@BuZz said in Updates broke Lighttpd:

Or use after apt update useaptitude install on lighttpd and go through the options when you get the dependency issue and choose to downgrade SSL.

@mitu said in Updates broke Lighttpd:

Looks like I have to brush up also on some advanced apt options :).
You can try @BuZz's suggestion, but aptitude is not installed by default on a Raspbian lite.
Try forcing apt to install the Raspbian version:

sudo apt install --reinstall libssl1.1=1.1.0l-1~deb9u1

You are the best!
Both of these solutions would work out (tried 1st one without answering yes, but it would downgrade libssl and install lighttpd).
I used the @mitu one and then installed lighttpd.

Thank you for being so helpful and knowledgeable. :)