This is a bug in macOS Catalina (still present with the latest patchlevel, i.e. 10.15 with the supplemental update from 15th October 2019). For some reason the Captive Portal Assistant (the app that produces the captive portal popup window whenever you connect to a WiFi hotspot) won't start automatically.
There are two workarounds:
option 1: Either you can manually start the Captive Portal Assistant app manually after you have connected to the WiFi network. This will bring up the captive portal popup window and you can unlock Internet access there. (Really no need to boot in recovery mode, etc. !)
option 2: From this blog post: To bring back the captive portal window automatically whenever you connect to a captive portal-protected WiFi network you can create a LaunchDaemon that watches for WiFi changes and automatically opens the Captive Portal Assistant app.
Create a plist file with the service definition somewhere:
<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple Computer//DTD PLIST 1.0//EN" \
"http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
<dict>
<key>Label</key>
<string>my.shim.catalina.captivenetworkassistant.plist</string>
<key>LowPriorityIO</key>
<true/>
<key>ProgramArguments</key>
<array>
<string>open</string>
<string>/System/Library/CoreServices/Captive Network Assistant.app</string>
</array>
<key>WatchPaths</key>
<array>
<string>/Library/Preferences/SystemConfiguration</string>
</array>
<key>RunAtLoad</key>
<true/>
</dict>
</plist>
and apply it:
launchctl load my.shim.catalina.captivenetworkassistant.plist
launchctl start my.shim.catalina.captivenetworkassistant
check https://poweruser.blog/macos-catalina-wifi-issue-captive-portal-broken-45610cc016b5 for more details.