I'm already too new. Should I just downgrade?
Downgrading would result in removal of a whole bunch of packages:
QuoteDisplay More~ # apt-get install libssl1.1=1.1.0k-1~deb9u1
Reading package lists... Done
Building dependency tree
Reading state information... Done
The following packages were automatically installed and are no longer required:
debhelper dh-autoreconf dh-strip-nondeterminism fonts-lato intltool-debian javascript-common libapr1-dev libaprutil1-dev
libarchive-zip-perl libexttextcat-2.0-0 libexttextcat-data libfastlz libfile-listing-perl libfile-stripnondeterminism-perl
libhtml-tree-perl libhttp-cookies-perl libhttp-negotiate-perl libicu57 libjansson4 libjs-jquery libjs-sphinxdoc
libjs-underscore liblzo2-2 libmail-sendmail-perl libnet-http-perl libpython3.5 libsctp-dev libsctp1 libstemmer0d
libsys-hostname-long-perl libtcl8.6 libwww-robotrules-perl libyaml-0-2 po-debconf postfix-sqlite python-backports-abc
python-cffi-backend python-chardet python-concurrent.futures python-croniter python-crypto python-cryptography
python-dateutil python-enum34 python-idna python-ipaddress python-jinja2 python-markupsafe python-msgpack python-openssl
python-pkg-resources python-psutil python-pyasn1 python-setuptools python-singledispatch python-six python-systemd
python-tz python-urllib3 python-yaml python-zmq python3-pycurl python3-urllib3 ruby-did-you-mean ruby-minitest
ruby-net-telnet ruby-power-assert ruby-test-unit sqlite3 uuid-dev vim-runtime
Use 'apt autoremove' to remove them.
The following packages will be REMOVED:
apache2-dev apt-listbugs bareos-common bareos-filedaemon ca-certificates dovecot-core dovecot-imapd dovecot-mysql
dovecot-pop3d liblwp-protocol-https-perl libruby2.3 libssl-dev libwww-perl libxml-parser-perl openssl postfix
python-pip-whl python-requests python-tornado python-virtualenv python3-debianbts python3-httplib2 python3-pysimplesoap
python3-reportbug python3-requests python3-virtualenv rake reportbug ruby ruby-debian ruby-domain-name ruby-gettext
ruby-http-cookie ruby-httpclient ruby-locale ruby-soap4r ruby-sqlite3 ruby-text ruby-unf ruby-unf-ext ruby-unicode
ruby-xmlparser ruby2.3 rubygems-integration salt-common salt-minion ssl-cert vim-nox virtualenv
The following packages will be DOWNGRADED:
libssl1.1
0 upgraded, 0 newly installed, 1 downgraded, 49 to remove and 0 not upgraded.