Chromecast & Bose WiFi Speakers (solved)
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For the benefit of others treading my path and related to this old post https://forum.pfsense.org/index.php?topic=65559
I recently had issues with a new Chromecast and then a new pair of Bose SoundTouch 10 WiFi speakers, both failed during final part of setup with not being able to connect to my WiFi despite appearing to authenticate etc. While at first I suspected the Chromecast, and even pfSense, once I tried to setup the Bose speakers, almost the identical symptoms. I did verify there were no entries in pfSense firewall logs, and that my WiFi router(s) TP-Link Archer C5 on same sub-net as pfSense were correctly setup, not blocking across WiFi clients etc. All other devices on WiFi iOS, Android, Linux & Windows worked fine (apart from poor roaming between APs, but separate issue) I gave up in frustration and flashed the WiFi routers stock firmware with OpenWrt using identical setup and WiFi credentials. Viola both Chromecast and Bose now setup and work flawlessly. Sorry for doubting you pfSense (I know after thinking things through, there is no way pfSense was involved here)
Hope it helps someone