Smoothwall MITM and Admin UI certs not working after migration to new on-premises box

[DeGrimmy]

Hi all,

 

I can't work out if I'm missing something obvious or not, hoping that someone else may have an answer...

 

We've just migrated from an older generation S9 box to a newer generation S9 box in the hopes that it doesn't lock up every few weeks - Apparently the older box was showing temperatures of 80 degrees plus! The new box is in as of yesterday afternoon, but we've been having the odd certificate issue since on BYOD devices and logging into the HTTPS admin UI. The root CA certificate we generated last summer is still valid, as is all the certs underneath it.

 

Smoothwall support mentioned something about exporting the certificates, but then I'm not sure what I'm doing with it after that. I've tried re-importing them back into Smoothwall, which appears to be successful, but that hasn't solved the issue. I have created a new certificate under the root CA and assigned those as the Admin UI and User-facing HTTPS services certs in the User Interface section, and while this appears to have got rid of constant insecure connection warnings when navigating through the admin panel, Chrome suggests that it is still not secure at one end of the address bar.

 

In my very limited testing on a mobile phone and a laptop, it looks like the BYOD MITM certificate is not working on the phone, but it's fine on the Windows laptop. People using their pre-configured BYOD devices have also mentioned that they're getting the insecure connection warnings.

 

I feel like such an idiot when it comes to certificates - Is there a way I can fix this without having to completely re-create the root CA and starting again with all the staff and students' BYOD devices?

[ITGuyNW]

Hi

 

I'm also seeing similar issues (I wonder if its a maiden update thing? also interesting you mention S9 box temps.... I'm getting the same!!!)

 

We have laptops that are off domain but connect via the Smoothwall SSL login page when brought into school. However it seems some have forgotten the certs (or behaves that way). I have looked and some mention certs being generated near the end of May, possible when an update was performed? I wonder if a recent update has messed with certs?

 

Anyway, I'm getting the same as you. Some devices are fine, others aren't. I'm also getting the "not secure" logo next to the address bar, even though everything else seems fine.

 

Wondering if its a dodgy update..

[tom_newton]

Not seeing anything broad enough that it would suggest so - I will keep an eye on things

[ITGuyNW]

Thanks Tom

 

Issue has only started since the 26th May, which was half term which is likely when I last pushed an update (we're on maiden 29)

 

We've made no changes to certs and they're in date until October 2025. 

 

I've also created a ticket, number 602283

 

 

Edited June 16, 2025 by ITGuyNW

[tom_newton]

I will get that escalated - in case it is something more rotten!

[DeGrimmy]

A slight update to this thread - The MITM issue is resolved, I think I cleared cached certificates in Guardian > HTTPS Inspection > Settings.

 

We've moved to the new S9 box as mentioned in the original post, although this hasn't resolved the lockup/reboot issues with Smoothwall. After 40 emails back and forth, we've been told this morning that it's a known issue with Maiden and the dev team is working on it. Unfortunately, since we've moved to the new box, we can no longer go back to the Leeds restore point we made before we originally updated to Maiden, so we're stuck with it now.

 

Lockups and restarts have been getting more frequent - It was once every two weeks, then once a week, and now it feels like it's almost daily.

 

If anyone reading this is still on Leeds and is thinking about updating to Maiden in the summer, my advice would be don't!

[matt_shakespeare]

@DeGrimmy What you support ticket number please? I would like to look into your support case and to get one of our developers to look into your box if possible.

 

We only have three open support tickets regarding lockups. We also have a large customer based running Maiden with no issues so I would like to understand your issue in more detail and get to a resolution as quickly as possible.

[3s-gtech]

I have a self-built HP server running Maiden on bare metal, it's working nicely. Another ancient Dell S8 we have, which is dying, is stable once it's booted.

[DeGrimmy]

3 hours ago, matt_shakespeare said:

@DeGrimmy What you support ticket number please? I would like to look into your support case and to get one of our developers to look into your box if possible.

 

We only have three open support tickets regarding lockups. We also have a large customer based running Maiden with no issues so I would like to understand your issue in more detail and get to a resolution as quickly as possible.

Hi Matt, thanks for replying. My ticket number is 597086, Alex has made a few changes this morning and I believe the dev team have been investigating on our box today.