Add X.509 path length rollover regression test

boring/src/x509/tests/mod.rs

@@ -16,6 +16,7 @@ use crate::x509::verify::X509CheckFlags;
 use crate::x509::{X509Extension, X509Name, X509Req, X509StoreContext, X509};
 const TEST_CERT_DIGEST: &str = "585e3a58acfd3b4e5e2825659407244ddd93539c";
 
+mod path_len;
 mod trusted_first;
 
 fn pkey() -> PKey<Private> {

boring/src/x509/tests/path_len.rs

@@ -0,0 +1,90 @@
+//! See https://github.com/google/boringssl/commit/ed00cfde0 and the
+//! `PathLenSelfIssuedNotCountedButStillVerified` test in `crypto/x509/x509_test.cc`.
+//!
+//! Fixtures are generated by `boring/test/generate-path-len-rollover-certs.sh`.
+
+use crate::stack::Stack;
+use crate::x509::store::X509StoreBuilder;
+use crate::x509::verify::X509VerifyParamRef;
+use crate::x509::{X509Ref, X509StoreContext, X509VerifyError, X509VerifyResult, X509};
+
+#[test]
+fn test_self_issued_rollover() {
+    let root = X509::from_pem(include_bytes!("../../../test/path-len-rollover-root.pem")).unwrap();
+    let int2 = X509::from_pem(include_bytes!("../../../test/path-len-rollover-int2.pem")).unwrap();
+    let int2_pathlen0 = X509::from_pem(include_bytes!(
+        "../../../test/path-len-rollover-int2-pathlen0.pem"
+    ))
+    .unwrap();
+    let rollover = X509::from_pem(include_bytes!(
+        "../../../test/path-len-rollover-rollover.pem"
+    ))
+    .unwrap();
+    let rollover_pathlen0 = X509::from_pem(include_bytes!(
+        "../../../test/path-len-rollover-rollover-pathlen0.pem"
+    ))
+    .unwrap();
+    let int1 = X509::from_pem(include_bytes!("../../../test/path-len-rollover-int1.pem")).unwrap();
+    let leaf = X509::from_pem(include_bytes!("../../../test/path-len-rollover-leaf.pem")).unwrap();
+
+    // Leaf -- Int1 -- Rollover -- Int2 -- Root
+    //
+    // Rollover is self-issued: it has Int2's name and is signed by Int2's old key, but carries
+    // Int2's new key. It does not count towards the path length, so pathlen 1 on both Int2 and
+    // Rollover is enough to cover Int1.
+    assert_eq!(
+        Ok(()),
+        verify(&leaf, &[&root], &[&int1, &rollover, &int2], |_| {})
+    );
+
+    // Rollover's own pathlen is still enforced, and pathlen 0 does not allow Int1 below it.
+    // BoringSSL ignored this before ed00cfde0.
+    assert_eq!(
+        Err(X509VerifyError::PATH_LENGTH_EXCEEDED),
+        verify(&leaf, &[&root], &[&int1, &rollover_pathlen0, &int2], |_| {})
+    );
+
+    // Int1 still counts against Int2's pathlen, even with Rollover in between.
+    assert_eq!(
+        Err(X509VerifyError::PATH_LENGTH_EXCEEDED),
+        verify(&leaf, &[&root], &[&int1, &rollover, &int2_pathlen0], |_| {})
+    );
+}
+
+fn verify(
+    cert: &X509Ref,
+    trusted: &[&X509Ref],
+    untrusted: &[&X509Ref],
+    configure: impl FnOnce(&mut X509VerifyParamRef),
+) -> X509VerifyResult {
+    let trusted = {
+        let mut builder = X509StoreBuilder::new().unwrap();
+
+        for cert in trusted {
+            builder.add_cert(cert).unwrap();
+        }
+
+        builder.build()
+    };
+
+    let untrusted = {
+        let mut stack = Stack::new().unwrap();
+
+        for cert in untrusted {
+            stack.push((**cert).to_owned()).unwrap();
+        }
+
+        stack
+    };
+
+    let mut store_ctx = X509StoreContext::new().unwrap();
+
+    store_ctx
+        .init(&trusted, cert, &untrusted, |ctx| {
+            configure(ctx.verify_param_mut());
+            ctx.verify_cert().unwrap();
+
+            Ok(ctx.verify_result())
+        })
+        .expect("failed to obtain X509VerifyResult")
+}

