HELP! Can't get my Unattended Bot to connect to Orchestrator

Ok so I clearly don’t know what I’m doing in Orchestrator. I tried to setup an Unattended robot but cannot get it to work. I can only get Floating robots to work. I listed my full setup below, but to summarize, all I want is to have a Developer Machine (let’s call it Dev12345) and a primary test server (call it Test67890). I want to develop on Dev12345 using account user_dev. I want an unattended bot called bot_alpha to run on server Test67890.

I can’t imagine it should be this difficult, but when I try to use UiPath Assistant from the server Test67890 to connect to Orchestrator, it says “Connection was lost”, and then “Connection Failed”.

Here’s my exact setup (these are all virtual if it matters):

Developer Machine (Dev12345)

  • Account user_dev
  • Has UiPath Studio and UiPath Assistant installed

Test Server (Test67890)

  • Account bot_alpha
  • Has UiPath Robot and UiPath Assistant

Orchestrator Tenant (accessed via Web)

  • Folders (Default)
    • user_dev (Robot type: Unattended, Roles: Administrator)
    • bot_alpha (Robot type: Unattended, Roles: Robot)
  • Users
    • user_dev (role Administrator)
    • bot_alpha (role Robot, no e-mail specified)
  • Machines
    • Dev12345
      . Standard
      . Installed Version 20.10.2: Disconnected
      . License: 1 Unattended, 1 NonProduction, 0 Testing
    • Test67890
      . Standard
      . Installed Version 20.10.2: Available (plus two 21.4.4 but both say Disconnected)
      . License: 1 Unattended, 1 NonProduction, 0 Testing

What am I doing wrong? Why is it not connecting??