Is the iCloud authorization issue the reason my Calendar events aren't showing up?

edit: Calendar is now working some of the time. It’s not as reliable as it used to be so I decided to use a bunch of sensors & input_booleans to build a calendar of my roster as a backup to trigger automations for if calendar.work has no events.

I use caldav component to have my work calendar show in HA and use the start/end time for automations. Until last week (I think) it was working perfectly.
When I went looking for why my work automations weren’t triggering, I found that my calendar.work had disappeared. Did some research, and changed my config to get rid of the specific work url.:

calendar:
  - platform: caldav
    url: https://caldav.icloud.com 
    username: !secret icloud_username
    password: !secret icloud_app_specific_password
    calendars:
      - 'Work' 

Calendar.work now appears. On first reset, an event appeared. But after that, there’s been nothing. Only attribute showing is friendly_name. Even when my ical shows me as being at work, there’s nothing showing in calendar.work
In the logs, I found this, but no errors:

2019-06-21 16:52:01 DEBUG (SyncWorker_7) [homeassistant.components.caldav.calendar] No matching event found in the 0 results for Work
I’m using Hass.io and updated to 0.94.4 yesterday, but I think I was on 0.94.2 when this issue started.

Could it be the issues with iCloud Authorization messing this CalDav, or is it something else?