diff --git a/tests/data_files/Makefile b/tests/data_files/Makefile
index 80bdd25..e638caf 100644
--- a/tests/data_files/Makefile
+++ b/tests/data_files/Makefile
@@ -1306,6 +1306,11 @@
 	$(FAKETIME) -f -3650d $(OPENSSL) req -x509 -subj="/C=NL/O=PKCS7/CN=PKCS7 Cert Expired" -sha256 -nodes -days 365  -newkey rsa:2048 -keyout pkcs7-rsa-expired.key -out pkcs7-rsa-expired.crt
 all_final += pkcs7-rsa-expired.crt
 
+# File with an otherwise valid signature signed with an expired cert
+pkcs7_data_rsa_expired.der: pkcs7-rsa-expired.key pkcs7-rsa-expired.crt pkcs7_data.bin
+	$(OPENSSL) smime -sign -binary -in pkcs7_data.bin -out $@ -md sha256 -inkey pkcs7-rsa-expired.key -signer pkcs7-rsa-expired.crt -noattr -outform DER -out $@
+all_final += pkcs7_data_rsa_expired.der
+
 # Convert signing certs to DER for testing PEM-free builds
 pkcs7-rsa-sha256-1.der: $(pkcs7_test_cert_1)
 	$(OPENSSL) x509 -in pkcs7-rsa-sha256-1.crt -out $@ -outform DER
@@ -1315,6 +1320,10 @@
 	$(OPENSSL) x509 -in pkcs7-rsa-sha256-2.crt -out $@ -outform DER
 all_final += pkcs7-rsa-sha256-2.der
 
+pkcs7-rsa-expired.der: pkcs7-rsa-expired.crt
+	$(OPENSSL) x509 -in pkcs7-rsa-expired.crt -out $@ -outform DER
+all_final += pkcs7-rsa-expired.der
+
 # pkcs7 signature file over zero-len data
 pkcs7_zerolendata_detached.der: pkcs7_zerolendata.bin pkcs7-rsa-sha256-1.key pkcs7-rsa-sha256-1.crt
 	$(OPENSSL) smime -sign -md sha256 -nocerts -noattr -in pkcs7_zerolendata.bin -inkey pkcs7-rsa-sha256-1.key -outform DER -binary -signer pkcs7-rsa-sha256-1.crt -out pkcs7_zerolendata_detached.der
diff --git a/tests/data_files/pkcs7-rsa-expired.der b/tests/data_files/pkcs7-rsa-expired.der
new file mode 100644
index 0000000..508ec5c
--- /dev/null
+++ b/tests/data_files/pkcs7-rsa-expired.der
Binary files differ
diff --git a/tests/data_files/pkcs7_data_rsa_expired.der b/tests/data_files/pkcs7_data_rsa_expired.der
new file mode 100644
index 0000000..63af49d
--- /dev/null
+++ b/tests/data_files/pkcs7_data_rsa_expired.der
Binary files differ