Forum Thread: Is the Social Engineering Spearphishing Attack Outdated?

Hi everyone,

Today I attempted OTW's spearphising tutorial as seen here. To summarise I chose to send an email via my gmail account to another gmail account of mine. I chose the fileformat option, meterpreter payload, the Microsoft word RTF MS087-10 exploit, but I got an error message the following:

! Unable to deliver email. Printing exceptions message below, this is most likely due to an illegal attachment. If using GMAIL they inspect PDFs and is most likely getting caught.

Press {return} to view error message.

(552, '5.7.0 This message was blocked because its content presents a potential\n5.7.0 security issue. Please visit\n5.7.0 to review our message\n5.7.0 content and attachment content guidelines. xt1sm9097446wjb.32 - gsmtp')

* SET has finished delivering the emails

I read more guides and they actually recommend the word exploit because its harder to detect. What should I try next? Is there a more useful method now?

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4 Responses

The default spearphishing attack (PDF) showed the same error message.

Is your file .pdf or .pdf.exe? beacuse as google says:

"You can't send or receive the following file types:

.ade, .adp, .bat, .chm, .cmd, .com, .cpl, .exe, .hta, .ins, .isp, .jar, .jse, .lib, .lnk, .mde, .msc, .msp, .mst, .pif, .scr, .sct, .shb, .sys, .vb, .vbe, .vbs, .vxd, .wsc, .wsf, .wsh"

Try to combine encoded with msfvenom payload with pdf file using metasploit and then send file .pdf. If that doesn't work I suggest you to write your own payload and add it to PDF.

Hi root toor thanks for the reply. I tried to reply earlier than this but kept getting AJAX errors.

I can't see what the filetype is, because I couldn't find the .rtf or .pdf payloads that I made. I checked the /usr/share/SET directory. I couldn't check on the email attachment of course, because it won't send.

If I encode a payload or make my own, would I add it to SET by copying and pasting it into the SET payloads directory and choosing it from the SET menu on the terminal?

Simply use msfvenom, msfconsol to create .pdf file and then send it.

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