SSL RENEWS EXPIRES

Question asked by Diego Discacciati - 3/4/2025 at 9:55 AM

Unanswered

Holy cow...

SmarterMail Professional Build 9091 on a windows 2019 just moved 2 weeks ago.

I have automatic renewal...

Here is what I see:

certificate expires before the renewal date... WTF???

Why? Anybody had any experience with this, I mean did you see it happening?

Enclosing screen shot I could not believe my eyes.

6 Replies

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Diego Discacciati Replied

3/4/2025 at 11:22 AM

OK, now this is very odd... enclosing picture...

in the certificate tab I have that problem (and on the email of course when I try to connect), however in the automatic certificate tab it seems ok.

There is a JSon file... should I deactivate the ssl, delete the jason file and repopulate the ssl?

I only have a handful of domains so I can do updates in DNS if I have to update the keys.

But also in the bindings. I use Let's encrypt certificates for the binding in IIS for any domainX.com and www.domainX.com on port 443.

In smartermail I set up certicficates requests for the following prefixes only:

autodiscover
imap
mail
pop
smtp
webmail

Anything I am doing wrong?

Kyle Kerst Replied

3/4/2025 at 1:22 PM

Employee Post

I wonder if the mismatch between the renewal date/expiration date is a byproduct of the move perhaps. Maybe you're getting data from both the new and old renewal procedures depending on the hostname you're looking at. I don't recommend deleting the JSON and repopulating it, this could lead to a large number of LE requests going out to renew/request certificates which could lead to you hitting some rate limiting. Can you submit a ticket on this so we can take a closer look please?

Kyle Kerst

Lead Internal Network/System Administrator

SmarterTools Inc.

smartertools.com

Diego Discacciati Replied

3/4/2025 at 4:07 PM

Can't, my subscription is expired, I was on a server 2012, and waited more than a year to get on a server 2019... I was told our old server was not supported anymore so didn't make much sense to renew the subscription... I think it expired in January... and of course... as soon as it expired or shortly after... we got a server 2019... Murphy's law!!!!

Gabriele Maoret - SERSIS Replied

3/5/2025 at 5:42 AM

You got 2019 server in January 2025?

We are already on 2022 by 2 years, and now we are migratig to 2025...

If you want support (sorry if I am a little rough...), you need to stay updated AND pay subscriptions...

Gabriele Maoret - Head of SysAdmins and CISO at SERSIS

Currently manages 7 SmarterMail installations (1 in the cloud for SERSIS which provides services to a few hundred third-party email domains + 6 on-premise for customers who prefer to have their mail server in-house)

Diego Discacciati Replied

3/5/2025 at 6:20 AM

Gabrie'... we have a lousy provider!!!

And we have a complicate set up... so I am grateful we received an updated machine to 2019!!!

It is still an improvement compared to the old 2012R.

Besides, old is not always that bad... I am more of an Apple guy, but I use the latest model with M3 to play with my 8 year old kid and a 2012 machine (taroccata come i nostri vecchi motorini), two actually as I like a back up... for what I do on a daily basis (anche perche' le nuove macchine sono difficili da taroccare, hanno messo tutto insieme sulla scheda madre, componenti registrati, hai bisogno di equipaggiamenti da laboratorio serio per metterci le mani sopra, ma da noi siamo piu' rudimentali artigiani!!!)

:-)

We'll hopefully make it to the next upgrade... switching to 2025 in the year 2030... with some luck... right behind you... well from a distance right behind you...

(I wrote in Italian all questionable things that people should not do, bad examples not to follow so... nobody is missing anything important in the conversation!!!)

Gabriele Maoret - SERSIS Replied

3/5/2025 at 9:10 AM

@Diego Discacciati : 🤣🤣🤣

Grandissimo!

Ciao!

Gabriele Maoret - Head of SysAdmins and CISO at SERSIS

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