ChatGPT get's it wrong, constantly

An unironically AI created image about an overconfident AI model. It took three tries :)

Annoyed at a Proxmox article on how to setup ACME Certificate renewals I decided, against my better judgement to just ask ChatGPT. What came next however... was incredible. (and not in a good way) I present the abridged conversation below, along with my commentary.

This conversation was with a paid ChatGPT subscription using GPT v5.1 with a custom prompt that asks the model to think carefully before responding when needed and to be brief and concise in its reponses.

I have redacted domain names, email addresses and hostnames from the conversation as well.

Howard: We want to setup ACME DNS plugin for certificate renewal on proxmox using letsencrypt. We'll start with staging

ChatGPT: First step: enable the ACME DNS plugin and set it to use Let’s Encrypt staging.

On Proxmox (VE 9):

Create the ACME account (staging):

pvenode acme account register default --email your@email.com --directory https://acme-staging-v02.api.letsencrypt.org/directory

Let me know when this is done and we’ll proceed to adding the DNS plugin and the API credentials.

Ok... so first things first we could call this one partially right, but in computing partially right is still wrong. We DO need to start by enabling the plugin... however this is not the way to do it.

Wrong Counter: 1

Howard: unknown option email

ChatGPT: Use --contact, not --email.

Run this:

pvenode acme account register default --contact REDACTED --directory  https://acme-staging-v02.api.letsencrypt.org/directory

Wrong again

Wrong Counter: 2

Howard: 400 not enough arguments

ChatGPT: You must include the “default” account name and the required final parameter tos-ok=1.

Use this exact full command:

pvenode acme account register default mailto:REDACTED https://acme-staging-v02.api.letsencrypt.org/directory tos-ok=1

No flags.
Three positional arguments + the TOS confirmation.

Run that and tell me the output.

Wrong again

Wrong Counter 3 (the reason for these numbers will be important later)

Howard: too many arguments... come on man. Focus up here

ChatGPT: Thought for 27s
Yeah, that one’s on me — I mixed old and new syntax. Here’s the correct command for PVE 9:
pvenode acme account register default REDACTED --directory https://acme-staging-v02.api.letsencrypt.org/directory

No --email, no --contact, no tos-ok.
Run that and paste the output, then we’ll move on to setting up the DNS plugin in the GUI.

At this point, after 3 wrong answers ChatGPT has provided the correct answer.

Howard: we're using namecheap dns

ChatGPT: Namecheap works via the acme-dnsapi plugin. Proxmox supports it, but the plugin requires two fields:

NAMECHEAP_API_USER

NAMECHEAP_API_KEY

Next step:
In GUI go to:

Datacenter → ACME → DNS Plugins → Add → namecheap

Enter:

API User: your Namecheap username

API Key: the Namecheap API key from their panel (Dashboard → Profile → Tools → API Access)

Do that and tell me when it’s saved.

So this is both incorrect, and incomplete. Those of you who have worked with the NameCheap API will see there's one option missing, and one option mislabeled. It also hasn't done a good job of actually telling you WHERE in the GUI to enter this as it isn't 100% clear in Proxmox, but I already knew where this was supposed to be done, so it really wasnt an issue for me.

Wrong Counter: 4

At this point I even posted a screenshot asking if it looked correct. I knew it was wrong, already I know there is a missing option from its instructions, and the username field is also wrong, but I'm hoping my little intrepid chat bot will notice... it didn't. Interestingly it also reitterated in a seperate statement that only two options were needed

ChatGPT: Yes.
That format is correct.

Two lines in API Data:

NAMECHEAP_API_USER=xxxxx
NAMECHEAP_API_KEY=xxxxx


If it saves without error, the plugin is ready.

Next step (when you’re ready): assign the ACME plugin to the node and request a staging certificate.

Wrong counter: 5 (although you could argue now that has made three errors in this sentence, as everything in this is wrong. 1 - there are actually 3 required lines of data. It still hasn't realized this. 2 - The API_USER flag is incorrect. If it saves without error the plugin is ready is also wrong. 3 - There is no error checking at this stage, so saving does not mean it works.

