1 files changed, 95 insertions, 14 deletions

diff --git a/src/lib/libcrypto/man/SMIME_write_CMS.3 b/src/lib/libcrypto/man/SMIME_write_CMS.3
index 1a691fc29a..5f4c43bb7c 100644
--- a/src/lib/libcrypto/man/SMIME_write_CMS.3
+++ b/src/lib/libcrypto/man/SMIME_write_CMS.3
@@ -1,7 +1,24 @@
-.\" $OpenBSD: SMIME_write_CMS.3,v 1.8 2025/06/11 14:23:14 schwarze Exp $
+.\" $OpenBSD: SMIME_write_CMS.3,v 1.9 2025/06/11 23:16:32 schwarze Exp $
 .\" full merge up to: OpenSSL 99d63d46 Oct 26 13:56:48 2016 -0400
 .\"
-.\" This file was written by Dr. Stephen Henson <steve@openssl.org>.
+.\" This file is a derived work.
+.\" The changes are covered by the following Copyright and license:
+.\"
+.\" Copyright (c) 2021, 2025 Ingo Schwarze <schwarze@openbsd.org>
+.\"
+.\" Permission to use, copy, modify, and distribute this software for any
+.\" purpose with or without fee is hereby granted, provided that the above
+.\" copyright notice and this permission notice appear in all copies.
+.\"
+.\" THE SOFTWARE IS PROVIDED "AS IS" AND THE AUTHOR DISCLAIMS ALL WARRANTIES
+.\" WITH REGARD TO THIS SOFTWARE INCLUDING ALL IMPLIED WARRANTIES OF
+.\" MERCHANTABILITY AND FITNESS. IN NO EVENT SHALL THE AUTHOR BE LIABLE FOR
+.\" ANY SPECIAL, DIRECT, INDIRECT, OR CONSEQUENTIAL DAMAGES OR ANY DAMAGES
+.\" WHATSOEVER RESULTING FROM LOSS OF USE, DATA OR PROFITS, WHETHER IN AN
+.\" ACTION OF CONTRACT, NEGLIGENCE OR OTHER TORTIOUS ACTION, ARISING OUT OF
+.\" OR IN CONNECTION WITH THE USE OR PERFORMANCE OF THIS SOFTWARE.
+.\"
+.\" The original file was written by Dr. Stephen Henson <steve@openssl.org>.
 .\" Copyright (c) 2008 The OpenSSL Project.  All rights reserved.
 .\"
 .\" Redistribution and use in source and binary forms, with or without
@@ -66,21 +83,35 @@
 .Fc
 .Sh DESCRIPTION
 .Fn SMIME_write_CMS
-adds the appropriate MIME headers to the
-.Fa cms
-structure to produce an S/MIME message and writes it to
-.Fa out .
+generates an S/MIME message on
+.Fa out
+by writing MIME 1.0 headers
+followed by a BER- and base64-encoded serialization of
+.Fa cms .
+The BER encoding uses the DER format except as described for
+.Dv CMS_STREAM
+below.
 If streaming is enabled, the content must be supplied in the
 .Fa data
 argument.
 .Pp
-The following
+The
 .Fa flags
-can be passed:
+can be the logical OR of zero or more of the following bits:
 .Bl -tag -width Ds
 .It Dv CMS_DETACHED
-Use cleartext signing.
-This option only makes sense if
+Use cleartext signing and generate a
+.Qq multipart/signed
+S/MIME message.
+The content is read from
+.Fa data .
+If
+.Fa data
+is a
+.Dv NULL
+pointer, this flag is ignored.
+.Pp
+This flag is only supported if
 .Fa cms
 is of the type
 .Vt SignedData
@@ -95,13 +126,46 @@ is not set, the data must be read twice:
 once to compute the signature in
 .Xr CMS_sign 3
 and once to output the S/MIME message.
-.It Dv CMS_TEXT
-Add MIME headers for type text/plain to the content.
-This only makes sense if
+.Pp
+If
+.Dv CMS_DETACHED
+is ignored or not specified, the smime-type is chosen according to
+.Xr CMS_get0_type 3 :
+.Bl -tag -width Ds
+.It Dv NID_pkcs7_enveloped
+.Qq enveloped-data
+.It Dv NID_pkcs7_signed
+.Bl -tag -width Msigned-receiptM -compact
+.It Qq signed-receipt
+if
+.Xr CMS_get0_eContentType 3
+is
+.Dv NID_id_smime_ct_receipt
+.It Qq signed-data
+if
+.Fa cms
+specifies any digest algorithm
+.It Qq certs-only
+otherwise
+.El
+.It Dv NID_id_smime_ct_compressedData
+.Qq compressed-data
+.El
+.It Dv CMS_REUSE_DIGEST
+Skip the calls to
+.Xr CMS_dataInit 3
+and
+.Xr CMS_dataFinal 3 .
+This flag has no effect unless
 .Dv CMS_DETACHED
 is also set.
 .It Dv CMS_STREAM
-Perform streaming.
+Perform streaming by reading the content from
+.Fa data .
+This only works if
+.Dv CMS_DETACHED
+is not specified.
+.Pp
 This flag should only be set if
 .Dv CMS_STREAM
 was also passed to the function that created
@@ -112,6 +176,23 @@ constructed encoding except in the case of
 .Vt SignedData
 with detached content where the content is absent and DER format is
 used.
+.It Dv CMS_TEXT
+Prepend the line
+.Qq Content-Type: text/plain
+to the content.
+This only makes sense if
+.Dv CMS_DETACHED
+is also set.
+It is ignored if the flag
+.Dv SMIME_BINARY
+is also set.
+.It Dv SMIME_BINARY
+If specified, this flag is passed through to
+.Xr SMIME_crlf_copy 3 .
+.It Dv SMIME_CRLFEOL
+End MIME header lines with pairs of carriage return and newline characters.
+By default, no carriage return characters are written
+and header lines are ended with newline characters only.
 .El
 .Sh RETURN VALUES
 .Fn SMIME_write_CMS