diff --git a/.github/workflows/docker.yaml b/.github/workflows/docker.yaml
index 079a8f7..e3da99b 100644
--- a/.github/workflows/docker.yaml
+++ b/.github/workflows/docker.yaml
@@ -25,7 +25,7 @@ jobs:
           - dockerfile: ./osmosisd/Dockerfile
             image: ghcr.io/defiantlabs/osmosisd
             platforms: linux/amd64
-            tag: v19.0.0
+            tag: v20.1.0
           - dockerfile: ./kujirad/Dockerfile
             image: ghcr.io/defiantlabs/kujirad
             platforms: linux/amd64
diff --git a/kujirad/Dockerfile b/kujirad/Dockerfile
index 2df44d3..389f0db 100644
--- a/kujirad/Dockerfile
+++ b/kujirad/Dockerfile
@@ -11,7 +11,7 @@ ARG LD_FLAGS=-linkmode=external \
 -extldflags '-Wl,-z,muldefs -static'
 
 # Install cli tools for building and final image
-RUN apk add --update --no-cache make git bash gcc linux-headers eudev-dev ncurses-dev openssh curl jq
+RUN apk update && apk add --no-cache make git bash gcc linux-headers eudev-dev ncurses-dev openssh curl jq
 RUN apk add --no-cache musl-dev
 
 # Build Chain Binary
@@ -86,8 +86,9 @@ COPY --from=build-env /usr/lib/libonig.so.5 /lib
 COPY --from=build-env /usr/lib/libcurl.so.4 /lib
 COPY --from=build-env /lib/libz.so.1 /lib
 COPY --from=build-env /usr/lib/libnghttp2.so.14 /lib
+
 COPY --from=build-env /lib/libssl.so.1.1 /lib
-COPY --from=build-env /lib/libcrypto.so.1.1 /lib
+COPY --from=build-env /lib/libcrypto.so.* /lib
 COPY --from=build-env /usr/lib/libbrotlidec.so.1 /lib
 COPY --from=build-env /usr/lib/libbrotlicommon.so.1 /lib
 
diff --git a/osmosisd/Dockerfile b/osmosisd/Dockerfile
index 7be1d90..02e6275 100644
--- a/osmosisd/Dockerfile
+++ b/osmosisd/Dockerfile
@@ -79,6 +79,7 @@ COPY --from=build-env /usr/lib/libbrotlicommon.so.1 /lib
 # Install trusted CA certificates for curl
 COPY --from=build-env /etc/ssl/cert.pem /etc/ssl/cert.pem
 COPY --from=build-env /etc/ssl/cert.pem /etc/ssl/ca-certificates.crt
+COPY --from=build-env /etc/ssl/cert.pem /etc/ssl/certs/ca-certificates.crt
 
 # Install cli tools from busybox
 COPY --from=busybox /bin/ln /bin/ln