[FuriouslyAdrift]

I just recently had a executive level manager ask if we could get a 100 year cert for our ERP as the hassle of cert management and the massive cost of missing a renewal made it worth it.

He said six figures for the price would be fine. This is an instance where business needs and technology have gotten really out of alignment.

[9dev]

How on earth would that make more sense than properly setting up ACME and forgetting about the problem for the next hundred years?? If your bespoke ERP system is really so hostile toward cert changes, put it behind a proper reverse proxy with modern TLS features and self-sign a certificate for a hundred years, and be done with it.

It'll take about fifteen minutes of time, and executive level won't ever have to concern themselves with something as mundane as TLS certificates again.

[FuriouslyAdrift]

Support contract states we cannot put it behind a proxy. We used to use HAProxy and multiple web server instances, but the support switched to India and they claimed they could no longer undertsand or support that configuration. Since it is a main system for the entire org and the support contract is part of our financial liability and data insurance, the load balancer had to go. This is corporate enterprise IT. Now you know why sysadmins are so grumpy.

[slipperydippery]

Most safety & security dysfunction stories: high level management-tier misaligned incentives, incompetence, and ignorance, overriding the expert advice of mere peons, leading to predictable catastrophes (not to mention, usually, extra costs in the meantime—just hidden ones).

Most solutions: make the peons watch a training video or attend a training session about how they should speak up more.

[9dev]

My condolences:)

[darkwater]

> How on earth would that make more sense than properly setting up ACME and forgetting about the problem for the next hundred years?? If your bespoke ERP system is really so hostile toward cert changes, put it behind a proper reverse proxy with modern TLS features and self-sign a certificate for a hundred years, and be done with it.

I completely agree with you but you would be astonished by how many companies, even small/medium companies that uses recent technologies and are otherwise pretty lean, still think that restarting/redeploying/renewing as less as possible is the best way to go instead of fixing the root issue that makes restarting/redeploying/renewing a pain in the ass.

[moduspol]

I don't know about OP but I've also worked plenty of places where I seem to be the only person who understands TLS.

And not even at the "math" level. I mean, like, how to get them into a Java keystore. Or how to get Apache or nginx to use them. That you need to include the intermediate certificate. How to get multiple SANs instead of a wildcard certificate. How to use certbot (with HTTP requests or DNS verification). How to get your client to trust a custom CA. How to troubleshoot what's wrong from a client.

I think the most rational takeaway is just that it's too difficult for a typical IT guy to understand, and most SMBs that aren't in tech don't have anyone more knowledgeable on staff.

[9dev]

> I think the most rational takeaway is just that it's too difficult for a typical IT guy to understand, and most SMBs that aren't in tech don't have anyone more knowledgeable on staff.

Where would that kind of thinking lead us..? Most medical procedures are too complex for someone untrained to understand. Does that mean clinics should just not offer those procedures anymore, or should they rather make sure to train their physicians appropriately so they’re able to… do their job properly?

[moduspol]

Well I mean there's no inherent requirement that PKI work the way it does. We've mostly just accepted it because it's good enough.

Even if your server admins fully understand TLS, there are still issues like clock skew on clients breaking things, old cipher suites needing to be reviewed / sunset, users clicking past certificate warnings despite training, and the list of (sometimes questionable) globally trusted CAs that the security of the Internet depends upon.

Of course they should do their job properly, but I'm skeptical that we (as software developers) can't come up with something that can more reliably work well.

[FuriouslyAdrift]

Yeah I have one specific enterprise app (the updater service for another piece of software) that will not work unless TLS 1.1 is turned on at the OS level. It doesn't do anything with it, but some hard coded phone-home function in the software must fire up each time it checks for updates (even though it doesn't use TLS for the connection, but unencrypted FTP) or it will hard fail and not even log the failure.

[FuriouslyAdrift]

I have to schedule at least 30 days out on any change or restart for main systems and I may be overruled by ANY manager.

I actually watched for crashes (thank you inventory control department shenanigans) so that I can sneak in changes during a reset.

[9dev]

> […] that restarting/redeploying/renewing as less as possible is the best way to go instead of fixing the root issue that makes restarting/redeploying/renewing a pain in the ass.

I mean… There's a tradeoff to be sure. I also have a list of things that could be solved properly, but can't justify the time expense to doing so compared to repeating the shortcut every so often.

It's like that expensive espresso machine I've been drooling over for years—I can go out and grab a lot of great coffee at a barista shop before the machine would have saved me money.

But in this particular instance, sure; once you factor the operational risk in, proper automation often is a no-brainer.

[zoeysmithe]

Yep this. This is just "we have so much technical debt, our square pegs should fit into all round holes!"

Business culture devaluing security is the root of this and I hope people see the above example of everything that's wrong with how some technology companies operate, and "just throw money at the problem because security in an annoying cost center" is super bad leadership. I'm going to guess this guy also have an MFA exception on his account and a 7 character password because "it just works! It just makes sense, nerds!" I've worked with these kinds of execs all my career and they are absolutely the problem here.

[FuriouslyAdrift]

IT serves business needs... not the other way around. If anything, cloud services and mobile device access has made securing anything just about impossible.

[Loudergood]

Classic case of business not understanding that it doesn't just need access to the data, it needs secure access to the data.

[FuriouslyAdrift]

That's what insurance and lawyers are for... so sayeth my management that pay me.

[op00to]

Start your own business - nginx proxy in front of ERP where you handle the SSL for them, put $$ in a trust to ensure there's enough money to pay for someone to update the cert.