diff --git a/tests/data_files/Makefile b/tests/data_files/Makefile
index d4aed67..b8cacdd 100644
--- a/tests/data_files/Makefile
+++ b/tests/data_files/Makefile
@@ -12,6 +12,7 @@
 
 ## Tools
 OPENSSL ?= openssl
+FAKETIME ?= faketime
 MBEDTLS_CERT_WRITE ?= $(PWD)/../../programs/x509/cert_write
 
 ## Build the generated test data. Note that since the final outputs
@@ -66,6 +67,18 @@
 	$(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-----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+-----END CERTIFICATE-----
+-----BEGIN CERTIFICATE-----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+-----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-----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+-----END CERTIFICATE-----
+-----BEGIN CERTIFICATE-----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+-----END CERTIFICATE-----