I already asked a similar question, "PE Header requirements", but I'm not really satisfied with it's answer.

I am building an assembler/linker, in Java SE 1.6. I have read about 5 different documentations/specifications about the PE/COFF header and file format, but I'm stuck at a problem:

My generated file is not valid, says Windows: "X is not a valid Win32 application." I'm clueless of what can be wrong; I have double-checked every entry in the PE Header and PE Optional Header, and all seems to be right.
I've got four sections:

• code (RVA 0x1000, File 0x400)
• data (RVA 0x2000, File 0x600)
• import (RVA 0x3000, File 0x800)
• reloc (RVA 0x4000, File 0xA00)

My entrypoint value is at 0x1000 (the beginning of code) and my imagebase is 0x400000. Section alignment is 0x1000 and file alignment is 0x200.

Here is the file (3 kb):

4D 5A 6C 00 01 00 00 00 04 00 11 00 FF FF 03 00 00 01 00 00 00 00 00 00 40 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 70 00 00 00 0E 1F BA 0E 00 B4 09 CD 21 B8 00 4C CD 21 54 68 69 73 20 70 72 6F 67 72 61 6D 20 72 65 71 75 69 72 65 73 20 57 69 6E 33 32 0D 0A 24 00 00 00 00 50 45 00 00 4C 01 04 00 6A C4 4D 69 00 00 00 00 00 00 00 00 E0 00 02 01 0B 01 08 00 00 10 00 00 00 10 00 00 00 00 00 00 00 10 00 00 00 10 00 00 00 20 00 00 00 00 40 00 00 10 00 00 00 02 00 00 04 00 00 00 0D 00 25 00 04 00 00 00 00 00 00 00 04 0A 00 00 00 04 00 00 00 00 00 00 02 00 00 00 00 00 04 00 00 10 01 00 00 00 10 00 00 10 00 00 00 00 00 00 10 00 00 00 00 00 00 00 00 00 00 00 00 30 00 00 00 10 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 40 00 00 00 10 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 2E 63 6F 64 65 00 00 00 00 10 00 00 00 10 00 00 23 00 00 00 00 04 00 00 00 00 00 00 00 00 00 00 00 00 00 00 20 00 00 60 2E 64 61 74 61 00 00 00 00 10 00 00 00 20 00 00 23 00 00 00 00 06 00 00 00 00 00 00 00 00 00 00 00 00 00 00 40 00 00 C0 2E 69 6D 70 6F 72 74 00 00 10 00 00 00 30 00 00 90 00 00 00 00 08 00 00 00 00 00 00 00 00 00 00 00 00 00 00 40 00 00 50 2E 72 65 6C 6F 63 00 00 00 10 00 00 00 40 00 00 04 00 00 00 00 0A 00 00 00 00 00 00 00 00 00 00 00 00 00 00 40 00 00 52 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 68 00 00 00 00 68 0D 20 40 00 68 00 20 40 00 68 00 00 00 00 E8 64 30 40 00 68 00 00 00 00 E8 6C 30 40 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 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00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 54 30 00 00 00 00 00 00 00 00 00 00 3C 30 00 00 64 30 00 00 5C 30 00 00 00 00 00 00 00 00 00 00 47 30 00 00 6C 30 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 75 73 65 72 33 32 2E 64 6C 6C 00 6B 65 72 6E 65 6C 33 32 2E 64 6C 6C 00 74 30 00 00 00 00 00 00 82 30 00 00 00 00 00 00 74 30 00 00 00 00 00 00 82 30 00 00 00 00 00 00 00 00 4D 65 73 73 61 67 65 42 6F 78 41 00 00 00 45 78 69 74 50 72 6F 63 65 73 73 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 74 65 73 74

So: I grabbed a valid PE file (a simple "Hello World" message box application), and started to modify it, with a hex-editor (HxD). I got a lot of different error messages, not the "X is not a valid Win32 application.":

I'm aware that my code content is not "valid" code, but I've tested it out: invalid code gives an Application Crash error.

If the import-section content is invalid in the "Hello World" PE file, it gives me the error "Procedure point cannot be found in [...]", or "Application has failed to start because [..] dll is not found.", or an Application Crash. These errors are all very useful; they all give me some clue what was wrong.

But my PE file, with the error "X is not a valid Win32 application.", drives me insane: What is wrong with my PE file?