Hi Amy!
Thanks for getting in touch with us! Let me try to help you with that.
As you might already know, the functionality you are looking for is not built in with our plugins. Like you say, you can export .ics files from our calendar and then import it in your Outlook calendar, but this is a process that will have to be done manually.
Automating this process could likely be done somehow, but would definitely require custom coding. I’m not very familiar with Outlook’s capabilities, but you might see if it can receive a subscription to an RSS feed, in which case you might want to have a look at the following article regarding The Events Calendar RSS Feed > https://theeventscalendar.com/knowledgebase/events-rss-feed/
I hope that helps! Let me know if you have any follow up questions.
Best,
Victor