Problems creating a cert on Ubuntu running Tomcat

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My domain is:
* (never provided this when I ran the command)

I ran this command:
sudo /usr/local/bin/certbot-auto certonly --apache

It produced this output:
Saving debug log to /var/log/letsencrypt/letsencrypt.log
Could not choose appropriate plugin: The apache plugin is not working; there may be problems with your existing configuration.
The error was: NoInstallationError(‘Cannot find Apache executable apache2ctl’,)
The apache plugin is not working; there may be problems with your existing configuration.
The error was: NoInstallationError(‘Cannot find Apache executable apache2ctl’,)

My web server is (include version):
Tomcat 8.5.47

The operating system my web server runs on is (include version):
Ubuntu 19.10

My hosting provider, if applicable, is:

I can login to a root shell on my machine (yes or no, or I don’t know):

I’m using a control panel to manage my site (no, or provide the name and version of the control panel):

The version of my client is (e.g. output of certbot --version or certbot-auto --version if you’re using Certbot):
certbot 0.40.1

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I’m pretty sure Tomcat isn’t the same as the webserver called Apache. It might be called “Apache Tomcat”, but that’s just the company name. I’m also pretty sure the --apache plugin doesn’t understand a bit of Tomcat.

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Yes, certbot --apache is not suitable for use with Tomcat, unless you want to run a separate Apache web server which proxies connections to your Tomcat server (which may be an appropriate way to go about things).


That said, you have options:

  • Simplest: Use --webroot -w /path/to/your/tomcat/root (instead of --apache)
    Does not require any Tomcat config modifications nor stopping service for cert issuance.
    [Cert replacement requires reload - Initial activation will require TLS config inclusion]
  • Easy: Use --standalone method
    Requires temporary shutdown of Tomcat to spin up a web server and process the cert request.
  • Complicated: Install a dedicated proxy to terminate TLS connections (Apache | NGINX).
    May require moving ports around (firewall forwarding or listening ports)
    Does not require any Tomcat config modifications nor service interruptions [after cut-over].
    [Cert replacement requires proxy reload - Initial activation will require proxy TLS config inclusion]
  • Harder: Use a DNS authentication method.
    Requires DNS service allowing automated updates (API) or manual actions (not recommended)
  • Insane: Write a custom program that integrates seamlessly with your Tomcat implementation.
    Requires in-depth knowledge of ACME client and your Tomcat implementation, etc.

The extra difficulty in these methods is converting the certificates into the format that Tomcat understands and configuring them (what you referred to as “initial activation will require TLS config inclusion”, but also note that the certificate may have to be converted again after each renewal).


Leave it to Tomcat, to make even the ordinary and simple difficult.


There is a PDF document online where it seems somebody made a PowerPoint presentation about implementing Let’s Encrypt on Tomcat. Seems quite straight forward to me:’s%20Encrypt%20Apache%20Tomcat.pdf

(Note: I am not at all familiar with Tomcat…)


Straight forward?
Did I miss something, uses iptables to redirect 80 > 8080 and 443 > 8443.
But what listens on 8080 and 8443?
[I read through it twice]

On the third read, it looks like the secret sauce is mostly the use of:
--webroot --webroot-path “${CATALINA_BASE}/webapps/ROOT"
openssl pkcs12 -export -in [cert] -inkey [key] -certfile [chain] -out [p12file]

Page 39:
Scripting will set you free*
* The actual script has a lot more detail that won’t fit here.

I do applaud him for trying to make a difficult thing simpler, but I think it may still be less than complete (at least for a novice).

Page 39 (last):
Slides available on the ApacheCon2018 web site and at’s%20Encrypt%20Apache%20Tomcat.odp Sample code available in the same directory.


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I agree with both of you! Automating Certbot with Tomcat can be straightforward for someone who’s familiar with all of the underlying technologies, and we’ve seen on this forum that it’s often a significant challenge for someone who’s trying to rely only on built-in Certbot functionality.

Just a question for clarity please. Ubuntu has a package/port called “tomcat-with-ssl”. The description says:

  • "Apache Tomcat with SSL activated and managed by Certbot.

  • Intended to use as a part to install Apache Tomcat with SSL enabled and the required certificate automatically managed by certbot (Lets Encrypt) including automatic renewals.

  • Note: currently if a renewal occurs tomcat will be restarted without warning.

So my question: Did you install tomcat from source, or a package manager?

In my experience, @rg305 “INSANE” method was the solution that worked. But in the time required to debug and test it you can spin up an apache server with dozens of virtual hosts and certificates to boot. @schoen politely touches on the core of the issue. This is a “significant challenge” even for a seasoned enterprise admin.

webroot can work.
certonly is a pain but can work also
@Osiris posted a good link you might seriously consider looking in to.

My doctor equates tomcat with chemotherapy. Unless you have been running your server for years and just love your experience with tomcat, consider a friendlier server or take a look at Brett Sutton’s **tomcat-with-ssl option. I haven’t seen anyone on this forum using it (might be wrong)

Whatever you do please update this thread so we can see the progress and learn from your experience.
Finished my rant.


I think 'certonly' is implied anyway, because there is no installer plugin for Tomcat. When you're using certbot run without an installer plugin, de facto you're running certbot certonly :wink:

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