diff --git a/test/recipes/25-test_x509.t b/test/recipes/25-test_x509.t
index 67abee1028..9e1cc0368e 100644
--- a/test/recipes/25-test_x509.t
+++ b/test/recipes/25-test_x509.t
@@ -16,7 +16,7 @@ use OpenSSL::Test qw/:DEFAULT srctop_file/;
 
 setup("test_x509");
 
-plan tests => 21;
+plan tests => 28;
 
 # Prevent MSys2 filename munging for arguments that look like file paths but
 # aren't
@@ -146,3 +146,58 @@ ok(run(app(["openssl", "x509", "-noout", "-dates", "-dateopt", "iso_8601",
 ok(!run(app(["openssl", "x509", "-noout", "-dates", "-dateopt", "invalid_format",
 	     "-in", srctop_file("test/certs", "ca-cert.pem")])),
    "Run with invalid -dateopt format");
+
+# extracts issuer from a -text formatted-output
+sub get_issuer {
+    my $f = shift(@_);
+    my $issuer = "";
+    open my $fh, $f or die;
+    while (my $line = <$fh>) {
+        if ($line =~ /Issuer:/) {
+            $issuer = $line;
+        }
+    }
+    close $fh;
+    return $issuer;
+}
+
+# Tests for signing certs (broken in 1.1.1o)
+my $a_key = "a-key.pem";
+my $a_cert = "a-cert.pem";
+my $a2_cert = "a2-cert.pem";
+my $ca_key = "ca-key.pem";
+my $ca_cert = "ca-cert.pem";
+my $cnf = srctop_file('apps', 'openssl.cnf');
+
+# Create cert A
+ok(run(app(["openssl", "req", "-x509", "-newkey", "rsa:2048",
+            "-config", $cnf,
+            "-keyout", $a_key, "-out", $a_cert, "-days", "365",
+            "-nodes", "-subj", "/CN=test.example.com"])));
+# Create cert CA - note key size
+ok(run(app(["openssl", "req", "-x509", "-newkey", "rsa:4096",
+            "-config", $cnf,
+            "-keyout", $ca_key, "-out", $ca_cert, "-days", "3650",
+            "-nodes", "-subj", "/CN=ca.example.com"])));
+# Sign cert A with CA (errors on 1.1.1o)
+ok(run(app(["openssl", "x509", "-in", $a_cert, "-CA", $ca_cert,
+            "-CAkey", $ca_key, "-set_serial", "1234567890",
+            "-preserve_dates", "-sha256", "-text", "-out", $a2_cert])));
+# verify issuer is CA
+ok (get_issuer($a2_cert) =~ /CN=ca.example.com/);
+
+# Tests for issue #16080 (fixed in 1.1.1o)
+my $b_key = "b-key.pem";
+my $b_csr = "b-cert.csr";
+my $b_cert = "b-cert.pem";
+# Create the CSR
+ok(run(app(["openssl", "req", "-new", "-newkey", "rsa:4096",
+            "-keyout", $b_key, "-out", $b_csr, "-nodes",
+            "-config", $cnf,
+            "-subj", "/CN=b.example.com"])));
+# Sign it - position of "-text" matters!
+ok(run(app(["openssl", "x509", "-req", "-text", "-CAcreateserial",
+            "-CA", $ca_cert, "-CAkey", $ca_key,
+            "-in", $b_csr, "-out", $b_cert])));
+# Verify issuer is CA
+ok(get_issuer($b_cert) =~ /CN=ca.example.com/);