Merge branch 'maint-3.2'

* maint-3.2:
  Fix modular square root test with LibreSSL >= 3.8
  pkcs7: raise PKCS7Error for PKCS7 without content in PKCS7.read_smime
  pkcs7: raise ArgumentError for PKCS7 with no content in PKCS7.new
  cipher: fix buffer overflow in Cipher#update
  ssl: allow failure on test_connect_certificate_verify_failed_exception_message
  .github/workflows/test.yml: synchronize with master
  Only CSR version 1 (encoded as 0) is allowed by PKIX standards
  test_asn1.rb: Remove the assertions of the time string format without second.
  test/openssl/test_asn1.rb: skip failing tests on LibreSSL 3.6.0
  Use EVP_Digest{Sign,Verify} when available
  Fix performance regression in do_write(s)

2 files changed, 22 insertions, 4 deletions

diff --git a/ext/openssl/ossl_cipher.c b/ext/openssl/ossl_cipher.c
index 1910a5cd..6f74c925 100644
--- a/ext/openssl/ossl_cipher.c
+++ b/ext/openssl/ossl_cipher.c
@@ -386,11 +386,23 @@ ossl_cipher_update(int argc, VALUE *argv, VALUE self)
     in = (unsigned char *)RSTRING_PTR(data);
     in_len = RSTRING_LEN(data);
     GetCipher(self, ctx);
-    out_len = in_len+EVP_CIPHER_CTX_block_size(ctx);
-    if (out_len <= 0) {
+
+    /*
+     * As of OpenSSL 3.2, there is no reliable way to determine the required
+     * output buffer size for arbitrary cipher modes.
+     * https://github.com/openssl/openssl/issues/22628
+     *
+     * in_len+block_size is usually sufficient, but AES key wrap with padding
+     * ciphers require in_len+15 even though they have a block size of 8 bytes.
+     *
+     * Using EVP_MAX_BLOCK_LENGTH (32) as a safe upper bound for ciphers
+     * currently implemented in OpenSSL, but this can change in the future.
+     */
+    if (in_len > LONG_MAX - EVP_MAX_BLOCK_LENGTH) {
 	ossl_raise(rb_eRangeError,
 		   "data too big to make output buffer: %ld bytes", in_len);
     }
+    out_len = in_len + EVP_MAX_BLOCK_LENGTH;
 
     if (NIL_P(str)) {
         str = rb_str_new(0, out_len);
@@ -401,7 +413,7 @@ ossl_cipher_update(int argc, VALUE *argv, VALUE self)
 
     if (!ossl_cipher_update_long(ctx, (unsigned char *)RSTRING_PTR(str), &out_len, in, in_len))
 	ossl_raise(eCipherError, NULL);
-    assert(out_len < RSTRING_LEN(str));
+    assert(out_len <= RSTRING_LEN(str));
     rb_str_set_len(str, out_len);
 
     return str;
diff --git a/ext/openssl/ossl_pkcs7.c b/ext/openssl/ossl_pkcs7.c
index 78dcbd66..aeeb4bf5 100644
--- a/ext/openssl/ossl_pkcs7.c
+++ b/ext/openssl/ossl_pkcs7.c
@@ -165,7 +165,11 @@ ossl_pkcs7_s_read_smime(VALUE klass, VALUE arg)
     out = NULL;
     pkcs7 = SMIME_read_PKCS7(in, &out);
     BIO_free(in);
-    if(!pkcs7) ossl_raise(ePKCS7Error, NULL);
+    if (!pkcs7)
+        ossl_raise(ePKCS7Error, "Could not parse the PKCS7");
+    if (!pkcs7->d.ptr)
+        ossl_raise(ePKCS7Error, "No content in PKCS7");
+
     data = out ? ossl_membio2str(out) : Qnil;
     SetPKCS7(ret, pkcs7);
     ossl_pkcs7_set_data(ret, data);
@@ -346,6 +350,8 @@ ossl_pkcs7_initialize(int argc, VALUE *argv, VALUE self)
     BIO_free(in);
     if (!p7)
         ossl_raise(rb_eArgError, "Could not parse the PKCS7");
+    if (!p7->d.ptr)
+        ossl_raise(rb_eArgError, "No content in PKCS7");
 
     RTYPEDDATA_DATA(self) = p7;
     PKCS7_free(p7_orig);