Apt-get update fails inside container yarn repo not signed

I am getting what looks like similar errors on an update.

Err:7 https://dl.yarnpkg.com/debian stable InRelease
  The following signatures were invalid: EXPKEYSIG 23E7166788B63E1E Yarn Packaging <yarn@dan.cx>
Get:13 http://apt.postgresql.org/pub/repos/apt bullseye-pgdg/main amd64 Packages [268 kB]
Reading package lists...
FAILED

--------------------

Pups::ExecError: cd /var/www/discourse && apt-get update && DEBIAN_FRONTEND=noninteractive apt-get install -y libsqlite3-dev failed with return #<Process::Status: pid 532 exit 100>

Location of failure: /usr/local/lib/ruby/gems/3.1.0/gems/pups-1.1.1/lib/pups/exec_command.rb:117:in `spawn'

exec failed with the params {"cd"=>"$home", "cmd"=>["apt-get update && DEBIAN_FRONTEND=noninteractive apt-get install -y libsqlite3-dev", "echo \"gem 'sqlite3'\" >> Gemfile", "su discourse -`Preformatted text`c 'bundle config unset deployment'", "su discourse -c 'bundle install --no-deployment --path vendor/bundle --jobs 4 --without test development'"]}

From discourse-doctor I get:

Checking your domain name . . .

Connection to xxx succeeded.

You should probably remove any non-standard plugins and rebuild.

Attempting to restart existing container. . .

x86_64 arch detected.

WARNING: containers/app.yml file is world-readable. You can secure this file by running: chmod o-rwx containers/app.yml

starting up existing container

+ /usr/bin/docker start app

Error response from daemon: driver failed programming external connectivity on endpoint app (c143632e34e1ae05e48759bdf163b4bbe5dc9aaf895f1fb7521f7e3784c26577): Error starting userland proxy: listen tcp 0.0.0.0:443: bind: address already in use

Error: failed to start containers: app

Failed to restart the container.

Anything I might be able do other than a new install?