Yesterday I ran into the same problem. After some trial
and error, I was able to get it to work by editing nt.mak and changing
the CFLAG variable to:

CFLAG= /MT /Od -DDEBUG -D_DEBUG /Gs0 /Zi /nologo -
DOPENSSL_SYSNAME_WIN32 -DWIN32_LEAN_AND_MEAN -DL_ENDIAN -DDSO_WIN32 -
D_CRT_SECURE_NO_DEPRECATE -D_CRT_NONSTDC_NO_DEPRECATE -DBN_ASM -
DMD5_ASM -DSHA1_ASM -DRMD160_ASM /Fdout32 -DOPENSSL_NO_CAMELLIA -
DOPENSSL_NO_RC5 -DOPENSSL_NO_MDC2 -DOPENSSL_NO_KRB5 -
DOPENSSL_NO_DYNAMIC_ENGINE

There are probably some extraneous changes there, but I can attest to the
fact that this configuration allowed me to step through OpenSSL code
in VS2005.
John

On Apr 17, 4:52 pm, bob.bar...@businesslink.com ("Bob Barnes") wrote:
> Good thought, but both nt.mak & ntdll.mak have the '/Od' argument set on
the
> 'CFLAG'. I've found that I can debug the assembler code, but needless to
say
> that's not really ideal.
>
> Bob
>
> -----Original Message-----
> From: owner-openssl-us...@openssl.org
>
> [mailto:owner-openssl-us...@openssl.org] On Behalf Of Carter Browne
> Sent: Friday, April 17, 2009 2:08 PM
> To: openssl-us...@openssl.org
> Subject: Re: Debugging OpenSSL with Visual Studio 2008
>
> If you use the step into option when you start debugging, then the
debugger
> will step through the program starting from the beginning.  Did you turn
off
> all optimizations (-Od)?  If you do not, then the debugger can not
associate
> the source code directly with the compiled code.
>
> Carter
>
> Carter Browne
> CBCS
> cbro...@cbcs-usa.com
> 781-721-2890
>
> Bob Barnes wrote:
> > Carter,
>
> >    That's exactly where I've tried to put the breakpoint, but I never
> > hit it and as I indicated earlier, the breakpoint symbol indicates
> > that symbols weren't loaded even though other information, like the
> > Module list and the debug output window, indicate that symbols were
> loaded.
>
> > Bob
>
> > -----Original Message-----
> > From: owner-openssl-us...@openssl.org
> > [mailto:owner-openssl-us...@openssl.org] On Behalf Of Carter Browne
> > Sent: Friday, April 17, 2009 1:38 PM
> > To: openssl-us...@openssl.org
> > Subject: Re: Debugging OpenSSL with Visual Studio 2008
>
> > It is hard to reply without knowing what you are trying to do, but if
> > you put a break point at the :"arg.data=NULL;" statement and then use
> > the step over, step into options of the debugger, you should be able
> > to get to the area you are looking for.  If VC tells you the
> > breakpoint won't be reached, you need to put it somewhere else.
>
> > Carter
>
> > Carter Browne
> > CBCS
> > cbro...@cbcs-usa.com
> > 781-721-2890
>
> > Bob Barnes wrote:
>
> >> hi,
>
> >>   I realize this may be slightly off-topic, but a search of the
> >> Microsoft forums hasn't turned up anything useful and I'm hoping that
> >> someone here has had some experience getting this to work. I've
> >> successfully built a debug version of OpenSSL on Windows and I'm now
> >> trying to use Visual Studio 2008 to debug it. I can see that the .pdb
> >> files have been created in the out32dll.dbg directory following the
> >> build. I then create a Visual Studio "solution" per the VS
> >> instructions for the executable openssl.exe, open the source file
> >> openssl.c and set a breakpoint in the main and select "Start
> >> Debugging" from the Debug menu. Mousing over the breakpoint symbol in
> >> the openssl.c main displays the source file name,line number and
> >> function along with the text "The breakpoint will not currently be
> >> hit. No symbols have been loaded for this document." The breakpoint
> >> is never hit, but the DOS command window opens and I get the initial
> >> OpenSSL> prompt so I know it's alive. However, when I select
> >> "Debug->Windows->Modules" I get a list of the OpenSSL modules,
> >> including openssl.exe, ssleay.dll and libeay.dll and they all show
> >> the "Symbol Status" as "Symbols loaded." and the correct path to the
> >> .pdb appears in the "Symbol File" column.
>
> >>   If anyone has any experience getting this to work I would greatly
> >> appreciate any help you could offer? Feel free to contact me off-list
> >> if you prefer.
>
> >> tia,
>
> >> Bob
>
> > ______________________________________________________________________
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>
> > ______________________________________________________________________
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> > User Support Mailing List                    openssl-us...@openssl.org
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>
> ______________________________________________________________________
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