diff --git a/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/golden/success_despite_failing_to_override_the_ssl_certficate_path b/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/golden/success_despite_failing_to_override_the_ssl_certficate_path
new file mode 100644
index 000000000..3ee8ae0a7
--- /dev/null
+++ b/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/golden/success_despite_failing_to_override_the_ssl_certficate_path
@@ -0,0 +1,4 @@
+[client]
+hello          = world
+ssl_public_key = D:\Users\TestUser\certificate
+computer_title = TEST_DISTRO
diff --git a/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/golden/success_overriding_the_ssl_certficate_path b/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/golden/success_overriding_the_ssl_certficate_path
new file mode 100644
index 000000000..e9563aa4f
--- /dev/null
+++ b/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/golden/success_overriding_the_ssl_certficate_path
@@ -0,0 +1,4 @@
+[client]
+hello          = world
+ssl_public_key = ${FILESYSTEM_ROOT}/mnt/d/Users/TestUser/certificate
+computer_title = TEST_DISTRO
diff --git a/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/success_despite_failing_to_override_the_SSL_certficate_path/landscape.conf b/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/success_despite_failing_to_override_the_SSL_certficate_path/landscape.conf
new file mode 100644
index 000000000..f256eee6e
--- /dev/null
+++ b/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/success_despite_failing_to_override_the_SSL_certficate_path/landscape.conf
@@ -0,0 +1,3 @@
+[client]
+hello = world
+ssl_public_key = D:\Users\TestUser\certificate
\ No newline at end of file
diff --git a/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/success_overriding_the_ssl_certficate_path/landscape.conf b/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/success_overriding_the_ssl_certficate_path/landscape.conf
new file mode 100644
index 000000000..f256eee6e
--- /dev/null
+++ b/wsl-pro-service/internal/system/testdata/TestLandscapeEnable/success_overriding_the_ssl_certficate_path/landscape.conf
@@ -0,0 +1,3 @@
+[client]
+hello = world
+ssl_public_key = D:\Users\TestUser\certificate
\ No newline at end of file