diff --git a/.devcontainer/Dockerfile b/.devcontainer/Dockerfile
index 43996e0b1fe03b..87427299eed987 100644
--- a/.devcontainer/Dockerfile
+++ b/.devcontainer/Dockerfile
@@ -90,7 +90,7 @@ ARG TARGETOS
 
 # Install dependencies
 USER root
-ARG LEEWAY_VERSION=0.9.6
+ARG LEEWAY_VERSION=0.10.2
 ENV LEEWAY_MAX_PROVENANCE_BUNDLE_SIZE=8388608
 ENV LEEWAY_WORKSPACE_ROOT=/workspace/gitpod
 ENV LEEWAY_REMOTE_CACHE_BUCKET=leeway-cache-dev-3ac8ef5
diff --git a/dev/image/Dockerfile b/dev/image/Dockerfile
index e4d48c48c53646..43e5a7195efbcc 100644
--- a/dev/image/Dockerfile
+++ b/dev/image/Dockerfile
@@ -45,7 +45,7 @@ RUN cd /usr/bin && curl -fsSL https://github.com/cert-manager/cert-manager/relea
 RUN cd /usr/bin && curl -fsSL https://github.com/praetorian-inc/gokart/releases/download/v0.5.1/gokart_0.5.1_linux_x86_64.tar.gz | tar xzv --no-anchored gokart
 
 # leeway
-ARG LEEWAY_VERSION=0.9.6
+ARG LEEWAY_VERSION=0.10.2
 ENV LEEWAY_MAX_PROVENANCE_BUNDLE_SIZE=8388608
 ENV LEEWAY_WORKSPACE_ROOT=/workspace/gitpod
 ENV LEEWAY_REMOTE_CACHE_BUCKET=leeway-cache-dev-3ac8ef5