I wish you could connect to the WD Wireless Pro drive wireless and be on the internet hotspot from my phone at the same time :(

WD External Drives My Passport Wireless
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I can’t figure out if there is a way. I only have a WiFi iPad.

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Would having a LTE iPad fix this issue or not really?

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You could always buy a small travel router https://amzn.to/37qm7sx. Have the internet hotspot on the phone on & then configure router to connect to the hotspot (in bridging mode). Then have the passport & any other device ( tablet / laptop ) connect to the routers wifi and they will share the hotspot.