Release 2.11

Signed-off-by: Michał Trojnara <Michal.Trojnara@stunnel.org>

.github/ISSUE_TEMPLATE.md

@@ -0,0 +1,8 @@
+<!--
+Please use one of the available issue templates.
+Bug reports without required information may be closed.
+-->
+
+If you are reporting a bug or crash, please use the appropriate issue template.
+
+For questions or support, use please use [Discussions](<https://github.com/mtrojnar/osslsigncode/discussions>).

.github/ISSUE_TEMPLATE/10_crash_report.md

@@ -0,0 +1,74 @@
+---
+name: Crash report
+about: Report a segmentation fault or other crash
+labels: crash
+---
+
+<!--
+Thank you for your crash report.
+Note: Please search to see if an issue already exists for the bug you encountered.
+-->
+
+### Segmentation Fault / Crash Details
+<!--
+Provide exact, reproducible steps.
+Include the complete command, exactly as executed.
+-->
+- Signal / exit code: <!-- SIGSEGV, SIGABRT -->
+- Reproducibility: <!-- always / sometimes / once -->
+- Affected command or operation: <!-- e.g. `osslsigncode sign`, `osslsigncode verify` -->
+- First observed version:
+- Last known working version (if any):
+
+#### Backtrace
+<!--
+Provide a backtrace from gdb or lldb.
+Build with debug symbols if possible. Use `bt full` if possible.
+Crash reports without a backtrace may be closed without investigation.
+-->
+- `(gdb) bt`
+
+#### Memory / Sanitizers
+<!--
+Attach relevant output if available.
+-->
+- [ ] Valgrind
+- [ ] ASan / UBSan
+- [ ] Other tools
+
+#### Crash Context
+<!--
+Anything that may be relevant:
+- OpenSSL provider / engine in use
+- PKCS#11 modules
+- Custom OpenSSL configuration
+- Threading or concurrency
+-->
+
+### Environment
+- Operating system and version (e.g. Ubuntu 24.04):
+- Architecture (x86_64, arm64, etc.):
+
+### Versions
+<!--
+Please verify that the issue is reproducible with the current upstream master.
+-->
+- osslsigncode built from:
+  - [ ] upstream master
+  - [ ] upstream release (tag):
+  - [ ] distribution package (name and version):
+- `openssl version -a`
+- `osslsigncode --version`
+
+### Configuration / Settings
+<!--
+Anything that could affect signing or verification:
+- Custom OpenSSL configuration
+- Engine / provider settings
+- Environment variables (OPENSSL_CONF, etc.)
+-->
+
+### Anything else
+<!--
+Links, references, related issues, workarounds or additional observations.
+-->

.github/ISSUE_TEMPLATE/20_documentation.md

@@ -0,0 +1,26 @@
+---
+name: Documentation
+about: Report an error in (or missing) documentation
+labels: documentation
+---
+
+<!--
+Thank you for taking the time to report a documentation issue.
+-->
+
+### Documentation Location
+<!--
+Where is the problem located?
+Provide a link, file path, or section name.
+-->
+
+### Issue Description
+<!--
+Describe what is wrong or missing.
+-->
+
+### Suggested Improvement (optional)
+<!--
+If you know how it should be fixed, describe it here.
+Proposed wording or examples are especially helpful.
+-->

.github/ISSUE_TEMPLATE/30_feature_request.md

@@ -0,0 +1,30 @@
+---
+name: Feature request
+about: Suggest a new feature or improvement
+labels: feature
+---
+
+<!--
+Thank you for your feature request.
+Please describe the use case and motivation as clearly as possible.
+-->
+
+### Use Case / Motivation
+<!--
+What problem are you trying to solve?
+Why is this feature needed?
+-->
+
+### Proposed Change
+<!--
+Describe the feature or improvement you are proposing.
+High-level description is sufficient.
+-->
+
+### Additional Notes (optional)
+<!--
+Anything else that may help:
+- examples
+- references
+- related issues
+-->

.github/ISSUE_TEMPLATE/40_questions.md

@@ -0,0 +1,17 @@
+---
+name: Questions / Support
+about: Please use Q&A in Discussions instead
+labels: question
+---
+
+### Questions and Support
+
+Please do **not** use GitHub issues for general questions or support requests.
+
+For:
+- usage questions
+- "how do I..." questions
+
+please use [Q&A category in Discussions](<https://github.com/mtrojnar/osslsigncode/discussions/new?category=q-a>)
+
+Bug reports and crashes should be reported using the appropriate issue templates.

.github/ISSUE_TEMPLATE/50_bug_report.md

@@ -0,0 +1,77 @@
+---
+name: Other bug report
+about: Report a bug
+labels: bug
+---
+
+<!--
+Thank you for your bug report.
+Note: Please search to see if an issue already exists for the bug you encountered.
+-->
+
+### Current Behavior
+<!--
+A concise description of what is happening.
+Include error messages or incorrect results.
+-->
+
+### Expected Behavior
+<!--
+A concise description of what you expected to happen instead.
+-->
+
+### Steps To Reproduce & Observed Output
+<!--
+Provide exact, reproducible steps together with full stdout/stderr for each.
+-->
+1. Signing with osslsigncode
+<!--
+Full `osslsigncode sign` command and complete stdout/stderr output.
+-->
+
+2. Verification with osslsigncode
+<!--
+Full `osslsigncode verify` command and complete stdout/stderr output.
+-->
+
+3. Signing / verification with Windows signtool (if applicable)
+<!--
+Full signtool command (`signtool verify /pa /v`) and complete stdout/stderr output.
+-->
+
+### Environment
+- Operating system and version (e.g. Ubuntu 24.04):
+- Architecture (x86_64, arm64, etc.):
+
+### Versions
+<!--
+Please verify that the issue is reproducible with the current upstream master.
+-->
+- osslsigncode built from:
+  - [ ] upstream master
+  - [ ] upstream release (tag):
+  - [ ] distribution package (name and version):
+- `openssl version -a`
+- `osslsigncode --version`
+
+### Files
+<!--
+Attach files if possible, or mention that you will share them privately.
+-->
+- [ ] unsigned file
+- [ ] file signed with osslsigncode
+- [ ] file signed with signtool or the other tool (for comparison)
+- [ ] certificate chain used for verification (PEM format)
+
+### Configuration / Settings
+<!--
+Anything that could affect signing or verification:
+- Custom OpenSSL configuration
+- Engine / provider settings
+- Environment variables (OPENSSL_CONF, etc.)
+-->
+
+### Anything else
+<!--
+Links, references, related issues, workarounds or additional observations.
+-->

