Support multiple timestamps per signature

NEWS.md

@@ -14,6 +14,13 @@
 - fixed heap out-of-bounds reads when parsing malformed APPX ZIP64 extra fields
 - fixed heap out-of-bounds reads when verifying malformed PKCS#7 signature attributes
 - fixed undefined behavior when copying an empty MSI signature blob
+- fixed RFC 3161 timestamp verification accepting tokens whose message
+  imprint is empty or shorter than its digest, which did not bind them to
+  the signature
+- added multiple timestamp support: `add` preserves existing timestamps and
+  `-timestamp-all` requires every specified Authenticode/RFC 3161 server
+- verification now tries all timestamps and accepts any trusted timestamp for
+  which the Authenticode signature also validates at the timestamp's time
 
 ### 2.14 (2026.07.20)
 

README.md

@@ -118,6 +118,20 @@ or if you want to add a timestamp as well:
     -t http://timestamp.digicert.com \
     -in yourapp.exe -out yourapp-signed.exe
 ```
+To require multiple timestamps, use `-timestamp-all` with repeated `-ts` or
+`-t` options (both protocols may be combined):
+```
+  osslsigncode add -timestamp-all \
+    -ts https://tsa1.example.com/ -ts https://tsa2.example.com/ \
+    -in yourapp-signed.exe -out yourapp-multistamped.exe
+```
+Every requested server must succeed. Without `-timestamp-all`, repeated URLs
+remain fallback servers, stopping after the first success. `add` preserves
+existing timestamps. Verification succeeds if at least one trusted timestamp
+and the signing certificate/signature validate at that timestamp's time;
+invalid alternatives do not invalidate a valid pair. Use `-ignore-timestamp`
+to verify at the requested/current time instead.
+
 You can use a certificate and key stored in a PKCS#12 container:
 ```
   osslsigncode sign -pkcs12 <pkcs12-file> -pass <pkcs12-password> \

cmake/CMakeTest.cmake

@@ -544,6 +544,20 @@ if(Python3_FOUND AND NOT cryptography_error)
             endforeach(cert ${pem_certs})
         endforeach(ext ${extensions_all})
 
+        # Append two more RFC3161 timestamps to the existing one
+        add_test(NAME "add_ts_all_exe"
+            COMMAND ${Python3_EXECUTABLE} ${EXEC} ${OSSLSIGNCODE} "add"
+            "-timestamp-all"
+            "-ts" "FILE ${LOGS}/url.log"
+            "-ts" "FILE ${LOGS}/url.log"
+            "-in" "${FILES}/ts_cert.exe"
+            "-out" "${FILES}/ts_all.exe")
+        set_tests_properties("add_ts_all_exe" PROPERTIES
+            ENVIRONMENT "HTTP_PROXY=;http_proxy="
+            DEPENDS "sign_ts_cert_exe"
+            RESOURCE_LOCK "tsa")
+        list(APPEND ALL_TESTS "add_ts_all_exe")
+
 
 ### Verify Time-Stamp Authority ###
 
@@ -561,6 +575,18 @@ if(Python3_FOUND AND NOT cryptography_error)
             list(APPEND ALL_TESTS "verify_ts_cert_${ext}")
         endforeach(ext ${extensions_all})
 
+        # Verify a signature with multiple timestamps
+        add_test(NAME "verify_ts_all_exe"
+            COMMAND ${Python3_EXECUTABLE} ${EXEC} ${OSSLSIGNCODE} "verify"
+            "-time" "1567296000" # Signature verification time: Sep  1 00:00:00 2019 GMT
+            "-CAfile" "${CERTS}/CACert.pem"
+            "-TSA-CAfile" "${CERTS}/TSACA.pem"
+            "-in" "${FILES}/ts_all.exe")
+        set_tests_properties("verify_ts_all_exe" PROPERTIES
+            ENVIRONMENT "HTTP_PROXY=;http_proxy=;"
+            DEPENDS "add_ts_all_exe")
+        list(APPEND ALL_TESTS "verify_ts_all_exe")
+
         # Verify with untrusted Time-Stamp Authority
         # This test is expected to fail
         foreach(ext ${extensions_all})
@@ -718,6 +744,7 @@ if(Python3_FOUND AND NOT cryptography_error)
         set(OUTPUT_FILES ${OUTPUT_FILES} "${FILES}/jreq.tsq")
         set(OUTPUT_FILES ${OUTPUT_FILES} "${FILES}/jresp.tsr")
     endforeach(ext ${extensions_all})
+    set(OUTPUT_FILES ${OUTPUT_FILES} "${FILES}/ts_all.exe")
 
     add_test(NAME "remove_files"
         COMMAND ${CMAKE_COMMAND} -E rm -f ${OUTPUT_FILES})