diff --git a/Dockerfile b/Dockerfile
index bb46c6a..0eb18e9 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,33 +1,27 @@
-FROM ubuntu:14.04
-MAINTAINER Andrew Ferrier <andrew.ferrier@example.com>
+FROM debian
+LABEL maintainer="Andrew Ferrier <andrew.ferrier@example.com>"
 RUN apt-get update && apt-get install -y git build-essential \
-        checkinstall \
         fontconfig \
         gdebi-core \
         getmail4 \
         libfontconfig1 \
         libfreetype6 \
-        libjpeg-turbo8 \
+        libjpeg62-turbo \
         libx11-6 \
         libxext6 \
         libxrender1 \
         python \
-        python3-dateutil \
-        python3-flake8 \
         python3-pip \
-        python3-reportlab \
         wget \
         xfonts-75dpi \
         xfonts-base
 WORKDIR /tmp
-RUN wget http://mirrors.kernel.org/ubuntu/pool/universe/p/pypdf2/python3-pypdf2_1.23+git20141008-1_all.deb
-RUN wget http://mirrors.kernel.org/ubuntu/pool/universe/f/freezegun/python3-freezegun_0.1.18-1_all.deb
-RUN fakeroot checkinstall --pkgname=python3-pdfminer3k --pkgversion=0.1 -y --fstrans=no --install=no pip3 install pdfminer3k
-RUN wget -O wkhtmltox.deb 'http://download.gna.org/wkhtmltopdf/0.12/0.12.2.1/wkhtmltox-0.12.2.1_linux-trusty-amd64.deb'
+RUN wget -O wkhtmltox.deb 'https://github.com/wkhtmltopdf/packaging/releases/download/0.12.6-1/wkhtmltox_0.12.6-1.buster_amd64.deb'
 RUN dpkg -i *.deb
-RUN wget -O /etc/vim/vimrc.local https://raw.githubusercontent.com/tpope/vim-sensible/master/plugin/sensible.vim
+RUN mkdir /etc/vim && wget -O /etc/vim/vimrc.local https://raw.githubusercontent.com/tpope/vim-sensible/master/plugin/sensible.vim
 COPY . /tmp/email2pdf/
 COPY docker/email2pdf/getmail /etc/cron.d/
 WORKDIR /tmp/email2pdf
+RUN pip3 install -r requirements_hacking.txt
 RUN make builddeb_real && sh -c 'ls -1 /tmp/email2pdf/*.deb | xargs -L 1 gdebi -n' && cp /tmp/email2pdf/*.deb /tmp
 RUN apt-get clean && rm -rf /var/lib/apt/lists/* /var/tmp/*
diff --git a/Makefile b/Makefile
index 85ccdf9..f11d292 100644
--- a/Makefile
+++ b/Makefile
@@ -18,7 +18,7 @@ builddeb: rundocker_getdebs
 endif
 
 builddeb_real:
-	sudo apt-get install build-essential
+	dpkg -s build-essential || sudo apt-get install build-essential
 	cp -R debian/DEBIAN/ $(TEMPDIR)
 	mkdir -p $(TEMPDIR)/usr/bin
 	mkdir -p $(TEMPDIR)/usr/share/doc/email2pdf