TL;DR
We can login anonymously to the WorkShares share on the SMB server, and then get the flag.
Recon
We start with the nmap
nmap -sVC -T4 $target

As we can see, it find 4 open ports:
135/tcp open msrpc Microsoft Windows RPC
139/tcp open netbios-ssn Microsoft Windows netbios-ssn
445/tcp open microsoft-ds?
5985/tcp open http Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
|_http-title: Not Found
|_http-server-header: Microsoft-HTTPAPI/2.0
Service Info: OS: Windows; CPE: cpe:/o:microsoft:windows
the interesting port is 445, which shows us there is an SMB service behind the scences.
Notice there is also an http server on port 5985, I tried to curl to see if there is something interesting, and i got 404 Not Found

Connecting anonymously to SMB and access WorkShares
When trying to connect with smbclient, with wrong creds, it still let us see all the shared folders, using the -L flag.

These are the folders we find:
Sharename Type Comment
--------- ---- -------
ADMIN$ Disk Remote Admin
C$ Disk Default share
IPC$ IPC Remote IPC
WorkShares Disk
Let’s try to connect to those folders anonymously, using the -N flag.
smbclient -N \\\\$target\\WorkShares

as we can see, ADMIN$ and C$ didn’t work, and IPC$ doesn’t show anything interesting.
However, when connect to WorkShares, we can see the folders.
Let’s cd to the folders, and retrieve the files using get.
And we can find the flag inside James.P folder

Flag:5f61c10dffbc77a704d76016a22f1664