diff --git a/CHANGELOG.md b/CHANGELOG.md
index 4da26d55c..12ef9cc91 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,7 @@
 - feat(maven): Support BOM files in `maven` target (#270)
 - feat(maven): Optional `android` config (#271)
 - feat(maven): Remove Gradle properties after publishing (#276)
+- upgrade(docker): Upgrade to Debain Bullseye and Node 14 (#282)
 
 ## 0.24.4
 
diff --git a/Dockerfile b/Dockerfile
index fae2abe06..dc509709a 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,4 +1,4 @@
-FROM node:12-buster
+FROM node:14-bullseye
 
 ENV DEBIAN_FRONTEND=noninteractive \
   DOTNET_CLI_TELEMETRY_OPTOUT=1 \
@@ -32,8 +32,6 @@ RUN apt-get -qq update \
   && curl --proto '=https' --tlsv1.2 -sSf https://sh.rustup.rs | sh -s --  --profile minimal -y \
   && cargo --version \
   && cargo install cargo-hack \
-  # Stick with 3.1.x as 3.2.x doesn't install on Debian Buster for some reason
-  && gem update --no-document --system 3.1.5 \
   && gem install cocoapods \
   # Install https://github.com/getsentry/symbol-collector
   && symbol_collector_url=$(curl -s https://api.github.com/repos/getsentry/symbol-collector/releases/tags/1.3.2 | \