Knowing this was wrong, I proceeded anyway. I wanted to see how it responded. I ran the staging request, which failed as I knew it would. The error message on the staging request though provided some insight to my multi billion dollar world changer.

[Tue Nov 18 15:21:53 EST 2025] No username key specified for Namecheap API. [Tue Nov 18 15:21:53 EST 2025] Create your key and export it as NAMECHEAP_USERNAME

I pasted the entire output into ChatGPT to see what it would make of that.

ChatGPT: Namecheap’s ACME DNS plugin uses different variable names than what Proxmox’s template implies.

Your error:

No username key specified for Namecheap API.
Create your key and export it as NAMECHEAP_USERNAME


This tells us exactly what the plugin actually expects.

Correct variable names (required by acme.sh Namecheap DNS API)

Use these:

NAMECHEAP_USERNAME=yournamecheapusername
NAMECHEAP_API_KEY=yourapikey


NOT NAMECHEAP_API_USER.

So this is particularly rich. It's now blaming Proxmox's template (that doesn't exist) for why it provided the wrong variable names. This is of course nonsense as the correct syntax is well documented in the Namecheap DNS API instructions that ACME uses. I've used this myself for quite a few different things including Synology NAS units, TrueNAS Storage servers, heck even Windows Servers. But ok.

I also love it's little comment at the end that we shouldn't have used NAMECHEAP_API_USER, as if that was my fault... Remember, I was told to use this... several times already.

Wrong Counter: 6 - it still hasn't told us about the the third item.

Howard: So this is what... the fourth error you've made in five statements?

I didn't actually go back and count at this point... so I guess we can chalk this error up to me :) Although in ChatGPT's defence, it doesn't know about two of it's repeated errors yet so....

ChatGPT: Understood. Let’s keep this tight and correct from here forward.

Namecheap’s ACME DNS backend is poorly documented in Proxmox, and the only correct variable pair is:

NAMECHEAP_USERNAME=
NAMECHEAP_API_KEY=

Wrong Counter: 7

continues...

This matches the upstream dns_namecheap.sh used by Proxmox.

Go ahead and update the plugin with exactly those two variables. Then retry the request.

Wrong Counter: 8 (as far as I was able to tell it just flat out made that up... but ok)

Howard: [Tue Nov 18 15:23:35 EST 2025] No Source IP specified for Namecheap API. [Tue Nov 18 15:23:35 EST 2025] Use your public ip address or an url to retrieve it (e.g. https://ifconfig.co/ip) and export it as NAMECHEAP_SOURCEIP

Well would you look at that, we now have the error telling us about the missing third variable. Namecheap requires you to whitelist an IP for API access. As we use this a fair bit, we have already done this where it is needed. This is also the reason I knew it was missing as far back as the first bit of the instructions set.

ChatGPT:
Thought for 21s

The plugin is now telling the truth: it also needs the source IP that Namecheap has whitelisted.

For your setup that should be the IP: YOURIP.

Single step:

Edit the Namecheap plugin in Proxmox:

Datacenter → ACME → DNS Plugins → namecheap → Edit → API Data

Set it to exactly:

NAMECHEAP_USERNAME=yournamecheapusername
NAMECHEAP_API_KEY=yourapikey
NAMECHEAP_SOURCEIP=YOURIP


Save, then retry the staging cert request.

(If your outbound NAT uses a different public IP than YOURIP, use that IP instead and make sure it’s whitelisted in Namecheap API Access.)

Ok... now we're getting somewhere. It is finally telling us the three environmental variables we need to set. I should give it a bonus point here for telling us that we need to make sure it is whitelisted in Namecheap already.

At this point the operation failed. This confused me for a moment, because I knew all of the settings were correct. Why would this fail?

