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Recently, after extending a wireless network on a setup with one Extreme and one Express (both AirPort base stations), I've been experiencing issues regarding which base station extends which on a certain iMac. Note that when it actually works, it works great.

I have the AirPort Extreme connected to a modem via Ethernet, but an AirPort Express that is generally closer to all of my devices extends this network (we can't change where our modem is without our ISP having to send someone over to re-wire practically everything). The screenshot below explains everything.

Bad Internet Connection! AirPort Express ahead of AirPort Extreme.

I cannot use Internet on this particular Mac when it is acting this way.

Any suggestions or explanations as to why AirPort Utility would show it in this strangely ordered diagram?

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I recently encountered the same issue and was able to resolve it by removing the Wifi connection in System Preferences > Network.

Here you can select the Wi-Fi interface from the left panel and click the "-" underneath this panel. Then, add back the Wi-Fi interface by pressing the "+", select Wi-Fi and attempt to connect to your desired network.

This should then place all devices in the correct order by connecting to the device that creates the wireless network as opposed to those devices that either join or extend it.

Best of luck.

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