I have a lot of customers that use Thunderbird, Outlook, iPhone, etc to access their mail.  All of these scream if the certificate is expired.

I'm not having any problems per se.  I use a three step process with LetsEncrypt, openssl, and keytool.  Everything functions fine.  LetsEncrypt has a command that you run as a cron job that will renew the certs automatically usually when they are 2 months into a 3-month expiration cycle.  It runs daily.  But it only triggers the cert renewals when it decides it's close enough to expiration.  I'm just worried about the cert auto-renewing, but in the process invalidating the keystore files I'm using for imap and smtp.  I agree that the process of running openssl and keytool is trivial.  But I just need to figure out a way to auto-run them as well if I discover that LetsEncrypt has auto-refreshed the certs and thereby invalidated the keystore.  The 'best' answer would be that the keystore will continue to work with a refreshed cert. But I guess I'll need to wait a couple of months until LetsEncrypt does its thing and I find out if everything dies.  Not a big deal.  Just trying to get ahead of the problem.

Thanks.

Jerry

On 5/12/2020 3:46 PM, David Matthews wrote:
David,

That's good info in the article.  But my question was does the
keytool-generated file expire as well when the underlying cert
(LetsEncrypt or self-signed cert) expires?  Or can I simply renew the
underlying cert without having to re-execute the keytool step each time
the cert auto-renews?

Short answer - I don't know.

But a couple of thoughts:-

1) That keytool command completes as you snap your fingers, it's not an 
intensive thing.

2)LetsEncrypt for https, I totally get (and use it myself); you do not want 
people having to ignore browser warnings to see your web site. I don't see it 
as an issue with imaps though. Dovecot is another imap server and depending on 
which version/distro you use, for imaps it comes with a certificate or offers a 
script to create one.

Seems to me that using keytool is just the equivalent for James - I guess you 
could also use openssl, which dovecot uses. I just checked that and saw the 
cert expires after 365 days, so I've certainly run on an out of date cert at 
times even if I'm not doing it now. :-)

Do I care? No, my webmail program doesn't check the cert for validity - it runs 
on the same machine as dovecot so that is hardly a serious issue -  I just want 
the encryption. I'm pretty sure there's no problem with sylpheed either, 
although it's a good while since I used it. May be things like thunderbird 
check cert validity? Not sure.

How many people are going to access their email on your server? It's not like a 
web page which is for the whole world.

--
David Matthews
m...@dmatthews.org


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