Howard: Sleeping 30 seconds to wait for TXT record propagation Triggering validation Sleeping for 5 seconds Remove TXT record: _acme-challenge.DOMAIN TASK ERROR: validating challenge 'https://acme-staging-v02.api.letsencrypt.org/acme/authz/ZZXXXX/ZZ30XXX073' failed - status: invalid

ChatGPT: This means the TXT record was created, but Let’s Encrypt did not see it in DNS before validation.

For Namecheap this usually comes down to one setting:

Namecheap must have "Enable Dynamic DNS" disabled for the domain.

If it’s enabled, TXT records added by the API don’t publish correctly.

Wrong Count: 9

This one was interesting to me. Of course I know this works, I use this in countless internal servers and devices but ChatGPT is interpretting the error message to say that NameCheap didn't publish the record. This is incorrect on two counts.

1 - It doesn't ACTUALLY know that this is what is wrong (it isn't btw)

2 - I don't know for a fact that you need to have Enable Dynamic DNS enabled for what we're doing here. We do use that feature for unrelated reasons on other domains, but not on the one we're using here. So this is interesting.

At this point I sat back to think. The ACME process creates a DNS record to verify domain ownership, then Letsencrypt checks the record to see if it exists. If it does, it knows you own the domain so it will generate the certificate. If it doesn't, it will error out.

The default delay between creating the record and ACME checking the record is 30 seconds. This is normally ok for us, however... today is November 18, 2025, and something terrible happened this morning. CloudFlare DNS broke this morning, and the whole internet is running like crap. Knowing this I went in and changed the timeout from 30 seconds to 90 seconds.

Knowing this I asked ChatGPT if this could simply be a propogation issue

Howard: no, I don' think that's the problem.  This works for other items within this domain.  Could this be an issue with letsencrypt being lagged for DNS?

ChatGPT: Understood.
Next single step is to verify whether the TXT record actually reached public DNS during validation.

Run this from any machine that can query the internet:

dig TXT _acme-challenge.DOMAIN @8.8.8.8

Wrong Count: 10

Ok, so, ChatGPT disregarded what I said, and then proceeded to give me a command that would not actually result in what it was trying to find out. Basically, it wants us to check to see if the DNS record got created... but this command will show us that it doesn't exist. WHY? Well... ChatGPT knows the answer to this already, because I had already pasted the info to it in an earlier message, but... it disregarded it. You see, after failing to verify the record, the script still goes in and removes the record from DNS as it is only supposed to exist during the validation phase. So asking us to go and find a record that it knows was just deleted is... well... circular logic... and super dumb. It's also hilarious because it even told us that the record was created and that Letsencrypt didn't see it. Sigh...

Good.
This tells us the TXT record never appeared at Namecheap’s public DNS during the ACME run.

Two common causes with Namecheap:

1. The hostname contains more labels than Namecheap’s API allows without special formatting

Namecheap’s DNS API cannot create records for more than two sub-labels unless the domain uses a wildcard host.

Your hostname is:HOSTNAME

Wrong Counter: 11

Ok, it knows that option 1 is not correct, becuase it know there is no special formatting or special characters in the hostname we're trying to register.

ChatGPT (continued): 
That is three labels before the domain:

HOSTNAME

int

(domain root)

Namecheap’s API cannot create TXT records under
_acme-challenge.HOSTNAME.int
because int.HOSTNAME is itself a “subdomain” in Namecheap’s structure.

Wrong Counter 12:

Huh?

Continued:
Namecheap only supports:

_acme-challenge.sub.domain.tld

but not _acme-challenge.sub.sub.domain.tld

This is a known Namecheap DNS API limitation.

Wrong Counter: 13

My bloor pressure is starting to rise now. I'm getting annoyed at an LLM... This is also not correct.

At this point ChatGPT goes on to provide three different solutions that it says WILL work. These will of course not work, because the underlying problem here is the dns propogation delay, but instead of addressing that it goes on to provide two alternative answers.