.github/PULL_REQUEST_TEMPLATE.md

@@ -0,0 +1,65 @@
+<!--
+Thank you for your pull request.
+Provide a concise summary of the changes in the PR title.
+-->
+
+### Pull Request Type
+<!--
+Limit this PR to a single type. If necessary, split changes into multiple PRs.
+-->
+
+- [ ] Bug fix
+- [ ] New feature
+- [ ] Code style / formatting / renaming
+- [ ] Refactoring (no functional or API changes)
+- [ ] Build / CI related changes
+- [ ] Documentation
+- [ ] Other (please describe):
+
+### Related Issue
+<!--
+If this fixes a GitHub issue, make sure to have a line saying 'Fixes #XXXX' (without quotes) in the commit message.
+-->
+Issue number: N/A
+
+### Current Behavior
+<!--
+Describe the current behavior or limitation this PR addresses.
+Include error messages or crash symptoms if relevant.
+-->
+
+### New Behavior
+<!--
+Describe the new or changed behavior introduced by this PR.
+-->
+
+### Scope of Changes
+<!--
+Briefly describe what was changed and why.
+Focus on relevant parts only.
+-->
+
+### Testing
+<!--
+Describe how the changes were tested.
+Include commands, environments, or platforms if relevant.
+-->
+- [ ] Existing tests
+- [ ] New tests added
+- [ ] Manual testing
+
+### Additional Notes
+<!--
+Any additional information relevant for reviewers:
+- design decisions
+- backward compatibility
+- known limitations
+-->
+
+## License Declaration
+<!--
+All contributions to this project are licensed under the project's license.
+By submitting this pull request, you confirm that you have the right to submit
+the code and agree to license it accordingly.
+-->
+- [ ] I hereby agree to license my contribution under the project's license.

.github/workflows/ci.yml

@@ -7,7 +7,7 @@ on:
 env:
   # Customize the CMake build type here (Release, Debug, RelWithDebInfo, etc.)
   BUILD_TYPE: Release
-  version: osslsigncode-2.10
+  version: osslsigncode-2.11
 
 jobs:
   build:

CMakeLists.txt

@@ -10,7 +10,7 @@ set(BUILTIN_SOCKET ON CACHE BOOL "") # for static Python
 
 # configure basic project information
 project(osslsigncode
-    VERSION 2.10
+    VERSION 2.11
     DESCRIPTION "OpenSSL based Authenticode signing for PE, CAB, CAT, MSI, APPX and script files"
     HOMEPAGE_URL "https://github.com/mtrojnar/osslsigncode"
     LANGUAGES C)

NEWS.md

@@ -1,5 +1,15 @@
 # osslsigncode change log
 
+### 2.11 (2026.01.20)
+- added keyUsage validation for signer certificate
+  (thanks to Hanqing Zhao and Zi-Quan You for reporting the issue)
+- added printing CRL details during signature verification
+- implemented a workaround for CRL servers returning the HTTP Content-Type
+  header other than application/pkix-crl (thanks to Chris Thibodeaux)
+- fixed HTTP keep-alive handling
+- fixed macOS compiler and linker flags
+- fixed undefined BIO_get_fp() behavior with BIO_FLAGS_UPLINK_INTERNAL
+
 ### 2.10 (2025.06.23)
 
