Testing Office 365 SMTP relay

In order to test Office 365 SMTP relay you will have to create a user with an Exchange online license. After the email is activated for this user you can test this user for relay with the following powershell.

First connect to Microsoft Online service with this user that you’ll be using for relaying.

$msolcred = Get-Credential

Next edit the following powershell with the user’s e-mail and the recipient’s too

Send-MailMessage -From Office365User@Domain.com -To info@moh10ly.com -Subject “Test Email” -Body “Test SMTP Relay Service” -SmtpServer smtp.office365.com -Credential $msolcred -UseSsl -Port 587



This test is known as Client SMTP submission you can also use a different method for multiple devices where you can configure them all to point to a single server (IIS) in a method known as IIS for relay with Office 365 however, all the methods what involve office 365 (Only) for relay will require a user with Exchange online license assigned to it.



The use of this command is not recommended for security reasons in particular for not supporting the modern protocols. use it on your own risk and make sure the user assigned to this service has no privilege’s or not any Office 365 feature admin or power user.

Securing and Testing your Exchange Server with Pfsense HAProxy

– Using the CVE-2021-26855 Payload

After the recent vulnerabilities that hit Exchange Servers On-premises I found sometime to install KaliLinux and try to check what kind of information would I get from the patched servers.

I downloaded the payloads and tried to run it against couple of clients that I have patched the servers for luckily no authentication was made.


– Using Nikto scanner

By using Nikto command from Kali Linux I could see what  Information could Exchange expose using

The command line is nikto –h mail.domain.com and the result of the scan would be exposing the Server’s name, local IP address, OWA Version,  ASP Net platform and version.


Since I have my Exchange Server published via HAProxy 1.8 on Pfsense then I had to tweak HAProxy to strengthen the ciphers, make sure that HSTS is in place and deny the headers that expose the server’s sensitive information.

The result is pretty good as it also has affected the server’s score on ssllabs.com

Prior to the tweaking  my owa scan result on SSL Labs would get an A


– Pfsense’s HAProxy Settings before

Before upgrading Pfsense to the latest version HAProxy was on 1.6 and the ssl/tls settings were also different as they were setup through the Advanced SSL options on the frontend however, now this is no longer supported and you’ll have to remove that and set it up on the “Global Advanced pass thru” in the General setting page.

ssl-default-bind-options ssl-min-ver TLSv1.2

tune.ssl.default-dh-param 2048



Right after you save this, you will still need to change another settings on the Frontend to protect your server’s information from being exposed.

In the HAProxy settings Go to Frontend > Scroll down all the way to “Advanced pass thru” and paste the following:


# Remove headers that expose security-sensitive information.

rspadd X-Frame-Options:\ SAMEORIGIN
rspidel X-FeServer:.*$
rspidel ^Server:.*$
rspidel ^X-Powered-By:.*$
rspidel ^X-AspNet-Version:.*$
rspidel X-WsSecurity-Enabled:.*$
rspidel X-WsSecurity-For:.*$
rspidel X-OAuth-Enabled:.*$
rspadd X-Xss-Protection:\ 1;\ mode=block
rspadd Strict-Transport-Security:\ max-age=31536000;includeSubDomains;preload
rspadd Referrer-Policy:\ no-referrer-when-downgrade
rspidel Request-Id:.*$
rspidel X-RequestId:.*$
rspadd X-Content-Type-Options:\ nosniff

In the below result, I have got almost everything protected well except for the OWA version which can be a bit problematic. In the next article I am going to try and mitigate this so the server can be protected in the expected manner.



– The Result

Now the server is showing a totally different result and the Nikto scan is not revealing anything anymore.




The reason why I got B on security headers is due to the fact that Content-Security-Policy header will malfunction the ECP and OWA Login pages. Permission Policy is new feature and I couldn’t find anything about it on HAProxy.


I hope this helps






Exchange Server backdoor investigation tools

The Story

After the disastrous exploit that was found in Microsoft Exchange Servers lots of corporations started immediately patching their servers with the latest Cumulative update and Security patches. The question is would those patches be enough if the server is already hacked or have a backdoor installed already?


What are those 0-day exploits ?

The vulnerabilities recently being exploited were CVE-2021-26855, CVE-2021-26857, CVE-2021-26858, and CVE-2021-27065 which are part of alleged “State-sponsored Chinese group” according to Microsoft.

Let’s get into details of those exploits one by one:

CVE-2021-26855 is a server-side request forgery (SSRF) vulnerability in Exchange which allowed the attacker to send arbitrary HTTP requests and authenticate as the Exchange server.

CVE-2021-26857 is an insecure deserialization vulnerability in the Unified Messaging service. Insecure deserialization is where untrusted user-controllable data is deserialized by a program. Exploiting this vulnerability gave HAFNIUM the ability to run code as SYSTEM on the Exchange server. This requires administrator permission or another vulnerability to exploit.

CVE-2021-26858 is a post-authentication arbitrary file write vulnerability in Exchange. If HAFNIUM could authenticate with the Exchange server then they could use this vulnerability to write a file to any path on the server. They could authenticate by exploiting the CVE-2021-26855 SSRF vulnerability or by compromising a legitimate admin’s credentials.

CVE-2021-27065 is a post-authentication arbitrary file write vulnerability in Exchange. If HAFNIUM could authenticate with the Exchange server then they could use this vulnerability to write a file to any path on the server. They could authenticate by exploiting the CVE-2021-26855 SSRF vulnerability or by compromising a legitimate admin’s credentials.

How to proceed ?

Microsoft released couple of tools that could diagnose your servers and check if you already have been infected with a backdoor or any of these nasty malware and also remove those infected files or clean them and ask you for a restart if it’s required.


  1. MSERT (Microsoft Safety Scanner) detects web shells, Download here .
  2. Health Checker (Scans your server for any vulnerabilities and whether you have updated Server CU and installed patches). Download here
  3. Exchange WebShell Detection (A simple PowerShell that is fast and checks if your IIS or Exchange directory has been exploited). Download here
  4. Scan your exchange server for proxy logon:
  5. Microsoft very recently created a mitigation tool for Exchange on-premises that would rewrite url for the infected servers and recover the files that were changed. You can download the tools from this github link.


    Copy the Test-ProxyLogon code into Notepad
    Save As “Test-ProxyLogon.ps1” with the quotes in your C:\Temp folder
    Run in Exchange Management Shell: .\Test-ProxyLogon.ps1 -OutPath C:\Temp

Scan Result

Scan result should show you the following if your servers has been exploited already.

This will remove the infections and asks for a restart.