I front all my honeypots with the IIS landing page precisely because it attracts black hat jagoffs.
Nothing makes me happier than knowing I've wasted hours of their time chasing their own tails.
themafia•Jun 17, 2026
Noise is a really underrated security layer.
YeahThisIsMe•Jun 17, 2026
That's just security by obscurity, which is rated pretty appropriately.
close04•Jun 17, 2026
Obscurity is a perfectly adequate layer of security. It shouldn't be the only layer but those who argue against adding it heard at some point "security through obscurity is not security" and never dug deeper.
seethishat•Jun 17, 2026
I agree. Hiding from a grizzly bear is a good strategy. But if that fails, you will need pepper spray and maybe a shotgun.
Bear Defense Plan: Hide, Non-lethal, Lethal.
Alphanymous•Jun 17, 2026
You've said it just like it is, prevention + preparation.
p1necone•Jun 17, 2026
Why stop there? Front the honeypot with a real IIS server, build a matryoshka doll of honeypots and see how far people get.
wil421•Jun 17, 2026
Tell me more…I opened a plex and Nintendo switch port, the scans were out of control. I’d love to screw over port scanner over.
fragmede•Jun 17, 2026
What does shodan.io run?
DaSHacka•Jun 17, 2026
Unless you're honeypotting in the IP range of an established organization, all you're doing is getting bot traffic.
High-tier blackhats focus on big targets, and low-tier ones focus on low-hanging fruits they find off shodan or application 0days they've found.
bitwize•Jun 17, 2026
"Guys, guys, guys, listen, listen, listen. So I'm in this computer, right? So I'm lookin' around, lookin' around, throwing commands at it, I don't know where it is or what it does or anything..."
forgetfreeman•Jun 17, 2026
Some ATM in bumsville Idaho spit $700 into the middle of the street.
wildlogic•Jun 17, 2026
joey, is that you!?
stavros•Jun 17, 2026
Where's that from?
bryanrasmussen•Jun 17, 2026
I think it's from hackers, Joey the youngest hacker found the bad guys computers, not sure if it's an accurate quote since it's been years since I saw it.
Sounds like creating an url like aspnet_client/admin.php returning a WebObjects header might be a good hobby
kreyenborgi•Jun 17, 2026
Add in a zip bomb or two?
hstaab•Jun 17, 2026
The tone of this is something else
andai•Jun 17, 2026
Several times, I wondered if Claude wrote it.
Stitch4223•Jun 17, 2026
One confusing part is that the blue screen is not a reference to BSOD but to the IIS default page with the blue squares. That’s probably jargon.
The article lists all the tricks I’ve collected over the years doing pentesting and then some, with great tool references. The signal to noise ratio is very high and there’s little “here’s why” filler which instead might just be someone’s way of storytelling. The article drones on, but with actual content as there is a lot to tell. It’s even light on features like trace.axd, but does mention them and their purposes.
I found it an entertaining overview of taking apart unassuming IIS servers and the point of “Recon harder. ” is made very well :)
Edit: s/boring/unassuming + added point was made very well
0x1d7•Jun 17, 2026
Yes, it's jargon. Blue screen is that default page. Yellow screen of death is another one, referring to when ASP.NET throws an exception and you have detailed exceptions turned on (which for public sites, you shouldn't).
Tiberium•Jun 17, 2026
It did, this article is clearly LLM-written/edited
merpkz•Jun 17, 2026
"This is the brute-force fallback when the smart approaches fail, and honestly, it works more often than you’d expect."
Found the LLM generated part.
suslik•Jun 17, 2026
Honestly, given how much claude-based prose I was recently reading, I am worried I will soon begin to write in this style naturally.
Would be a feat on its own to get Claude to write on a topic like this.
andai•Jun 17, 2026
I do think there was a lot of human effort involved. The llm-isms (whether human or machine generated!) cheapen the whole thing, which is a shame.
I rather read bad awkward human writing than LLM generated paragraph number 9 billion.
kitd•Jun 17, 2026
Get Claude to fix IIS, or is that not allowed any more?
AuthAuth•Jun 17, 2026
Ah webpage formatting cooked but otherwise a fun read
sytelus•Jun 17, 2026
This is extremely well done design (at least on full desktop browsers). Amazing content as well.
mopsi•Jun 17, 2026
"Amazing" is a little generous for script kiddie stuff from the early 2000s.
