I have the same problem. First time I get prompted for the pass phrase,
I hit cancel and manually tell NM to connect to my router. Usually it
connects after trying 2 or 3 times. This not only happens when I try to
connect to my router but also with other routers.

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nm-applet can't connect to wireless network during the first connection
https://bugs.launchpad.net/bugs/212366
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