 - added JavaScript signing

README.md

@@ -133,8 +133,9 @@ To sign a CAB file containing Java class files:
 ```
 Only the 'low' parameter is currently supported.
 
-If you want to use a PKCS#11 token, you should specify the PKCS#11 engine and module.
-An example of using osslsigncode with SoftHSM:
+### Using the PKCS#11 Engine with osslsigncode
+If you want to use a PKCS#11 token, specify the PKCS#11 engine and module.
+Example usage with SoftHSM:
 ```
   osslsigncode sign \
     -engine /usr/lib64/engines-1.1/pkcs11.so \
@@ -144,8 +145,10 @@ An example of using osslsigncode with SoftHSM:
     -in yourapp.exe -out yourapp-signed.exe
 ```
 
-Since OpenSSL 3.0, you can use a PKCS#11 token with the PKCS#11 provider.
-An example of using osslsigncode with OpenSC:
+### Using the PKCS#11 Provider with osslsigncode (OpenSSL 3.x only)
+OpenSSL 3.0 introduced a new provider-based architecture. To use a PKCS#11 token
+ with `osslsigncode`, specify the PKCS#11 provider and module.
+Example usage with OpenSC:
 ```
   osslsigncode sign \
     -provider /usr/lib64/ossl-modules/pkcs11prov.so \
@@ -155,26 +158,40 @@ An example of using osslsigncode with OpenSC:
     -in yourapp.exe -out yourapp-signed.exe
 ```
 
-You can use a certificate and key stored in the Windows Certificate Store with
-the CNG engine version 1.1 or later. For more information, refer to
+### Using the CNG Engine with osslsigncode (Windows only)
+The CNG engine allows using certificates and keys stored in the Windows
+Certificate Store. It requires CNG engine version 1.1 or later. For more
+information, refer to
 
   https://www.stunnel.org/cng-engine.html
 
 A non-commercial edition of CNG engine is available for testing, personal,
 educational, or research purposes.
 
-To use the CNG engine with osslsigncode, ensure that the `cng.dll` library is
-placed in the same directory as the `osslsigncode.exe` executable.
+To ensure `osslsigncode` can locate and load the CNG engine module (`cng.dll`)
+even when it is not installed in the default system engine directory, you can:
 
-Below is an example of how to use osslsigncode with the CNG engine:
+- Specify the full or relative path to `cng.dll`:
 ```
-  osslsigncode sign \
-    -engine cng \
-    -pkcs11cert osslsigncode_cert \
-    -key osslsigncode_cert \
-    -engineCtrl store_flags:0 \
-    -engineCtrl store_name:MY \
-    -engineCtrl PIN:yourpass \
+  osslsigncode sign -engine C:\my\engines\cng.dll ...
+```
+- Or set the `OPENSSL_ENGINES` environment variable to the directory containing
+`cng.dll`, and refer to the engine by its ID:
+```
+  set OPENSSL_ENGINES=C:\my\engines
+  osslsigncode sign -engine cng ...
+```
+
+Below is an example of how to use `osslsigncode` with the CNG engine on Windows:
+```
+  set OPENSSL_ENGINES=C:\my\engines
+  osslsigncode sign ^
+    -engine cng ^
+    -pkcs11cert osslsigncode_cert ^
+    -key osslsigncode_cert ^
+    -engineCtrl store_flags:0 ^
+    -engineCtrl store_name:MY ^
+    -engineCtrl PIN:yourpass ^
     -in yourapp.exe -out yourapp-signed.exe
 ```
 

appx.c

@@ -2744,7 +2744,10 @@ static int get_current_position(BIO *bio, uint64_t *offset)
     FILE *file = NULL;
     int64_t pos;
 
-    BIO_get_fp(bio, &file);
+    if (BIO_get_fp(bio, &file) != 1 || file == NULL) {
+        fprintf(stderr, "BIO_get_fp() failed\n");
+        return 0; /* FAILED */
+    }
     pos = ftello(file);
     if (pos < 0) {
         return 0; /* FAILED */

cmake/SetCompilerFlags.cmake

@@ -96,16 +96,11 @@ function(add_compile_flags target)
                 message(WARNING "No stack protection supported")
             endif(HAVE_STACK_PROTECTOR)
         endif(HAVE_STACK_PROTECTOR_ALL)
-        # Support address space layout randomization (ASLR)
-        if(NOT (MINGW OR CYGWIN OR CMAKE_C_COMPILER_ID STREQUAL "AppleClang"
-            OR ((CMAKE_SYSTEM_NAME MATCHES Darwin) AND (CMAKE_C_COMPILER_ID MATCHES Clang))))
+        # Support address space layout randomization (ASLR) / PIE
+        if(UNIX AND NOT APPLE)
             target_compile_options(${target} PRIVATE -fPIE)
-            target_link_options(${target} PRIVATE -fPIE -pie)
-            target_link_options(${target} PRIVATE -Wl,-z,relro)
-            target_link_options(${target} PRIVATE -Wl,-z,now)
-            target_link_options(${target} PRIVATE -Wl,-z,noexecstack)
-        endif(NOT (MINGW OR CYGWIN OR CMAKE_C_COMPILER_ID STREQUAL "AppleClang"
-            OR ((CMAKE_SYSTEM_NAME MATCHES Darwin) AND (CMAKE_C_COMPILER_ID MATCHES Clang))))
+            target_link_options(${target} PRIVATE -fPIE -pie -Wl,-z,relro,-z,now,-z,noexecstack)
+        endif(UNIX AND NOT APPLE)
         target_link_options(${target} PRIVATE -fstack-check)
         add_compile_flag_to_targets(${target})
     endif(MSVC)

get_code_signing_ca.py

@@ -10,6 +10,7 @@ from csv import reader
 from requests import get
