diff --git a/CHANGELOG.md b/CHANGELOG.md
index eb94958f5..bbf54796f 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -66,6 +66,7 @@ The table below shows which release corresponds to each branch, and what date th
 - [#1742][1742] New `baremetal` os to debug binaries executed with qemu-system-$(arch)
 - [#1757][1757] update cache directories
 - [#1758][1758] Remove eval from cli
+- [#1780][1780] Re-add Python2 to the official Dockerfile
 
 [1261]: https://github.com/Gallopsled/pwntools/pull/1261
 [1695]: https://github.com/Gallopsled/pwntools/pull/1695
@@ -74,6 +75,7 @@ The table below shows which release corresponds to each branch, and what date th
 [1742]: https://github.com/Gallopsled/pwntools/pull/1742
 [1757]: https://github.com/Gallopsled/pwntools/pull/1757
 [1758]: https://github.com/Gallopsled/pwntools/pull/1758
+[1780]: https://github.com/Gallopsled/pwntools/pull/1780
 
 ## 4.4.0 (`beta`)
 
diff --git a/extra/docker/base/Dockerfile b/extra/docker/base/Dockerfile
index e45f1ac8d..490e95ba2 100644
--- a/extra/docker/base/Dockerfile
+++ b/extra/docker/base/Dockerfile
@@ -6,12 +6,17 @@
 FROM ubuntu:bionic
 MAINTAINER Maintainer Gallopsled et al.
 
+env DEBIAN_FRONTEND=noninteractive
+
 RUN apt-get update \
     && apt-get install -y \
         build-essential \
         git \
         libssl-dev \
         libffi-dev \
+        python \
+        python-pip \
+        python-dev \
         python3 \
         python3-pip \
         python3-dev \
@@ -23,6 +28,8 @@ RUN apt-get update \
         binutils-powerpc-linux-gnu \
         binutils-powerpc64-linux-gnu \
         binutils-sparc64-linux-gnu \
+    && pip install --upgrade pip \
+    && python -m pip install --upgrade pwntools \
     && pip3 install --upgrade pip \
     && python3 -m pip install --upgrade pwntools \
     && PWNLIB_NOTERM=1 pwn update \
diff --git a/extra/docker/beta/Dockerfile b/extra/docker/beta/Dockerfile
index 7caea59ba..d4df4e3c1 100644
--- a/extra/docker/beta/Dockerfile
+++ b/extra/docker/beta/Dockerfile
@@ -1,6 +1,7 @@
 FROM pwntools/pwntools:stable
 
 USER root
+RUN pip install --upgrade git+https://github.com/Gallopsled/pwntools@beta
 RUN pip3 install --upgrade git+https://github.com/Gallopsled/pwntools@beta
 RUN PWNLIB_NOTERM=1 pwn update
 USER pwntools
diff --git a/extra/docker/dev/Dockerfile b/extra/docker/dev/Dockerfile
index 3eed782a7..365213aa8 100644
--- a/extra/docker/dev/Dockerfile
+++ b/extra/docker/dev/Dockerfile
@@ -1,6 +1,7 @@
 FROM pwntools/pwntools:stable
 
 USER root
+RUN pip install --upgrade git+https://github.com/Gallopsled/pwntools@dev
 RUN pip3 install --upgrade git+https://github.com/Gallopsled/pwntools@dev
 RUN PWNLIB_NOTERM=1 pwn update
 USER pwntools
diff --git a/extra/docker/stable/Dockerfile b/extra/docker/stable/Dockerfile
index 4250e3e8b..43a3ae1bd 100644
--- a/extra/docker/stable/Dockerfile
+++ b/extra/docker/stable/Dockerfile
@@ -1,6 +1,7 @@
 FROM pwntools/pwntools:base
 
 USER root
+RUN pip install --upgrade git+https://github.com/Gallopsled/pwntools@stable
 RUN pip3 install --upgrade git+https://github.com/Gallopsled/pwntools@stable
 RUN PWNLIB_NOTERM=1 pwn update
 USER pwntools