Hey there wvdurren,
It sounds like you are not able to reliably connect to your Airport Express unless it is in bridged mode. I would recommend the troubleshooting in the following article for you, to help resolve the issue here:
- Tap Settings > Wi-Fi and turn Wi-Fi off and on. If your Wi-Fi setting is dimmed, follow these steps.
- Restart your iOS device.
- Tap Settings > Wi-Fi and locate the Wi-Fi network to which you're connected.
- Tap and Forget this Network.
- Try to connect to your desired Wi-Fi network.
Note: You may need to enter your Wi-Fi password again if your network requires one.
- Turn your Wi-Fi router off and on2. If your ISP also provides cable or phone service, check with them before attempting this step to avoid interruption of service.
- Update your device to the latest version of software.
- Update your Wi-Fi router to the latest firmware2. For AirPort Base Stations, install updates using the AirPort Utility.
- Verify that you're attempting to connect to your desired Wi-Fi network.
- Make sure you're entering your Wi-Fi password correctly. Passwords may be case sensitive and may contain numbers or special characters.
- Reset network settings by tapping Settings > General > Reset > Reset Network Settings. Note: This will reset all network settings including:
- previously connected Wi-Fi networks and passwords
- recently used Bluetooth accessories
- VPN and APN settings
Thank you for using Apple Support Communities.