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Sign detached signatures over raw bytes with openssl -binary - #20
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15081 The cms -sign invocation in OpenSslOptions omitted -binary, so openssl ran the content through SMIME_crlf_copy and digested a CRLF-rewritten copy rather than the bytes on disk. This is OpenSSL library behaviour, not host behaviour. The manifest is only the visible symptom. Text canonicalization also rewrites every lone LF inside a zip, dll or exe before hashing, so detached signatures over binaries have never covered the shipped bytes either. The verify command documented in Readme.md passes -binary and therefore could not have succeeded against these signatures for any real archive. Two things kept that hidden: the client's HasValidDetachedSignature was reduced to a structural check because the canonicalized digest could not be reproduced in .NET, and the one test that did verify byte-exactly fell back to asserting the .sig merely exists and is non-empty whenever validation failed. Adds -binary to the service and test-harness templates, restores the client check to a real CheckSignature(verifySignatureOnly: true) against the raw bytes, drops the fallback assertion, and adds LF/CRLF cases that fail without the flag. Signatures issued before this change verify only without -binary and ones issued after only with it.
JoshuaPeddle
approved these changes
Aug 25, 2026
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15081
The cms -sign invocation in OpenSslOptions omitted -binary, so openssl ran the content through SMIME_crlf_copy and digested a CRLF-rewritten copy rather than the bytes on disk. This is OpenSSL library behaviour, not host behaviour.
The manifest is only the visible symptom. Text canonicalization also rewrites every lone LF inside a zip, dll or exe before hashing, so detached signatures over binaries have never covered the shipped bytes either. The verify command documented in Readme.md passes -binary and therefore could not have succeeded against these signatures for any real archive. Two things kept that hidden: the client's HasValidDetachedSignature was reduced to a structural check because the canonicalized digest could not be reproduced in .NET, and the one test that did verify byte-exactly fell back to asserting the .sig merely exists and is non-empty whenever validation failed.
Adds -binary to the service and test-harness templates, restores the client check to a real CheckSignature(verifySignatureOnly: true) against the raw bytes, drops the fallback assertion, and adds LF/CRLF cases that fail without the flag. Signatures issued before this change verify only without -binary and ones issued after only with it.