 from requests.exceptions import RequestException
 from concurrent.futures import ThreadPoolExecutor
+from re import search
 
 def download_cert(hash):
     for attempt in range(10):
@@ -17,23 +18,33 @@ def download_cert(hash):
             sleep(10)
         try:
             creds = f'{attempt}{hash}:{attempt}{hash}'
-            resp = get(f'https://crt.sh/?d={hash}',
-                proxies=dict(https=f'socks5://{creds}@127.0.0.1:9050'))
+            proxies = dict(https=f'socks5://{creds}@127.0.0.1:9050')
+
+            url = f'https://crt.sh/?sha1={hash}&match=='
+            resp = get(url, proxies=proxies)
             resp.raise_for_status()
+
+            m = search(r'\bid=(\d+)\b', resp.content.decode('ascii', 'replace'))
+            id = m.group(1)
+
+            url = f'https://crt.sh/?d={id}'
+            resp = get(url, proxies=proxies)
+            resp.raise_for_status()
+
             print('.', file=stderr, end='')
             stderr.flush()
-            return resp.content.decode('utf-8')
-        except RequestException as e:
-            print(f'\nAttempt {attempt}: {e}', file=stderr)
+            return resp.content.decode('utf-8', 'replace')
+        except Exception as e:
+            print(f'\n{url} attempt {attempt}: {e}', file=stderr)
     print('\nGiving up on', hash, file=stderr)
 
-resp = get('https://ccadb-public.secure.force.com/microsoft/IncludedCACertificateReportForMSFTCSV')
+resp = get('https://ccadb.my.salesforce-sites.com/microsoft/IncludedCACertificateReportForMSFTCSV')
 resp.raise_for_status()
 lines = resp.content.decode('utf-8').splitlines()[1:]
 hashes = [row[4] for row in reader(lines)
     if row[0] != 'Disabled'
         or row[4] == 'F38406E540D7A9D90CB4A9479299640FFB6DF9E224ECC7A01C0D9558D8DAD77D']
-with ThreadPoolExecutor(max_workers=20) as executor:
+with ThreadPoolExecutor(max_workers=10) as executor:
     certs = executor.map(download_cert, hashes)
 for cert in certs:
     if cert is not None:

helpers.c

@@ -17,6 +17,7 @@ static int pkcs7_signer_info_add_purpose(PKCS7_SIGNER_INFO *si, FILE_FORMAT_CTX
 static int pkcs7_signer_info_add_sequence_number(PKCS7_SIGNER_INFO *si, FILE_FORMAT_CTX *ctx);
 static STACK_OF(X509) *X509_chain_get_sorted(FILE_FORMAT_CTX *ctx, int signer);
 static int X509_compare(const X509 *const *a, const X509 *const *b);
+static void sk_X509_remove_duplicates(STACK_OF(X509) *chain);
 
 /*
  * Common functions
@@ -763,6 +764,9 @@ static STACK_OF(X509) *X509_chain_get_sorted(FILE_FORMAT_CTX *ctx, int signer)
     }
     /* sort certificate chain using the supplied comparison function */
     sk_X509_sort(chain);
+    /* remove duplicates */
+    sk_X509_remove_duplicates(chain);
+
     return chain;
 }
 
@@ -814,6 +818,35 @@ static int X509_compare(const X509 *const *a, const X509 *const *b)
     return ret;
 }
 
+/*
+ * Remove duplicate certificates from a sorted STACK_OF(X509).
+ *
+ * This function assumes the stack is sorted according to X.690-compliant
+ * certificate comparison, so duplicate certificates appear consecutively.
+ * It iterates through the stack and removes any duplicate certificates
+ * by comparing each element with its immediate predecessor.
+ * The stack is modified in place.
+ */
+static void sk_X509_remove_duplicates(STACK_OF(X509) *chain)
+{
+    int i, n = sk_X509_num(chain);
+
+    if (n < 2)
+        return;
+
+    /* start from the second element */
+    for (i = 1; i < n; ) {
+        if (!X509_cmp(sk_X509_value(chain, i - 1), sk_X509_value(chain, i))) {
+            /* duplicate found: remove the certificate at index i */
+            (void)sk_X509_delete(chain, i);
+            n--; /* reduce stack size since one element was removed */
+            /* do not increment i, as next element shifts into index i */
+        } else {
+            i++; /* advance only if no removal was done */
+        }
+    }
+}
+
 /*
 Local Variables:
    c-basic-offset: 4

osslsigncode.c

@@ -244,6 +244,7 @@ static PKCS7 *pkcs7_get_sigfile(FILE_FORMAT_CTX *ctx);
 static void print_cert(X509 *cert, int i);
 static int x509_store_load_crlfile(X509_STORE *store, char *cafile, char *crlfile);
 static void load_objects_from_store(const char *url, char *pass, EVP_PKEY **pkey, STACK_OF(X509) *certs, STACK_OF(X509_CRL) *crls);
+static BIO *bio_new_file(const char *filename, const char *mode);
 #ifndef OPENSSL_NO_ENGINE
 static void engine_control_set(GLOBAL_OPTIONS *options, const char *arg);
 #endif /* OPENSSL_NO_ENGINE */
@@ -797,63 +798,37 @@ static int verify_callback(int ok, X509_STORE_CTX *ctx)
 /*
  * Read data from socket BIO
  * [in] s_bio: socket BIO
- * [in] rctx: open connection context
- * [in] use_ssl: HTTPS request switch
  * [returns] memory BIO
  */
-static BIO *socket_bio_read(BIO *s_bio, OSSL_HTTP_REQ_CTX *rctx, int use_ssl)
+static BIO *socket_bio_read(BIO *s_bio)
 {
