diff --git a/tests/data_files/Makefile b/tests/data_files/Makefile
index f7826d4..521e4a2 100644
--- a/tests/data_files/Makefile
+++ b/tests/data_files/Makefile
@@ -12,6 +12,7 @@
 
 ## Tools
 OPENSSL ?= openssl
+FAKETIME ?= faketime
 
 ## Build the generated test data. Note that since the final outputs
 ## are committed to the repository, this target should do nothing on a
@@ -64,6 +65,18 @@
 	$(OPENSSL) x509 -req -extfile $(cli_crt_extensions_file) -extensions cli-rsa -CA test-ca-sha256.crt -CAkey $(test_ca_key_file_rsa) -passin "pass:$(test_ca_pwd_rsa)" -set_serial 4 -days 3653 -sha256 -in server2-rsa.csr -out $@
 all_final += server2-sha256.crt
 
+test_ca_int_rsa1 = test-int-ca.crt
+
+server7.csr: server7.key
+	$(OPENSSL) req -new -key server7.key -subj "/C=NL/O=PolarSSL/CN=localhost" -out $@
+all_intermediate += server7.csr
+server7-expired.crt: server7.csr $(test_ca_int_rsa1)
+	$(FAKETIME) -f -3653d $(OPENSSL) x509 -req -extfile $(cli_crt_extensions_file) -extensions cli-rsa -CA $(test_ca_int_rsa1) -CAkey test-int-ca.key -set_serial 16 -days 3653 -sha256 -in server7.csr | cat - $(test_ca_int_rsa1) > $@
+all_final += server7-expired.crt
+server7-future.crt: server7.csr $(test_ca_int_rsa1)
+	$(FAKETIME) -f +3653d $(OPENSSL) x509 -req -extfile $(cli_crt_extensions_file) -extensions cli-rsa -CA $(test_ca_int_rsa1) -CAkey test-int-ca.key -set_serial 16 -days 3653 -sha256 -in server7.csr | cat - $(test_ca_int_rsa1) > $@
+all_final += server7-future.crt
+
 
 
 ################################################################
diff --git a/tests/data_files/server7-expired.crt b/tests/data_files/server7-expired.crt
new file mode 100644
index 0000000..a25ce4b
--- /dev/null
+++ b/tests/data_files/server7-expired.crt
@@ -0,0 +1,47 @@
+-----BEGIN CERTIFICATE-----
+MIIDwjCCAaqgAwIBAgIBEDANBgkqhkiG9w0BAQsFADBIMQswCQYDVQQGEwJOTDER
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+-----END CERTIFICATE-----
+-----BEGIN CERTIFICATE-----
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+Af5cNR8KhzegznL6amRObGGKmX1F
+-----END CERTIFICATE-----
diff --git a/tests/data_files/server7-future.crt b/tests/data_files/server7-future.crt
new file mode 100644
index 0000000..eeb596f
--- /dev/null
+++ b/tests/data_files/server7-future.crt
@@ -0,0 +1,47 @@
+-----BEGIN CERTIFICATE-----
+MIIDwjCCAaqgAwIBAgIBEDANBgkqhkiG9w0BAQsFADBIMQswCQYDVQQGEwJOTDER
+MA8GA1UEChMIUG9sYXJTU0wxJjAkBgNVBAMTHVBvbGFyU1NMIFRlc3QgSW50ZXJt
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+WKW7hd8h
+-----END CERTIFICATE-----
+-----BEGIN CERTIFICATE-----
+MIIEATCCA4egAwIBAgIBDjAKBggqhkjOPQQDAjA+MQswCQYDVQQGEwJOTDERMA8G
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+Af5cNR8KhzegznL6amRObGGKmX1F
+-----END CERTIFICATE-----
diff --git a/tests/suites/test_suite_x509parse.data b/tests/suites/test_suite_x509parse.data
index cd9ec81..e497869 100644
--- a/tests/suites/test_suite_x509parse.data
+++ b/tests/suites/test_suite_x509parse.data
@@ -411,6 +411,14 @@
 depends_on:MBEDTLS_PEM_PARSE_C:MBEDTLS_SHA256_C:MBEDTLS_ECP_C:MBEDTLS_ECP_DP_SECP256R1_ENABLED:MBEDTLS_ECP_DP_SECP384R1_ENABLED:MBEDTLS_SHA1_C
 x509_verify:"data_files/server5-future.crt":"data_files/test-ca2.crt":"data_files/crl-ec-sha1.pem":"NULL":MBEDTLS_ERR_X509_CERT_VERIFY_FAILED:MBEDTLS_X509_BADCERT_FUTURE:"compat":"NULL"
 
+X509 Certificate verification #8c (Expired Cert, longer chain)
+depends_on:MBEDTLS_PEM_PARSE_C:MBEDTLS_SHA256_C:MBEDTLS_ECP_C:MBEDTLS_ECP_DP_SECP256R1_ENABLED:MBEDTLS_ECP_DP_SECP384R1_ENABLED:MBEDTLS_SHA1_C:MBEDTLS_RSA_C
+x509_verify:"data_files/server7-expired.crt":"data_files/test-ca2.crt":"data_files/crl-ec-sha1.pem":"NULL":MBEDTLS_ERR_X509_CERT_VERIFY_FAILED:MBEDTLS_X509_BADCERT_EXPIRED:"compat":"NULL"
+
+X509 Certificate verification #8d (Future Cert, longer chain)
+depends_on:MBEDTLS_PEM_PARSE_C:MBEDTLS_SHA256_C:MBEDTLS_ECP_C:MBEDTLS_ECP_DP_SECP256R1_ENABLED:MBEDTLS_ECP_DP_SECP384R1_ENABLED:MBEDTLS_SHA1_C:MBEDTLS_RSA_C
+x509_verify:"data_files/server7-future.crt":"data_files/test-ca2.crt":"data_files/crl-ec-sha1.pem":"NULL":MBEDTLS_ERR_X509_CERT_VERIFY_FAILED:MBEDTLS_X509_BADCERT_FUTURE:"compat":"NULL"
+
 X509 Certificate verification #9 (Not trusted Cert)
 depends_on:MBEDTLS_PEM_PARSE_C:MBEDTLS_SHA1_C:MBEDTLS_RSA_C:MBEDTLS_PKCS1_V15
 x509_verify:"data_files/server2.crt":"data_files/server1.crt":"data_files/crl.pem":"NULL":MBEDTLS_ERR_X509_CERT_VERIFY_FAILED:MBEDTLS_X509_BADCERT_NOT_TRUSTED:"compat":"NULL"