diff --git a/pkg/Dockerfile.base.deb b/pkg/Dockerfile.base.deb
index 4e16437e9..4062d0a13 100644
--- a/pkg/Dockerfile.base.deb
+++ b/pkg/Dockerfile.base.deb
@@ -10,6 +10,7 @@ RUN apt-get update -q && \
     lintian \
     procps \
     zsh \
+    tree \
     rsync \
     gdebi \
     ca-certificates \
diff --git a/pkg/Dockerfile.deb b/pkg/Dockerfile.deb
index ce8661809..7766b8d42 100644
--- a/pkg/Dockerfile.deb
+++ b/pkg/Dockerfile.deb
@@ -7,5 +7,6 @@ ARG PKG_DIR
 COPY pkg pkg
 RUN rsync -avz pkg/skel/* pkg/$PKG_DIR/
 RUN rsync -avz _build/prod/rel/firezone/* pkg/$PKG_DIR/usr/lib/firezone/
+RUN mkdir -p pkg/$PKG_DIR/usr/bin
 RUN cd pkg/$PKG_DIR/usr/bin && ln -s ../lib/firezone/bin/firezone
 RUN cd pkg && dpkg-deb --build $PKG_DIR
diff --git a/pkg/Dockerfile.release b/pkg/Dockerfile.release
index fbd718e67..d206324ae 100644
--- a/pkg/Dockerfile.release
+++ b/pkg/Dockerfile.release
@@ -23,5 +23,6 @@ RUN npm run --prefix ./apps/fz_http/assets deploy && \
 COPY rel rel
 COPY config config
 COPY apps apps
+RUN tree .
 COPY deps deps
 RUN mix release