I just compiled static builds of Openssl from the head snapshot
"openssl-SNAP-20091111.tar.gz" for DJGPP and for Mingw (under Cygwin
using -mno-cygwin). Both build and test without difficulty except for 2
changes needed in one of the test modules. One change includes the
".exe" suffix for the executable. The other change is to prevent failure
due to perl syntax problems (seen in perl 5.6.0 for Cygwin). The patch
is attached.

The perl error report is:
CMS consistency test
/usr/local/bin/perl.exe cms-test.pl
In string, @openssl now must be written as \...@openssl at cms-test.pl line 
238, near "-receipt_request_to t...@openssl"
Execution of cms-test.pl aborted due to compilation errors.


The DJGPP version was configured:
WATT_ROOT=/dev/env/DJDIR/watt32 && \
perl ./Configure no-threads no-idea 386 --prefix=/dev/env/DJDIR DJGPP

and openssl version -a shows:
OpenSSL 1.1.0-dev xx XXX xxxx
built on: Wed Nov 11 19:34:12 PST 2009
platform: DJGPP
options:  bn(64,32) rc4(4x,int) des(ptr,risc1,16,long) blowfish(idx) 
compiler: gcc -I/dev/env/WATT_ROOT/inc -DTERMIOS -DL_ENDIAN 
-fomit-frame-pointer -O2 -Wall -DOPENSSL_BN_ASM_PART_WORDS 
-DOPENSSL_BN_ASM_MONT -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DMD5_ASM 
-DRMD160_ASM -DAES_ASM
OPENSSLDIR: "/dev/env/DJDIR/ssl"

The Mingw version was configured:
./Configure no-shared no-idea --prefix=d\:/cygwin/mingw mingw

and openssl version -a shows:
OpenSSL 1.1.0-dev xx XXX xxxx
built on: Wed Nov 11 22:05:36 PST 2009
platform: mingw
options:  bn(64,32) rc4(4x,int) des(ptr,risc1,16,long) blowfish(idx) 
compiler: gcc -DOPENSSL_THREADS  -DDSO_WIN32 -mno-cygwin -DL_ENDIAN 
-DOPENSSL_NO_CAPIENG -fomit-frame-pointer -O3 -march=i486 -Wall 
-DOPENSSL_BN_ASM_PART_WORDS -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT 
-DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DMD5_ASM -DRMD160_ASM -DAES_ASM 
-DWHIRLPOOL_ASM
OPENSSLDIR: "d:/cygwin/mingw/ssl"

Doug

-- 
Doug Kaufman
Internet: [email protected]
--- test/cms-test.pl.orig       2008-04-18 05:00:22.000000000 -0700
+++ test/cms-test.pl    2009-11-12 06:10:02.000000000 -0800
@@ -58,6 +58,9 @@
 if ( -f "../apps/openssl" ) {
     $ossl_path = "../util/shlib_wrap.sh ../apps/openssl";
 }
+elsif ( -f "../apps/openssl.exe" ) {
+    $ossl_path = "../util/shlib_wrap.sh ../apps/openssl.exe";
+}
 elsif ( -f "..\\out32dll\\openssl.exe" ) {
     $ossl_path = "..\\out32dll\\openssl.exe";
 }
@@ -232,7 +235,7 @@
     [
         "signed content MIME format, RSA key, signed receipt request",
         "-sign -in smcont.txt -signer $smdir/smrsa1.pem -nodetach"
-          . " -receipt_request_to [email protected] -receipt_request_all"
+          . " -receipt_request_to [email protected] -receipt_request_all"
           . " -out test.cms",
         "-verify -in test.cms "
           . " -CAfile $smdir/smroot.pem -out smtst.txt"

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