error while loading shared libraries: libssl.so.1.0.2:

Running Ubuntu on Digital Ocean droplet

Description:    Ubuntu 20.04.4 LTS
Release:    20.04
Codename:   focal

Try to upgrade to latest version of rstudio-server
Fails.

...
Setting up libclang-dev (1:10.0-50~exp1) ...
Processing triggers for libc-bin (2.31-0ubuntu9.7) ...
Selecting previously unselected package rstudio-server.
(Reading database ... 189246 files and directories currently installed.)
Preparing to unpack rstudio-server-2022.02.2-485-amd64.deb ...
Unpacking rstudio-server (2022.02.2+485) ...
Setting up rstudio-server (2022.02.2+485) ...
useradd: user 'rstudio-server' already exists
Created symlink /etc/systemd/system/multi-user.target.wants/rstudio-server.service → /lib/systemd/system/rstudio-server.service.
/usr/lib/rstudio-server/bin/rserver: error while loading shared libraries: libssl.so.1.0.2: cannot open shared object file: No such file or directory
● rstudio-server.service - RStudio Server
     Loaded: loaded (/lib/systemd/system/rstudio-server.service; enabled; vendor preset: enabled)
     Active: inactive (dead) since Tue 2022-05-10 13:45:43 EDT; 7min ago
   Main PID: 176199
      Tasks: 0 (limit: 4611)
     Memory: 23.9M
     CGroup: /system.slice/rstudio-server.service

May 09 20:59:01 ubuntu-1vcpu-1gb rserver[176199]: CLIENT EXCEPTION (rsession-law): (Error) : The range…
May 09 20:59:31 ubuntu-1vcpu-1gb rserver[176199]: CLIENT EXCEPTION (rsession-law): (Error) : The range…
May 09 21:11:39 ubuntu-1vcpu-1gb rsession-law[295260]: ERROR r error 4 (R code execution error) [error…
May 10 11:56:36 ubuntu-1vcpu-1gb rserver[176199]: ERROR Invalid method PRI requested for uri: *; LOGGE…
May 10 11:56:37 ubuntu-1vcpu-1gb rserver[176199]: ERROR Invalid method PRI requested for uri: *; LOGGE…
May 10 13:45:42 ubuntu-1vcpu-1gb systemd[1]: Stopping RStudio Server...
May 10 13:45:43 ubuntu-1vcpu-1gb systemd[1]: rstudio-server.service: Succeeded.
May 10 13:45:43 ubuntu-1vcpu-1gb systemd[1]: Stopped RStudio Server.
May 10 13:45:44 ubuntu-1vcpu-1gb systemd[1]: 0m
May 10 13:45:45 ubuntu-1vcpu-1gb rsession-law[295260]: ERROR r error 4 (R code execution error) [error…
Hint: Some lines were ellipsized, use -l to show in full.

Which URL did you use for downloading the DEB file? The error looks as if you downloaded a version meant for an older distribution.

The URL that resulted in an error is what I understand to be the latest version:
wget https://download2.rstudio.org/server/bionic/amd64/rstudio-server-2022.02.2-485-amd64.deb

What I eventually found that worked was to go to this page and use this url: https://s3.amazonaws.com/rstudio-ide-build/server/bionic/amd64/rstudio-server-2022.02.1-461-amd64.deb

It got me up and running again. Not ideal, since not the latest version.
Any thoughts on how I can get, rstudio-server-2022.02.2-485-amd64.deb to work?

I tested this right now in the rstudio/r-base:4.2-focal Docker container:

My suggestion is to re-download the package making sure that you are using the correct URL and try installing it again. You can also verify that your download is good using

$ md5sum rstudio-server-2022.02.2-485-amd64.deb 
0fb9fe6002d4808834cfbdaed3364b29  rstudio-server-2022.02.2-485-amd64.deb