-    int retry = 1, ok = 0, written = 0, resp_len = 0;
+    int retry = 1, ok = 0;
     char *buf = OPENSSL_malloc(OSSL_HTTP_DEFAULT_MAX_RESP_LEN);
     BIO *resp = BIO_new(BIO_s_mem());
 
-    if (rctx) {
-        resp_len = (int)OSSL_HTTP_REQ_CTX_get_resp_len(rctx);
-    }
-    if (resp_len == 0) {
-        if (use_ssl)
-            BIO_ssl_shutdown(s_bio);
-        else {
-            int fd = (int)BIO_get_fd(s_bio, NULL);
-
-            if (fd >= 0) {
-#ifdef WIN32
-                (void)shutdown(fd, SD_SEND);
-#else /* WIN32 */
-                (void)shutdown(fd, SHUT_WR);
-#endif /* WIN32 */
-            }
-        }
-    }
-    ERR_clear_error();
     while (retry) {
         int n;
 
         errno = 0;
         n = BIO_read(s_bio, buf, OSSL_HTTP_DEFAULT_MAX_RESP_LEN);
         if (n > 0) {
-            written += BIO_write(resp, buf, n);
+            (void)BIO_write(resp, buf, n);
         } else if (BIO_eof(s_bio) == 1) {
             ok = 1;
-            retry = 0; /* EOF */
+            retry = 0; /* HTTP EOF */
         } else if (BIO_should_retry(s_bio)) {
         } else {
             unsigned long err = ERR_get_error();
 
             if (err == 0) {
                 ok = 1;
-                retry = 0; /* use_ssl EOF */
+                retry = 0; /* HTTPS EOF */
             } else {
                 fprintf(stderr, "\nHTTP failure: error %ld: %s\n", err, ERR_reason_error_string(err));
                 retry = 0; /* FAILED */
             }
         }
-        if (resp_len > 0 && resp_len == written) {
-            ok = 1;
-            retry = 0; /* all response has been read */
-        }
     }
-    OSSL_HTTP_close(rctx, ok);
     OPENSSL_free(buf);
     if (!ok) {
         BIO_free_all(resp);
@@ -915,12 +890,10 @@ static void check_authenticode_timestamp(BIO **resp)
 static BIO *bio_get_http(char *url, BIO *req, char *proxy, int rfc3161, char *cafile, char *crlfile)
 {
     BIO *tmp_bio = NULL, *s_bio = NULL, *resp = NULL;
-    OSSL_HTTP_REQ_CTX *rctx = NULL;
     HTTP_TLS_Info info;
     SSL_CTX *ssl_ctx = NULL;
     char *server = NULL, *port = NULL, *path = NULL;
     int timeout = -1; /* blocking mode, exactly one try, see BIO_do_connect_retry() */
-    int keep_alive = 1; /* prefer */
     int use_ssl = 0;
 
     if (!url) {
@@ -956,10 +929,16 @@ static BIO *bio_get_http(char *url, BIO *req, char *proxy, int rfc3161, char *ca
     info.ssl_ctx = ssl_ctx;
 
     if (!req) { /* GET */
-        const char *expected_content_type = "application/pkix-crl";
-
+        /*
+         * HTTP server implementations accessed via the URI SHOULD specify the
+         * media type application/pkix-crl in the Content-Type header field of
+         * the response (RFC 5280, section 4.2.1.13).
+         * In practice, some CRL distribution points return "application/octet-stream"
+         * instead. Therefore, do not enforce the Content-Type and rely on the CRL
+         * parser to validate the response content.
+         */
         s_bio = OSSL_HTTP_get(url, proxy, NULL, NULL, NULL, http_tls_cb, &info, 0,
-            NULL, expected_content_type, 0, 0, timeout);
+            NULL, NULL, 0, 0, timeout);
     } else { /* POST */
         const char *content_type = "application/timestamp-query"; /* RFC3161 Timestamp */
         const char *expected_content_type = "application/timestamp-reply";
@@ -974,9 +953,9 @@ static BIO *bio_get_http(char *url, BIO *req, char *proxy, int rfc3161, char *ca
             content_type = "application/octet-stream"; /* Authenticode Timestamp */
             expected_content_type = "application/octet-stream";
         }
-        s_bio = OSSL_HTTP_transfer(&rctx, server, port, path, use_ssl, proxy, NULL,
+        s_bio = OSSL_HTTP_transfer(NULL, server, port, path, use_ssl, proxy, NULL,
             NULL, NULL, http_tls_cb, &info, 0, NULL, content_type, req,
-            expected_content_type, 0, 0, timeout, keep_alive);
+            expected_content_type, 0, 0, timeout, 0);
         BIO_free(tmp_bio);
     }
     OPENSSL_free(server);
@@ -985,7 +964,7 @@ static BIO *bio_get_http(char *url, BIO *req, char *proxy, int rfc3161, char *ca
     SSL_CTX_free(ssl_ctx);
 
     if (s_bio) {
-        resp = socket_bio_read(s_bio, rctx, use_ssl);
+        resp = socket_bio_read(s_bio);
         BIO_free_all(s_bio);
         if (resp && req && !rfc3161)
             check_authenticode_timestamp(&resp);
@@ -1277,7 +1256,7 @@ static int add_timestamp_builtin(PKCS7 *p7, FILE_FORMAT_CTX *ctx)
     TS_RESP *response = NULL;
     int i, res = 1;
 
-    btmp = BIO_new_file(ctx->options->tsa_certfile, "rb");
+    btmp = bio_new_file(ctx->options->tsa_certfile, "rb");
     if (!btmp) {
         fprintf(stderr, "Failed to read Time-Stamp Authority certificate file: %s\n", ctx->options->tsa_certfile);
         return 0; /* FAILED */
@@ -1285,7 +1264,7 @@ static int add_timestamp_builtin(PKCS7 *p7, FILE_FORMAT_CTX *ctx)