boring/test/generate-path-len-rollover-certs.sh

@@ -0,0 +1,101 @@
+#!/usr/bin/env bash
+# Generates the certificates used by `boring/src/x509/tests/path_len.rs`.
+#
+# The chain models a CA key rollover, where Int2 re-keys itself by issuing a
+# self-issued (same subject and issuer name, different key) certificate:
+#
+#   Root
+#    └─ Int2      (old key, pathlen 1 or 0)
+#        └─ Rollover  (Int2 name, new key, signed by old key, pathlen 1 or 0)
+#            └─ Int1
+#                └─ Leaf
+#
+# RFC 5280 says self-issued intermediates do not count towards the path length,
+# but their own pathLenConstraint still applies. BoringSSL only enforces the
+# latter since ed00cfde0.
+#
+# The *-pathlen0 variants are reissued from the same key and name as their
+# pathlen 1 counterparts, so the rest of the chain is shared.
+#
+# CA keys are committed so the chain can be reissued (e.g. to extend validity)
+# without changing key identifiers. Missing keys are generated. The leaf key is
+# discarded.
+set -euo pipefail
+
+cd "$(dirname "$0")"
+NAME=path-len-rollover
+DAYS=7300
+
+ROOT_SUBJ="/CN=Path Len Rollover Test Root"
+INT2_SUBJ="/CN=Path Len Rollover Test Int2"
+INT1_SUBJ="/CN=Path Len Rollover Test Int1"
+LEAF_SUBJ="/CN=localhost"
+
+for key in root int2 int2-new int1; do
+    if [[ ! -f "${NAME}-${key}.key" ]]; then
+        openssl genrsa -traditional -out "${NAME}-${key}.key" 2048
+    fi
+done
+openssl genrsa -out "${NAME}-leaf-key.pem" 2048
+
+# issue OUT KEY SUBJECT CA_CERT CA_KEY EXTENSION...
+issue() {
+    local out=$1 key=$2 subj=$3 ca_cert=$4 ca_key=$5
+    shift 5
+    openssl req -new -key "${key}" -subj "${subj}" -out "${NAME}.csr"
+    openssl x509 -req \
+        -in "${NAME}.csr" \
+        -CA "${ca_cert}" \
+        -CAkey "${ca_key}" \
+        -CAserial "${NAME}.srl" \
+        -CAcreateserial \
+        -out "${out}" \
+        -days "${DAYS}" \
+        -extfile <(printf '%s\n' "$@" \
+            'subjectKeyIdentifier=hash' \
+            'authorityKeyIdentifier=keyid:always')
+}
+
+CA_KEY_USAGE='keyUsage=critical,keyCertSign,cRLSign'
+
+# Self-signed root.
+openssl req -new -x509 \
+    -key "${NAME}-root.key" \
+    -out "${NAME}-root.pem" \
+    -days "${DAYS}" \
+    -subj "${ROOT_SUBJ}" \
+    -addext "basicConstraints=critical,CA:TRUE" \
+    -addext "${CA_KEY_USAGE}" \
+    -addext "subjectKeyIdentifier=hash" \
+    -addext "authorityKeyIdentifier=keyid:always"
+
+# Int2 with its old key, issued by Root.
+for pathlen in 1 0; do
+    suffix=$([[ ${pathlen} == 0 ]] && echo "-pathlen0" || true)
+    issue "${NAME}-int2${suffix}.pem" "${NAME}-int2.key" "${INT2_SUBJ}" \
+        "${NAME}-root.pem" "${NAME}-root.key" \
+        "basicConstraints=critical,CA:TRUE,pathlen:${pathlen}" "${CA_KEY_USAGE}"
+done
+
+# Rollover: Int2's name and new key, signed by Int2's old key.
+for pathlen in 1 0; do
+    suffix=$([[ ${pathlen} == 0 ]] && echo "-pathlen0" || true)
+    issue "${NAME}-rollover${suffix}.pem" "${NAME}-int2-new.key" "${INT2_SUBJ}" \
+        "${NAME}-int2.pem" "${NAME}-int2.key" \
+        "basicConstraints=critical,CA:TRUE,pathlen:${pathlen}" "${CA_KEY_USAGE}"
+done
+
+# Int1, issued by Int2's new key (i.e. by Rollover).
+issue "${NAME}-int1.pem" "${NAME}-int1.key" "${INT1_SUBJ}" \
+    "${NAME}-rollover.pem" "${NAME}-int2-new.key" \
+    "basicConstraints=critical,CA:TRUE" "${CA_KEY_USAGE}"
+
+# Leaf, issued by Int1.
+issue "${NAME}-leaf.pem" "${NAME}-leaf-key.pem" "${LEAF_SUBJ}" \
+    "${NAME}-int1.pem" "${NAME}-int1.key" \
+    "basicConstraints=critical,CA:FALSE" \
+    "keyUsage=critical,digitalSignature" \
+    "extendedKeyUsage=serverAuth" \
+    "subjectAltName=DNS:localhost"
+
+rm -f "${NAME}.csr" "${NAME}.srl" "${NAME}-leaf-key.pem"

boring/test/path-len-rollover-int1.key

@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIEpQIBAAKCAQEAohf4cV7gujHnSmqLa0n468DkUYFs6SNOVsawrPskqpXPUg0l
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+tszEh1HO8D3MzIEJ0a2eQLvMyZCORW0jKIlvmO5e/2C8bQetiA/dzOE=
+-----END RSA PRIVATE KEY-----

boring/test/path-len-rollover-int1.pem

@@ -0,0 +1,20 @@
+-----BEGIN CERTIFICATE-----
+MIIDPTCCAiWgAwIBAgIUZ9Wex0ml6IMTL1w76kF31xMl8ZgwDQYJKoZIhvcNAQEL
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+NyMgtrAVx02M/mGBCWcQLpI=
+-----END CERTIFICATE-----

boring/test/path-len-rollover-int2-new.key

@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIEpAIBAAKCAQEA1typ8Otnz6qOpnXyf+QVNe0wpRgAGcS8jVF6T7RN9KENnPhV
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+-----END RSA PRIVATE KEY-----

boring/test/path-len-rollover-int2-pathlen0.pem

@@ -0,0 +1,20 @@
+-----BEGIN CERTIFICATE-----
+MIIDQDCCAiigAwIBAgIUZ9Wex0ml6IMTL1w76kF31xMl8ZUwDQYJKoZIhvcNAQEL
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+-----END CERTIFICATE-----

boring/test/path-len-rollover-int2.key

@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIEpAIBAAKCAQEAtdNVtkOd0QZLoSO8+4BtBiokB9aCPFxNdpKisVDwKmvzeAM5
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