https://www.cvedetails.com/vendor/26/Microsoft.html

Several vulnerabilities in the Windows operating system and their corresponding attacks are some of the most exploited vulnerabilities

Let's discuss those for a minute:

Vulnerability Description
MS08-067 MS08-067 was a critical patch pushed out to many different Windows revisions due to an SMB flaw. This flaw made it extremely easy to infiltrate a Windows host. It was so efficient that the Conficker worm was using it to infect every vulnerable host it came across. Even Stuxnet took advantage of this vulnerability.
Eternal Blue MS17-010 is an exploit leaked in the Shadow Brokers dump from the NSA. This exploit was most notably used in the WannaCry ransomware and NotPetya cyber attacks. This attack took advantage of a flaw in the SMB v1 protocol allowing for code execution. EternalBlue is believed to have infected upwards of 200,000 hosts just in 2017 and is still a common way to find access into a vulnerable Windows host.
PrintNightmare A remote code execution vulnerability in the Windows Print Spooler. With valid credentials for that host or a low privilege shell, you can install a printer, add a driver that runs for you, and grants you system-level access to the host. This vulnerability has been ravaging companies through 2021. 0xdf wrote an awesome post on it here.
BlueKeep CVE 2019-0708 is a vulnerability in Microsoft's RDP protocol that allows for Remote Code Execution. This vulnerability took advantage of a miss-called channel to gain code execution, affecting every Windows revision from Windows 2000 to Server 2008 R2.
Sigred CVE 2020-1350 utilized a flaw in how DNS reads SIG resource records. It is a bit more complicated than the other exploits on this list, but if done correctly, it will give the attacker Domain Admin privileges since it will affect the domain's DNS server which is commonly the primary Domain Controller.
SeriousSam CVE 2021-36934 exploits an issue with the way Windows handles permission on the C:\\Windows\\system32\\config folder. Before fixing the issue, non-elevated users have access to the SAM database, among other files. This is not a huge issue since the files can't be accessed while in use by the pc, but this gets dangerous when looking at volume shadow copy backups. These same privilege mistakes exist on the backup files as well, allowing an attacker to read the SAM database, dumping credentials.
Zerologon CVE 2020-1472 is a critical vulnerability that exploits a cryptographic flaw in Microsoft’s Active Directory Netlogon Remote Protocol (MS-NRPC). It allows users to log on to servers using NT LAN Manager (NTLM) and even send account changes via the protocol. The attack can be a bit complex, but it is trivial to execute since an attacker would have to make around 256 guesses at a computer account password before finding what they need. This can happen in a matter of a few seconds.

Enumerating Windows & Fingerprinting Methods

Bats, DLLs, & MSI Files, Oh My!

When it comes to creating payloads for Windows hosts, we have plenty of options to choose from. DLLs, batch files, MSI packages, and even PowerShell scripts are some of the most common methods to use. Each file type can accomplish different things for us, but what they all have in common is that they are executable on a host. Try to keep your delivery mechanism for the payload in mind, as this can determine what type of payload you use.

Payload Types to Consider

Tools, Tactics, and Procedures for Payload Generation, Transfer, and Execution

Below you will find examples of different payload generation methods and ways to transfer our payloads to the victim. We will talk about some of these methods at a high level since our focus is on the payload generation itself and the different ways to acquire a shell on the target.

Payload Generation

We have plenty of good options for dealing with generating payloads to use against Windows hosts. We touched on some of these already in previous sections. For example, the Metasploit-Framework and MSFVenom is a very handy way to generate payloads since it is OS agnostic. The table below lays out some of our options. However, this is not an exhaustive list, and new resources come out daily.

Resource Description
MSFVenom & Metasploit-Framework Source MSF is an extremely versatile tool for any pentester's toolkit. It serves as a way to enumerate hosts, generate payloads, utilize public and custom exploits, and perform post-exploitation actions once on the host. Think of it as a swiss-army knife.
Payloads All The Things Source Here, you can find many different resources and cheat sheets for payload generation and general methodology.
Mythic C2 Framework Source The Mythic C2 framework is an alternative option to Metasploit as a Command and Control Framework and toolbox for unique payload generation.
Nishang Source Nishang is a framework collection of Offensive PowerShell implants and scripts. It includes many utilities that can be useful to any pentester.
Darkarmour Source Darkarmour is a tool to generate and utilize obfuscated binaries for use against Windows hosts.

Payload Transfer and Execution:

Besides the vectors of web-drive-by, phishing emails, or dead drops, Windows hosts can provide us with several other avenues of payload delivery. The list below includes some helpful tools and protocols for use while attempting to drop a payload on a target.