The author has yet to learn the extent to which civilization depends on people not being cunts to one another for no good reason.
caspper69•Jun 17, 2026
Ah yes, the lulz, the great American pastime.
deadbabe•Jun 17, 2026
Civilization has a way of dealing with these individuals: prison.
dakolli•Jun 17, 2026
There's like 90,000 computer fraud reports sent to the federal government every year and about 400 prosecutions total. Most of those are concentrated in whatever niche abuse category the government is focused on at the time (right now, crypto/phishing/ransomware).
note: Don't take this as your cue to start messing around with black hat. Don't become the guy trying to explain to your cell mate who's doing 50 years for a violent crimes what a unauthenticated supabase table is and why you deleted it.
BalinKing•Jun 17, 2026
The lead says "how I approach IIS targets during bug bounty" (emphasis mine), so (assuming the author is being truthful) I'm guessing the tone of the title is just for fun.
aix1•Jun 17, 2026
> This is extremely well done design (at least on full desktop browsers).
I can't tell if you're being sarcastic, but on my full desktop browser the side bar overlaps the main panel, putting text on top of other text.
P.S. Other than this, I do like the presentation.
Shellban•Jun 17, 2026
It looks decent on my 1920x1080p window running on a 4K monitor, but I have overlapping problems on my M1 Macbook.
Group_B•Jun 17, 2026
Would love to see a write yo on nginx!
Lammy•Jun 17, 2026
> IIS has a legacy behavior inherited from the old DOS 8.3 filename convention.
Is this exposing the underlying OS's behavior coupled with the fact that the IIS document root is `C:\Inetpub` by default? Eight-dot-three filenames are enabled by default on the C drive but disabled by default on all other drives on Windows 10/11:
PS> (Get-ItemProperty -Path 'HKLM:\SOFTWARE\Microsoft\Windows NT\CurrentVersion').DisplayVersion
24H2
PS> fsutil 8dot3name query C:
The volume state is: 0 (8dot3 name creation is ENABLED)
The registry state is: 2 (Per volume setting - the default)
Based on the above settings, 8dot3 name creation is ENABLED on "C:"
PS> fsutil 8dot3name query U:
The volume state is: 1 (8dot3 name creation is DISABLED)
The registry state is: 2 (Per volume setting - the default)
Based on the above settings, 8dot3 name creation is DISABLED on "U:"
Terr_•Jun 17, 2026
Tangentially, that reminds me of how a Windows update created c:\inetpub on everybody's non-server computers, to "increase protection" for unspecified reasons.
While that's still pretty vague, it sounds like the issue was that something running as SYSTEM (the page seems to indicate some part of Windows Update) was not correctly checking if inetpub was a symlink or something along those lines. It also links to a script to set ACLs on that directory; presumably that's not possible to do if the directory doesn't exist.
It would probably be better to fix whatever component to not have the link traversal bug, but maybe there's some reason that makes the proper fix infeasible…
Yeah, I regularly speak to folks still running IIS on Windows Server. There are a lot of old apps out there, sadly. Some really, really important ones.
mpyne•Jun 17, 2026
Tons of the Navy's public websites still run on it.
thedougd•Jun 17, 2026
Amazingly some companies like Hyland still ship software that requires IIS. Bonus add are the pages and pages of setup instructions.
robotnikman•Jun 17, 2026
And NCR from my experience.
naturalmovement•Jun 17, 2026
Some banks still use IIS.
Every large company big enough to host an intranet is running IIS somewhere, possibly everywhere. It integrates well with AD so some really complex tasks become stupid simple.
It's seeing less and less usage as the world moves to AWS which is equally stupid because you're tied to one vendor's proprietary products (Amazon) again. Except this time you don't own the hardware.
Public sector IT loves IIS. Check your municipality's tax or property website it's probably got .aspx scripts out the ass.
I've seen it hosting European web apps, public sector if I recall. Lots of bespoke .NET applications out there with SQL Server backends running entire local governments.
Asian countries especially China and Taiwan love IIS and use it to host anything and everything. This is a personal observation.
Sure the world has mostly moved on, but there's tons of legacy code out there that keeps cities and really important organizations humming that runs on IIS and it's never changing.
You think that's bad, there's still places out there running AS/400 stuff on the web, Lotus Notes, and Novell Groupwise (gasp).
forkerenok•Jun 17, 2026
Heyyy what's wrong with novel groupwise?
raesene9•Jun 17, 2026
Well its document management feature didn't used to have Anti-Virus support which caused me a load of problems back in the 90's when Word Macro viruses were common. :P
samplatt•Jun 17, 2026
Way, WAY too many corporate IT divisions.
esikich•Jun 17, 2026
Yes, but typically just internal corporate intraweb stuff from what I've seen.
