diff --git a/tests/data_files/Makefile b/tests/data_files/Makefile
index d6df19c..01d2379 100644
--- a/tests/data_files/Makefile
+++ b/tests/data_files/Makefile
@@ -1765,6 +1765,22 @@
 	$(MBEDTLS_CERT_WRITE) request_file=server2.req.sha256 serial=2 issuer_crt=$(test_ca_crt) issuer_key=$(test_ca_key_file_rsa) issuer_pwd=$(test_ca_pwd_rsa) not_before=20190210144406 not_after=20290210144406 md=SHA256 version=3 output_file=$@
 all_final += server2-sha256.crt
 
+server2-sha256.ku-ka.crt: SERVER2_CRT_SERIAL=22
+server2-sha256.ku-ka.crt: SERVER2_KEY_USAGE=key_agreement
+server2-sha256.ku-ke.crt: SERVER2_CRT_SERIAL=23
+server2-sha256.ku-ke.crt: SERVER2_KEY_USAGE=key_encipherment
+server2-sha256.ku-ds.crt: SERVER2_CRT_SERIAL=24
+server2-sha256.ku-ds.crt: SERVER2_KEY_USAGE=digital_signature
+server2-sha256.ku-ds_ke.crt: SERVER2_CRT_SERIAL=28
+server2-sha256.ku-ds_ke.crt: SERVER2_KEY_USAGE=digital_signature,key_encipherment
+server2-sha256.ku-%.crt: server2.req.sha256
+	$(MBEDTLS_CERT_WRITE) request_file=server2.req.sha256 serial=$(SERVER2_CRT_SERIAL) \
+		issuer_crt=$(test_ca_crt) issuer_key=$(test_ca_key_file_rsa) issuer_pwd=$(test_ca_pwd_rsa) \
+		key_usage="$(SERVER2_KEY_USAGE)" \
+		not_before=20190210144406 not_after=20290210144406 md=SHA256 version=3 output_file=$@
+all_final += server2-sha256.ku-ka.crt server2-sha256.ku-ke.crt server2-sha256.ku-ds.crt server2-sha256.ku-ds_ke.crt
+
+all_final += server2.ku-ka.crt server2.ku-ke.crt server2.ku-ds.crt server2.ku-ds_ke.crt
 server2.ku-ka.crt: SERVER2_CRT_SERIAL=42
 server2.ku-ka.crt: SERVER2_KEY_USAGE=key_agreement
 server2.ku-ke.crt: SERVER2_CRT_SERIAL=43
diff --git a/tests/data_files/server2-sha256.ku-ds.crt b/tests/data_files/server2-sha256.ku-ds.crt
new file mode 100644
index 0000000..0d4866c
--- /dev/null
+++ b/tests/data_files/server2-sha256.ku-ds.crt
@@ -0,0 +1,20 @@
+-----BEGIN CERTIFICATE-----
+MIIDRzCCAi+gAwIBAgIBGDANBgkqhkiG9w0BAQsFADA7MQswCQYDVQQGEwJOTDER
+MA8GA1UECgwIUG9sYXJTU0wxGTAXBgNVBAMMEFBvbGFyU1NMIFRlc3QgQ0EwHhcN
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+A1UECgwIUG9sYXJTU0wxEjAQBgNVBAMMCWxvY2FsaG9zdDCCASIwDQYJKoZIhvcN
+AQEBBQADggEPADCCAQoCggEBAMFNo93nzR3RBNdJcriZrA545Do8Ss86ExbQWuTN
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+FoAUtFrkpbPe0lL2udWmlQ/rPrzH/f8wDgYDVR0PAQH/BAQDAgeAMA0GCSqGSIb3
+DQEBCwUAA4IBAQAtKutVrQunnzOQg3TP2vnOT8Qr5LrbvsSBaPEm21Oxkpr0gJcC
+/BgON5WrBdfpEDZ5jOMGgqdF3AxFzh/Zw1EBr2y2wIcleodtzV5j2fTQV9MPYJ9z
