diff --git a/lib/hx509/data/gen-req.sh b/lib/hx509/data/gen-req.sh
index fd6d4ad5e..4e0d79760 100644
--- a/lib/hx509/data/gen-req.sh
+++ b/lib/hx509/data/gen-req.sh
@@ -152,6 +152,26 @@ openssl smime \
     -rc2-128 \
     test.crt
 
+openssl smime \
+    -encrypt \
+    -nodetach \
+    -binary \
+    -in static-file \
+    -outform DER \
+    -out test-enveloped-des \
+    -des \
+    test.crt
+
+openssl smime \
+    -encrypt \
+    -nodetach \
+    -binary \
+    -in static-file \
+    -outform DER \
+    -out test-enveloped-des-ede3 \
+    -des3 \
+    test.crt
+
 openssl smime \
     -encrypt \
     -nodetach \
@@ -162,6 +182,16 @@ openssl smime \
     -aes128 \
     test.crt
 
+openssl smime \
+    -encrypt \
+    -nodetach \
+    -binary \
+    -in static-file \
+    -outform DER \
+    -out test-enveloped-aes-256 \
+    -aes256 \
+    test.crt
+
 echo ocsp requests
 
 openssl ocsp \