diff --git a/dev/image/Dockerfile b/dev/image/Dockerfile
index cc4397a1068519..909f29e35806b5 100644
--- a/dev/image/Dockerfile
+++ b/dev/image/Dockerfile
@@ -58,7 +58,7 @@ RUN cd /usr/bin && curl -fsSL https://github.com/praetorian-inc/gokart/releases/
 
 # leeway
 ENV LEEWAY_MAX_PROVENANCE_BUNDLE_SIZE=8388608
-RUN cd /usr/bin && curl -fsSL https://github.com/gitpod-io/leeway/releases/download/v0.2.20/leeway_0.2.20_Linux_x86_64.tar.gz | tar xz
+RUN cd /usr/bin && curl -fsSL https://github.com/gitpod-io/leeway/releases/download/v0.2.21/leeway_0.2.21_Linux_x86_64.tar.gz | tar xz
 
 # evans (gRPC client)
 RUN cd /usr/bin && curl -fsSL https://github.com/ktr0731/evans/releases/download/v0.10.6/evans_linux_amd64.tar.gz | tar xz evans