$ perl -MCrypt::SSLeay -e "print 'OK'"
Can't find 'boot_Crypt__SSLeay' symbol in c:/Perl/site/lib/auto/Crypt/
+SSLeay/SSL
eay.dll
 at -e line 0
Compilation failed in require.
BEGIN failed--compilation aborted.
[download]

That's very strange. I've just downloaded the binary that ppm should have installed and the SSLeay.dll that ships with it definitely exports that symbol:

C:\temp\blib\arch\auto\Crypt\SSLeay>dumpbin /EXPORTS SSLeay.dll
Microsoft (R) COFF/PE Dumper Version 7.00.9466
Copyright (C) Microsoft Corporation.  All rights reserved.


Dump of file SSLeay.dll

File Type: DLL

  Section contains the following exports for SSLeay.dll

    00000000 characteristics
    476CA7C2 time date stamp Sat Dec 22 13:59:30 2007
        0.00 version
           1 ordinal base
           2 number of functions
           2 number of names

    ordinal hint RVA      name

          1    0 00003FD7 _boot_Crypt__SSLeay
          2    1 00003FD7 boot_Crypt__SSLeay

  Summary

        1000 .data
        1000 .rdata
        1000 .reloc
        4000 .text
[download]

You can see quite clearly that boot_Crypt__SSLeay is there.

I can only conclude that either:
1) that's not the binary that was installed;
or
2) another different SSLeay.dll (one that doesn't export that symbol) is being found first.

You could check that 1) is not the problem by downloading the same binary as I did, extracting it to a temporary location, and copying SSLeay.dll across to your C:/Perl/site/lib/auto/Crypt/SSLeay directory. If, having done that, you still get the same error, then you will know for sure that a different SSLeay.dll is being found first.

Cheers,
Rob