diff --git a/.dockerignore b/.dockerignore
index 16a13794bf..944b62eb98 100644
--- a/.dockerignore
+++ b/.dockerignore
@@ -76,6 +76,7 @@ cpu.out
 /.go-licenses
 Dockerfile
 Dockerfile.rootless
+
 # Files and folders that were previously generated
 /public/assets/img/webpack
 
diff --git a/Dockerfile b/Dockerfile
index 31959d42c2..774084ba82 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -26,6 +26,16 @@ RUN --mount=type=cache,target=/go/pkg/mod \
     --mount=type=bind,source=".git/",target=".git/" \
     make
 
+COPY docker/root /tmp/local
+
+# Set permissions for builds that made under windows which strips the executable bit from file
+RUN chmod 755 /tmp/local/usr/bin/entrypoint \
+              /tmp/local/usr/local/bin/* \
+              /tmp/local/etc/s6/gitea/* \
+              /tmp/local/etc/s6/openssh/* \
+              /tmp/local/etc/s6/.s6-svscan/* \
+              /go/src/code.gitea.io/gitea/gitea
+
 FROM docker.io/library/alpine:3.22 AS gitea
 
 EXPOSE 22 3000
@@ -55,7 +65,7 @@ RUN addgroup \
     git && \
   echo "git:*" | chpasswd -e
 
-COPY docker/root /
+COPY --from=build-env /tmp/local /
 COPY --chmod=755 --from=build-env /go/src/code.gitea.io/gitea/gitea /app/gitea/gitea
 
 ENV USER=git
diff --git a/Dockerfile.rootless b/Dockerfile.rootless
index ec9a91d611..d709d99b59 100644
--- a/Dockerfile.rootless
+++ b/Dockerfile.rootless
@@ -26,6 +26,12 @@ RUN --mount=type=cache,target=/go/pkg/mod \
     --mount=type=bind,source=".git/",target=".git/" \
     make
 
+COPY docker/rootless /tmp/local
+
+# Set permissions for builds that made under windows which strips the executable bit from file
+RUN chmod 755 /tmp/local/usr/local/bin/* \
+              /go/src/code.gitea.io/gitea/gitea
+
 FROM docker.io/library/alpine:3.22 AS gitea-rootless
 
 EXPOSE 2222 3000
@@ -54,7 +60,7 @@ RUN addgroup \
 RUN mkdir -p /var/lib/gitea /etc/gitea
 RUN chown git:git /var/lib/gitea /etc/gitea
 
-COPY docker/rootless /
+COPY --from=build-env /tmp/local /
 COPY --from=build-env --chmod=755 --chown=root:root /go/src/code.gitea.io/gitea/gitea /app/gitea/gitea
 
 # git:git