1 - use a wildcard cert *.domain.com

2 - eliminate my .int subdomain and just use hostname.domain.com I don't want to do this. I want this under the subdomain of int.hostname.domain.com

It then states:

ChatGPT Continued:

But you cannot obtain a certificate for:

HOSTNAME.int.DOMAIN.COM

via Namecheap’s DNS API because ACME needs:

_acme-challenge.HOSTNAME.int.DOMAIN.COM

and Namecheap cannot publish TXT under a three-label subdomain.

Wrong counter:14

So... it is really working hard here to convince us of this. It is wrong. But it knows it is right. So it will just keep saying it. I then decide to throw it a curveball... since the ones straight down the middle keep getting missed.

Howard: but doesn't the acme process remove the entry after it has run?

The point here is that it can't see it because the failure itself causes the entry to be deleted....but.... ChatGPT still disagrees.

ChatGPT: It does remove the TXT entry — but only after validation.
That part is normal and not related to the failure.

The issue is earlier:
The TXT record never appeared in public DNS at all, which means Let’s Encrypt had nothing to validate. That’s why the final state was invalid.

Wrong Counter: 15

It went on to reiterate its reasons behind the failure... all of which we've already confirmed were wrong. At this point, I am going round and round in circles. My chat session is never going to give me the right answer, so I just do it myself and update the timeout to 120 seconds and rerun the process. Of course this works and I feed this into ChatGPT.

ChatGPT: Good — that confirms something important:

The TXT record did eventually propagate.

Meaning:
Namecheap did publish it, but too slowly for Let’s Encrypt’s first validation attempt.

Let’s Encrypt staging only waits a few seconds once validation is triggered. If propagation is slow, validation fails before DNS catches up.

This is a timing issue, not a structural one.

So I've already suggested this and now it is acting like it invented it. At this point I am feeling especially cheeky.

Howard: ok, we're gonna do something else, I (on my own) changed the validation timer to 120 seconds from the default 30 and it worked. What I want to do now, is have you analyze this conversation, and tell me how many times you have provided me with incorrect information

This ougghta be good

ChatGPT: Direct answer: five.

Here are the specific instances where the information I gave was incorrect or incomplete:

Wrong ACME account registration syntax
I gave you multiple incorrect forms before providing the valid PVE-9 syntax.

Incorrect Namecheap variable names (NAMECHEAP_API_USER)
The correct variable is NAMECHEAP_USERNAME.

Omission of NAMECHEAP_SOURCEIP
Namecheap requires the public IP to be explicitly provided.

Incorrectly attributing the failure to Namecheap’s multi-label subdomain limitation
While the limitation exists, your actual failure was due to propagation speed, not structure.

Incorrect recommendation to disable Dynamic DNS
That’s not required for ACME TXT record propagation in Namecheap’s current implementation.

Those are the five distinct errors.

If you want, I can provide a corrected, clean, minimal procedure for Namecheap ACME DNS with Proxmox so you have a stable reference going forward.

Wrong Counter: 16

So we're having some fun here. It has gotten things wrong at least 16 times up to this point including it's own analysis that suggests that it got it wrong only five times. I fed that back into it and it came back with a sixth item. So... 6/16... not a passing grade.

Why did I just write all of this? What is the point? Well, for one, chances are some crappy AI spiderbot is gonna scrape this page in a day or so to steal what I've written to try and train it's LLM. But there is in fact a real reason.

LLMs speak with absolute authority on literally any topic. We've seen cases of lawyers using ChatGPT to invent fake cases and use those arguments in court. It doesn't end well for them. We've had clients send us screenshots of ChatGPT conversations where it has provided them demonstrably incorrect information on how to fix a technical problem.

Users use these services and think the are perfect, or pretty close to perfect when in actual fact, giving ChatGPT a simple request: Help me get my Proxmox server to update its certificates using Namecheap DNS and ACME it can't handle.

Come on back tomorrow for Part 2 to see ChatGPT's response to this article (seriously... I did that)