Metasploit Gmail pdf with embedded exe

[parrotface]

Hi
Trying to send an email using sendEmail and Gmail with attached PDF with embedded exe file but gmail fails with "illegal attachment on your message". This used to work, has google now blocked these things as I can't get Social Engineerig Tooolkit to send either.

The PDF file is one I have created and this sends OK.

The exe file is windows notepad.exe which is Not detected by AV's.
This fails using the same Gmail set-up as when sending the pdf only.

Using msf exploit/windows/fileformat/adobe_pdf_embedded_exe to add the exe to the PDF.

Any pointers please

[sickness]

I don't really understand what you sent ... but I think I know what you are trying to do.
If you want to send a malicious .pdf with a payload incorporated in it. Gmail/Yahoo/Msn woun't work, because they have their own scanners when you attach something to an email or download an attachment.
Either you try to encode it really good, either you find another way.

[parrotface]

Thanks for reply I guessed this was the problem thats why I tried notepad.exe as the attachment. I have tried various encoders and even two encoders at the same time with different count values. The problem came to light when I tried running SET which I think used to work. Just wondered if I was missing something.
thanks

I am still having problems trying to send an Email using googlemail with an attached PDF with embedded exe.
I am using sendEmail with just the PDF attached and this works OK.
I have created the exe from metersploit payload and msfencode single and multi times. My AV does not detect it and tested it against Virus Total also clean.
As soon as I try to send Email I get the message "illegal attachment"
I am also having the same problem using SET

I hope this is not classed as a DOUBLE POSTING as I got into trouble once before for double posting. If so I am sorry.
I know this used to work as I have gone back through my old notes. Therefore google has blocked this please can some kind member point me in the right direction or has anyone got a working sample exe file for me to test. Wasted 2 weeks on this now. Many Thanks

edit
Is there another way by not using Gmail

[sickness]

I am still having problems trying to send an Email using googlemail with an attached PDF with embedded exe.
I am using sendEmail with just the PDF attached and this works OK.
I have created the exe from metersploit payload and msfencode single and multi times. My AV does not detect it and tested it against Virus Total also clean.
As soon as I try to send Email I get the message "illegal attachment"
I am also having the same problem using SET

I hope this is not classed as a DOUBLE POSTING as I got into trouble once before for double posting. If so I am sorry.
I know this used to work as I have gone back through my old notes. Therefore google has blocked this please can some kind member point me in the right direction or has anyone got a working sample exe file for me to test. Wasted 2 weeks on this now. Many Thanks

edit
Is there another way by not using Gmail

Google will detect those as viruses stop trying to send them via google or yahoo or msn.

[halfdone]

so what is name of that file you are trying to send. Try not to use sendEmail to send your file, use gmail.com

get a virus friendly email, I dont know any. use open relay smtp servers and you can also spoof senders email. (use sendEmail and ISP smtp server. or something similar.)