps1
+++ b/windows/helpers/phase2/install_embedded_pythons.ps1
@@ -1,5 +1,5 @@
 #
-# Installs embedded python2 and python3 for use in unit testing.
+# Installs embedded python for use in unit testing.
 # Be careful to use unique environment variables indicating location
 # of the python files.
 #
@@ -8,7 +8,6 @@
 #
 
 # Uses:
-# EMBEDDED_PYTHON_2_VERSION
 # EMBEDDED_PYTHON_3_VERSION
 
 # this downloads the necessary file
@@ -22,17 +21,12 @@ if($Env:DD_DEV_TARGET -ne "Container") {
    return
 }
 
-$py2 = "https://s3.amazonaws.com/dd-agent-omnibus/python-windows-${Env:EMBEDDED_PYTHON_2_VERSION}-amd64.zip"
 $py3 = "https://s3.amazonaws.com/dd-agent-omnibus/python-windows-${Env:EMBEDDED_PYTHON_3_VERSION}-amd64.zip"
 
-$py2Target = "c:\embeddedpy\py${Env:EMBEDDED_PYTHON_2_VERSION}"
 $py3Target = "c:\embeddedpy\py${Env:EMBEDDED_PYTHON_3_VERSION}"
 
-DownloadAndExpandTo -TargetDir $py2Target -SourceURL $py2 -Sha256 "$Env:EMBEDDED_PYTHON_2_SHA256"
-
 DownloadAndExpandTo -TargetDir $py3Target -SourceURL $py3 -Sha256 "$Env:EMBEDDED_PYTHON_3_SHA256"
 
-Add-EnvironmentVariable -Variable "TEST_EMBEDDED_PY2" -Value $py2Target -Global
 Add-EnvironmentVariable -Variable "TEST_EMBEDDED_PY3" -Value $py3Target -Global
 
 # Read DD_PIP_VERSION{,_PY3} and DD_SETUPTOOLS_VERSION{,_PY3} to variables
@@ -41,15 +35,6 @@ Get-Content \python-packages-versions.txt | Where-Object { $_.Trim() -ne '' } |
    Add-EnvironmentVariable -Variable $var[0] -Value $var[1] -Local
 }
 
-# Python 2
-$py2getpip = "https://raw.githubusercontent.com/pypa/get-pip/38e54e5de07c66e875c11a1ebbdb938854625dd8/public/2.7/get-pip.py"
-$py2getpipsha256 = "40ee07eac6674b8d60fce2bbabc148cf0e2f1408c167683f110fd608b8d6f416"
-Get-RemoteFile -LocalFile "get-pip.py" -RemoteFile $py2getpip -VerifyHash $py2getpipsha256
-& "$py2Target\python" get-pip.py pip==${Env:DD_PIP_VERSION}
-If ($lastExitCode -ne "0") { throw "Previous command returned $lastExitCode" }
-& "$py2Target\python" -m pip install -r ../requirements-py2.txt
-If ($lastExitCode -ne "0") { throw "Previous command returned $lastExitCode" }
-
 # Python 3
 $py3getpip = "https://raw.githubusercontent.com/pypa/get-pip/66d8a0f637083e2c3ddffc0cb1e65ce126afb856/public/get-pip.py"
 $py3getpipsha256 = "6fb7b781206356f45ad79efbb19322caa6c2a5ad39092d0d44d0fec94117e118"
diff --git a/windows/helpers/phase2/install_python.ps1 b/windows/helpers/phase2/install_python.ps1
index a8b3809e..c3570190 100644
--- a/windows/helpers/phase2/install_python.ps1
+++ b/windows/helpers/phase2/install_python.ps1
@@ -4,7 +4,7 @@ param (
 )
 
 
-# https://www.python.org/ftp/python/3.9.1/python-3.9.1-amd64.exe
+# https://www.python.org/ftp/python/X.Y.Z/python-X.Y.Z-amd64.exe
 $pyexe = "https://www.python.org/ftp/python/$($Version)/python-$($Version)-amd64.exe"
 
 $isInstalled, $isCurrent = Get-InstallUpgradeStatus -Component "Python" -Keyname "version" -TargetValue $Version
diff --git a/windows/versions.ps1 b/windows/versions.ps1
index a859ff7d..5740d1a9 100644
--- a/windows/versions.ps1
+++ b/windows/versions.ps1
@@ -40,8 +40,6 @@ $SoftwareTable = @{
     "NUGET_SHA256"="5c5b9c96165d3283b2cb9e5b65825d343e0e7139b9e70a250b4bb24c2285f3ba";
     "WINGET_VERSION"="1.6.5.0";
     "WINGET_SHA256"="2CCED75B1830246A78FF0E57F18133807F78BA484CCA2D369CBDDF490DDAC1AF";
-    "EMBEDDED_PYTHON_2_VERSION"="2.7.17";
-    "EMBEDDED_PYTHON_2_SHA256"="557ea6690c5927360656c003d3114b73adbd755b712a2911975dde813d6d7afb";
     "EMBEDDED_PYTHON_3_VERSION"="3.12.6";
     "EMBEDDED_PYTHON_3_SHA256"="045d20a659fe80041b6fd508b77f250b03330347d64f128b392b88e68897f5a0";
     "EMBEDDED_PIP_VERSION"="20.3.4";