Welcome to RStudio community! I suspect the problem is your Server.Address value in your /etc/rstudio-connect/rstudio-connect.gcfg file
For example:
[Server]
Address = https://myaddress.com:444
There are certain parts of Connect that (for security and other reasons) depend on that value being the correct "front door" of your Connect server (where users go to interact with the root of the server).
For instance, we use that address to generate links in emails, etc.