     /* .pem certificate file */
     chain = X509_chain_read_certs(btmp, NULL);
     BIO_free(btmp);
-    btmp = BIO_new_file(ctx->options->tsa_keyfile, "rb");
+    btmp = bio_new_file(ctx->options->tsa_keyfile, "rb");
     if (!btmp) {
         fprintf(stderr, "Failed to read private key file: %s\n", ctx->options->tsa_keyfile);
         return 0; /* FAILED */
@@ -1766,7 +1745,7 @@ static char *x509_name_to_utf8(const X509_NAME *name)
 
     flags = XN_FLAG_RFC2253 | ASN1_STRFLGS_UTF8_CONVERT |
             ASN1_STRFLGS_ESC_CTRL;
-    flags &= ~ASN1_STRFLGS_ESC_MSB;
+    flags &= ~(unsigned long)ASN1_STRFLGS_ESC_MSB;
 
     bio = BIO_new(BIO_s_mem());
     if (!bio)
@@ -1922,11 +1901,22 @@ static int verify_ca_callback(int ok, X509_STORE_CTX *ctx)
 
 static int verify_crl_callback(int ok, X509_STORE_CTX *ctx)
 {
+    X509_CRL *crl;
     int error = X509_STORE_CTX_get_error(ctx);
     int depth = X509_STORE_CTX_get_error_depth(ctx);
-
     X509 *current_cert = X509_STORE_CTX_get_current_cert(ctx);
+
     print_cert(current_cert, depth);
+
+    crl = X509_STORE_CTX_get0_current_crl(ctx);
+    if (crl) {
+        BIO *bio = BIO_new_fp(stdout, BIO_NOCLOSE);
+
+        X509_CRL_print(bio, crl);
+        BIO_free(bio);
+        printf("\n");
+    }
+
     if (!ok) {
         if (trusted_cert(current_cert, error)) {
             return 1;
@@ -2534,9 +2524,14 @@ static int verify_authenticode(FILE_FORMAT_CTX *ctx, PKCS7 *p7, time_t time, X50
         if (!crlok)
             goto out;
     }
-    /* check extended key usage flag XKU_CODE_SIGN */
+    /* keyUsage, if present, must permit digitalSignature (RFC 5280 section 4.2.1.3) */
+    if (!(X509_get_key_usage(signer) & X509v3_KU_DIGITAL_SIGNATURE)) {
+        fprintf(stderr, "Signer certificate rejected: keyUsage does not permit digitalSignature\n");
+        goto out;
+    }
+    /* extendedKeyUsage, if present, must permit codeSigning (RFC 5280 section 4.2.1.12) */
     if (!(X509_get_extended_key_usage(signer) & XKU_CODE_SIGN)) {
-        fprintf(stderr, "Unsupported Signer's certificate purpose XKU_CODE_SIGN\n");
+        fprintf(stderr, "Signer certificate rejected: extendedKeyUsage does not permit codeSigning\n");
         goto out;
     }
 
@@ -3605,11 +3600,11 @@ static void usage(const char *argv0, const char *cmd)
         printf("%1s[ --help ]\n\n", "");
     }
     if (on_list(cmd, cmds_sign)) {
-        printf("%1s[ sign ] -pkcs12 <pkcs12file> | ( [ -certs <certfile> | -spc <certfile> ]\n", "");
+        printf("%1s[ sign ] -pkcs12 <file> | ( [ -certs <file|URI> | -spc <file> ]\n", "");
 #if !defined(OPENSSL_NO_ENGINE) || OPENSSL_VERSION_NUMBER>=0x30000000L
-        printf("%12s( -key <keyfile> | ( -key <pkcs11 key URI> -pkcs11module <module> [ -pkcs11cert <pkcs11 cert URI> ] )\n", "");
+        printf("%12s( -key <file|URI> [ -pkcs11module <module> ] [ -pkcs11cert <pkcs11 cert URI> ] )\n", "");
 #else /* !defined(OPENSSL_NO_ENGINE) || OPENSSL_VERSION_NUMBER>=0x30000000L */
-        printf("%12s-key <keyfile> )\n", "");
+        printf("%12s-key <file|URI> )\n", "");
 #endif /* !defined(OPENSSL_NO_ENGINE) || OPENSSL_VERSION_NUMBER>=0x30000000L */
 #if OPENSSL_VERSION_NUMBER>=0x30000000L
         printf("%12s[ -provider <provider> | ", "");
@@ -3619,7 +3614,7 @@ static void usage(const char *argv0, const char *cmd)
 #endif /* OPENSSL_NO_ENGINE */
 #endif /* OPENSSL_VERSION_NUMBER>=0x30000000L */
 #ifndef OPENSSL_NO_ENGINE
-        printf("%s( -engine <engine> [ -login ] [ -engineCtrl <command[:parameter]> ] ) ] ) )\n", "");
+        printf("%s( -engine <engine> [ -login ] [ -engineCtrl <command[:parameter]> ] ) ] )\n", "");
 #endif /* OPENSSL_NO_ENGINE */
 #if OPENSSL_VERSION_NUMBER>=0x30000000L
         printf("%12s[ -nolegacy ]\n", "");
@@ -3630,73 +3625,73 @@ static void usage(const char *argv0, const char *cmd)
 #endif /* PROVIDE_ASKPASS */
         printf("%1s[ -readpass <file> ]\n", "");
         printf("%12s(use \"-\" with readpass to read from stdin)\n", "");
-        printf("%12s[ -ac <crosscertfile> ]\n", "");
+        printf("%12s[ -ac <file> ]\n", "");
         printf("%12s[ -h {md5,sha1,sha2(56),sha384,sha512} ]\n", "");
         printf("%12s[ -n <desc> ] [ -i <url> ] [ -jp <level> ] [ -comm ]\n", "");
         printf("%12s[ -ph ]\n", "");
         printf("%12s[ -t <timestampurl> [ -t ... ] [ -p <proxy> ] [ -noverifypeer  ]\n", "");
         printf("%12s[ -ts <timestampurl> [ -ts ... ] [ -p <proxy> ] [ -noverifypeer ] ]\n", "");
-        printf("%12s[ -TSA-certs <TSA-certfile> ] [ -TSA-key <TSA-keyfile> ]\n", "");
+        printf("%12s[ -TSA-certs <file> ] [ -TSA-key <file> ]\n", "");
         printf("%12s[ -TSA-time <unix-time> ]\n", "");
-        printf("%12s[ -HTTPS-CAfile <infile> ]\n", "");
-        printf("%12s[ -HTTPS-CRLfile <infile> ]\n", "");