+XYfhNsr9idt/i4YCqJSe6lB/+GG/p+9jtMLGMjfSkNnG7ppa7Sv6NVsAxgbKskTw
+WU/z7T7Y/afK5omAPpHfWddzCl5o+o9VFi5scYyjv2iNPkRiTMDh4bE8RVm9vxcf
+TMH14TSa1Y6OkaTuzJLbU3V8yJZ67s2SK89Trd75SQ+B62nZYe+0NG+6b2s+D97y
+ex2x2EbfK/nxEL2Gv7/xG4gcpzxmKObhPpsS
+-----END CERTIFICATE-----
diff --git a/tests/data_files/server2-sha256.ku-ds_ke.crt b/tests/data_files/server2-sha256.ku-ds_ke.crt
new file mode 100644
index 0000000..e89e17d
--- /dev/null
+++ b/tests/data_files/server2-sha256.ku-ds_ke.crt
@@ -0,0 +1,20 @@
+-----BEGIN CERTIFICATE-----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+HT4P6DSYW8tzS1KW2BGiLICIaTla0w+w3lkvEcf36hIBMJcCAwEAAaNdMFswCQYD
+VR0TBAIwADAdBgNVHQ4EFgQUpQXoZLjc32APUBJNYKhkr02LQ5MwHwYDVR0jBBgw
+FoAUtFrkpbPe0lL2udWmlQ/rPrzH/f8wDgYDVR0PAQH/BAQDAgWgMA0GCSqGSIb3
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+OLwjjuWRdKT+SPrm+42db4j++KcPVk/HwPNkbcXF7sAHy13DGi47mi7ySKqCiOZ8
+RVnpBWjZJpMzXi5l8RgXGK10v2C4iPX3E7iRw+CYTZjOWfjnzHUWqQ93eu3s6OU3
+3FobrPFKYkS9CvqvbGBIqpv8TTAoAvUAsjUbQHY2SlqlJLw2DUmewmeBzS2ItNyp
+BO367lTm03z+nG77pZYOhgxch8EA2RcIuoEExj0tHZcG3JLOz60ijqqG1lxjrTXV
+qMDRttuL8jisekj4gZD90T9JdMHpz8goNhO7
+-----END CERTIFICATE-----
diff --git a/tests/data_files/server2-sha256.ku-ka.crt b/tests/data_files/server2-sha256.ku-ka.crt
new file mode 100644
index 0000000..326876b
--- /dev/null
+++ b/tests/data_files/server2-sha256.ku-ka.crt
@@ -0,0 +1,20 @@
+-----BEGIN CERTIFICATE-----
+MIIDRzCCAi+gAwIBAgIBFjANBgkqhkiG9w0BAQsFADA7MQswCQYDVQQGEwJOTDER
+MA8GA1UECgwIUG9sYXJTU0wxGTAXBgNVBAMMEFBvbGFyU1NMIFRlc3QgQ0EwHhcN
+MTkwMjEwMTQ0NDA2WhcNMjkwMjEwMTQ0NDA2WjA0MQswCQYDVQQGEwJOTDERMA8G
+A1UECgwIUG9sYXJTU0wxEjAQBgNVBAMMCWxvY2FsaG9zdDCCASIwDQYJKoZIhvcN
+AQEBBQADggEPADCCAQoCggEBAMFNo93nzR3RBNdJcriZrA545Do8Ss86ExbQWuTN
+owCIp+4ea5anUrSQ7y1yej4kmvy2NKwk9XfgJmSMnLAofaHa6ozmyRyWvP7BBFKz
+NtSj+uGxdtiQwWG0ZlI2oiZTqqt0Xgd9GYLbKtgfoNkNHC1JZvdbJXNG6AuKT2kM
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+PNG8gfhW71rcMRTxwKM5qziJ8h6PeomSglsO
+-----END CERTIFICATE-----
diff --git a/tests/data_files/server2-sha256.ku-ke.crt b/tests/data_files/server2-sha256.ku-ke.crt
new file mode 100644
index 0000000..ca5c3c7
--- /dev/null
+++ b/tests/data_files/server2-sha256.ku-ke.crt
@@ -0,0 +1,20 @@
+-----BEGIN CERTIFICATE-----
+MIIDRzCCAi+gAwIBAgIBFzANBgkqhkiG9w0BAQsFADA7MQswCQYDVQQGEwJOTDER
+MA8GA1UECgwIUG9sYXJTU0wxGTAXBgNVBAMMEFBvbGFyU1NMIFRlc3QgQ0EwHhcN
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+Gmp9IkBVZKQci1NbTY18l/2wxFYICv486sAV
+-----END CERTIFICATE-----