diff --git a/windows-agent/internal/proservices/landscape/testdata/TestConnect/certificates/bad-certificate.pem b/windows-agent/internal/proservices/landscape/testdata/TestConnect/certificates/bad-certificate.pem
new file mode 100644
index 000000000..13f344e2e
--- /dev/null
+++ b/windows-agent/internal/proservices/landscape/testdata/TestConnect/certificates/bad-certificate.pem
@@ -0,0 +1 @@
+This is not a valid certificate
diff --git a/windows-agent/internal/proservices/landscape/testdata/TestConnect/certificates/generate-certificate.sh b/windows-agent/internal/proservices/landscape/testdata/TestConnect/certificates/generate-certificate.sh
index ecf27cce6..4c30a2ce8 100644
--- a/windows-agent/internal/proservices/landscape/testdata/TestConnect/certificates/generate-certificate.sh
+++ b/windows-agent/internal/proservices/landscape/testdata/TestConnect/certificates/generate-certificate.sh
@@ -9,3 +9,5 @@ openssl req                                                 \
     -nodes                                                  \
     -addext 'subjectAltName = IP:127.0.0.1'                 \
     -subj "/C=US/O=Canonical/CN=CanonicalGroupLimited"
+
+echo This is not a valid certificate > bad-certificate.pem
\ No newline at end of file
diff --git a/windows-agent/internal/proservices/landscape/testdata/TestConnect/error_when_the_config_cannot_be_parsed/landscape.conf b/windows-agent/internal/proservices/landscape/testdata/TestConnect/error_when_the_config_cannot_be_parsed/landscape.conf
new file mode 100644
index 000000000..699784501
--- /dev/null
+++ b/windows-agent/internal/proservices/landscape/testdata/TestConnect/error_when_the_config_cannot_be_parsed/landscape.conf
@@ -0,0 +1,6 @@
+{
+    "client": {
+        "tags": "wsl",
+    },
+    "problem": "This should be an ini file"
+}
\ No newline at end of file
diff --git a/windows-agent/internal/proservices/landscape/testdata/TestConnect/error_when_the_ssl_certificate_cannot_be_read/landscape.conf b/windows-agent/internal/proservices/landscape/testdata/TestConnect/error_when_the_ssl_certificate_cannot_be_read/landscape.conf
new file mode 100644
index 000000000..e3d102467
--- /dev/null
+++ b/windows-agent/internal/proservices/landscape/testdata/TestConnect/error_when_the_ssl_certificate_cannot_be_read/landscape.conf
@@ -0,0 +1,2 @@
+[client]
+ssl_public_key = testdata/TestConnect/this_path_does_not_exist/certificate.pem
\ No newline at end of file
diff --git a/windows-agent/internal/proservices/landscape/testdata/TestConnect/error_when_the_ssl_certificate_is_not_valid/landscape.conf b/windows-agent/internal/proservices/landscape/testdata/TestConnect/error_when_the_ssl_certificate_is_not_valid/landscape.conf
new file mode 100644
index 000000000..fa967798f
--- /dev/null
+++ b/windows-agent/internal/proservices/landscape/testdata/TestConnect/error_when_the_ssl_certificate_is_not_valid/landscape.conf
@@ -0,0 +1,2 @@
+[client]
+ssl_public_key = testdata/TestConnect/certificates/bad-certificate.pem
\ No newline at end of file