diff --git a/components/ide/code/codehelper/leeway.Dockerfile b/components/ide/code/codehelper/leeway.Dockerfile
index 41138f0d5eb87d..a4592cfee01c8d 100644
--- a/components/ide/code/codehelper/leeway.Dockerfile
+++ b/components/ide/code/codehelper/leeway.Dockerfile
@@ -2,7 +2,7 @@
 # Licensed under the GNU Affero General Public License (AGPL).
 # See License.AGPL.txt in the project root for license information.
 
-FROM alpine:3.16 as base_builder
+FROM alpine:3.19 as base_builder
 RUN mkdir /ide
 
 FROM scratch
diff --git a/components/supervisor/leeway.Dockerfile b/components/supervisor/leeway.Dockerfile
index 8758485fbb783d..6c7c859d859d28 100644
--- a/components/supervisor/leeway.Dockerfile
+++ b/components/supervisor/leeway.Dockerfile
@@ -2,7 +2,7 @@
 # Licensed under the GNU Affero General Public License (AGPL).
 # See License.AGPL.txt in the project root for license information.
 
-FROM alpine:3.16 as docker_cli_builder
+FROM alpine:3.19 as docker_cli_builder
 
 RUN apk add wget tar
 
diff --git a/components/supervisor/openssh/leeway.Dockerfile b/components/supervisor/openssh/leeway.Dockerfile
index e30129f4e704bc..9a6190650d392c 100644
--- a/components/supervisor/openssh/leeway.Dockerfile
+++ b/components/supervisor/openssh/leeway.Dockerfile
@@ -20,9 +20,9 @@
 # WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
 
 # This Dockerfile was taken from https://github.com/ep76/docker-openssh-static and adapted.
-FROM alpine:3.18 AS builder
+FROM alpine:3.19 AS builder
 
-ARG openssh_url=https://github.com/openssh/openssh-portable/archive/refs/tags/V_9_3_P2.tar.gz
+ARG openssh_url=https://github.com/openssh/openssh-portable/archive/refs/tags/V_9_5_P1.tar.gz
 
 WORKDIR /build
 
@@ -52,7 +52,8 @@ RUN ./configure \
     --sysconfdir=/etc/ssh \
     --with-ldflags=-static \
     --with-privsep-user=nobody \
-    --with-ssl-engine
+    --with-ssl-engine \
+    --with-pie
 
 ENV aports=https://raw.githubusercontent.com/alpinelinux/aports/master/main/openssh
 RUN curl -fsSL \