diff --git a/changelog/bugfixes/2023-11-30-gce-oslogin.md b/changelog/bugfixes/2023-11-30-gce-oslogin.md
new file mode 100644
index 0000000000..7083bcd4e7
--- /dev/null
+++ b/changelog/bugfixes/2023-11-30-gce-oslogin.md
@@ -0,0 +1 @@
+- GCP: Fixed OS Login enabling ([scripts#1445](https://github.com/flatcar/scripts/pull/1445))
diff --git a/sdk_container/src/third_party/coreos-overlay/coreos-base/oem-gce/files/units/oem-gce-enable-oslogin.service b/sdk_container/src/third_party/coreos-overlay/coreos-base/oem-gce/files/units/oem-gce-enable-oslogin.service
index 2451522672..8b09d5dd69 100644
--- a/sdk_container/src/third_party/coreos-overlay/coreos-base/oem-gce/files/units/oem-gce-enable-oslogin.service
+++ b/sdk_container/src/third_party/coreos-overlay/coreos-base/oem-gce/files/units/oem-gce-enable-oslogin.service
@@ -8,6 +8,7 @@ Before=sshd.socket
 
 [Service]
 Type=oneshot
+RemainAfterExit=true
 
 ExecStart=/oem/bin/enable-oslogin
 
diff --git a/sdk_container/src/third_party/coreos-overlay/net-misc/openssh/openssh-9.5_p1.ebuild b/sdk_container/src/third_party/coreos-overlay/net-misc/openssh/openssh-9.5_p1-r1.ebuild
similarity index 98%
rename from sdk_container/src/third_party/coreos-overlay/net-misc/openssh/openssh-9.5_p1.ebuild
rename to sdk_container/src/third_party/coreos-overlay/net-misc/openssh/openssh-9.5_p1-r1.ebuild
index c4c68abbcc..fddfbe6e64 100644
--- a/sdk_container/src/third_party/coreos-overlay/net-misc/openssh/openssh-9.5_p1.ebuild
+++ b/sdk_container/src/third_party/coreos-overlay/net-misc/openssh/openssh-9.5_p1-r1.ebuild
@@ -232,6 +232,10 @@ insert_include() {
 	local src_config="${1}" options="${2}" includedir="${3}"
 	local name copy regexp_options regexp lineno comment_options
 
+	if [[ ! "${includedir}" =~ ^/.* ]]; then
+		die "includir must be an absolute path (i.e, starting with /). Got: ${includedir}"
+	fi
+
 	name=${src_config##*/}
 	copy="${T}/${name}"
 	cp -a "${src_config}" "${copy}" || die
@@ -251,7 +255,7 @@ insert_include() {
 		head -n "${lineno}" "${copy}" || die
 		cat <<-EOF || die
 		# Make sure that all ${comment_options} options are below this Include!
-		Include "${EPREFIX}/${includedir}/*.conf"
+		Include "${EPREFIX}${includedir}/*.conf"
 
 		EOF
 		tail -n "+${lineno}" "${copy}" || die