I took a stab at organizing our CLI options. At the time of writing, we have 42 top-level categories. The presentation can be drastically improved by grouping them (and hiding ones that are pretty irrelevant to 99% of users)

I used https://coder.yourdomain.com/api/v2/config/deployment to get the top-level config options

General

"access_url",
"address",
"redirect_to_access_url",
"wildcard_access_url"
"http_address",
"tls",
"pg_connection_url",
"cache_directory",
"telemetry",
"update_check",

Authentication

"scim_api_key",
"oauth2",
"oidc",
"gitauth",

Workspace builds

"provisioner",

Workspace connections

"derp",

Security

"max_session_expiry",
"max_token_lifetime",
"browser_only",
"secure_auth_cookie",
"ssh_keygen_algorithm",
"rate_limit",
"disable_password_auth",
"audit_logging",

Monitoring & documentation

"logging",
"pprof",
"prometheus",
"trace",
"swagger",

Extras

"agent_fallback_troubleshooting_url",
"agent_stat_refresh_interval",
"autobuild_poll_interval",
"dangerous",
"disable_path_apps",
"disable_session_expiry_refresh",
"experimental",
"experiments",
"in_memory_database",
"metrics_cache_refresh_interval",
"proxy_trusted_headers",
"proxy_trusted_origins",

One concept

$ coder server --help

Showing general configuration options: 

      For a list of all options: `coder server help --all`
      or visit https://coder.com/docs/v2/latest/cli/coder_server

General:
      --access-url string                                 External URL to access your
        (consumes $CODER_ACCESS_URL)                      deployment. This must be accessible
                                                          by all provisioned workspaces.
      
      --http-address string                               HTTP bind address of the server.
        (consumes $CODER_HTTP_ADDRESS)                    Unset to disable the HTTP endpoint.
                                                          (default "127.0.0.1:3000")
      ...all general options

Authentication:
      Run `coder server --help authentication` to see available options

Workspace builds:
      Run `coder server --help workspace-builds` to see available options

...all categories

Then we could also change https://coder.com/docs/v2/latest/cli/coder_server or https://coder.com/docs/v2/latest/admin/configure to have different groups and display the options in a table.

Open to other ideas though!

I've found it quite clunky to inform users about new flags via email or Slack. I end up sending them a snippet of the --help output, but it'd be super nice if I could send a docs link or a specific CLI command they could type to see the flag.

This seems to be fixed by the flags work!