I doubt it.
browser cache
I wonder if a browser caching issue could be involved. You might try clearing your browser’s cache for this site, generally viewing it in incognito mode or private browsing tab, and maybe clear hsts headers.
.dev 
.test
You might consider adjusting your dev site(s) to use .test instead of .dev. See details…
So, you’d edit site_hosts in group_vars/development/wordpress_sites.yml.
If you do this, consider whether you need to search/replace example.dev to example.test in your dev database. You could use wp-cli or a plugin like WP Migrate DB Pro.
Also, I’d recommend not defining wp_home and wp_siteurl in the env of wordpress_sites.yml so that Trellis will use its dynamic default values instead. Maybe you weren’t defining those values anyway.
MacOS High Sierra
Whether it’s relevant to this issue or not, you may want to check whether you are affected by this issue with the High Sierra filesystem.
https://discourse.roots.io/t/high-sierra-upgrade-issues-with-filesystem/10594/8
/etc/hosts
You could double-check your local machine’s /etc/hosts files for any potential conflicting entries related to your dev VM’s IP (probably 192.168.50.5).
Reload or Destroy and Rebuild
If this is an older existing VM that you’ve started back up, maybe the issue would resolve itself if you were to export the DB (if you need it) and vagrant reload or vagrant destroy -f && vagrant up.