Back in the early-2000s, I passed the Microsoft certification exam for IIS. I had never even heard of the product (I was told my company had some extra credits at the testing center, I was there taking another exam (Solaris 8 certification), so I figured why not?) I know, MCSE exams were notoriously simple back then, but good god - usually, for every question, 3 of the 4 possible answers didn't even make sense. Anyway, I figured there was no way IIS would last if any dipshit could become "certified" in the product.
bitwize•Jun 17, 2026
That's the value add. Any dipshit can be trained in the Windows server stack, so you can staff your back office with dipshits. For a while in the early 2000s—before the cloud era—Windows was routinely found to have a lower TCO than Linux as a server OS for precisely this reason. More actual deployments too, especially in corporate intranets.
swarnie•Jun 17, 2026
I would say 75% of my webservers are IIS.
Nothing internet facing mind.
forgetfreeman•Jun 17, 2026
but...why?
swarnie•Jun 17, 2026
Really simple.
I read the prerequisites of whatever software im asked to install and do what it says.
I'm not spending the next 3 years of my life trying to make some monitoring platform run on WebLogic i have other jobs to do in 4-8-12 hours.
jabroni_salad•Jun 17, 2026
this is one of the funniest recurring threads on HN. developers finding out what other developers are requiring from their customers. Bonus points for developers finding out that non-cloud solutions still dominate some industries.
forgetfreeman•Jun 17, 2026
Cloud's got nothing to do with it. The thought of standing up a windows box to serve anything other than profiles and user surveillance is simply foreign. Budget webhosting has been a thing for a long time and standing up a *nix VM is also no big deal. In 25 years in industry I never once saw an IIS server used in the wild. shrug
formerly_proven•Jun 17, 2026
The text uses target.com as a placeholder but they actually also have an IIS blue screen: https://knslsd.target.com/
dagaci•Jun 17, 2026
IIS also sits at the back of a many "modern" cloud web type services.
y2244•Jun 17, 2026
Lots and lots
A lot of Microsoft devs know very little Linux historically as they used windows and are comfortable with it
Decreasing due to cloud and Nodejs takeup
catmanjan•Jun 17, 2026
SharePoint uses it extensively
prussian•Jun 17, 2026
I do. As others have replied, Windows Server--including IIS, means you have a domain joined machine, likely with an SPN of HOST/MACHINE.DOMAIN.
Windows services and IIS App Pool Identities log in with an (g)MSA or virtual accounts (NT Service*) and you get a fully working and managed Kerberos experience without having to deal with 30, 60, 90 day password rotations.
Log into your MS SQL Server with Kerberos, log into some other webapp's oauth2 flow with Kerberos, etc, it all just works.
You can use WinRM with your native Windows shell without having to do anything special, and even technically bypass 2FA since that's just how it really works.
Can you do all this on Linux? Yes.
Will it ever be set up correctly? Depends where you work, but based on my experience so far, not likely.
zamalek•Jun 17, 2026
> with Kerberos, etc, it all just works
I worked with customer's AD environments in the 2010's and I remember whiteboards of figuring out customer Kerberos config. "it all just works" is not my recollection of that 3-headed beast lmao.
bartnp•Jun 17, 2026
Yep.
And as an ignoramus: what it is that you are supposed to be using nowadays?
Think in the context of a small company making enterprise .NET (framework) code where Windows is the world, cloud wouldn't fly with the customers, SOAP is still king and your one IT guy is too busy to notice anything happened after 2010. Suppose also that entire software rewrites are impossibly impractical, and that while you'd love to take some security gains, you just don't have the capacity to do configuration deep dives let alone to gamble on something complex like Kubernetes.
chainingsolid•Jun 17, 2026
I've seen it used to deliver 'apps' that 90% of a business's employees use. (EX: Met/Team) in the Metrology (calibration) space.
NooneAtAll3•Jun 17, 2026
what's the deal with left sidebar overlapping the main text?
kahf56•Jun 17, 2026
good entertainment
xmcp123•Jun 17, 2026
Oh man this takes me back.
Once upon a time, all server logs were basically unusable because of the amount of IIS scanners out there. There was a directory traversal that was literally just url encoding “../“ that absolutely lit the internet on fire for many months.
0x1d7•Jun 17, 2026
Those traversal attempts are still very common, right next to the PHP/WordPress script kiddie attacks.
10 Comments
Nothing makes me happier than knowing I've wasted hours of their time chasing their own tails.