+        printf("%12s[ -HTTPS-CAfile <file> ]\n", "");
+        printf("%12s[ -HTTPS-CRLfile <file> ]\n", "");
         printf("%12s[ -time <unix-time> ]\n", "");
-        printf("%12s[ -addUnauthenticatedBlob [ -blobFile <blobfile> ] ]\n", "");
+        printf("%12s[ -addUnauthenticatedBlob [ -blobFile <file> ] ]\n", "");
         printf("%12s[ -nest ]\n", "");
         printf("%12s[ -verbose ]\n", "");
         printf("%12s[ -add-msi-dse ]\n", "");
         printf("%12s[ -pem ]\n", "");
-        printf("%12s[ -in ] <infile> [-out ] <outfile>\n\n", "");
+        printf("%12s[ -in ] <file> [-out ] <file>\n\n", "");
     }
     if (on_list(cmd, cmds_extract_data)) {
         printf("%1sextract-data [ -pem ]\n", "");
         printf("%12s[ -h {md5,sha1,sha2(56),sha384,sha512} ]\n", "");
         printf("%12s[ -ph ]\n", "");
         printf("%12s[ -add-msi-dse ]\n", "");
-        printf("%12s[ -in ] <infile> [ -out ] <datafile>\n\n", "");
+        printf("%12s[ -in ] <file> [ -out ] <file>\n\n", "");
     }
     if (on_list(cmd, cmds_add)) {
-        printf("%1sadd [ -addUnauthenticatedBlob [ -blobFile <blobfile> ] ]\n", "");
+        printf("%1sadd [ -addUnauthenticatedBlob [ -blobFile <file> ] ]\n", "");
         printf("%12s[ -t <timestampurl> [ -t ... ] [ -p <proxy> ] [ -noverifypeer  ]\n", "");
         printf("%12s[ -ts <timestampurl> [ -ts ... ] [ -p <proxy> ] [ -noverifypeer ] ]\n", "");
-        printf("%12s[ -TSA-certs <TSA-certfile> ] [ -TSA-key <TSA-keyfile> ]\n", "");
+        printf("%12s[ -TSA-certs <file> ] [ -TSA-key <file> ]\n", "");
         printf("%12s[ -TSA-time <unix-time> ]\n", "");
-        printf("%12s[ -HTTPS-CAfile <infile> ]\n", "");
-        printf("%12s[ -HTTPS-CRLfile <infile> ]\n", "");
+        printf("%12s[ -HTTPS-CAfile <file> ]\n", "");
+        printf("%12s[ -HTTPS-CRLfile <file> ]\n", "");
         printf("%12s[ -h {md5,sha1,sha2(56),sha384,sha512} ]\n", "");
         printf("%12s[ -index <index> ]\n", "");
         printf("%12s[ -verbose ]\n", "");
         printf("%12s[ -add-msi-dse ]\n", "");
-        printf("%12s[ -in ] <infile> [ -out ] <outfile>\n\n", "");
+        printf("%12s[ -in ] <file> [ -out ] <file>\n\n", "");
     }
     if (on_list(cmd, cmds_attach)) {
-        printf("%1sattach-signature [ -sigin ] <sigfile>\n", "");
-        printf("%12s[ -CAfile <infile> ]\n", "");
-        printf("%12s[ -CRLfile <infile> ]\n", "");
-        printf("%12s[ -TSA-CAfile <infile> ]\n", "");
-        printf("%12s[ -TSA-CRLfile <infile> ]\n", "");
+        printf("%1sattach-signature [ -sigin ] <file>\n", "");
+        printf("%12s[ -CAfile <file> ]\n", "");
+        printf("%12s[ -CRLfile <file> ]\n", "");
+        printf("%12s[ -TSA-CAfile <file> ]\n", "");
+        printf("%12s[ -TSA-CRLfile <file> ]\n", "");
         printf("%12s[ -time <unix-time> ]\n", "");
         printf("%12s[ -h {md5,sha1,sha2(56),sha384,sha512} ]\n", "");
         printf("%12s[ -require-leaf-hash {md5,sha1,sha2(56),sha384,sha512}:XXXXXXXXXXXX... ]\n", "");
         printf("%12s[ -nest ]\n", "");
         printf("%12s[ -add-msi-dse ]\n", "");
-        printf("%12s[ -in ] <infile> [ -out ] <outfile>\n\n", "");
+        printf("%12s[ -in ] <file> [ -out ] <file>\n\n", "");
     }
     if (on_list(cmd, cmds_extract)) {
         printf("%1sextract-signature [ -pem ]\n", "");
-        printf("%12s[ -in ] <infile> [ -out ] <sigfile>\n\n", "");
+        printf("%12s[ -in ] <file> [ -out ] <file>\n\n", "");
     }
     if (on_list(cmd, cmds_remove))
-        printf("%1sremove-signature [ -in ] <infile> [ -out ] <outfile>\n\n", "");
+        printf("%1sremove-signature [ -in ] <file> [ -out ] <file>\n\n", "");
     if (on_list(cmd, cmds_verify)) {
-        printf("%1sverify [ -in ] <infile>\n", "");
-        printf("%12s[ -c | -catalog <infile> ]\n", "");
-        printf("%12s[ -CAfile <infile> ]\n", "");
-        printf("%12s[ -CRLfile <infile> ]\n", "");
-        printf("%12s[ -HTTPS-CAfile <infile> ]\n", "");
-        printf("%12s[ -HTTPS-CRLfile <infile> ]\n", "");
-        printf("%12s[ -TSA-CAfile <infile> ]\n", "");
-        printf("%12s[ -TSA-CRLfile <infile> ]\n", "");
+        printf("%1sverify [ -in ] <file>\n", "");
+        printf("%12s[ -c | -catalog <file> ]\n", "");
+        printf("%12s[ -CAfile <file> ]\n", "");
+        printf("%12s[ -CRLfile <file> ]\n", "");
+        printf("%12s[ -HTTPS-CAfile <file> ]\n", "");
+        printf("%12s[ -HTTPS-CRLfile <file> ]\n", "");
+        printf("%12s[ -TSA-CAfile <file> ]\n", "");
+        printf("%12s[ -TSA-CRLfile <file> ]\n", "");
         printf("%12s[ -p <proxy> ]\n", "");
         printf("%12s[ -index <index> ]\n", "");
         printf("%12s[ -ignore-timestamp ]\n", "");
@@ -3857,7 +3852,7 @@ static void help_for(const char *argv0, const char *cmd)
     if (on_list(cmd, cmds_CAfile))
