I don't have enough skills to help you or troubleshoot the mess in your FreeBSD OS
Personally, I always start with basics and then progress into more advanced applications or TCP/IP services such as personal cloud. If I was in your situation, I would redo FreeBSD installation and then go step by step and:
Make sure that the OS is up to date
Make sure that my pkg(s) are up to date
Make sure that my configuration files are correct
Make sure to look at the system logs for critical error messages
Make sure that the basic system utilities and apps work as intended
Then, I try to install some kind of developmental framework for TCP/IP server like Apache to play with.
After I felt comfortable and understood the language of the framework and the functions of httpd server, I'd deploy something to play with and learn from. Tho, I would not open my TCP/IP service port(s) to the outside world, until I was more/less sure that my system is secured and fully functional, at its basic level
I can install almost anything and make it run somehow in FreeBSD. But ..., maybe I'm just lucky - heh
That said, here is my
pkg install run of basic system utility developed by those who know better for someone like I who doesn't know that much:
$ uname -a
FreeBSD fbsd12 12.0-RELEASE-p7 FreeBSD 12.0-RELEASE-p7 GENERIC amd64
pkg install py36-certbot
Updating FreeBSD repository catalogue...
FreeBSD repository is up to date.
All repositories are up to date.
The following 12 package(s) will be affected (of 0 checked):
New packages to be INSTALLED:
py36-certbot: 0.35.1,1
py36-josepy: 1.2.0
py36-acme: 0.35.1,1
py36-requests-toolbelt: 0.8.0
py36-pytz: 2019.1,1
py36-pyrfc3339: 1.1
py36-zope.interface: 4.6.0
py36-zope.component: 4.2.2
py36-zope.event: 4.1.0
py36-parsedatetime: 2.4_1
py36-configobj: 5.0.6_1
py36-configargparse: 0.14.0
Number of packages to be installed: 12
The process will require 17 MiB more space.
6 MiB to be downloaded.
Proceed with this action? [y/N]: y
This port installs the "standalone" client only, which does not use and is not the certbot-auto bootstrap/wrapper script.
The simplest form of usage to obtain certificates is:
# sudo certbot certonly --standalone -d <domain>, [domain2, ... domainN]>
NOTE:
The client requires the ability to bind on TCP port 80 or 443 (depending on the --preferred-challenges option used). If a server is running on that port, it will need to be temporarily stopped so that the standalone server
can listen on that port to complete the challenge authentication process.
For more information on the 'standalone' mode, see: https://certbot.eff.org/docs/using.html#standalone
The certbot plugins to support apache and nginx certificate installation will be made available in the following ports:
* Apache plugin: security/py-certbot-apache
* Nginx plugin: security/py-certbot-nginx
And the cerbot-3.6 run:
certbot-3.6 --dry-run certonly
Saving debug log to /var/log/letsencrypt/letsencrypt.log
How would you like to authenticate with the ACME CA?
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1: Spin up a temporary webserver (standalone)
2: Place files in webroot directory (webroot)
- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
Select the appropriate number [1-2] then [enter] (press 'c' to cancel):
And Yes, I do use certbot-3.6 for Let's Encrypt to maintain and update my httpd, smtpd and imap4 (more/less) secured TCP/IP connectivity