Bear Defense Plan: Hide, Non-lethal, Lethal.
High-tier blackhats focus on big targets, and low-tier ones focus on low-hanging fruits they find off shodan or application 0days they've found.
https://memes.getyarn.io/yarn-clip/e9d8176d-e936-4224-a1d1-f...
The article lists all the tricks I’ve collected over the years doing pentesting and then some, with great tool references. The signal to noise ratio is very high and there’s little “here’s why” filler which instead might just be someone’s way of storytelling. The article drones on, but with actual content as there is a lot to tell. It’s even light on features like trace.axd, but does mention them and their purposes.
I found it an entertaining overview of taking apart unassuming IIS servers and the point of “Recon harder. ” is made very well :)
Edit: s/boring/unassuming + added point was made very well
Found the LLM generated part.
https://github.com/blader/humanizer/blob/main/SKILL.md#33-co...
I rather read bad awkward human writing than LLM generated paragraph number 9 billion.
The author has yet to learn the extent to which civilization depends on people not being cunts to one another for no good reason.
note: Don't take this as your cue to start messing around with black hat. Don't become the guy trying to explain to your cell mate who's doing 50 years for a violent crimes what a unauthenticated supabase table is and why you deleted it.
I can't tell if you're being sarcastic, but on my full desktop browser the side bar overlaps the main panel, putting text on top of other text.
P.S. Other than this, I do like the presentation.
Is this exposing the underlying OS's behavior coupled with the fact that the IIS document root is `C:\Inetpub` by default? Eight-dot-three filenames are enabled by default on the C drive but disabled by default on all other drives on Windows 10/11:
https://www.pcworld.com/article/2684062/why-is-windows-11-la...
Everything old is new again https://devblogs.microsoft.com/oldnewthing/20041116-00/?p=37... (2004)
While that's still pretty vague, it sounds like the issue was that something running as SYSTEM (the page seems to indicate some part of Windows Update) was not correctly checking if inetpub was a symlink or something along those lines. It also links to a script to set ACLs on that directory; presumably that's not possible to do if the directory doesn't exist.
It would probably be better to fix whatever component to not have the link traversal bug, but maybe there's some reason that makes the proper fix infeasible…
I got no response to that command on my W10 box, turns out for older (eg LTSC) versions it appears to need:
Every large company big enough to host an intranet is running IIS somewhere, possibly everywhere. It integrates well with AD so some really complex tasks become stupid simple.
It's seeing less and less usage as the world moves to AWS which is equally stupid because you're tied to one vendor's proprietary products (Amazon) again. Except this time you don't own the hardware.
Public sector IT loves IIS. Check your municipality's tax or property website it's probably got .aspx scripts out the ass.
I've seen it hosting European web apps, public sector if I recall. Lots of bespoke .NET applications out there with SQL Server backends running entire local governments.
Asian countries especially China and Taiwan love IIS and use it to host anything and everything. This is a personal observation.
Sure the world has mostly moved on, but there's tons of legacy code out there that keeps cities and really important organizations humming that runs on IIS and it's never changing.
You think that's bad, there's still places out there running AS/400 stuff on the web, Lotus Notes, and Novell Groupwise (gasp).
https://bloomberry.com/data/windows-server/
Nothing internet facing mind.
I read the prerequisites of whatever software im asked to install and do what it says.
I'm not spending the next 3 years of my life trying to make some monitoring platform run on WebLogic i have other jobs to do in 4-8-12 hours.
A lot of Microsoft devs know very little Linux historically as they used windows and are comfortable with it
Decreasing due to cloud and Nodejs takeup
Can you do all this on Linux? Yes. Will it ever be set up correctly? Depends where you work, but based on my experience so far, not likely.
I worked with customer's AD environments in the 2010's and I remember whiteboards of figuring out customer Kerberos config. "it all just works" is not my recollection of that 3-headed beast lmao.
And as an ignoramus: what it is that you are supposed to be using nowadays?
Think in the context of a small company making enterprise .NET (framework) code where Windows is the world, cloud wouldn't fly with the customers, SOAP is still king and your one IT guy is too busy to notice anything happened after 2010. Suppose also that entire software rewrites are impossibly impractical, and that while you'd love to take some security gains, you just don't have the capacity to do configuration deep dives let alone to gamble on something complex like Kubernetes.
Once upon a time, all server logs were basically unusable because of the amount of IIS scanners out there. There was a directory traversal that was literally just url encoding “../“ that absolutely lit the internet on fire for many months.