         printf("%-24s= the file containing one or more trusted certificates in PEM format\n", "-CAfile");
     if (on_list(cmd, cmds_certs))
-        printf("%-24s= the signing certificate to use\n", "-certs, -spc");
+        printf("%-24s= certificate chain (signing cert + intermediates)\n", "-certs, -spc");
     if (on_list(cmd, cmds_comm))
         printf("%-24s= set commercial purpose (default: individual purpose)\n", "-comm");
     if (on_list(cmd, cmds_CRLfile))
@@ -3882,7 +3877,7 @@ static void help_for(const char *argv0, const char *cmd)
         printf("%-24s= disable legacy mode and don't automatically load the legacy provider\n", "-nolegacy");
 #endif /* OPENSSL_VERSION_NUMBER>=0x30000000L */
     if (on_list(cmd, cmds_key))
-        printf("%-24s= the private key to use or PKCS#11 URI identifies a key in the token\n", "-key");
+        printf("%-24s= private key (optionally with signing cert) from file or URI\n", "-key");
     if (on_list(cmd, cmds_n))
         printf("%-24s= specifies a description of the signed content\n", "-n");
     if (on_list(cmd, cmds_nest))
@@ -4104,7 +4099,7 @@ err:
  */
 static int read_der_keyfile(GLOBAL_OPTIONS *options)
 {
-    BIO *btmp = BIO_new_file(options->keyfile, "rb");
+    BIO *btmp = bio_new_file(options->keyfile, "rb");
 
     if (!btmp) {
         fprintf(stderr, "Failed to read private key file: %s\n", options->keyfile);
@@ -4130,7 +4125,7 @@ static int read_der_keyfile(GLOBAL_OPTIONS *options)
 static int read_pkcs7_certfile(GLOBAL_OPTIONS *options)
 {
     PKCS7 *p7;
-    BIO *btmp = BIO_new_file(options->certfile, "rb");
+    BIO *btmp = bio_new_file(options->certfile, "rb");
 
     if (!btmp) {
         fprintf(stderr, "Failed to read certificate from: %s\n",
@@ -4364,8 +4359,8 @@ static int read_crypto_params(GLOBAL_OPTIONS *options)
             (void)provider_load(options->provider);
         }
 #endif /* OPENSSL_VERSION_NUMBER>=0x30000000L */
-        /* Load the private key ('-key' option) */
-        load_objects_from_store(options->keyfile, options->pass, &options->pkey, NULL, NULL);
+        /* Load the private key and the signing certificate ('-key' option) */
+        load_objects_from_store(options->keyfile, options->pass, &options->pkey, options->certs, NULL);
     }
 #if OPENSSL_VERSION_NUMBER<0x1010108f
     /* Workaround for OpenSSL 1.1.1g and older, where the store API does not
@@ -4609,6 +4604,26 @@ static int file_exists(const char *filename)
     return 0; /* File does not exist */
 }
 
+static BIO *bio_new_file(const char *filename, const char *mode)
+{
+    FILE *file;
+    BIO *bio;
+
+    if (!filename)
+        return NULL;
+
+    file = fopen(filename, mode);
+    if (!file)
+        return NULL;
+
+    bio = BIO_new_fp(file, BIO_CLOSE);
+    if (!bio) {
+        fclose(file);
+        return NULL;
+    }
+    return bio;
+}
+
 /*
  * [in] argc, argv
  * [in, out] options: structure holds the input data
@@ -5122,14 +5137,12 @@ int main(int argc, char **argv)
 #if defined(__GNUC__)
 #pragma GCC diagnostic pop
 #endif
-        /* Create outdata file */
-        outdata = BIO_new_file(options.outfile, "w+bx");
-        if (!outdata && errno != EEXIST)
-            outdata = BIO_new_file(options.outfile, "w+b");
+        /* Create output file — file existence already verified via file_exists() */
+        outdata = bio_new_file(options.outfile, "w+b");
         if (!outdata) {
             BIO_free_all(hash);
             DO_EXIT_1("Failed to create file: %s\n", options.outfile);
-        }
+         }
     }
     ctx = file_format_script.ctx_new(&options, hash, outdata);
     if (!ctx)

tests/make_certificates.py

@@ -338,6 +338,17 @@ class LeafCertificate(X509Extensions):
         authority_key = AuthorityKeyIdentifier.from_issuer_subject_key_identifier(
             self.issuer_cert.extensions.get_extension_for_class(SubjectKeyIdentifier).value
         )
+        key_usage = KeyUsage(
+            digital_signature=True,
+            content_commitment=False,
+            key_encipherment=False,
+            data_encipherment=False,
+            key_agreement=False,
+            key_cert_sign=False,
+            crl_sign=False,
+            encipher_only=False,
+            decipher_only=False
+        )
         extended_key_usage = ExtendedKeyUsage(
             [ExtendedKeyUsageOID.CODE_SIGNING]
         )
@@ -352,6 +363,7 @@ class LeafCertificate(X509Extensions):
             .add_extension(BasicConstraints(ca=False, path_length=None), critical=False)
             .add_extension(SubjectKeyIdentifier.from_public_key(public_key), critical=False)
             .add_extension(authority_key, critical=False)
+            .add_extension(key_usage, critical=False)
             .add_extension(extended_key_usage, critical=False)
             .add_extension(self.create_x509_crldp(), critical=False)
             .sign(self.issuer_key, SHA256())