correction: regarding needing to exclude zlib, that was apparently due
to an error
on my part. I have now gotten apache 2.2.14 to compile with openssl
0.9.8l and zlib.

So I am amending my instructions to these:
Yes you can compile apache 2.2.14 with openssl-0.9.8l and zlib
with vs2008 professional.
These instructions are correct but it's possible to trip on some details
in executing them.  So I am adding a bit more detail.
http://httpd.apache.org/docs/2.2/platform/win_compiling.html

I have visual studio professional 2008 (v9) installed on 2003. and I
had windows sdk 7 installed, should this make a difference. I
'registered" sdk 7 with visual studio. I have no idea if that was
necessary.
I did install this version of awk per the instructions.
http://www.cs.princeton.edu/~bwk/btl.mirror/awk95.exe
I deleted some awk and gawk items from a cygwin install on this
machine.
I used this checksum program
http://www.microsoft.com/downloads/details.aspx?FamilyID=B3C93558-31B7-47E2-A663-7365C1686C08&displaylang=en
I used the cygwin patch program.
I had the activestate perl version 5.8.9.

I used the visual studio 2008 tools, command prompt to do further work.
Having extracted the apache source somewhere (check checksum before extracting),

Download zlib to a directory somewhere.
http://www.zlib.net/zlib-1.2.3.tar.gz, check checksum.
Create the directory zlib under the existing srclib directory in the
apache source. xcopy all the zlib-1.2.3 content to the srclib\zlib
directory. Being
in the srclib\zlib\win32 directory, download this patch:
http://www.apache.org/dist/httpd/binaries/win32/patches_applied/zlib-1.2.3-vc32-2005-rcver.patch
Apply it:
patch -s < zlib-1.2.3-vc32-2005-rcver.patch
Then being above that directory, in the srclib/zlib directory,
issue these commands from the vs2008 command prompt:
nmake -f win32\Makefile.msc
nmake -f win32\Makefile.msc test

Download openssl-0.9.8l
http://www.openssl.org/source/
to a directory somewhere
Check the checksum and gzip -d and tar -xvf .
Create a directory openssl under the already existing srclib directory.
Copy all the files from the subdirectory openssl-0.9.8l to the
srclib\openssl directory (eg using xcopy src dest /s/c ).
Download this patch to the srclib\openssl directory:
http://www.apache.org/dist/httpd/binaries/win32/patches_applied/openssl-0.9.8k-vc32.patch
It works without modification. To apply, do this being in the
srclib\openssl directory:
patch -s < openssl-0.9.8k-vc32.patch

Then being in the srclib\openssl directory (this command has to be
customized for your situation:
[For comparison, the actual installed location of compiled zlib in my
case was e:\apachezlib\httpd-2.2.14\srclib\zlib]
perl Configure no-rc5 no-idea enable-mdc2 enable-zlib VC-WIN32
-I/apachezlib/httpd-2.2.14/srclib/zlib
-L/apachezlib/httpd-2.2.14/srclib/zlib
ms\do_masm.bat
nmake -f ms\ntdll.mak

If you get link complaints about multiply defined items I think (but I
could be wrong) it probably means the zlib patch didn't get applied
correctly.
I didn't tackle mod_dbd or mod_authn_dbm

And then one can proceed to the top source level and do:
nmake /f Makefile.win _apacher
and follow the rest of the instructions.

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